Name: 1883-75-6|Furan-2,5-diyldimethanol|98%
Brand: Ambeed
SKU: A136022
Price: 5.0 USD
Availability: InStock
Rating: 95 (27 reviews)

1
[ 67-47-0 ]
[ 1883-75-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen In ethanol at 20℃; for 48h;	4 Example 4.; Batch experiment with hydrogenation/etherification of 5- ( hy d roxy methyl )f u rf u ra I In a 7.5 ml batch reactor, 0.06 mmol 5-(hydroxymethyl)furfural (HMF) in 1 mL ethanol and 5 bars of hydrogen was reacted with 3 mol% of a Pt/C catalyst for 2 days at room temperature. The starting material was completely converted in 100% selectivity to 2,5- di(hydroxymethyl)furan. Subsequently, the mixture was heated to 75 0C for 1 day without hydrogen. The 2,5-di(hydroxymethyl)furan was fully converted and 2,5- bis(ethoxymethyl)furan was obtained in 75% yield. 25% Side products are ring opened levulinate derivatives. The experiment was successfully repeated on a 20 gram scale.
100%	With methanol; magnesium(II) oxide at 160℃; for 3h; Autoclave; Inert atmosphere; chemoselective reaction;	The following reagents and products were used for reactivity experiments: furfural (FAL) (Sigma-Aldrich), 5-hydroxymethylfurfural (HMF) (Sigma-Aldrich), furfuryl alcohol (FFA) (Sigma-Aldrich), and 2,5-bis(hydroxymethyl)furan (BHMF) (Toronto Research Chemicals). The hydrogenation of FAL and HMF was carried out using a Parr Instrument 4561 autoclave reactor (300 mL capacity). The reaction was carried out in methanol, using the appropriate amount of catalyst. If not otherwise indicated, each test was conducted for 3 h at 160 °C, with the following amounts of reagents: 50 mL methanol; 1.21 mmol FAL or HMF; 0.5 g MgO; 1 bar of nitrogen. After loading the methanol, reactant, and catalyst, the autoclave reactor was purged 3 times with N2 (20 bar) and then pressurized at 1 bar (N2). The temperature was increased up to 160 °C and the reaction mixture was stirred at 400 rpm for the time needed. At the end of the reaction, the reaction mixture was cooled in an ice bath and the MgO was separated by filtration.
100%	With sodium tetrahydridoborate In lithium hydroxide monohydrate	2.2. Synthesis of 2,5-bishydroxymethylfuran (BHMF) In a 50 mL round bottom flask 0.63 g (5 mmol) HMF was dissolvedin 10 mL distilled water. In another flask, 0.19 g (5 mmol) NaBH4 was dissolved in 3 mL distilled water. Then NaBH4 solutionwas added drop wise to the HMF solution with continuous stirring.The reduction process was very fast. After the complete reduction,the product (BHMF) was isolated by extracting with ethyl acetate(4 20 mL). Here the aqueous phase was saturated with NaCl forthe quantitative extraction of BHMF. After evaporation of ethylacetate, BHMF was obtained as white solid product (0.64 g, 100%yield) and characterized by NMR studies. 1H NMR (400 MHz,CDCl3): δ 6.16 (s, 2H, 2CH), 4.50 (s, 4H, 2CH2). 13C NMR(100 MHz, CDCl3): d 154.0, 108.5, 57.4.

100%	With carbon monoxide; lithium hydroxide monohydrate at 90℃; for 3h;
100%	With hydrogen In lithium hydroxide monohydrate at 130℃; for 4h; Autoclave;
99%	With formic acid In dimethyl sulfoxide at 40℃; for 2h;	20 Conversion of HMF to BHMF using Ir Catalysts This example demonstrates the use of various transfer hydrogenation Ir catalysts and formic acid as the hydrogen donor in the hydrogenation of HMF to BHMF.The different catalysts vary in terms of their stabilities toward formic acid. To test the stability of the catalyst, the iridium catalyst and formic acid was combined in a 1:10 ratio in 1 mL d6-DMSO. Catalyst decomposition was monitored by 1H NMR at 20° C. CpIr(TsDPEN) was found to have a half life of about 2 hours whereas CpIr(NHCPh2C6H4) and CP*IrH(TsDACH-H) have half-lives of minutes after exposure to formic acid.The catalysts were evaluated in the transfer hydrogenation of HMF. HMF (0.25 g), was combined with DMSO (3 mL) and 0.1-1% of an iridium based catalyst. Formic acid in DMSO was dispensed via a syringe pump at a rate of 2 mL/h to minimize catalyst decomposition. The reaction of HMF and formic acid occurred quantitatively in the presence of 0.1-1% catalyst at 40° C. in 1-4 hours. Methanol, which is traditionally employed for transfer hydrogenation catalysis, was also evaluated as a hydrogen donor (entry 3). Combining HMF (2 mmol), catalyst and methanol (5 mL) results in a much longer reaction time of 16 hours to produce a 99% yield of BHMF. The results are summarized in the table below. This experiment shows that formic acid is a highly effective hydrogen donor.
99%	With hydrogen In lithium hydroxide monohydrate at 29.84℃; for 6h; Autoclave; Sealed tube; chemoselective reaction;
99%	With Shvo's catalyst; hydrogen In toluene at 90℃; for 1h; Autoclave; Inert atmosphere;
99.2%	With formic acid; O₄S^(2-)*C₂₀H₂₈IrN₄O⁽²⁺⁾; anhydrous sodium formate at 130℃; for 2h;	34 Weigh 1mmol5-HMF (126mg), using 1mol / L of formic acid 5mlpH = 2 / dissolving sodium formate buffer solution and transferred to a 35mL glass pressure tube was added 200μL 2 catalyst (catalyst concentration: [Cp * Ir- (di-R -bpy) (OH2)] SO4Complexes 0.50mmol / L), i.e. 100ppm (when compared to a dual site catalyst Ir 50ppm) catalyst, with magnetic stirring and the reaction was heated in an oil bath 120 2H; After completion of the reaction, ice-water bath and cool to room temperature.The 5-HMF feedstock quality similar dimethyl phthalate internal standard added to the reaction mixture, washed with methanol and 20ml wall.After the mixed reaction liquid to take appropriate centrifuge tube, with a larger volume of the reaction solution was taken in methanol and then diluted into after centrifugation centrifuge.Gas chromatography (GC (2104, Shimazu, FID) fitted on the DM-WAX (30m × 0.32mm × 0.25μm) for detecting the column combination in gasifier temperature setting 250 , detector temperature setting 280 , column oven temperature setting 180 holding 20min. linear velocity of 45cm / s, split ratio was 50.) reacting a compound of quantitative detection system, measured HHD yield was 36.2%pecific reaction and detecting the same manner as in Example 1, except that the catalyst was changed to the catalyst 6, formic acid / sodium formate buffer solution was adjusted to pH 5.5.The resulting product furandimethanol (BHMF) in a yield of 99.2%
99%	With sodium tetrahydridoborate In lithium hydroxide monohydrate at 24 - 60℃; for 3h;
99%	With sodium tetrahydridoborate In lithium hydroxide monohydrate
99.1%	With Hf-DPBDS-SO₃H In iso-butanol at 120 - 160℃; for 10h; Inert atmosphere; Sealed tube;	1; 2; 3; 4; 5; 6 Example 5 Add 30 mmol of ruthenium tetrachloride and 15 mmol of 2,5-diphosphonic phenyl-1,4-disulfonic acid to 500 mL of dimethylIn the formamide solvent, stir to complete dissolution with ultrasonic assistance; slowly add the ruthenium tetrachloride solution to the 2,5-diphosphonic acid group.In the phenyl-1,4-disulfonic acid solution, stirring was continued for 4 h at room temperature, and the temperature was raised to 90 ° C for standing for 5 h; the solid precipitate was passed throughAfter filtration, it was washed repeatedly with dimethylformamide and ethanol until no chloride ions were detected;The body precipitate is dried under vacuum at 90 ° C for 12 h, and ground and pulverized to about 200 mesh to obtain a sulfonic acid functionalized inorganic organic impurity.Polymerized Catalyst 5, abbreviated as Hf-DPBDS-SO3H; characterized by NH3-TPD, CO2-TPD and Py-IR, the Lewis acid site content of Hf-DPBDS-SO3H is 0.876 mmol/g, Lewis alkaline The site content was 1.322 mmol/g and the Brφnsted acid site content was 0.824 mmol/g. Next, 1 g of 5-hydroxymethylfurfural, 25 sec-butanol, and 0.9 g of Hf-DPBDS-SO3H were placed in a 100 mL reactor, and the air in the kettle was continuously replaced with nitrogen five times after sealing; the temperature was raised to 120 at a stirring speed of 300 rpm. After °C, after 7h reaction, the conversion rate of HMF reached 100%, the yield of 2,5-dihydroxymethylfuran reached 97.7%, and the temperature was further increased to 160 °C, and then reacted for 3 hours to obtain the corresponding 2, 5-Dialkyloxymethylfuran. As a result of gas chromatography, the conversion of 2,5-dihydroxymethylfuran was 99.1%, and the final yield of 2,5-dialkoxymethylfuran was 95.2% (Fig. 5).
99%	With hydrogen In ethanol at 140℃; for 3h;	1-5 Example 1 5-hydroxymethylfurfural (0.5 mmol),Catalyst CuNPsZIF-8 (7.2% mol Cu, relative to 5-hydroxymethylfurfural)Add 5mL of ethanol to the stainless steel closed reactor and charge 2Mpa H2.The reaction was heated to 140 ° C at a stirring speed of 600 rpm for 3 hours, and after the reaction was completed,Cool to room temperature. The catalyst was centrifuged and the reaction solution was tested.After gas chromatography analysis,Calculate the selectivity of 2,5-furandimethanol over 99%,The molar yield was 99%.
99.6%	With (OC-6-52)-[2-[bis(1-methylethyl)phosphino-κP]-N-[2-[bis(1-methylethyl)phosphino-κP]ethyl]ethanamine-κN](carbonyl)(chloro)(hydrido)ruthenium(II); hydrogen; potassium etoxide In ethanol at 25℃; for 2h; Autoclave; Green chemistry;
98%	With hydrogen In ethanol at 120℃; for 15h; Autoclave;
98%	With copper(II) bis(2,4-pentanedionate); hydrogen In methanol at 90℃; for 20h; Autoclave;
98.9%	With hydrogen at 120℃;
98.66%	With zirconium hydroxycarbonate In isopropanol at 80℃; for 9h; Autoclave; Sealed tube;
98.5%	With hydrogen In methanol at 100℃; for 4h; Autoclave; Sealed tube;	Hydrogenation of HMF to BHMF/BHMTHF General procedure: Hydrogenation experiments of HMF to BHMF/BHMTHF were conductedin 100 mL of Parr reactor (Parr Instrument Company, Moline, IL,USA). For this purpose, 1.0 g (8.0 mmol) of HMF, 30 mL of methanol asa solvent, and 0.40 g of Ru-based catalyst (mole ratio of HMF/Ru =50)was taken into the reactor and sealed. In order to eliminate the air fromthe reactor, H2 gas was passed into the reactor three times. When thereactor was heated to the desired reaction temperature, the reactor waspressurized with H2 gas. During the reaction, the pressure was maintainedconstantly using a gas reservoir equipped with a back-pressureregulator and a transducer. After completion of the reaction, the reactorwas allowed to room temperature and depressurized. The productmixture was filtered to remove the insoluble catalyst, and the finalsolution was analyzed using High-Performance Liquid Chromatography(HPLC) instrument (Agilent Technologies 1200 series) equipped withUV-detector. Bio-Rad Aminex HPX-87 H pre-packed column was usedas column material and dilute solution of H2SO4 (0.0005 M) in waterwas used as mobile phase. Based on the calibration curves obtainedfrom the standard solutions of products (BHMF/ or BHMTHF), and HMFreactant, the conversion of HMF (CHMF,%), yield of product (BHMF/ orBHMTHF) (Y BHMF/BHMTHF,%), and the selectivity of product (BHMF/ orBHMTHF) (SBHMF/BHMTHF,%) were calculated using the following expressions.
98.6%	With hydrogen In ethanol at 70℃; for 3.5h;	1-6 General procedure: During the hydrogenation reaction, 15 g of ethanol as a solvent, 500 mg of HMF and 100 mg of a catalyst were mixed, and then hydrogenation was performed with a stirring rate of 900 RPM at a reaction temperature of 70° C. under a hydrogen pressure of 50 bar for 3.5 hours. The results are shown in Table 3 below.
98.6%	With lithium hydroxide monohydrate In aq. buffer at 23℃; Electrochemical reaction;	1 Electrochemical HMF Reduction To investigate the catalytic abilities of Cu foil, Aggd, and Agsp electrodes to reduce HMF, linear sweep voltammetry (LSV) was performed using solutions with and without HMF. The general experimental setup consisted of a three-electrode system (Cu or Ag working electrode, Pt counter electrode, and a Ag/AgCl (4 M KCl) reference electrode) in an undivided cell controlled by a Bio-Logic VMP2 potentiostat. A 0.5 M borate buffer solution (pH 9.2) with and without 0.02 M HMF was used as the electrolyte, which was purged with N2 to remove dissolved oxygen prior to obtaining LSVs. The potential was swept to the negative direction from the open circuit potential to -1.5 V vs. Ag/AgCl at 5 mV/s without stirring. All current densities reported in this example were calculated based on the geometric area of the working electrode.
97%	With sodium tetrahydridoborate In methanol at 20℃; for 0.25h;
97%	With hydrogen In ethanol at 100℃; for 3h; Autoclave;
97%	With hydrogen at 90℃; for 5h;	1-7 Example 3: Hydrogenation reaction using a Cu-based catalyst containing 50% by weight of Cu - 3 The reaction was carried out in the same manner as in Example 1 except that the reaction was carried out for 5 hours while maintaining the temperature and the pressure at 90 ° C and 15 bar, respectively.After the reaction was completed, the solution was analyzed by gas chromatography to find that the conversion of 5-hydroxymethylfurfural was 100% and the yield of dihydroxymethylfuran was 97%.
96%	With Au/Al₂O₃; hydrogen at 119.84℃; for 2h;
96.2%	With isopropanol at 82℃; for 2h; Sealed tube;
96%	With hydrogen In ethanol at 80℃; for 1h;
95%	With hydrogen at 150℃; for 3h;
95%	With Ni_2.1/CN In ethanol at 160℃; for 3h; Inert atmosphere;	1-5 Example 1 Add 0.126g 5-hydroxymethyl furfural, 0.04g Ni2.1/CN and 10mL ethanol into a stainless steel closed reactor, replace the air with nitrogen, heat to 160 with a stirring speed of 600rpm for reaction for 3h, after the reaction, cool to Room temperature. The catalyst is separated by centrifugation, and the reaction liquid is tested. After gas chromatography analysis (external standard method), the selectivity of 2,5-furandimethanol was calculated to be 96%, and the molar yield was 95%.
95%	With hydrogen In methanol at 100℃; for 16h; Sealed tube;
94%	With formic acid In tetrahydrofuran for 4h; Reflux;	1 This example demonstrates the reduction of HMF to BHMF with formic acid and palladium catalyst. To a 100-mL Schlenk flask, HMF (0.25 g, 2 mmol) was dissolved in THF (15 mL). Formic acid (0.31 mL, 8 mmol) and Pd/C (0.2 g) were subsequently added. The slurry was heated at reflux for 4 h. Pd/C was removed by filtration (catalyst recovered: 0.39 g). The colorless filtrate was concentrated under reduced pressure to yield light orange oil of BHMF (FIGS. 1 and 2). Yield: 0.24 g (94%).
94%	With CuZn; hydrogen In ethanol at 120℃; for 3h; Autoclave;	6 EXAMPLE 6: HMF reduction to FDM EXAMPLE 6: HMF reduction to FDMCopper zinc nanopowder and some commercial catalysts were also tested the hydrogenation of HMF at mild temperature for the achievement of useful diol building blocks (suppliers are indicated in table 6). Table 7. Composition details (and suppliers) of the commercial catalysts used.The vessel was pressurized with 70 bar H2 and subsequently heated to 120 C for 3 hours. In the adopted experimental conditions, all commercial catalysts showed good to excellent activity in the hydrogenation of HMF to FDM (2,5-furandimethanol) and THFDM (2,5-tetrahydrofurandimethanol), which account together for a combined selectivity of >80% (see Scheme 3).Scheme 3. Commercial compositions, such as catalyst D and catalyst G, both based on copper and nickel supported on S1O2 and Si02 Zr02, respectively, showed good selectivity to FDM (Table 8, entry 1 and 2) but no complete conversion of HMF, especially with catalyst G, which is characterized by a lower content of Cu and Ni than catalyst D. Ni Raney alloy showed complete conversion of HMF and high selectivity to THFDM (94%, table 8, entry 3), while Ni supported on ceria and zirconia (table 8, entry 4) led to an approximately equimolar mixture of FDM and THFDM. The strong interaction between nickel and the support might cause a reduced hydrogenation activity. Also the simultaneous presence of copper and nickel centres may attenuate the hydrogenation activity of nickel, which is very active in the reduction of C=C bonds (Table 8, entry 1 and 2 vs. entry 3).Interestingly, Cu-Zn alloy showed quantitative conversion of HMF and excellent selectivity to FDM (94%, table 8, entry 5), with no ring- hydrogenation. With the exception of Pt/C, which also selectively reduced HMF to FDM (table 8, entry 6), other hydrogenation catalysts based on noble metals preferably gave THFDM or a mixture of FDM and THFDM. Interestingly, Pd/A Oe and Pd/C showed high selectivity to THFDM by hydrogenation of both C=0 and C=C bonds (table 8, entry 7 and 8).
94.2%	With formic acid In 1,4-dioxane at 130℃; for 10h; Autoclave;	1-52 Example 1 In a 500 mL stirred high temperature and high pressure reaction kettle, add 200 mL of 1,4-dioxane, 2g 5-hydroxymethylfurfural, where the mass concentration of 5-hydroxymethylfurfural is 10g / L, Then add 4.2 mL of formic acid and 0.7 g of Co-MNC-700 catalyst, the molar ratio of formic acid to 5-hydroxymethylfurfural is 7: 1, and the mass ratio of Co-NMC-700 catalyst to 5-hydroxymethylfurfural is 1: 3; turn on the stirring, and the stirring speed is 500 rpm, After replacing with 0.5MPa nitrogen three times, filling with 1MPa nitrogen,Heating to 130 °C, catalytic transfer hydrogenation reaction for 10h; After the reaction is completed, cool to room temperature and filter. reuse as catalyst after drying; the filtrate (analyzed by HPLC after sampling, the molar yield of 2,5-furan dimethanol is 94.2%). The 1,4-dioxane obtained at the top of the tower was recycled and the bottom of 2,5-furandimethanol was obtained. after recrystallization, 2,5-furandimethanol product was obtained.
94.1%	With isopropanol at 82℃; for 2h;	<Range of Substrate> General procedure: In addition to the hydrogenation reaction of FUR, the activity of the MOF catalyst according to the present disclosure was measured for hydrogenation reactions using various substrates. A hydrogenation reaction experiment was performed using representative aldehydes and ketones and other biomass-derived carbonyl compounds as the range of the substrate, and the results are shown in Table 5 below (reaction condition: 2.6 mmol of the substrate, 416 mmol of IPA, 0.1 g (10.6 mol %) of the catalyst, and a temperature of 82° C. (reflux)).
93%	With sodium tetrahydridoborate In methanol at 0 - 25℃;
93%	Stage #1: 5-hydroxymethyl-2-furfuraldehyde With [Ru(2-(ethylthio)-N-[(pyridin-2-yl)methyl]ethan-1-amine)(triphenylphosphine)Cl₂]; potassium-t-butoxide In isopropanol Autoclave; Inert atmosphere; Stage #2: With hydrogen In isopropanol at 80℃; for 1h;
93%	With Cu⁽⁵⁰⁾-SiO<SUB>2</SUB>; hydrogen In butan-1-ol at 100℃; for 4h;
93%	With MnO(at)CN calcined at 700 °C In ethanol at 170℃; for 25h; Autoclave; Green chemistry;	1-5 Example 1 0.26 g of 5-hydroxymethylfurfural, 0.1 g of catalyst MnO CN (700) and 20 mL of ethanol were placed in a stainless steel sealed reactor, and the mixture was heated to 170 ° C at a stirring speed of 600 rpm to carry out a reaction. Reaction for 25 hours. After the reaction was completed, the mixture was cooled to room temperature. The catalyst was centrifuged and the reaction solution was tested. After gas chromatography analysis, the selectivity of 2,5-furandiethanol was calculated to be greater than 95%, and the molar yield was 93%.
93.7%	With trimethyl-(2-hydroxyethyl)ammonium chloride; hydrogen at 100℃; for 3h; Autoclave;	1-20 Examples 14-15 Add 1g of choline chloride to the 25mL autoclave,Add 5-hydroxymethylfurfural at a molar ratio of 1: 2 and mix evenly to form a clear fluid.Add 15wt% Raney cobalt to seal the reaction kettle, feed 5MPa hydrogen, stir vigorously (500rpm), heat to 100 and keep for 1h, 3h, finish the reaction, cool to room temperature and take samplesQualitative and quantitative detection using GC-MS (Shimadzu) and GC (Agilent),The test results are listed in Table 1 with serial numbers 14-15.
92%	With isopropanol at 100℃; for 1.5h;
92%	With sodium tetrahydridoborate In methanol at 0℃; Inert atmosphere;
92.3%	With sodium tetrahydridoborate; trimethyl-(2-hydroxyethyl)ammonium chloride; urea at 40℃; for 4h;	1-3 Examples 1-3 In a three-necked flask, Accurately weigh 1.200g of choline chloride, Urea was added at a molar ratio of 1:1, 1:2, 1:3, and magnetically stirred at 40 ° C for 15 min to obtain a colorless transparent low phase transfer temperature blending system. 0.400 g of 5-hydroxymethylfurfural (as shown in Fig. 2) and 0.100 g of sodium borohydride were accurately weighed in the above low phase transfer temperature blending system, and the reaction was carried out at a temperature of 40 ° C for 240 min. After the reaction is completed, the system is dissolved in 8 g of ethanol, filtered to remove excess sodium borohydride, and then subjected to rotary evaporation. The sample after spinning is dissolved in a mixed solvent of methanol and acetone, filtered to remove choline chloride, and then subjected to rotary distillation. The obtained sample was extracted with a toluene solution to obtain a solid of 2,5-furan dimethanol. Qualitative and quantitative detection was carried out by GC-MS and GC. The qualitative test results are shown in Fig. 2 and Fig. 3, and the serial numbers are shown in Table 1 as Examples 1 to 3. The quantitative detection of Example 2 is shown in Fig. 1.
92%	With hydrogen In ethanol at 20℃; for 3h;
92%	With isopropanol at 100℃; for 4h;	2.4. Catalytic reaction General procedure: The MPV reaction of the biomass-derived compounds with 2-propanol was carried out in an oil-heated condition in a 15 ml Ace pressure tube (Synthware, Beijing). Typically, aldehydes (1.0 mmol), catalysts (0.1 g), and 2-propanol (10 mL) were added into the reactor, and then placed into the oil bath at stated temperature of 80-140 °C, followed bythe magnetic stirring for specific time at 600 rpm. After completion, the reaction tube was cooled to room temperature with cold water in a beaker. The reaction mixture was centrifuged and collected for analysis. Quantitative analysis of reactants and products on a standard sample using toluene as an internal standard on a GC (Shimadzu Nexis GC-2030) equipped with an HP-5 capillary column (30.0m×250mm×0.25 mm) and a flame ionization detector. Identification of products were observed using GC-MS (GCMS-QP2010 Ultra) equipped with HP-5MS capillary column (30.0m×250mm×0.25 mm).
90%	With sodium tetrahydridoborate; ruthenium on carbon In ethanol at 0 - 20℃;
90%	With [RuCl(6-(4-methoxyphenyl)-2-aminomethylpyridine)(1,4-bis(diphenylphosphino)butane)]; sodium isopropanolate; isopropanol for 0.5h; Inert atmosphere; Schlenk technique; Reflux;
89.4%	With hydrogen In isopropanol at 110℃; for 3h; Autoclave;	2.3. Hydrogenation reactions General procedure: FFR (99%, Sigma-Aldrich) 1 mL and various amounts of thenickel catalysts were added to 30 mL of a solvent (methanol(99.8%, Duksan), ethanol, IPA, or methyl isobutyl ketone (MIBK;99.5%, TCI)). Raney Ni (Ni 92.5%, TCI) was washed with ethanoland distilled water twice each and dried in a vacuum oven at50 °C before use. The mixed solution was placed in a 100 mL Teflonliner with a magnetic stir-bar and sealed in a stainless steel autoclave.Then the reactor was purged with H2 three times to excludeother gases. The autoclave was heated to 110 °C at which temperaturethe hydrogenation reaction was performed under 30 bar H2and stirring at 700 rpm. After the reaction, the autoclave wascooled, and the solution was subsequently centrifuged at11,000 rpm for 10 min to separate the liquid-phase products fromthe catalyst. For the recycling tests, 1 mL of FFR and 30 mL of IPAwere added to the centrifuged Ni catalyst without any furthertreatment. The products were analyzed by a gas chromatograph(GC; YL 6100) equipped with a capillary column (DB-624, AgilentTechnologies, 30 m 0.53 mm 3.00 lm) and flame ionizationdetector (FID).The selective hydrogenation of various unsaturated aldehydesand ketones was performed according to the following protocol.The reactant 1 mL (3-cyclohexene-1-carboxaldehyde (97%,Sigma-Aldrich), 5-hydroxymethyl-2-furaldehyde (99%, Sigma-Aldrich), 5-methylfurfural (99%, Sigma-Aldrich), 2-thiophenecarboxaldehyde (98%, Sigma-Aldrich), pyrrole-2-carboxaldehyde (98%, Sigma-Aldrich), 3-furancarboxaldehyde(P97%, Sigma-Aldrich), 2-furyl methyl ketone (99%, Sigma-Aldrich), acetophenone (99%, Sigma-Aldrich), cinnamaldehyde(99%, Sigma-Aldrich), or trans-2-hexen-1-al (98%, Sigma-Aldrich))was added to 30 mL of IPA. The 6.8 nm Ni nanoparticle catalyst(20 mg) was charged to the reactor. The hydrogenation reactionswere then performed according to the FFR hydrogenation protocol,except the reaction temperature was 100 °C for 3-cyclohexene-1-carboxaldehyde.
89%	With D-glucose In aq. phosphate buffer at 35℃; for 7h; Microbiological reaction;
89.09%	at 160℃; for 9h; Autoclave;	2.3 CTH reaction and sample analysis General procedure: CTH reaction of ML was performed without stirring in a steel alloy autoclave (Fe-Cr-Ni alloy, GB1220-92) with an internal volume of 35 ML. Typically, carbonyl compounds (0.67 mmol), solvents (20 mL), and catalyst (0.1 g) were charged into the reactor, which was then sealed and heated to a designed temperature (140-220 °C) for an intended reaction time (1-24 h). After the reaction, the autoclave was taken out and cooled to ambient temperature. Identification of liquid products in the reaction mixture wasachieved by the TRACE ISQ GC-MS (Thermo Scientific Co,TR-WAX-MS column 30.0m×320 μm×0.25 μm). The temperatureprogram started at 60 °C for 1 min, then increased from 60 °C to 230 °Cat a rate of 15 °C /min and held for 2 min. Identification of liquid products in the reaction mixture wasachieved by the TRACE ISQ GC-MS (Thermo Scientific Co,TR-WAX-MS column 30.0m×320 μm×0.25 μm). The temperature program started at 60 °C for 1 min, then increased from 60 °C to 230 °C at a rate of 15 °C /min and held for 2 min.
88%	With sodium tetrahydridoborate In tetrahydrofuran at 0℃; for 0.166667h;
87%	With hexadecyltrimethylammonium bromide and mesitylene treated zirconium furandicarboxylate In isopropanol at 140℃; for 8h;
86.2%	With Zr-thiophenedicarboxylate hybrid catalyst In isopropanol at 130℃; for 6h; High pressure;	2.4 Catalytic Tests General procedure: In a typical experiment, the cylindrical stainless steel highpressurevessel was loaded with FAL (1mmol), 2-propanol(5mL) and the catalyst (0.1g), and then heated at a certaindesignated temperature for the desired reaction time withmagnetic stirring. Upon completion, the resulting liquidproducts were analyzed quantitatively by gas chromatography(GC 9790 II) using naphthalene as the internal standard,and identification of the products was done by GC-MS(GCMS-QP2010 Ultra). The yield of FOL, the conversionof FAL and the selectivity to FOL were calculated on thebasis of the following formula.
85%	With 5 wt% platinum/alumina; hydrogen In ethanol at 23℃; for 18h; Autoclave;
85.8%	With ethanol In isopropanol at 150℃; for 3.5h; Autoclave;	14 A 50 mL autoclave was charged with 1 g of 5-hydroxymethylfurfural and 19 g of ethanol (5 wt%),Then add 0.2gBaO-ZrO2 / SBA-15 as a catalyst,Sealed reactor,Stirring vigorously (500 rpm),Respectively heated to 120 ~ 150 and maintained2.5 ~ 6h, the reaction was cooled to room temperature and sampling,Qualitative and quantitative tests were performed using GC-MS (Shimadzu) and GC (Agilent)
82%	With methanol; C₂₅H₂₉ClNO₂Rh; Cs₂CO₃ at 90℃; for 1h;
82%	With sodium tetrahydridoborate; ethanol at 0 - 20℃; for 13h; Inert atmosphere;	5-Hydroxymethylfurfural 14 (5.0 g, 1.0 equiv, 39.6 mmol,) was dissolved in 5 mL of absolute ethanol and the solution was cooled to 0 °C for ~ 10 min. Sodium borohydride (0.46 g, 12 mmol, 30 mol%) was added slowly to the cooled solution and allowed to stir on an ice bath for an hour. After 1 hour, the resultant mixture was warmed to room temperature and stirred for 12 h. Afterwards, ~5 g of silica gel was added to the reaction, and ethanol was removed under reduced pressure. The obtained solid slurry was used in flash chromatography with dichloromethane/methanol as mobile phase. 2,5- Dialkylsubstituted furan ring was detected by a 225 nm detection mode in the instrument. A yellowish viscous liquid was obtained after the removal of solvent and a white powder material was formed upon addition of diethyl ether. [00217] Rf = 0.36 (95% Dichloromethane: 5% Methanol), Yield = 82%. 1H NMR (500 MHz, CDCl3, δ ppm) 6.26 (s, 1H), 4.61 (s, 2H), 1.96 (s, 1H). 13C NMR (125 MHz, CDCl3, δ ppm) 154.0, 108.6, 57.5. FIG.13A shows the 1H NMR spectrum of 15, and FIG.13B shows the 13C NMR spectrum of 15.
82%	With sodium tetrahydridoborate; ethanol at 0 - 20℃; for 13h; Inert atmosphere;	5-Hydroxymethylfurfural 14 (5.0 g, 1.0 equiv, 39.6 mmol,) was dissolved in 5 mL of absolute ethanol and the solution was cooled to 0 °C for ~ 10 min. Sodium borohydride (0.46 g, 12 mmol, 30 mol%) was added slowly to the cooled solution and allowed to stir on an ice bath for an hour. After 1 hour, the resultant mixture was warmed to room temperature and stirred for 12 h. Afterwards, ~5 g of silica gel was added to the reaction, and ethanol was removed under reduced pressure. The obtained solid slurry was used in flash chromatography with dichloromethane/methanol as mobile phase. 2,5- Dialkylsubstituted furan ring was detected by a 225 nm detection mode in the instrument. A yellowish viscous liquid was obtained after the removal of solvent and a white powder material was formed upon addition of diethyl ether. [00217] Rf = 0.36 (95% Dichloromethane: 5% Methanol), Yield = 82%. 1H NMR (500 MHz, CDCl3, δ ppm) 6.26 (s, 1H), 4.61 (s, 2H), 1.96 (s, 1H). 13C NMR (125 MHz, CDCl3, δ ppm) 154.0, 108.6, 57.5. FIG.13A shows the 1H NMR spectrum of 15, and FIG.13B shows the 13C NMR spectrum of 15.
80%	With sodium tetrahydridoborate
78%	With sodium tetrahydridoborate In ethanol at 20℃; for 12h;
77%	With sodium tetrahydridoborate In methanol at 0℃; for 4h;
75%	With hydrogen In butan-1-ol at 84℃; for 2h;
74%	With sodium tetrahydridoborate; ethanol at 0℃; for 12h; Sealed tube;	I.M Synthesis of 2,5-furylbis(propenoic acid) (2nd Procedure) M. Synthesis of 2,5-bis(hydroxymethyl)furan 3 Reaction scheme for the synthesis of 2,5-bis(hydroxymethyl)furan from HMF Hydroxymethylfurfural (10.0 g, 0.079 mol) was dissolved in absolute EtOH (100 mL) and cooled to 0° C. Sodium borohydride, NaBH4 (2.0 mg, 0.053 mol) was slowly added. The reaction flask was then sealed and allowed to stir for 12 h. The EtOH was evaporated under reduced pressure using a rotary evaporator. Pure compound was obtained by column chromatography using Dichloromethane-Methanol (95:5) as an eluent and silica gel (300-400 Mesh) as a stationary phase.
73.5%	With nickel(II) oxide; isopropanol In neat (no solvent) at 150℃; for 4h; Sealed tube;
73.2%	With isopropanol at 140℃; for 8h; Autoclave;
71%	With hydrogen In lithium hydroxide monohydrate at 50℃; for 3h;	2 Typical conversion process of fructose for the production of DHMF and DHMTF General procedure: 0.18 g fructose and 0.5 g [BMIm]Cl was charged in an open autoclave and was heated to 130°C for 20 min to afford HMF. About 20 mg samples were withdrawn, weighed, quenched with cold water, and subjected to HPLC analysis. 35 ml cool water and 50 mg metal catalyst were added to the residue reaction mixture. After the solution was mixed uniformly, the hydrogenation reaction was carried out with an initial H2 pressure of 6 MPa (measured at room temperature) at 50°C for set time. After the one-pot transformation, the reaction solution was filtered and the clear filtrate was analyzed by HPLC.
71%	With isopropanol at 180℃; for 4h;
67%	With sodium tetrahydridoborate In isopropanol at 20℃; for 0.5h;
64%	With MnBr(CO)2[NH(CH₂CH₂P(iPr)2)2]; hydrogen; sodium tertiary butoxide In toluene at 100℃; for 24h; Autoclave; chemoselective reaction;
55%	With sodium tetrahydridoborate In methanol at -0.16 - 19.84℃;
52%	With hydrogen In lithium hydroxide monohydrate at 160℃; for 2.5h; Autoclave;
51.7%	With hydrogen In 1,4-dioxane at 180℃; for 2h;
48.4%	With hydrogen; 20Cu/Al₂O₃ In methanol at 150℃; for 4.5h;
42.4%	With hydrogen at 160℃; for 2h; chemoselective reaction;
25%	With isopropanol In decane at 160℃; for 8h; Autoclave; Inert atmosphere;	3; 5 Example 3: Hydrogenolysis of HMF or Furfural: General procedure: Example 3: Hydrogenolysis of HMF or Furfural: All the reactions were carried out using 100 mL Parr autoclave (SS316). In a typical experiment, the reactor was charged with 1 mmol HMF (or 5 mmol furfural), hydrogen donor (25 mL), n-decane (0.2 g, internal standard) and required amount of freshly prepared catalyst. The reactor contents were mixed thoroughly and the reactor was sealed, purged 2-3 times with N2 and pressurized to 20 bar N2 pressure. Subsequently, the reaction vessel was heated under stirring at required temperature for a desired duration. Liquid samples were withdrawn periodically during the reaction and analyzed by GC (Agilent 7890A) equipped with a flame ionization detector (FID) having CP Sil 8CB capillary column (30 m length, 0.25 mm diameter). Product identification was done using authentic standards and GC-MS (Varian, Saturn 2200) analysis.
6.5%	With lithium hydroxide monohydrate; triethylamine at 20℃; for 4h; Irradiation;
	With sodium hydroxide; formalin
	With diethyl ether; nickel at 75℃; Hydrogenation;
100 % Chromat.	With hydrogen In lithium hydroxide monohydrate at 140℃; for 0.5h;
	With hydrogen at 60 - 100℃; for 2h;	2; 5 EXAMPLE 2 Reduction of HMF Utilizing RANEY Metals Reduction reactions were performed utilizing RANEY cobalt, RANEY copper and RANEY nickel in independent reactions. The reduction reactions were performed at 60° C. and 500 psi H2 for at least 2 hours. The experiment conducted utilizing RANEY cobalt resulted in a 100% HMF conversion with 97% selectivity for FDM upon reacting for 2 hours. As indicated above, RANEY copper was less reactive and resulted in a different product distribution.EXAMPLE 5 Reduction of HMF in the Presence of Fructose Batch-wise experiments were conducted with an aqueous solution of 15 wt % each of HMF and fructose under 500 psi H2 between 75 and 100° C. using Ge-promoted 5% Pt on carbon (Engelhard No.43932) for at least 2 h. In a sample taken at 1 h, LC and 13C NMR analysis showed that HMF was converted to FDM with good selectivity but that essentially no fructose was converted to sorbitol or mannitol even at high HMF conversion. Only trace amounts of levulinic and formic acids were formed. FIGS. 71-80 show the results of a number of batchwise HMF conversion reactions utilizing RANEY Co-2724 (FIG. 71); 5% Pt(Ge)/C (FIG. 72); 5% Pd/C (FIG. 73); 5% Ru/C (FIG. 74); RANEY Co-2700 (FIGS. 75-76); and RANEY Cu (FIG. 77) catalysts. The effect of H2 pressure was investigated utilizing a 5% Pt(Ge)/C catalyst as shown in FIG. 78. FIG. 79 shows the effect of temperature on HMF conversion using the Pt(Ge)/C catalyst, and FIG. 80 shows the effect of temperature on FDM selectivity for the Pt(Ge)/C catalyst.
	With palladium 10% on activated carbon; hydrogen In 1,4-dioxane; propyl alcohol at 60℃; for 12.3333h;
	With oxygen; Adenine-flavine dinucleotide at 30℃; Microbiological reaction; Enzymatic reaction;
	With formic acid; palladium on carbon In tetrahydrofuran for 4h; Reflux;
	With tripotassium phosphate tribasic; recombinant rat brain aldo-keto reductase R₁B₁₀; NADP In methanol Enzymatic reaction;
0.24 g	With formic acid; Cp*Ir(TsDPEN) In tetrahydrofuran at 40℃; for 2h;
99 %Chromat.	With hydrogen In methanol at 100℃; for 15.5h; Inert atmosphere;	14 In a stirred autoclave of 100 ml 0.05 g of 5 Mol% Ru/C (Aldrich) was added to a solution of 0.5 g of HMF in 30 ml of methanol. The lid of the autoclave was closed, stirring was started at 1000 rpm and after three vacuum/nitrogen cycles the autoclave was pressurised at 50 bar H2 and the temperature was raised to 75 °C. After 1.5 h the hydrogen pressure was raised to 90 bar and the temperature to 200 °C. The autoclave was kept stirred under these conditions for a further 14 h. After cooling to ambient temperature the pressure was released and the contents of the autoclave were subjected to GC analysis, which showed the presence of 30% of THFDM. In the same manner several other catalysts were tested in this hydrogenation and the results are collected in Table 1 Table 1 Hydrogenation of HMF to 2,5-THF-dimethanol a ExampleCatalyst%-2,5-THF-dimethanol 2 Ru/C (ALD) 5% 30 3 Ru/C (JM) 5% 46 4 Ru/C (JM) 0.5% 12 5 Pd/C 10% 38 6 G-69B (Sud) 55 7 Ra-Ni 79 8 CuCr (ALD) 9 9 CuCr (AC) 11 10 CuCr-Pd/C 62Suppliers between brackets: ALD=Aldrich; JM=Johnson Matthey; Sud=sudchemie; AC=Across a In all cases 100% conversion of the starting material was observed. From these results it is clear that Raney nickel (Ra-Ni) is a very good catalyst for this conversion. Examples 11-15 (summarised in Table 2) show the effect of the temperature on the hydrogenation of HMF with Raney nickel at 90 bar in methanol. Table 2: Hydrogenation of HMF with Ra-Ni at different temperatures.a Examples Temperature Yield of 2,5-THF-dimethanol 11 250 50 12 200 79 13 150 88 14 100 99 15 75 91a In all cases 100% conversion of the starting material was observed. From these examples it is clear that 100 °C is an optimal temperature for the hydrogenation of HMF to THFDM with Ra-Ni, and that Ra-Ni is a suitable catalyst.
	With 5% ruthenium on carbon; hydrogen at 99.84℃; Inert atmosphere; Sealed tube;
	With C₂₃H₃₁ClN₃Ru⁽¹⁺⁾*F₆P^(1-); potassium-t-butoxide; hydrogen In tetrahydrofuran at 70℃; for 2h; Inert atmosphere; Autoclave;
	With D-glucose; Sodium sulfate [anhydrous] at 20℃; Electrochemical reaction;
	With Si-beta zeolite In isopropanol at 179.84℃; for 6.5h; Inert atmosphere; Autoclave;
0.65 g	With sodium tetrahydridoborate In methanol at 0 - 20℃; for 0.25h;
	With sodium tetrahydridoborate
	With Cu/SiO₂; hydrogen In methanol at 100℃; for 8h; Autoclave;	Typical experimental procedures Hydrogenation of HMF was carried out in a 250 mL autoclave.0.5 g Cu/SiO2 catalyst and 10 g HMF pre-dissolved in 50 mLmethanol were charged into the autoclave, which was purgedthree times and then pressurized to 2.5 MPa with H2. Zero timeand mechanical stirring started after the autoclave was heatedto 100 C. After the reaction had proceeded for 8 h, the autoclavewas cooled down to room temperature. The Cu/SiO2 catalystand methanol were removed by filtration and vacuum distillation,respectively. The remaining solid product was dried in vacuum,weighed and then analyzed by NMR and element analysis. The solidproduct diluted with acetone to 5 g/L was further analyzed by highresolutionmass spectrometer. The recovered Cu/SiO2 catalyst afterbeing washed by methanol was then used for the next run.
	With hydrogen In lithium hydroxide monohydrate at 35℃; for 2h;
	With Zn-Cu couple; hydrogen In ethanol at 120℃; for 3h;
	With hydrogen In ethanol at 70℃; for 0.5h; chemoselective reaction;
	With hydrogen In butan-1-ol at 109.84℃; for 18h; Autoclave;
	With 2CuO*ZnO; hydrogen for 1h;
10 %Spectr.	With 1,2-diaminoethane-bis-borane In lithium hydroxide monohydrate at 80℃; for 1h; Sealed tube; chemoselective reaction;	3.2.2. Metal-Free Transfer Hydrogenation in Water General procedure: Exemplary procedure (Table 1; entry 2): A vial was charged with 2.3 mmol acetophenone (Table 1) and 5 mL demineralized water. After adding 0.5 mmol of EDAB (four H2 equivalents), the vial was sealed, placed in an aluminum heating block at 80 °C, and the mixture was stirred for the given time (Table 1). Subsequently, the aqueous suspension was cooled down and extracted three times with 5 mL Et2O. The organic layers were combined and the solvent was removed under reduced pressure. The product yield was determined by NMR spectroscopy using a defined amount of Si2Me6 as internal standard.
	With ZrO(OH)2 In ethanol at 149.84℃; for 2.5h; Inert atmosphere;
	With 5% ruthenium on carbon; hydrogen In lithium hydroxide monohydrate at 54.84℃; for 1h; Green chemistry; chemoselective reaction;

Reference： [1]Current Patent Assignee: AVANTIUM N.V. - WO2009/30509, 2009, A2 Location in patent: Page/Page column 11
[2]Pasini, Thomas; Lolli, Alice; Albonetti, Stefania; Cavani, Fabrizio; Mella, Massimo [Journal of Catalysis, 2014, vol. 317, p. 206 - 219]
[3]De, Sudipta; Kumar, Tarun; Bohre, Ashish; Singh, Laishram R.; Saha, Basudeb [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 4, p. 791 - 796]
[4]Dong, Jing; Zhu, Mingming; Zhang, Gaoshuo; Liu, Yongmei; Cao, Yong; Liu, Su; Wang, Yangdong [Cuihua Xuebao/Chinese Journal of Catalysis, 2016, vol. 37, # 10, p. 1669 - 1675]
[5]Ishikawa, Hiroya; Sheng, Min; Nakata, Ayako; Nakajima, Kiyotaka; Yamazoe, Seiji; Yamasaki, Jun; Yamaguchi, Sho; Mizugaki, Tomoo; Mitsudome, Takato [ACS Catalysis, 2021, vol. 11, # 2, p. 750 - 757]
[6]Current Patent Assignee: UNIVERSITY OF ILLINOIS (SYSTEM) - US2011/263880, 2011, A1 Location in patent: Page/Page column 17
[7]Tamura, Masazumi; Tokonami, Kensuke; Nakagawa, Yoshinao; Tomishige, Keiichi [Chemical Communications, 2013, vol. 49, # 63, p. 7034 - 7036]
[8]Pasini, Thomas; Solinas, Gavino; Zanotti, Valerio; Albonetti, Stefania; Cavani, Fabrizio; Vaccari, Angelo; Mazzanti, Andrea; Ranieri, Silvia; Mazzoni, Rita [Dalton Transactions, 2014, vol. 43, # 26, p. 10224 - 10234]
[9]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; HEFEI LEAF BIO TECH - CN105712854, 2016, A Location in patent: Paragraph 0074; 0075
[10]Kucherov; Galkin; Gordeev; Ananikov [Green Chemistry, 2017, vol. 19, # 20, p. 4858 - 4864]
[11]Galkin, Konstantin I.; Kucherov, Fedor A.; Markov, Oleg N.; Egorova, Ksenia S.; Posvyatenko, Alexandra V.; Ananikov, Valentine P. [Molecules, 2017, vol. 22, # 12]
[12]Current Patent Assignee: HUAIYIN NORMAL UNIVERSITY - CN109734687, 2019, A Location in patent: Paragraph 0042; 0043; 0044; 0045; 0046; 0047
[13]Current Patent Assignee: XIAMEN UNIVERSITY - CN110128378, 2019, A Location in patent: Paragraph 0030-0040
[14]Koranchalil, Sakhitha; Nielsen, Martin; Padilla, Rosa [Green Chemistry, 2020, vol. 22, # 20, p. 6767 - 6772]
[15]Chen, Feng; Topf, Christoph; Radnik, Jörg; Kreyenschulte, Carsten; Lund, Henrik; Schneider, Matthias; Surkus, Annette-Enrica; He, Lin; Junge, Kathrin; Beller, Matthias [Journal of the American Chemical Society, 2016, vol. 138, # 28, p. 8781 - 8788]
[16]Watari, Ryo; Matsumoto, Norio; Kuwata, Shigeki; Kayaki, Yoshihito [ChemCatChem, 2017, vol. 9, # 24, p. 4501 - 4507]
[17]Hu, Danxin; Hu, Hualei; Zhou, Hao; Li, Guozheng; Chen, Chunlin; Zhang, Jian; Yang, Yong; Hu, Yaoping; Zhang, Yajie; Wang, Lei [Catalysis science and technology, 2018, vol. 8, # 23, p. 6091 - 6099]
[18]Ma, Mingwei; Hou, Pan; Cao, Jingjie; Liu, Hui; Yan, Xinyu; Xu, Xingliang; Yue, Huijuan; Tian, Ge; Feng, Shouhua [Green Chemistry, 2019, vol. 21, # 21, p. 5969 - 5979]
[19]Mishra, Dinesh Kumar; Lee, Hye Jin; Truong, Cong Chien; Kim, Jinsung; Suh, Young-Wong; Baek, Jayeon; Kim, Yong Jin [Molecular catalysis, 2020, vol. 484]
[20]Current Patent Assignee: HANYANG UNIVERSITY - US2021/146341, 2021, A1 Location in patent: Paragraph 0131; 0137; 0140; 0143; 0146
[21]Current Patent Assignee: UNIVERSITY OF WISCONSIN SYSTEM; WARF (in: University of Wisconsin) - US11008662, 2021, B2 Location in patent: Page/Page column 6-14
[22]Cottier, Louis; Descotes, Gerard; Soro, Yaya [Synthetic Communications, 2003, vol. 33, # 24, p. 4285 - 4295]
[23]Kumalaputri, Angela J.; Bottari, Giovanni; Erne, Petra M.; Heeres, Hero J.; Barta, Katalin [ChemSusChem, 2014, vol. 7, # 8, p. 2266 - 2275]
[24]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - KR101936789, 2019, B1 Location in patent: Paragraph 0069-0095
[25]Ohyama, Junya; Esaki, Akihiko; Yamamoto, Yuta; Arai, Shigeo; Satsuma, Atsushi [RSC Advances, 2013, vol. 3, # 4, p. 1033 - 1036]
[26]Cha, Ga-Young; Chang, Jong-San; Hong, Do-Young; Hwang, Young Kyu; Jung, Jaehoon; Kwak, Jaesung; Kwon, Young-Uk; Lee, Minhui; Oh, Kyung-Ryul; Valekar, Anil H.; Yoon, Ji Woong [ACS Catalysis, 2020, vol. 10, # 6, p. 3720 - 3732]
[27]Lan, Fujun; Zhang, Huiling; Zhao, Chaoyue; Shu, Yu; Guan, Qingxin; Li, Wei [ACS Catalysis, 2022, vol. 12, # 9, p. 5711 - 5725]
[28]Gupta, Dinesh; Saha, Basudeb [Catalysis Communications, 2017, vol. 100, p. 206 - 209]
[29]Current Patent Assignee: XIAMEN UNIVERSITY - CN112979588, 2021, A Location in patent: Paragraph 0023-0036
[30]Chandrashekhar, Vishwas G.; Natte, Kishore; Alenad, Asma M.; Alshammari, Ahmad S.; Kreyenschulte, Carsten; Jagadeesh, Rajenahally V. [ChemCatChem, 2022, vol. 14, # 1]
[31]Current Patent Assignee: UNIVERSITY OF ILLINOIS (SYSTEM) - US2011/263880, 2011, A1 Location in patent: Page/Page column 10
[32]Current Patent Assignee: UNIVERSITY OF GRONINGEN - WO2016/43589, 2016, A1 Location in patent: Page/Page column 25; 26; 27
[33]Current Patent Assignee: ZHEJIANG UNIVERSITY - CN110283147, 2019, A Location in patent: Paragraph 0030-0133
[34]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY - US2022/62880, 2022, A1 Location in patent: Paragraph 0202; 0208
[35]Balakrishnan, Madhesan; Sacia, Eric R.; Bell, Alexis T. [Green Chemistry, 2012, vol. 14, # 6, p. 1626 - 1634]
[36]Puylaert, Pim; van Heck, Richard; Fan, Yuting; Spannenberg, Anke; Baumann, Wolfgang; Beller, Matthias; Medlock, Jonathan; Bonrath, Werner; Lefort, Laurent; Hinze, Sandra; de Vries, Johannes G. [Chemistry - A European Journal, 2017, vol. 23, # 35, p. 8473 - 8481]
[37]Upare, Pravin P.; Hwang, Young Kyu; Hwang, Dong Won [Green Chemistry, 2018, vol. 20, # 4, p. 879 - 885]
[38]Current Patent Assignee: XIAMEN UNIVERSITY - CN110204519, 2019, A Location in patent: Paragraph 0028-0038
[39]Current Patent Assignee: XIAMEN UNIVERSITY - CN110698440, 2020, A Location in patent: Paragraph 0019-0033
[40]Rojas-Buzo, Sergio; García-García, Pilar; Corma, Avelino [ChemSusChem, 2018, vol. 11, # 2, p. 432 - 438]
[41]Li, Xing-Long; Zhang, Kun; Chen, Shi-Yan; Li, Chuang; Li, Feng; Xu, Hua-Jian; Fu, Yao [Green Chemistry, 2018, vol. 20, # 5, p. 1095 - 1105]
[42]Current Patent Assignee: XIAMEN UNIVERSITY - CN108084119, 2018, A Location in patent: Paragraph 0028-0030; 0031-0042; 0044-0045
[43]Redina, Elena A.; Vikanova, Kseniia V.; Kapustin, Gennady I.; Mishin, Igor V.; Tkachenko, Olga P.; Kustov, Leonid M. [European Journal of Organic Chemistry, 2019, vol. 2019, # 26, p. 4159 - 4170]
[44]Dai, Fanglin; Zhou, Shenghui; Qin, Xingzhen; Liu, Detao; Qi, Haisong [Molecular catalysis, 2019, vol. 479]
[45]Saha, Basudeb; Bohn, Christine M.; Abu-Omar, Mahdi M. [ChemSusChem, 2014, vol. 7, # 11, p. 3095 - 3101]
[46]Figliolia, Rosario; Cavigli, Paolo; Comuzzi, Clara; Del Zotto, Alessandro; Lovison, Denise; Strazzolini, Paolo; Susmel, Sabina; Zuccaccia, Daniele; Ballico, Maurizio; Baratta, Walter [Dalton Transactions, 2020, vol. 49, # 2, p. 453 - 465]
[47]Jeong, Hojin; Kim, Chanyeon; Yang, Sungeun; Lee, Hyunjoo [Journal of Catalysis, 2016, vol. 344, p. 609 - 615]
[48]Li, Yan-Mei; Zhang, Xue-Ying; Li, Ning; Xu, Pei; Lou, Wen-Yong; Zong, Min-Hua [ChemSusChem, 2017, vol. 10, # 2, p. 372 - 378]
[49]Ma, Mingwei; Liu, Hui; Cao, Jingjie; Hou, Pan; Huang, Jiahui; Xu, Xingliang; Yue, Huijuan; Tian, Ge; Feng, Shouhua [Molecular catalysis, 2019, vol. 467, p. 52 - 60]
[50]Zeng, Chao; Seino, Hidetake; Ren, Jie; Hatanaka, Kenichi; Yoshie, Naoko [Macromolecules, 2013, vol. 46, # 5, p. 1794 - 1802]
[51]Li, Hu; Liu, Xiaofang; Yang, Tingting; Zhao, Wenfeng; Saravanamurugan, Shunmugavel; Yang, Song [ChemSusChem, 2017, vol. 10, # 8, p. 1761 - 1770]
[52]Wang, Tao; Hu, Aiyun; Xu, Guangzhi; Liu, Chen; Wang, Haijun; Xia, Yongmei [Catalysis Letters, 2019]
[53]Balakrishnan, Madhesan; Sacia, Eric R.; Bell, Alexis T. [Green Chemistry, 2012, vol. 14, # 6, p. 1626 - 1634]
[54]Current Patent Assignee: XIAMEN UNIVERSITY - CN106946820, 2017, A Location in patent: Paragraph 0032-0033; 0037
[55]Aboo, Ahmed H.; Bennett, Elliot L.; Deeprose, Mark; Robertson, Craig M.; Iggo, Jonathan A.; Xiao, Jianliang [Chemical Communications, 2018, vol. 54, # 83, p. 11805 - 11808]
[56]Current Patent Assignee: UNIVERSITY SYSTEM OF OHIO - WO2021/236489, 2021, A1 Location in patent: Paragraph 00192; 00214-00217
[57]Current Patent Assignee: UNIVERSITY SYSTEM OF OHIO - WO2021/236489, 2021, A1 Location in patent: Paragraph 00192; 00214-00217
[58]Cho, Dong-Gyu; Choi, Sunju; Kim, Eun Ki; Kim, Gayeong; Lee, Hyang Bok; Rao, P. Sankara; Shin, Jeonghyun; Song, Jae-Won [Molecules, 2022, vol. 27, # 7]
[59]Goswami, Shyamaprosad; Dey, Swapan; Jana, Subrata [Tetrahedron, 2008, vol. 64, # 27, p. 6358 - 6363]
[60]Dunbabin, Alice; Subrizi, Fabiana; Ward, John M.; Sheppard, Tom D.; Hailes, Helen C. [Green Chemistry, 2017, vol. 19, # 2, p. 397 - 404]
[61]Gyergyek, Sašo; Grilc, Miha; Likozar, Blaž; Makovec, Darko [Green Chemistry, 2022, vol. 24, # 7, p. 2788 - 2794]
[62]Current Patent Assignee: NDSU RESEARCH FOUNDATION - US2017/233325, 2017, A1 Location in patent: Paragraph 0180-0184
[63]He, Jian; Nielsen, Monia Runge; Hansen, Thomas Willum; Yang, Song; Riisager, Anders [Catalysis science and technology, 2019, vol. 9, # 5, p. 1289 - 1300]
[64]Wang, Tao; Hu, Aiyun; Wang, Haijun; Xia, Yongmei [Journal of the Chinese Chemical Society, 2019, vol. 66, # 12, p. 1610 - 1618]
[65]Cai, Haile; Li, Changzhi; Wang, Aiqin; Zhang, Tao [Catalysis Today, 2014, vol. 234, p. 59 - 65]
[66]He, Jian; Li, Hu; Riisager, Anders; Yang, Song [ChemCatChem, 2018, vol. 10, # 2, p. 430 - 438]
[67]Wrigstedt, Pauli; Keskiväli, Juha; Perea-Buceta, Jesús E.; Repo, Timo [ChemCatChem, 2017, vol. 9, # 22, p. 4244 - 4255]
[68]Elangovan, Saravanakumar; Topf, Christoph; Fischer, Steffen; Jiao, Haijun; Spannenberg, Anke; Baumann, Wolfgang; Ludwig, Ralf; Junge, Kathrin; Beller, Matthias [Journal of the American Chemical Society, 2016, vol. 138, # 28, p. 8809 - 8814]
[69]Aellig, Christof; Jenny, Florian; Scholz, David; Wolf, Patrick; Giovinazzo, Isabella; Kollhoff, Fabian; Hermans, Ive [Catalysis science and technology, 2014, vol. 4, # 8, p. 2326 - 2331]
[70]Fang, Ruiqi; Liu, Hongli; Luque, Rafael; Li, Yingwei [Green Chemistry, 2015, vol. 17, # 8, p. 4183 - 4188]
[71]Fang, Zhen; Kong, Xiao; Li, Luping; Peng, Bo; Zhu, Yifeng; Zhu, Yulei [Catalysis science and technology, 2020, vol. 10, # 21, p. 7323 - 7330]
[72]Hu, Yulin; Rao, Kasanneni Tirumala Venkateswara; Xu, Chunbao Charles; Yuan, Zhongsun; Zhang, Yongsheng [Applied Catalysis A: General, 2021, vol. 609]
[73]Meng, Ge; Ji, Kaiyue; Zhang, Wei; Kang, Yiran; Wang, Yu; Zhang, Ping; Wang, Yang-Gang; Li, Jun; Cui, Tingting; Sun, Xiaohui; Tan, Tianwei; Wang, Dingsheng; Li, Yadong [Chemical Science, 2021, vol. 12, # 11, p. 4139 - 4146]
[74]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - WO2017/42838, 2017, A1 Location in patent: Page/Page column 17; 21-28
[75]Guo, Yuanyuan; Chen, Jinzhu [RSC Advances, 2016, vol. 6, # 104, p. 101968 - 101973]
[76]Turner et al. [Analytical Chemistry, 1954, vol. 26, p. 898]
[77]Newth; Wiggins [Research (London), 1950, vol. 3, p. 50]
[78]Schiavo, V.; Descotes, G.; Mentech, J. [Bulletin de la Societe Chimique de France, 1991, # 5, p. 704 - 711]
[79]Current Patent Assignee: BATTELLE MEMORIAL INSTITUTE - US2007/287845, 2007, A1 Location in patent: Page/Page column 6; 8
[80]Location in patent: experimental part Luijkx, Gerard C.A.; Huck, Nina P.M.; Van Rantwijk, Fred; Maat, Leendert; Van Bekkum, Herman [Heterocycles, 2009, vol. 77, # 2, p. 1037 - 1044]
[81]Location in patent: experimental part Koopman, Frank; Wierckx, Nick; De Winde, Johannes H.; Ruijssenaars, Harald J. [Proceedings of the National Academy of Sciences of the United States of America, 2010, vol. 107, # 11, p. 4919 - 4924]
[82]Thananatthanachon, Todsapon; Rauchfuss, Thomas B. [Angewandte Chemie - International Edition, 2010, vol. 49, # 37, p. 6616 - 6618]
[83]Location in patent: experimental part Endo, Satoshi; Matsunaga, Toshiyuki; Kuragano, Tsukasa; Ohno, Satoshi; Kitade, Yukio; Tajima, Kazuo; El-Kabbani, Ossama; Hara, Akira [Archives of Biochemistry and Biophysics, 2010, vol. 503, # 2, p. 230 - 237]
[84]Location in patent: experimental part Thananatthanachon, Todsapon; Rauchfuss, Thomas B. [ChemSusChem, 2010, vol. 3, # 10, p. 1139 - 1141]
[85]Current Patent Assignee: NETHERLANDS ORGANISATION FOR SCIENTIFIC RESEARCH - EP2390247, 2011, A1 Location in patent: Page/Page column 7-8
[86]Jae, Jungho; Zheng, Weiqing; Lobo, Raul F.; Vlachos, Dionisios G. [ChemSusChem, 2013, vol. 6, # 7, p. 1158 - 1162]
[87]Jansen, Eveline; Jongbloed, Linda S.; Tromp, Dorette S.; Lutz, Martin; De Bruin, Bas; Elsevier, Cornelis J. [ChemSusChem, 2013, vol. 6, # 9, p. 1737 - 1744]
[88]Kwon, Youngkook; De Jong, Ed; Raoufmoghaddam, Saeed; Koper, Marc T. M. [ChemSusChem, 2013, vol. 6, # 9, p. 1659 - 1667]
[89]Jae, Jungho; Mahmoud, Eyas; Lobo, Raul F.; Vlachos, Dionisios G. [ChemCatChem, 2014, vol. 6, # 2, p. 508 - 513]
[90]Scholz, David; Aellig, Christof; Hermans, Ive [ChemSusChem, 2014, vol. 7, # 1, p. 268 - 275]
[91]Sacia, Eric R.; Balakrishnan, Madhesan; Bell, Alexis T. [Journal of Catalysis, 2014, vol. 313, p. 70 - 79]
[92]Cao, Quan; Liang, Wenyuan; Guan, Jing; Wang, Lei; Qu, Qian; Zhang, Xinzhi; Wang, Xicheng; Mu, Xindong [Applied Catalysis A: General, 2014, vol. 481, p. 49 - 53]
[93]Chatterjee, Maya; Ishizaka, Takayuki; Kawanami, Hajime [Green Chemistry, 2014, vol. 16, # 11, p. 4734 - 4739]
[94]Bottari, Giovanni; Kumalaputri, Angela J.; Krawczyk, Krzysztof K.; Feringa, Ben L.; Heeres, Hero J.; Barta, Katalin [ChemSusChem, 2015, vol. 8, # 8, p. 1323 - 1327]
[95]Shi, Juanjuan; Zhang, Mengyuan; Du, Weichen; Ning, Wensheng; Hou, Zhaoyin [Catalysis Science and Technology, 2015, vol. 5, # 6, p. 3108 - 3112]
[96]Yu, Lili; He, Le; Chen, Jin; Zheng, Jianwei; Ye, Linmin; Lin, Haiqiang; Yuan, Youzhu [ChemCatChem, 2015, vol. 7, # 11, p. 1701 - 1707]
[97]Zhu, Yifeng; Kong, Xiao; Zheng, Hongyan; Ding, Guoqiang; Zhu, Yulei; Li, Yong-Wang [Catalysis science and technology, 2015, vol. 5, # 8, p. 4208 - 4217]
[98]Sahler, Sebastian; Scott, Martin; Gedig, Christian; Prechtl, Martin H.G. [Molecules, 2015, vol. 20, # 9, p. 17058 - 17069]
[99]Hao, Weiwei; Li, Weifeng; Tang, Xing; Zeng, Xianhai; Sun, Yong; Liu, Shijie; Lin, Lu [Green Chemistry, 2016, vol. 18, # 4, p. 1080 - 1088]
[100]Jain, Anandkumar B.; Vaidya, Prakash D. [International Journal of Chemical Kinetics, 2016, vol. 48, # 6, p. 318 - 328]

2
[ 823-82-5 ]
[ 1883-75-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium <i>tert</i>-butylate; hydrogen; C₁₈H₂₆Br₂MnN₃P In methanol at 130℃; for 48h; Inert atmosphere; Autoclave; chemoselective reaction;
94%	With sodium tetrahydroborate In methanol Cooling;
87%	Stage #1: 2,5-diformylfurane With phenylsilane; caesium carbonate In 2-methyltetrahydrofuran at 25℃; for 1h; Green chemistry; Stage #2: With ethanol In 2-methyltetrahydrofuran at 80℃; for 2h; Green chemistry; chemoselective reaction;

52%	With trans-Ru(mer-2-(4-phenyl-1H-1,2,3-triazol-1-yl)-N-(pyridin-2-ylmethyl)ethan-1-amine)(PPh<SUB>3</SUB>)Cl<SUB>2</SUB>; potassium <i>tert</i>-butylate; hydrogen In tetrahydrofuran at 80℃; Autoclave; Sealed tube;
	With formic acid In toluene at 90℃; for 2h; Yield given;
	With 2,4,6-trimethyl-pyridine; hydrogen In isopropyl alcohol at 100℃; for 24h;	General procedure for hydrogenation of aldehydes General procedure: A typical procedure for the hydrogenation of aldehydesis as follows: aldehyde (1 mmol), Au catalyst, and 2 mL ofsolvent were placed in a modified Fischer-Porter 100 mLglass reactor. The reactor was purged five times with H2,leaving the vessel at the desired pressure. The resultingmixture was vigorously stirred, and the temperature wasmaintained with an oil bath. After the desired time, thecatalyst was removed by centrifugation and the productswere analyzed by GC with an internal standard to determinethe conversion and selectivity
95 %Chromat.	With trans-[Ru(6-(4-methoxyphenyl)-2-aminomethylpyridine)(CO)(PCy₃)(PPh₃)][BAr^f₄]; potassium carbonate; isopropyl alcohol at 82℃; for 1h; Inert atmosphere; Schlenk technique;
	With hydrogen In water at 79.84℃; for 5h; Autoclave;

Reference： [1]Gholap, Sandeep Suryabhan; Dakhil, Abdullah Al; Chakraborty, Priyanka; Li, Huaifeng; Dutta, Indranil; Das, Pradip K.; Huang, Kuo-Wei [Chemical Communications, 2021, vol. 57, # 89, p. 11815 - 11818]
[2]Ziach, Krzysztof; Obrocka-Hrycyna, Aleksandra; Jurczak, Janusz [Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10334 - 10341]
[3]Li, Hu; Zhao, Wenfeng; Dai, Wenshuai; Long, Jingxuan; Watanabe, Masaru; Meier, Sebastian; Saravanamurugan, Shunmugavel; Yang, Song; Riisager, Anders [Green Chemistry, 2018, vol. 20, # 23, p. 5327 - 5335]
[4]Sole, Roberto; Bortoluzzi, Marco; Spannenberg, Anke; Tin, Sergey; Beghetto, Valentina; De Vries, Johannes G. [Dalton Transactions, 2019, vol. 48, # 36, p. 13580 - 13588]
[5]Yuskovets, Zh. G.; Shimanskaya, M. V. [Chemistry of Heterocyclic Compounds, 1990, vol. 26, # 6, p. 620 - 624][Khimiya Geterotsiklicheskikh Soedinenii, 1990, # 6, p. 745 - 749]
[6]Silva, Rerison J. M.; Fiorio, Jhonatan L.; Vidinha, Pedro; Rossi, Liane M. [Journal of the Brazilian Chemical Society, 2019, vol. 30, # 10, p. 2162 - 2169]
[7]Figliolia, Rosario; Cavigli, Paolo; Comuzzi, Clara; Del Zotto, Alessandro; Lovison, Denise; Strazzolini, Paolo; Susmel, Sabina; Zuccaccia, Daniele; Ballico, Maurizio; Baratta, Walter [Dalton Transactions, 2020, vol. 49, # 2, p. 453 - 465]
[8]Bal, Rajaram; Kumar, Abhinav; Srivastava, Rajendra [Catalysis science and technology, 2021, vol. 11, # 12, p. 4133 - 4148]

3
[ 67-47-0 ]
[ 1883-75-6 ]
[ 2144-40-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In water at 140℃; different temperatures, pressures, reaction times and concentrations of catalyst, other catalysts;
1: 71 %Spectr. 2: 28 %Spectr.	With bis(acetato){2,2'-bis(diphenylphosphino)-1,1'-binaphthyl}ruthenium(II); hydrogen In toluene at 120℃; for 16h;

Reference： [1]Schiavo, V.; Descotes, G.; Mentech, J. [Bulletin de la Societe Chimique de France, 1991, # 5, p. 704 - 711]
[2]Cadu, Alban; Sekine, Kohei; Mormul, Jaroslaw; Ohlmann, Dominik M.; Schaub, Thomas; Hashmi, A. Stephen K. [Green Chemistry, 2018, vol. 20, # 14, p. 3386 - 3393]

4
[ 1883-75-6 ]
[ 823-82-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With Rh/Al2O3; oxygen; In toluene; at 80℃; for 24.0h;	General procedure: Furfuryl alcohol (1 mmol, 98 mg), Toluene (5 mL) was added, and Ru / Al 2 O 3 (Wako Pure Chemical Industries, Ltd.) (5 mol% Ru) was suspended.A gas collecting bag filled with oxygen gas was attached,The interior of the reaction vessel was replaced with oxygen using an aspirator.The reaction solution was reacted at 80 C. for 24 hours with vigorous stirring, then the catalyst was removed by filtration, and the mother liquor was distilled off under reduced pressure.As a result of analyzing the obtained product, the raw material completely disappeared and the yield of the objective furfural was 98%.In addition, no by-products insoluble in the solvent were produced.
98%	With pyridine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; iodine; sodium hydrogencarbonate; In dichloromethane; water; at 20 - 25℃; for 1.0h;	General procedure: A mixture of 10 mL of 0.1 mol/L solution of sodium hydrocarbonate and 0.084 g (0.4 mmol) of compound 1 were charged into a 50 mL flat-bottom flask equipped with a reflux condenser and a magnetic stirrer. 4 mmol of an alcohol dissolved in 10 mL of methylene chloride (alcohol-nitroxyl 1 molar ratio1 : 0.1) was added to the solution, and then 0.4 mmolof an amine was introduced (alcohol-amine 1 : 0.1; 1-amine 1 : 1). 2.0 g (8 mmol) of crystalline iodine was added at vigorous stirring to the two-phase system; the mixture was stirred during 3 h at 20-25 and then treated with 20% solution of sodium thiosulfate for elimination of excess iodine. Aqueous and organic layers were separated, and the product was additionally extracted from the aqueous layer with methylene chloride (2×10 mL). The organic phases were combined and analyzed by means of chromatography.

Reference： [1]Patent: JP2017/109959,2017,A .Location in patent: Paragraph 0034
[2]Russian Journal of General Chemistry,2016,vol. 86,p. 2423 - 2426
Zh. Obshch. Khim.,2016,vol. 86,p. 1779 - 1783,5
[3]Chemistry - A European Journal,1997,vol. 3,p. 268 - 278
[4]Liebigs Annalen der Chemie,1985,p. 813 - 821
[5]Green Chemistry,2017,vol. 19,p. 1315 - 1326
[6]Journal of the American Chemical Society,2017,vol. 139,p. 15584 - 15587

5
[ 1883-75-6 ]
[ 6214-02-4 ]

Yield	Reaction Conditions	Operation in experiment
58%	With pyridine; thionyl chloride In dichloromethane at 0℃; Inert atmosphere;
45%	With pyridine; thionyl chloride In chloroform at -10℃; for 2h;
25%	With hydrogenchloride In dichloromethane; water at 20℃; for 16h;

	With thionyl chloride In ethyl acetate at 0℃; for 0.5h;
	With thionyl chloride In pyridine
	With thionyl chloride In pyridine; chloroform
	With thionyl chloride; potassium carbonate In ethyl acetate at -10℃; for 0.75h;

Reference： [1]Özcan, Hafize; Erkuş, Betül; Zaim, Ömer [Journal of Heterocyclic Chemistry, 2020]
[2]Tarrago, Georges; Marzin, Claude; Najimi, Ouafa; Pellegrin, Valdo [Journal of Organic Chemistry, 1990, vol. 55, # 2, p. 420 - 425]
[3]Dunbabin, Alice; Subrizi, Fabiana; Ward, John M.; Sheppard, Tom D.; Hailes, Helen C. [Green Chemistry, 2017, vol. 19, # 2, p. 397 - 404]
[4]Cammidge, Andrew N.; Cook, Michael J.; Harrison, Kenneth J.; McKeown, Neil B. [Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 3053 - 3058]
[5]Jen, Kwan-Yue; Jow, Richard; Shacklette, L. W.; Maxfield, M.; Eckhardt, Helmut; Elsenbaumer, Ronald L. [Molecular Crystals and Liquid Crystals (1969-1991), 1988, vol. 160, p. 69 - 78]
[6]Jen, Kwan-Yue; Jow, T. R.; Elsenbaumer, Ronald L. [Journal of the Chemical Society. Chemical communications, 1987, # 14, p. 1113 - 1115]
[7]Haibach, Michael C.; Wang, David Y.; Emge, Thomas J.; Krogh-Jespersen, Karsten; Goldman, Alan S. [Chemical Science, 2013, vol. 4, # 9, p. 3683 - 3692]

6
[ 1883-75-6 ]
[ 2144-40-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With Raney Ni (W-5); hydrogen In ethanol at 100℃;

Reference： [1]Naemura; Fukuda; Takahashi; Konishi; Hirose; Tobe [Tetrahedron Asymmetry, 1993, vol. 4, # 5, p. 911 - 918]

7
[ 1883-75-6 ]
[ 120040-07-5 ]

Yield	Reaction Conditions	Operation in experiment
95.2%	With dihydrogen peroxide In water at 30℃; for 0.5h; Molecular sieve;	1-20; 1 Example 1 Add 2,5-furandimethanol (0.05g, 5g/L), titanium silicon molecular sieve TS-1 (Si/Ti molar ratio of 30:1, 0.1g), and H2O2 (30wt%, 0.06mol/L) into 10mL In H2O, and stir at 30°C for 30 min. After cooling, take 5 mL of the reaction solution to a 100 mL volumetric flask, pass it through a 0.22 μm microporous membrane, and perform HPLC determination. The conversion rate of 2,5-furandimethanol is 100%, The yield of 6-hydroxy-6(hydroxymethyl)-2H-pyran-3(6H)-one (the structural formula is shown below) was 95.2%. Please refer to Fig. 1 and the product form is a yellow oil.
	With oxygen; 5,15,10,20-tetraphenylporphyrin; triphenylphosphine 1.) acetone, irradiation, -70 deg C, 2 h, 2.) -70 deg C, 10 min; Yield given. Multistep reaction;
	With 3,3-dimethyldioxirane In acetone Ambient temperature;

With choline chloride; 3-chloro-benzenecarboperoxoic acid for 1h; Milling;

6-Hydroxy-6-(hydroxymethyl)-2H-pyran-3(6H)-one (3d) The agate beaker was equipped with ten agate milling balls, 2d (41 mg, 0.32 mmol), choline chloride (40 mg) and mCPBA (111 mg, 0.64 mmol) and milling was performed for 60 min. The reaction mixture was diluted with EtOAc (20 mL), filtered and the solvent was removed under reduced pressure. The crude product was dissolved in water (20 mL), filtered and the water was removed by lyophilization to obtain a 5:1 mixture of 3d (29 mg, 63%) and the corresponding hemiacetal 5 as red brown oil. 1H-NMR (400 MHz, CDCl3): 3d: δ = 6.84 (d, 1H, J = 10.4 Hz), 6.19 (d, 1H, J = 10.4 Hz), 4.61 (d, 1H, J = 16.9 Hz), 4.16 (d, 1H, J = 16.9 Hz), 3.81 (d, 1H, J = 11.4 Hz), 3.64 (d, 1H, J = 11.5 Hz); 5: 6.90 (d, 1H, J = 10.4 Hz), 6.18 (d, 1H, J = 10.4 Hz), 4.60 (d, 1H, J = 16.9 Hz), 4.46 (d, 1H, J = 11.7 Hz), 4.19 (d, 1H, J = 16.9 Hz), 4.08 (d, 1H, J = 11.8 Hz).

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Ningbo Institute of Material Technology and Engineering (in: CAS) - CN112920150, 2021, A Location in patent: Paragraph 0040-0071
[2]Kuo, Yueh-Hsiung; Shih, Kae-Shyang [Heterocycles, 1990, vol. 31, # 11, p. 1941 - 1949]
[3]Adger; Barrett; Brennan; McKervey; Murray [Journal of the Chemical Society. Chemical communications, 1991, # 21, p. 1553 - 1554]
[4]Falenczyk, Carolin; Pölloth, Benjamin; Hilgers, Petra; König, Burkhard [Synthetic Communications, 2015, vol. 45, # 3, p. 348 - 354]

8
[ 1883-75-6 ]
[ 143-15-7 ]
2,5-bis((dodecyloxy)methyl)furan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium hydroxide; Aliquat 336 at 180℃; for 0.166667h; Irradiation;
39%	Stage #1: 2,5-bis-(hydroxymethyl)furan With potassium <i>tert</i>-butylate In dimethyl sulfoxide at -10℃; for 0.5h; Stage #2: 1-dodecylbromide In dimethyl sulfoxide at -10 - 20℃; Inert atmosphere;	11 Experimental: An oven dried, single neck 10 mL round bottomed flask equipped with a PTFE coated magnetic stir bar was charged with 100 mg of FDM A (0.780 mmol) and 5 mL of anhydrous DMSO. The flask was then immersed in an ice-brine bath (- 10°C) and, while stirring, 219 mg of potassium t- butoxide (1.95 mmol) added in portions and the mixture stirred for 30 minutes at this temperature. At this time, the neck was stoppered with a rubber septum and an argon gas inlet affixed via a 14" needle. While vigorously stirring and under an argon blanket, 412 μ^ of 1 -bromododecane (1.72 mmol) was added via syringe. The mixture was then warmed to room temperature and continued to react overnight. After this time, an aliquot was removed and spotted on a silica gel TLC plate, which exhibited a single band (cerium molybdate stain) after developing in 10: 1 hexanes/ethyl acetate. The signature band for FDM A (baseline) was noticeably absent, suggesting this reagent had fully converted. Here, the mixture was diluted with 5 mL of water and 5 mL of methylene chloride and partitioned and the aqueous layer extracted with 3-5 mL volumes of methylene chloride. The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under vacuum. The oily residue was dissolved in a minimum amount of methylene chloride and added to 20 g of silica gel, which was then dried under vacuum, furnishing product adsorbed silica gel. This material was added to a pre-fabricated silica gel column, where flash chromatography with hexanes to 9% ethyl acetate in hexanes afforded 139 mg of a B as a beige solid after concentration (39%> of theoretical). NMR (400 MHz, CDCI3) δ (ppm) 6.42 (2, 2H), 4.67 (s, 4H), 3.42-3.39 (m, 4H), 2.06 (m, 2H), 1.58 (m, 2H), 1.47 (t, J = 6.4 Hz, 4H), 1.40 (m, 4H), 1.38-1.30 (m, 34H), 0.91 (t, J = 7.0 Hz, 6H); 13C NMR (100 MHz, CDCI3) δ (ppm) 152.4, 108.5, 73.4, 69.9, 33.0, 31.2, 30.9, 29.8, 28.7, 26.2, 25.4, 24.9, 24.1, 23.3, 22.1, 13.3.

Reference： [1]Majdoub, Mustapha; Loupy, Andre; Petit, Alain; Roudesli, Sadok [Tetrahedron, 1996, vol. 52, # 2, p. 617 - 628]
[2]Current Patent Assignee: ARCHER-DANIELS-MIDLAND CO - WO2015/94970, 2015, A1 Location in patent: Page/Page column 35

9
[ 1883-75-6 ]
[ 112-89-0 ]
2,5-bis((octadecyloxy)methyl)furan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium hydroxide; Aliquat 336 at 198℃; for 0.166667h; Irradiation;
35%	Stage #1: 2,5-bis-(hydroxymethyl)furan With potassium <i>tert</i>-butylate In dimethyl sulfoxide at -10℃; for 0.5h; Stage #2: 1-Bromooctadecane In dimethyl sulfoxide at -10 - 20℃; Inert atmosphere;	12 Example 12: Synthesis of 2,5-bis((octadecyloxy)methyl)furan, B Example 12: Synthesis of 2,5-bis((octadecyloxy)methyl)furan, B Experimental: An oven dried, single neck 10 mL round bottomed flask equipped with a PTFE coated magnetic stir bar was charged with 100 mg of FDM A (0.780 mmol) and 5 mL of anhydrous DMSO. The flask was then immersed in an ice-brine bath (- 10°C) and, while stirring, 219 mg of potassium t- butoxide (1.95 mmol) added in portions and the mixture stirred for 30 minutes at this temperature. At this time, the neck was stoppered with a rubber septum and an argon gas inlet affixed via a 14" needle. While vigorously stirring and under an argon blanket, 586 of 1 -bromooctadecane (1.72 mmol) was added via syringe. The mixture was then warmed to room temperature and continued to react overnight. After this time, an aliquot was removed and spotted on a silica gel TLC plate, which exhibited a single band (cerium molybdate stain) after developing in 11 : 1 hexanes/ethyl acetate. The signature band for FDM A (baseline) was noticeably absent, suggesting this reagent had fully converted. Here, the mixture was diluted with 5 mL of water and 5 mL of methylene chloride and partitioned and the aqueous layer extracted with 3-5 mL volumes of methylene chloride. The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under vacuum. The oily residue was dissolved in a minimum amount of methylene chloride and added to 20 g of silica gel, which was then dried under vacuum, furnishing product adsorbed silica gel. This material was added to a pre-fabricated silica gel column, where flash chromatography with hexanes to 6% ethyl acetate in hexanes afforded 171 mg of a B as an off- white solid after concentration (35% of theoretical). NMR (400 MHz, CDC13), δ (ppm) 6.40 (s, 2H), 4.52 (s, 4H), 3.41-3.38 (m, 4H), 2.08 (m, 2H), 1.65 (m, 2H), 1.48 (t, J= 6.2 Hz, 4H), 1.41 (m, 4H), 1.40-1.28 (m, 58H), 0.89 (t, J= 6.8 Hz, 6H); 13C NMR (100 MHz, CDCI3) δ (ppm) 152.7, 108.6, 73.6, 69.0, 33.0, 31.2, 30.9, 29.8, 28.7, 26.2, 25.4, 24.9, 24.1, 23.8, 23.3, 22.9, 22.5, 22.1, 21.7, 21.3, 13.3.

Reference： [1]Majdoub, Mustapha; Loupy, Andre; Petit, Alain; Roudesli, Sadok [Tetrahedron, 1996, vol. 52, # 2, p. 617 - 628]
[2]Current Patent Assignee: ARCHER-DANIELS-MIDLAND CO - WO2015/94970, 2015, A1 Location in patent: Page/Page column 35; 36

10
[ 1883-75-6 ]
[ 108-24-7 ]
[ 5076-10-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With pyridine at 24℃; for 6h;
92%	With pyridine In acetonitrile at 20℃; for 3h; Inert atmosphere;	12 preparation of 2,5-bis[(acetoxy)methyl]furan This example demonstrates the conversion of BHMF to BAMF with acetic anhydride, and base. In a 50-mL Schlenk flask, pyridine (0.5 mL, 6.24 mmol) was added to a solution of BHMF (1.0 g, 7.80 mmol) and acetic anhydride (2.20 mL, 23.4 mmol) in 20 mL MeCN under argon atmosphere. The resulting orange solution was stirred at RT for 3 h. Solvent and volatile compounds were removed under vacuum to yield BAMF as a brown oil. Yield: 1.50 g (92%).
86%	With pyridine In 2-methyltetrahydrofuran at 24℃; for 24h; Autoclave;

72%	With sodium acetate at 20℃; for 6h;	2.3. Synthesis of 2,5-bisacetyloxymethylfuran (BAMF) In a 10 mL round bottom flask 0.512 g (4 mmol) BHMF was dissolved in 1.89 mL (20 mmol) of acetic anhydride. Then sodium acetate(0.066 g, 0.8 mmol) was added into the mixture as a catalystand it was stirred for 6 h at room temperature. After the reaction,2 mL of distilled water was added into the reaction mixture veryslowly to consume the excess acetic anhydride. Reaction product was isolated by extracting with dichloromethane (5 8 mL). After evaporation of dichloromethane BAMF was obtained as white solidproduct (0.611 g, 72% yield). 1H NMR (400 MHz, CDCl3): d 6.35 (s,2H, 2CH), 5.01 (s, 4H, 2CH2), 2.06 (s, 6H, 2CH3). 13C NMR(100 MHz, CDCl3): d 170.5 (CO), 150 (C-O), 111.4 (CH), 57.9(CH2), 20.7 (CH3). Melting point = 62 °C.
	With pyridine
	With pyridine In acetonitrile at 20℃; for 3h; Inert atmosphere;
	With dmap; triethylamine

Reference： [1]Kucherov; Galkin; Gordeev; Ananikov [Green Chemistry, 2017, vol. 19, # 20, p. 4858 - 4864]
[2]Current Patent Assignee: UNIVERSITY OF ILLINOIS (SYSTEM) - US2011/263880, 2011, A1 Location in patent: Page/Page column 13-14
[3]Arias, Karen S.; Carceller, Jose M.; Climent, Maria J.; Corma, Avelino; Iborra, Sara [ChemSusChem, 2020, vol. 13, # 7, p. 1864 - 1875]
[4]De, Sudipta; Kumar, Tarun; Bohre, Ashish; Singh, Laishram R.; Saha, Basudeb [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 4, p. 791 - 796]
[5]Brooker, Sally; Kelly, Robert J. [Journal of the Chemical Society, Dalton Transactions, 1996, # 10, p. 2117 - 2122]
[6]Thananatthanachon, Todsapon; Rauchfuss, Thomas B. [Angewandte Chemie - International Edition, 2010, vol. 49, # 37, p. 6616 - 6618]
[7]Galkin, Konstantin I.; Ananikov, Valentine P. [ChemSusChem, 2019, vol. 12, # 1, p. 185 - 189]

11
[ 1883-75-6 ]
[ 823-82-5 ]
[ 67-47-0 ]
[ 6338-41-6 ]
[ 3238-40-2 ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 229 - 231

12
[ 67-47-0 ]
2,5-bis(hydroxymethyl)tetrahydrofuran [ No CAS ]
[ 1883-75-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 78% 2: 17%	With hydrogen In methanol at 100℃; for 16h; Autoclave; Sealed tube;
1: 71% 2: 25%	With Ni_0.53Al_0.47O_1.10H_0.39; hydrogen In lithium hydroxide monohydrate at 79.84℃; for 6h; Autoclave; Inert atmosphere;
34.7%	With hydrogen In lithium hydroxide monohydrate at 40℃; for 1h; Autoclave;	13 [Synthesis of 2,5-dihydroxymethyltetrahydrofuran] General procedure: 100 mg of "Pd - Mo / SiO 2 catalyst (1)" obtained in Example 1 and 10 ml of 0.5 M 5 - hydroxymethylfurfural aqueous solution were placed in an autoclave having an internal volume of 50 ml equipped with a glass inner tube . Then, the inside of the autoclave was pressurized with hydrogen, and the mixture was stirred at 2 ° C. for 6 hours under a hydrogen atmosphere of 8 MPa. As a result, the reduction reaction shown in the following reaction formula (4) was carried out. After completion of the reduction reaction, the obtained reaction solution was filtered through a syringe equipped with a membrane filter (0.45 μm) to obtain a filtrate. Analysis of this filtrate by gas chromatography revealed that the conversion of 5-hydroxymethylfurfural was 99.7% and the yield of 2,5-dihydroxymethyltetrahydrofuran was 93.5%.The reaction was carried out in the same manner as in Example 8, except that the "Pd - Mo / SiO 2 catalyst (2)" obtained in Example 13 was used in place of the Pd - Rh / SiO 2 catalyst used in Example 8 went. As a result, the conversion of 5-hydroxymethylfurfural was 98.0% and the yield of 2,5-dihydroxymethyltetrahydrofuran was 34.7%.

1: 7% 2: 33%	With palladium on activated charcoal; hydrogen; sodium hydroxide In lithium hydroxide monohydrate at 139.84℃; for 2h; Autoclave;
	With hydrogen In lithium hydroxide monohydrate at 60 - 100℃; for 2h;	1; 3; 4; 5 EXAMPLE 1 Selective Reduction of HMF Utilizing Pd/C To 10 mL of water in a small pressure autoclave (45 mL total volume) was added 0.2289 g of dry Pd/C catalyst (commercially available 0.8% Pd on carbon). A magnetic stir bar was added and the vessel was sealed. The reactor was purged with N2 and was pressure tested for leaks at 500 psi. After confirming an absence of leaks, the vessel was vented, the line was removed and 0.4513 g of HMF dissolved in 5 mL of water was added utilizing a small syringe and needle through the 1/16 inch fitting on the head of the vessel. The vessel was then purged with N2, purged with H2 and pressurized to 500 psi H2. The reaction vessel was isolated from the H2 feed line by a valve downstream from the pressure gauge. The reactor was brought to a reaction temperature of 60° C. in less than 5 minutes. After 2 hours reaction time (measured from the point of reaching 60° C.) the pressure within the vessel was determined to be 330 psi. The vessel was then vented and purged with N2 and the gas line removed to allow sampling of vessel contents. Approximately 1 mL of sample was removed utilizing an approximately 5 inch needle, and the sample was filtered utilizing a 0.2 micron syringe filter. The gas line was then reconnected and the vessel purged with N2 followed by H2 and was re-pressurized to 500 psi H2. Sampling was repeated after 4 hours and the reaction was stopped after removing the 4 hour sample. Each of the 2 hour and 4 hour samples was diluted by 50% and was analyzed by liquid chromatography (LC). The results showed that by 2 hours the HMF conversion was 100% with 51% selectivity to FDM due to over-reduction (as apparent by the presence of THF dimethanol).; EXAMPLE 3 Reduction of HMF with Production of THF Dimethanol A commercially available nickel powder catalyst (Mallinckrodt Specialty Chemical Company, Calsicat, S-96-674, No.69F-093A, E-473P L, Dec. 6, 1996) was utilized. The catalyst was received and stored under water. 1 mL of catalyst slurry was placed in a glass liner and 9 mL of water added. A magnetic stir bar was added and the liner sealed in a 45 mL autoclave. The autoclave was purged and pressure/leak tested to 500 psi with hydrogen. The autoclave was vented and 0.45 grams of HMF dissolved in 5 mL of water was added. The reactor was purged again, and pressurized to 500 psi with hydrogen. The desired temperature of 60° C. was achieved upon heating for approximately 5 minutes and was maintained for 2 hours at which time the first sample was removed and analyzed by LC. HMF conversion was 99% with selectivity to FDM of 84%. Over reduction of FDM to THF dimethanol occurred with a selectivity to THF dimethanol of 10%. After 4 hours at 60° C. a second sample was removed and analyzed. Conversion of HMF was 100% with more over reduction, selectivity to FDM dropped to 77% and selectivity to THF dimethanol increased to 17%. At 4 hours the temperature was increased to 100° C. and pressure increased to 950 psi hydrogen. After 3 hours of additional reaction under these conditions, FDM selectivity had dropped to 3% and THF dimethanol selectivity increased to 95%. In fixed-bed continuous flow experiments using the same or similar catalysts and reaction conditions described above, alternative parameters such as gas and liquid flow rates, and feed concentrations were also independently varied to study the effect of such variations on conversion, yield and selectivity. A first set of studies was performed utilizing cobalt metal on SiO2 support material with varying parameters including temperature, H2 pressure, feed concentration, and flow rate parameters. The results of such studies are presented in a series of graphs set forth in FIGS. 1-14. Similar studies were performed utilizing a palladium metal on carbon support catalyst. For both the palladium and the cobalt catalyst studies, a fixed-bed reactor was utilized to allow sample flow rate to be studied. The results of independent variants of flow rate, reaction temperature, and pressure for the Pd/C catalyst studies are presented in FIGS. 15-21. Tables 3 and 4 show the effect of pressure at 70° C. and 100° C. respectively utilizing the Pd/C catalyst. Additional flow reactor studies were conducted utilizing alternative catalysts. Presented herewith are results of flow reactor studies conducted utilizing Pt/SiO2 (FIG. 22), an alternative Co/SiO2 catalyst (FIGS. 23-38), a copper-chromite catalyst (FIGS. 39-42), or Pt/Al2O3 (FIGS. 43-56). The enclosed sets of results for the alternative Co/SiO2 catalyst, Cu-chromite, and Pt/Al2O3 include effects on conversion and product selectivity of varied reaction parameters including gas and liquid flow rates, HMF feed concentration, H2 pressure, and/or temperature. Table 5 shows the effect of pretreatment temperature for the alternative Co/SiO2 catalyst (Engelhard Co-0179). Table 6 shows the effect of pressure for continuous flow reaction utilizing the Pt/Al2O3 catalyst.EXAMPLE 4 Reduction of HMF with Production of FDM in a Fixed-Bed Continuous Flow Reactor A tubular reactor made of inch stainless-steel thick-wall tubing (0.065 inch wall thickness) was utilized. 2 mL (1.11 g) of dry Pt/Al2O3 catalyst (prepared with 5% Pt on 40-80 mesh alumina support) was reduced before testing at 150° C. at atmospheric pressure with a hydrogen flow of 20 mL/minute. The reactor was then cooled to 40° C. and water was introduced at a flow rate of 0.5 mL/min with a high pressure liquid pump. The hydrogen gas flow was increased to approximately 120 mL/minute until the system pressure increased to 500 psig, at which time the hydrogen flow rate was decreased to 14 mL/minute. The temperature operating set point of the system was increased to 70° C. and upon achieving 70° C., a 1% feed solution of HMF (optionally purged with nitrogen) was fed to the catalyst bed at a rate of 0.5 mL/minute. At 20 minute reaction time intervals (measured from the time feed was started) liquid samples of the product exiting the reactor were collected for LC analysis. LC results for each sample taken showed 100% conversion of HMF and 95% selectivity to FDM. After 1 hour and 40 minutes of testing the liquid feed rate of the 1% HMF solution was decreased to 0.3 mL/minute. Sampling and analysis was repeated at 20 minute intervals for an additional 1 hour and 40 min. The results indicate no observed over-reduction at this lower liquid flow rate (as apparent by the absence of THF dimethanol) and that HMF conversion remained at 100% with 95% selectivity to FDM. As can be observed in the forgoing figures, under certain conditions products other than FDM can be selectively produced from HMF with particular catalysts. Further studies sere conducted to selectively produce non-FDM products utilizing HMF, FDM or tetrahydrofuran dimethanol (THFDM, THF diol) starting material. The Co-179 catalyst in a continuous flow reactor at 70° C. resulted in high selectivity (>95%) to FDM (see FIGS. 28, 29 and 36), with only moderate selectivities to THFDM when the temperature is raised to 120° C. Referring to FIG. 57, at about 100% HMF conversion at 120° C. a THFDM selectivity of about 70% was achieved. Reduction to THFDM was incomplete and significant by-products were observed at the higher temperature. Referring to FIG. 58, Ni/SiO2 reduced FDM nearly quantitatively to THFDM at 70° C. However, under identical conditions utilizing HMF (FIG. 59), only 80% HMF conversion was obtained and selectivity to THFDM was about 40%. When the feed was switched again to FDM, only about 20% FDM conversion was observed (FIG. 60), indicating that HMF poisons the Ni catalyst. A staged bed (segregated catalysts in the same bed) containing cobalt catalyst and nickel catalyst was tested for production of THFDM from HMF. The HMF feed first passed through the Co catalyst which primarily reduced the HMF to FDM, then through the Ni catalyst which primarily reduced the FDM to THFDM. Very high HMF conversion and selectivity to THFDM was obtained as shown in FIG. 61. The Ni catalyst appeared to remain active for THFDM production when HMF was reduced first to FDM with the Co catalyst. HMF feed concentrations of 1%, 3%, and 6%, were tested, all giving similar conversions and selectivities. Additional experiments were conducted utilizing the staged Co/Ni catalysts at high temperatures with either HMF or FDM feeds to examine polyol production (FIGS. 62-70). Temperatures as high as 180° C. were evaluated. The major product was 1,2,6-hexanetriol but yields decreased with increased temperatures with production of may unknown products. One major by-product was identified as 2,5-hexanediol. When the feed was THFDM however, almost no ring-opening occurred. THFDM was quite stable up to 200° C. Ring-opened polyols therefore likely are formed via HMF or FDM, not via THFDM. FIGS. 62-70 show the results obtained under a variety of temperatures, feed (FDM vs. HMF) feed concentration and space velocity. A batch-wise experiment was conducted to study the effect of organic solvent on the catalytic hydrogenation of HMF to FDM utilizing two different catalysts. Selectivity toward FDM production was compared for reactions conducted in ethanol and reactions conducted in water. As shown in Table 7, conversion and selectivity toward FDM are lower in ethanol than in water under the same reaction conditions and reaction times. The impact of various impurities on the hydrogenation of HMF was investigated in both batch-wise and flow reactor studies. Impurities included fructose, ethyl acetate, dimethylacetamide, methyl t-butyl ether, methyl iso-butyl ketone, levulinic acid, formic acid, acetic acid, sodium sulfate, and N-methyl pyrrolidinone. These impurities were found to be non-detrimental to HMF conversion within the accuracy of the experiments. Of particular interest were the results with fructose impurity in batch experiments conducted between 60 and 100° C. and 500 psi for at least 2 h. Both Pt(Ge)/C (Engelhard No.43932) and Co/SiO2 (Sud Chemie G62aRS) catalysts converted HMF to reduced products without reducing fructose to sorbitol or mannitol, even at high HMF conversions. FDM can be formed in high yield. In the absence of HMF, fructose is easily reduced under these reaction conditions, suggesting that HMF either inhibits fructose reduction or is reduced at a faster rate. These results indicate that highly selective reduction of HMF is possible with the HMF precursor fructose present in the feed and that fructose need not be separated from the HMF solution prior to reduction.EXAMPLE 5 Reduction of HMF in the Presence of Fructose Batch-wise experiments were conducted with an aqueous solution of 15 wt % each of HMF and fructose under 500 psi H2 between 75 and 100° C. using Ge-promoted 5% Pt on carbon (Engelhard No.43932) for at least 2 h. In a sample taken at 1 h, LC and 13C NMR analysis showed that HMF was converted to FDM with good selectivity but that essentially no fructose was converted to sorbitol or mannitol even at high HMF conversion. Only trace amounts of levulinic and formic acids were formed. FIGS. 71-80 show the results of a number of batchwise HMF conversion reactions utilizing RANEY Co-2724 (FIG. 71); 5% Pt(Ge)/C (FIG. 72); 5% Pd/C (FIG. 73); 5% Ru/C (FIG. 74); RANEY Co-2700 (FIGS. 75-76); and RANEY Cu (FIG. 77) catalysts. The effect of H2 pressure was investigated utilizing a 5% Pt(Ge)/C catalyst as shown in FIG. 78. FIG. 79 shows the effect of temperature on HMF conversion using the Pt(Ge)/C catalyst, and FIG. 80 shows the effect of temperature on FDM selectivity for the Pt(Ge)/C catalyst.
	With hydrogen In lithium hydroxide monohydrate at 70℃;	3 EXAMPLE 3 Reduction of HMF with Production of THF Dimethanol A commercially available nickel powder catalyst (Mallinckrodt Specialty Chemical Company, Calsicat, S-96-674, No.69F-093A, E-473P L, Dec. 6, 1996) was utilized. The catalyst was received and stored under water. 1 mL of catalyst slurry was placed in a glass liner and 9 mL of water added. A magnetic stir bar was added and the liner sealed in a 45 mL autoclave. The autoclave was purged and pressure/leak tested to 500 psi with hydrogen. The autoclave was vented and 0.45 grams of HMF dissolved in 5 mL of water was added. The reactor was purged again, and pressurized to 500 psi with hydrogen. The desired temperature of 60° C. was achieved upon heating for approximately 5 minutes and was maintained for 2 hours at which time the first sample was removed and analyzed by LC. HMF conversion was 99% with selectivity to FDM of 84%. Over reduction of FDM to THF dimethanol occurred with a selectivity to THF dimethanol of 10%. After 4 hours at 60° C. a second sample was removed and analyzed. Conversion of HMF was 100% with more over reduction, selectivity to FDM dropped to 77% and selectivity to THF dimethanol increased to 17%. At 4 hours the temperature was increased to 100° C. and pressure increased to 950 psi hydrogen. After 3 hours of additional reaction under these conditions, FDM selectivity had dropped to 3% and THF dimethanol selectivity increased to 95%. In fixed-bed continuous flow experiments using the same or similar catalysts and reaction conditions described above, alternative parameters such as gas and liquid flow rates, and feed concentrations were also independently varied to study the effect of such variations on conversion, yield and selectivity. A first set of studies was performed utilizing cobalt metal on SiO2 support material with varying parameters including temperature, H2 pressure, feed concentration, and flow rate parameters. The results of such studies are presented in a series of graphs set forth in FIGS. 1-14. Similar studies were performed utilizing a palladium metal on carbon support catalyst. For both the palladium and the cobalt catalyst studies, a fixed-bed reactor was utilized to allow sample flow rate to be studied. The results of independent variants of flow rate, reaction temperature, and pressure for the Pd/C catalyst studies are presented in FIGS. 15-21. Tables 3 and 4 show the effect of pressure at 70° C. and 100° C. respectively utilizing the Pd/C catalyst. Additional flow reactor studies were conducted utilizing alternative catalysts. Presented herewith are results of flow reactor studies conducted utilizing Pt/SiO2 (FIG. 22), an alternative Co/SiO2 catalyst (FIGS. 23-38), a copper-chromite catalyst (FIGS. 39-42), or Pt/Al2O3 (FIGS. 43-56). The enclosed sets of results for the alternative Co/SiO2 catalyst, Cu-chromite, and Pt/Al2O3 include effects on conversion and product selectivity of varied reaction parameters including gas and liquid flow rates, HMF feed concentration, H2 pressure, and/or temperature. Table 5 shows the effect of pretreatment temperature for the alternative Co/SiO2 catalyst (Engelhard Co-0179). Table 6 shows the effect of pressure for continuous flow reaction utilizing the Pt/Al2O3 catalyst.
	With hydrogen In lithium hydroxide monohydrate at 60 - 100℃; for 2.08333 - 7h;	3 EXAMPLE 3 Reduction of HMF with Production of THF Dimethanol A commercially available nickel powder catalyst (Mallinckrodt Specialty Chemical Company, Calsicat, S-96-674, No.69F-093A, E-473P L, Dec. 6, 1996) was utilized. The catalyst was received and stored under water. 1 mL of catalyst slurry was placed in a glass liner and 9 mL of water added. A magnetic stir bar was added and the liner sealed in a 45 mL autoclave. The autoclave was purged and pressure/leak tested to 500 psi with hydrogen. The autoclave was vented and 0.45 grams of HMF dissolved in 5 mL of water was added. The reactor was purged again, and pressurized to 500 psi with hydrogen. The desired temperature of 60° C. was achieved upon heating for approximately 5 minutes and was maintained for 2 hours at which time the first sample was removed and analyzed by LC. HMF conversion was 99% with selectivity to FDM of 84%. Over reduction of FDM to THF dimethanol occurred with a selectivity to THF dimethanol of 10%. After 4 hours at 60° C. a second sample was removed and analyzed. Conversion of HMF was 100% with more over reduction, selectivity to FDM dropped to 77% and selectivity to THF dimethanol increased to 17%. At 4 hours the temperature was increased to 100° C. and pressure increased to 950 psi hydrogen. After 3 hours of additional reaction under these conditions, FDM selectivity had dropped to 3% and THF dimethanol selectivity increased to 95%. In fixed-bed continuous flow experiments using the same or similar catalysts and reaction conditions described above, alternative parameters such as gas and liquid flow rates, and feed concentrations were also independently varied to study the effect of such variations on conversion, yield and selectivity. A first set of studies was performed utilizing cobalt metal on SiO2 support material with varying parameters including temperature, H2 pressure, feed concentration, and flow rate parameters. The results of such studies are presented in a series of graphs set forth in FIGS. 1-14. Similar studies were performed utilizing a palladium metal on carbon support catalyst. For both the palladium and the cobalt catalyst studies, a fixed-bed reactor was utilized to allow sample flow rate to be studied. The results of independent variants of flow rate, reaction temperature, and pressure for the Pd/C catalyst studies are presented in FIGS. 15-21. Tables 3 and 4 show the effect of pressure at 70° C. and 100° C. respectively utilizing the Pd/C catalyst. Additional flow reactor studies were conducted utilizing alternative catalysts. Presented herewith are results of flow reactor studies conducted utilizing Pt/SiO2 (FIG. 22), an alternative Co/SiO2 catalyst (FIGS. 23-38), a copper-chromite catalyst (FIGS. 39-42), or Pt/Al2O3 (FIGS. 43-56). The enclosed sets of results for the alternative Co/SiO2 catalyst, Cu-chromite, and Pt/Al2O3 include effects on conversion and product selectivity of varied reaction parameters including gas and liquid flow rates, HMF feed concentration, H2 pressure, and/or temperature. Table 5 shows the effect of pretreatment temperature for the alternative Co/SiO2 catalyst (Engelhard Co-0179). Table 6 shows the effect of pressure for continuous flow reaction utilizing the Pt/Al2O3 catalyst.
	With hydrogen In lithium hydroxide monohydrate at 70 - 180℃;	3; 4 EXAMPLE 3 Reduction of HMF with Production of THF Dimethanol A commercially available nickel powder catalyst (Mallinckrodt Specialty Chemical Company, Calsicat, S-96-674, No.69F-093A, E-473P L, Dec. 6, 1996) was utilized. The catalyst was received and stored under water. 1 mL of catalyst slurry was placed in a glass liner and 9 mL of water added. A magnetic stir bar was added and the liner sealed in a 45 mL autoclave. The autoclave was purged and pressure/leak tested to 500 psi with hydrogen. The autoclave was vented and 0.45 grams of HMF dissolved in 5 mL of water was added. The reactor was purged again, and pressurized to 500 psi with hydrogen. The desired temperature of 60° C. was achieved upon heating for approximately 5 minutes and was maintained for 2 hours at which time the first sample was removed and analyzed by LC. HMF conversion was 99% with selectivity to FDM of 84%. Over reduction of FDM to THF dimethanol occurred with a selectivity to THF dimethanol of 10%. After 4 hours at 60° C. a second sample was removed and analyzed. Conversion of HMF was 100% with more over reduction, selectivity to FDM dropped to 77% and selectivity to THF dimethanol increased to 17%. At 4 hours the temperature was increased to 100° C. and pressure increased to 950 psi hydrogen. After 3 hours of additional reaction under these conditions, FDM selectivity had dropped to 3% and THF dimethanol selectivity increased to 95%. In fixed-bed continuous flow experiments using the same or similar catalysts and reaction conditions described above, alternative parameters such as gas and liquid flow rates, and feed concentrations were also independently varied to study the effect of such variations on conversion, yield and selectivity. A first set of studies was performed utilizing cobalt metal on SiO2 support material with varying parameters including temperature, H2 pressure, feed concentration, and flow rate parameters. The results of such studies are presented in a series of graphs set forth in FIGS. 1-14. Similar studies were performed utilizing a palladium metal on carbon support catalyst. For both the palladium and the cobalt catalyst studies, a fixed-bed reactor was utilized to allow sample flow rate to be studied. The results of independent variants of flow rate, reaction temperature, and pressure for the Pd/C catalyst studies are presented in FIGS. 15-21. Tables 3 and 4 show the effect of pressure at 70° C. and 100° C. respectively utilizing the Pd/C catalyst. Additional flow reactor studies were conducted utilizing alternative catalysts. Presented herewith are results of flow reactor studies conducted utilizing Pt/SiO2 (FIG. 22), an alternative Co/SiO2 catalyst (FIGS. 23-38), a copper-chromite catalyst (FIGS. 39-42), or Pt/Al2O3 (FIGS. 43-56). The enclosed sets of results for the alternative Co/SiO2 catalyst, Cu-chromite, and Pt/Al2O3 include effects on conversion and product selectivity of varied reaction parameters including gas and liquid flow rates, HMF feed concentration, H2 pressure, and/or temperature. Table 5 shows the effect of pretreatment temperature for the alternative Co/SiO2 catalyst (Engelhard Co-0179). Table 6 shows the effect of pressure for continuous flow reaction utilizing the Pt/Al2O3 catalyst.EXAMPLE 4 Reduction of HMF with Production of FDM in a Fixed-Bed Continuous Flow Reactor A tubular reactor made of inch stainless-steel thick-wall tubing (0.065 inch wall thickness) was utilized. 2 mL (1.11 g) of dry Pt/Al2O3 catalyst (prepared with 5% Pt on 40-80 mesh alumina support) was reduced before testing at 150° C. at atmospheric pressure with a hydrogen flow of 20 mL/minute. The reactor was then cooled to 40° C. and water was introduced at a flow rate of 0.5 mL/min with a high pressure liquid pump. The hydrogen gas flow was increased to approximately 120 mL/minute until the system pressure increased to 500 psig, at which time the hydrogen flow rate was decreased to 14 mL/minute. The temperature operating set point of the system was increased to 70° C. and upon achieving 70° C., a 1% feed solution of HMF (optionally purged with nitrogen) was fed to the catalyst bed at a rate of 0.5 mL/minute. At 20 minute reaction time intervals (measured from the time feed was started) liquid samples of the product exiting the reactor were collected for LC analysis. LC results for each sample taken showed 100% conversion of HMF and 95% selectivity to FDM. After 1 hour and 40 minutes of testing the liquid feed rate of the 1% HMF solution was decreased to 0.3 mL/minute. Sampling and analysis was repeated at 20 minute intervals for an additional 1 hour and 40 min. The results indicate no observed over-reduction at this lower liquid flow rate (as apparent by the absence of THF dimethanol) and that HMF conversion remained at 100% with 95% selectivity to FDM. As can be observed in the forgoing figures, under certain conditions products other than FDM can be selectively produced from HMF with particular catalysts. Further studies sere conducted to selectively produce non-FDM products utilizing HMF, FDM or tetrahydrofuran dimethanol (THFDM, THF diol) starting material. The Co-179 catalyst in a continuous flow reactor at 70° C. resulted in high selectivity (>95%) to FDM (see FIGS. 28, 29 and 36), with only moderate selectivities to THFDM when the temperature is raised to 120° C. Referring to FIG. 57, at about 100% HMF conversion at 120° C. a THFDM selectivity of about 70% was achieved. Reduction to THFDM was incomplete and significant by-products were observed at the higher temperature. Referring to FIG. 58, Ni/SiO2 reduced FDM nearly quantitatively to THFDM at 70° C. However, under identical conditions utilizing HMF (FIG. 59), only 80% HMF conversion was obtained and selectivity to THFDM was about 40%. When the feed was switched again to FDM, only about 20% FDM conversion was observed (FIG. 60), indicating that HMF poisons the Ni catalyst. A staged bed (segregated catalysts in the same bed) containing cobalt catalyst and nickel catalyst was tested for production of THFDM from HMF. The HMF feed first passed through the Co catalyst which primarily reduced the HMF to FDM, then through the Ni catalyst which primarily reduced the FDM to THFDM. Very high HMF conversion and selectivity to THFDM was obtained as shown in FIG. 61. The Ni catalyst appeared to remain active for THFDM production when HMF was reduced first to FDM with the Co catalyst. HMF feed concentrations of 1%, 3%, and 6%, were tested, all giving similar conversions and selectivities. Additional experiments were conducted utilizing the staged Co/Ni catalysts at high temperatures with either HMF or FDM feeds to examine polyol production (FIGS. 62-70). Temperatures as high as 180° C. were evaluated. The major product was 1,2,6-hexanetriol but yields decreased with increased temperatures with production of may unknown products. One major by-product was identified as 2,5-hexanediol. When the feed was THFDM however, almost no ring-opening occurred. THFDM was quite stable up to 200° C. Ring-opened polyols therefore likely are formed via HMF or FDM, not via THFDM. FIGS. 62-70 show the results obtained under a variety of temperatures, feed (FDM vs. HMF) feed concentration and space velocity. A batch-wise experiment was conducted to study the effect of organic solvent on the catalytic hydrogenation of HMF to FDM utilizing two different catalysts. Selectivity toward FDM production was compared for reactions conducted in ethanol and reactions conducted in water. As shown in Table 7, conversion and selectivity toward FDM are lower in ethanol than in water under the same reaction conditions and reaction times. The impact of various impurities on the hydrogenation of HMF was investigated in both batch-wise and flow reactor studies. Impurities included fructose, ethyl acetate, dimethylacetamide, methyl t-butyl ether, methyl iso-butyl ketone, levulinic acid, formic acid, acetic acid, sodium sulfate, and N-methyl pyrrolidinone. These impurities were found to be non-detrimental to HMF conversion within the accuracy of the experiments. Of particular interest were the results with fructose impurity in batch experiments conducted between 60 and 100° C. and 500 psi for at least 2 h. Both Pt(Ge)/C (Engelhard No.43932) and Co/SiO2 (Sud Chemie G62aRS) catalysts converted HMF to reduced products without reducing fructose to sorbitol or mannitol, even at high HMF conversions. FDM can be formed in high yield. In the absence of HMF, fructose is easily reduced under these reaction conditions, suggesting that HMF either inhibits fructose reduction or is reduced at a faster rate. These results indicate that highly selective reduction of HMF is possible with the HMF precursor fructose present in the feed and that fructose need not be separated from the HMF solution prior to reduction.
	With hydrogen In lithium hydroxide monohydrate at 60 - 70℃;	3; 5 EXAMPLE 3 Reduction of HMF with Production of THF Dimethanol A commercially available nickel powder catalyst (Mallinckrodt Specialty Chemical Company, Calsicat, S-96-674, No.69F-093A, E-473P L, Dec. 6, 1996) was utilized. The catalyst was received and stored under water. 1 mL of catalyst slurry was placed in a glass liner and 9 mL of water added. A magnetic stir bar was added and the liner sealed in a 45 mL autoclave. The autoclave was purged and pressure/leak tested to 500 psi with hydrogen. The autoclave was vented and 0.45 grams of HMF dissolved in 5 mL of water was added. The reactor was purged again, and pressurized to 500 psi with hydrogen. The desired temperature of 60° C. was achieved upon heating for approximately 5 minutes and was maintained for 2 hours at which time the first sample was removed and analyzed by LC. HMF conversion was 99% with selectivity to FDM of 84%. Over reduction of FDM to THF dimethanol occurred with a selectivity to THF dimethanol of 10%. After 4 hours at 60° C. a second sample was removed and analyzed. Conversion of HMF was 100% with more over reduction, selectivity to FDM dropped to 77% and selectivity to THF dimethanol increased to 17%. At 4 hours the temperature was increased to 100° C. and pressure increased to 950 psi hydrogen. After 3 hours of additional reaction under these conditions, FDM selectivity had dropped to 3% and THF dimethanol selectivity increased to 95%. In fixed-bed continuous flow experiments using the same or similar catalysts and reaction conditions described above, alternative parameters such as gas and liquid flow rates, and feed concentrations were also independently varied to study the effect of such variations on conversion, yield and selectivity. A first set of studies was performed utilizing cobalt metal on SiO2 support material with varying parameters including temperature, H2 pressure, feed concentration, and flow rate parameters. The results of such studies are presented in a series of graphs set forth in FIGS. 1-14. Similar studies were performed utilizing a palladium metal on carbon support catalyst. For both the palladium and the cobalt catalyst studies, a fixed-bed reactor was utilized to allow sample flow rate to be studied. The results of independent variants of flow rate, reaction temperature, and pressure for the Pd/C catalyst studies are presented in FIGS. 15-21. Tables 3 and 4 show the effect of pressure at 70° C. and 100° C. respectively utilizing the Pd/C catalyst. Additional flow reactor studies were conducted utilizing alternative catalysts. Presented herewith are results of flow reactor studies conducted utilizing Pt/SiO2 (FIG. 22), an alternative Co/SiO2 catalyst (FIGS. 23-38), a copper-chromite catalyst (FIGS. 39-42), or Pt/Al2O3 (FIGS. 43-56). The enclosed sets of results for the alternative Co/SiO2 catalyst, Cu-chromite, and Pt/Al2O3 include effects on conversion and product selectivity of varied reaction parameters including gas and liquid flow rates, HMF feed concentration, H2 pressure, and/or temperature. Table 5 shows the effect of pretreatment temperature for the alternative Co/SiO2 catalyst (Engelhard Co-0179). Table 6 shows the effect of pressure for continuous flow reaction utilizing the Pt/Al2O3 catalyst.EXAMPLE 5 Reduction of HMF in the Presence of Fructose Batch-wise experiments were conducted with an aqueous solution of 15 wt % each of HMF and fructose under 500 psi H2 between 75 and 100° C. using Ge-promoted 5% Pt on carbon (Engelhard No.43932) for at least 2 h. In a sample taken at 1 h, LC and 13C NMR analysis showed that HMF was converted to FDM with good selectivity but that essentially no fructose was converted to sorbitol or mannitol even at high HMF conversion. Only trace amounts of levulinic and formic acids were formed. FIGS. 71-80 show the results of a number of batchwise HMF conversion reactions utilizing RANEY Co-2724 (FIG. 71); 5% Pt(Ge)/C (FIG. 72); 5% Pd/C (FIG. 73); 5% Ru/C (FIG. 74); RANEY Co-2700 (FIGS. 75-76); and RANEY Cu (FIG. 77) catalysts. The effect of H2 pressure was investigated utilizing a 5% Pt(Ge)/C catalyst as shown in FIG. 78. FIG. 79 shows the effect of temperature on HMF conversion using the Pt(Ge)/C catalyst, and FIG. 80 shows the effect of temperature on FDM selectivity for the Pt(Ge)/C catalyst.
	With hydrogen In lithium hydroxide monohydrate at 60℃;	5 EXAMPLE 5 Reduction of HMF in the Presence of Fructose Batch-wise experiments were conducted with an aqueous solution of 15 wt % each of HMF and fructose under 500 psi H2 between 75 and 100° C. using Ge-promoted 5% Pt on carbon (Engelhard No.43932) for at least 2 h. In a sample taken at 1 h, LC and 13C NMR analysis showed that HMF was converted to FDM with good selectivity but that essentially no fructose was converted to sorbitol or mannitol even at high HMF conversion. Only trace amounts of levulinic and formic acids were formed. FIGS. 71-80 show the results of a number of batchwise HMF conversion reactions utilizing RANEY Co-2724 (FIG. 71); 5% Pt(Ge)/C (FIG. 72); 5% Pd/C (FIG. 73); 5% Ru/C (FIG. 74); RANEY Co-2700 (FIGS. 75-76); and RANEY Cu (FIG. 77) catalysts. The effect of H2 pressure was investigated utilizing a 5% Pt(Ge)/C catalyst as shown in FIG. 78. FIG. 79 shows the effect of temperature on HMF conversion using the Pt(Ge)/C catalyst, and FIG. 80 shows the effect of temperature on FDM selectivity for the Pt(Ge)/C catalyst.
	With hydrogen In lithium hydroxide monohydrate at 70℃;	4 EXAMPLE 4 Reduction of HMF with Production of FDM in a Fixed-Bed Continuous Flow Reactor A tubular reactor made of inch stainless-steel thick-wall tubing (0.065 inch wall thickness) was utilized. 2 mL (1.11 g) of dry Pt/Al2O3 catalyst (prepared with 5% Pt on 40-80 mesh alumina support) was reduced before testing at 150° C. at atmospheric pressure with a hydrogen flow of 20 mL/minute. The reactor was then cooled to 40° C. and water was introduced at a flow rate of 0.5 mL/min with a high pressure liquid pump. The hydrogen gas flow was increased to approximately 120 mL/minute until the system pressure increased to 500 psig, at which time the hydrogen flow rate was decreased to 14 mL/minute. The temperature operating set point of the system was increased to 70° C. and upon achieving 70° C., a 1% feed solution of HMF (optionally purged with nitrogen) was fed to the catalyst bed at a rate of 0.5 mL/minute. At 20 minute reaction time intervals (measured from the time feed was started) liquid samples of the product exiting the reactor were collected for LC analysis. LC results for each sample taken showed 100% conversion of HMF and 95% selectivity to FDM. After 1 hour and 40 minutes of testing the liquid feed rate of the 1% HMF solution was decreased to 0.3 mL/minute. Sampling and analysis was repeated at 20 minute intervals for an additional 1 hour and 40 min. The results indicate no observed over-reduction at this lower liquid flow rate (as apparent by the absence of THF dimethanol) and that HMF conversion remained at 100% with 95% selectivity to FDM. As can be observed in the forgoing figures, under certain conditions products other than FDM can be selectively produced from HMF with particular catalysts. Further studies sere conducted to selectively produce non-FDM products utilizing HMF, FDM or tetrahydrofuran dimethanol (THFDM, THF diol) starting material. The Co-179 catalyst in a continuous flow reactor at 70° C. resulted in high selectivity (>95%) to FDM (see FIGS. 28, 29 and 36), with only moderate selectivities to THFDM when the temperature is raised to 120° C. Referring to FIG. 57, at about 100% HMF conversion at 120° C. a THFDM selectivity of about 70% was achieved. Reduction to THFDM was incomplete and significant by-products were observed at the higher temperature. Referring to FIG. 58, Ni/SiO2 reduced FDM nearly quantitatively to THFDM at 70° C. However, under identical conditions utilizing HMF (FIG. 59), only 80% HMF conversion was obtained and selectivity to THFDM was about 40%. When the feed was switched again to FDM, only about 20% FDM conversion was observed (FIG. 60), indicating that HMF poisons the Ni catalyst. A staged bed (segregated catalysts in the same bed) containing cobalt catalyst and nickel catalyst was tested for production of THFDM from HMF. The HMF feed first passed through the Co catalyst which primarily reduced the HMF to FDM, then through the Ni catalyst which primarily reduced the FDM to THFDM. Very high HMF conversion and selectivity to THFDM was obtained as shown in FIG. 61. The Ni catalyst appeared to remain active for THFDM production when HMF was reduced first to FDM with the Co catalyst. HMF feed concentrations of 1%, 3%, and 6%, were tested, all giving similar conversions and selectivities. Additional experiments were conducted utilizing the staged Co/Ni catalysts at high temperatures with either HMF or FDM feeds to examine polyol production (FIGS. 62-70). Temperatures as high as 180° C. were evaluated. The major product was 1,2,6-hexanetriol but yields decreased with increased temperatures with production of may unknown products. One major by-product was identified as 2,5-hexanediol. When the feed was THFDM however, almost no ring-opening occurred. THFDM was quite stable up to 200° C. Ring-opened polyols therefore likely are formed via HMF or FDM, not via THFDM. FIGS. 62-70 show the results obtained under a variety of temperatures, feed (FDM vs. HMF) feed concentration and space velocity. A batch-wise experiment was conducted to study the effect of organic solvent on the catalytic hydrogenation of HMF to FDM utilizing two different catalysts. Selectivity toward FDM production was compared for reactions conducted in ethanol and reactions conducted in water. As shown in Table 7, conversion and selectivity toward FDM are lower in ethanol than in water under the same reaction conditions and reaction times. The impact of various impurities on the hydrogenation of HMF was investigated in both batch-wise and flow reactor studies. Impurities included fructose, ethyl acetate, dimethylacetamide, methyl t-butyl ether, methyl iso-butyl ketone, levulinic acid, formic acid, acetic acid, sodium sulfate, and N-methyl pyrrolidinone. These impurities were found to be non-detrimental to HMF conversion within the accuracy of the experiments. Of particular interest were the results with fructose impurity in batch experiments conducted between 60 and 100° C. and 500 psi for at least 2 h. Both Pt(Ge)/C (Engelhard No.43932) and Co/SiO2 (Sud Chemie G62aRS) catalysts converted HMF to reduced products without reducing fructose to sorbitol or mannitol, even at high HMF conversions. FDM can be formed in high yield. In the absence of HMF, fructose is easily reduced under these reaction conditions, suggesting that HMF either inhibits fructose reduction or is reduced at a faster rate. These results indicate that highly selective reduction of HMF is possible with the HMF precursor fructose present in the feed and that fructose need not be separated from the HMF solution prior to reduction.
	With hydrogen In lithium hydroxide monohydrate at 60℃;	4; 5 EXAMPLE 4 Reduction of HMF with Production of FDM in a Fixed-Bed Continuous Flow Reactor A tubular reactor made of inch stainless-steel thick-wall tubing (0.065 inch wall thickness) was utilized. 2 mL (1.11 g) of dry Pt/Al2O3 catalyst (prepared with 5% Pt on 40-80 mesh alumina support) was reduced before testing at 150° C. at atmospheric pressure with a hydrogen flow of 20 mL/minute. The reactor was then cooled to 40° C. and water was introduced at a flow rate of 0.5 mL/min with a high pressure liquid pump. The hydrogen gas flow was increased to approximately 120 mL/minute until the system pressure increased to 500 psig, at which time the hydrogen flow rate was decreased to 14 mL/minute. The temperature operating set point of the system was increased to 70° C. and upon achieving 70° C., a 1% feed solution of HMF (optionally purged with nitrogen) was fed to the catalyst bed at a rate of 0.5 mL/minute. At 20 minute reaction time intervals (measured from the time feed was started) liquid samples of the product exiting the reactor were collected for LC analysis. LC results for each sample taken showed 100% conversion of HMF and 95% selectivity to FDM. After 1 hour and 40 minutes of testing the liquid feed rate of the 1% HMF solution was decreased to 0.3 mL/minute. Sampling and analysis was repeated at 20 minute intervals for an additional 1 hour and 40 min. The results indicate no observed over-reduction at this lower liquid flow rate (as apparent by the absence of THF dimethanol) and that HMF conversion remained at 100% with 95% selectivity to FDM. As can be observed in the forgoing figures, under certain conditions products other than FDM can be selectively produced from HMF with particular catalysts. Further studies sere conducted to selectively produce non-FDM products utilizing HMF, FDM or tetrahydrofuran dimethanol (THFDM, THF diol) starting material. The Co-179 catalyst in a continuous flow reactor at 70° C. resulted in high selectivity (>95%) to FDM (see FIGS. 28, 29 and 36), with only moderate selectivities to THFDM when the temperature is raised to 120° C. Referring to FIG. 57, at about 100% HMF conversion at 120° C. a THFDM selectivity of about 70% was achieved. Reduction to THFDM was incomplete and significant by-products were observed at the higher temperature. Referring to FIG. 58, Ni/SiO2 reduced FDM nearly quantitatively to THFDM at 70° C. However, under identical conditions utilizing HMF (FIG. 59), only 80% HMF conversion was obtained and selectivity to THFDM was about 40%. When the feed was switched again to FDM, only about 20% FDM conversion was observed (FIG. 60), indicating that HMF poisons the Ni catalyst. A staged bed (segregated catalysts in the same bed) containing cobalt catalyst and nickel catalyst was tested for production of THFDM from HMF. The HMF feed first passed through the Co catalyst which primarily reduced the HMF to FDM, then through the Ni catalyst which primarily reduced the FDM to THFDM. Very high HMF conversion and selectivity to THFDM was obtained as shown in FIG. 61. The Ni catalyst appeared to remain active for THFDM production when HMF was reduced first to FDM with the Co catalyst. HMF feed concentrations of 1%, 3%, and 6%, were tested, all giving similar conversions and selectivities. Additional experiments were conducted utilizing the staged Co/Ni catalysts at high temperatures with either HMF or FDM feeds to examine polyol production (FIGS. 62-70). Temperatures as high as 180° C. were evaluated. The major product was 1,2,6-hexanetriol but yields decreased with increased temperatures with production of may unknown products. One major by-product was identified as 2,5-hexanediol. When the feed was THFDM however, almost no ring-opening occurred. THFDM was quite stable up to 200° C. Ring-opened polyols therefore likely are formed via HMF or FDM, not via THFDM. FIGS. 62-70 show the results obtained under a variety of temperatures, feed (FDM vs. HMF) feed concentration and space velocity. A batch-wise experiment was conducted to study the effect of organic solvent on the catalytic hydrogenation of HMF to FDM utilizing two different catalysts. Selectivity toward FDM production was compared for reactions conducted in ethanol and reactions conducted in water. As shown in Table 7, conversion and selectivity toward FDM are lower in ethanol than in water under the same reaction conditions and reaction times. The impact of various impurities on the hydrogenation of HMF was investigated in both batch-wise and flow reactor studies. Impurities included fructose, ethyl acetate, dimethylacetamide, methyl t-butyl ether, methyl iso-butyl ketone, levulinic acid, formic acid, acetic acid, sodium sulfate, and N-methyl pyrrolidinone. These impurities were found to be non-detrimental to HMF conversion within the accuracy of the experiments. Of particular interest were the results with fructose impurity in batch experiments conducted between 60 and 100° C. and 500 psi for at least 2 h. Both Pt(Ge)/C (Engelhard No.43932) and Co/SiO2 (Sud Chemie G62aRS) catalysts converted HMF to reduced products without reducing fructose to sorbitol or mannitol, even at high HMF conversions. FDM can be formed in high yield. In the absence of HMF, fructose is easily reduced under these reaction conditions, suggesting that HMF either inhibits fructose reduction or is reduced at a faster rate. These results indicate that highly selective reduction of HMF is possible with the HMF precursor fructose present in the feed and that fructose need not be separated from the HMF solution prior to reduction.EXAMPLE 5 Reduction of HMF in the Presence of Fructose Batch-wise experiments were conducted with an aqueous solution of 15 wt % each of HMF and fructose under 500 psi H2 between 75 and 100° C. using Ge-promoted 5% Pt on carbon (Engelhard No.43932) for at least 2 h. In a sample taken at 1 h, LC and 13C NMR analysis showed that HMF was converted to FDM with good selectivity but that essentially no fructose was converted to sorbitol or mannitol even at high HMF conversion. Only trace amounts of levulinic and formic acids were formed. FIGS. 71-80 show the results of a number of batchwise HMF conversion reactions utilizing RANEY Co-2724 (FIG. 71); 5% Pt(Ge)/C (FIG. 72); 5% Pd/C (FIG. 73); 5% Ru/C (FIG. 74); RANEY Co-2700 (FIGS. 75-76); and RANEY Cu (FIG. 77) catalysts. The effect of H2 pressure was investigated utilizing a 5% Pt(Ge)/C catalyst as shown in FIG. 78. FIG. 79 shows the effect of temperature on HMF conversion using the Pt(Ge)/C catalyst, and FIG. 80 shows the effect of temperature on FDM selectivity for the Pt(Ge)/C catalyst.
	With hydrogen In lithium hydroxide monohydrate at 30 - 120℃;	3; 4 EXAMPLE 3 Reduction of HMF with Production of THF Dimethanol A commercially available nickel powder catalyst (Mallinckrodt Specialty Chemical Company, Calsicat, S-96-674, No.69F-093A, E-473P L, Dec. 6, 1996) was utilized. The catalyst was received and stored under water. 1 mL of catalyst slurry was placed in a glass liner and 9 mL of water added. A magnetic stir bar was added and the liner sealed in a 45 mL autoclave. The autoclave was purged and pressure/leak tested to 500 psi with hydrogen. The autoclave was vented and 0.45 grams of HMF dissolved in 5 mL of water was added. The reactor was purged again, and pressurized to 500 psi with hydrogen. The desired temperature of 60° C. was achieved upon heating for approximately 5 minutes and was maintained for 2 hours at which time the first sample was removed and analyzed by LC. HMF conversion was 99% with selectivity to FDM of 84%. Over reduction of FDM to THF dimethanol occurred with a selectivity to THF dimethanol of 10%. After 4 hours at 60° C. a second sample was removed and analyzed. Conversion of HMF was 100% with more over reduction, selectivity to FDM dropped to 77% and selectivity to THF dimethanol increased to 17%. At 4 hours the temperature was increased to 100° C. and pressure increased to 950 psi hydrogen. After 3 hours of additional reaction under these conditions, FDM selectivity had dropped to 3% and THF dimethanol selectivity increased to 95%. In fixed-bed continuous flow experiments using the same or similar catalysts and reaction conditions described above, alternative parameters such as gas and liquid flow rates, and feed concentrations were also independently varied to study the effect of such variations on conversion, yield and selectivity. A first set of studies was performed utilizing cobalt metal on SiO2 support material with varying parameters including temperature, H2 pressure, feed concentration, and flow rate parameters. The results of such studies are presented in a series of graphs set forth in FIGS. 1-14. Similar studies were performed utilizing a palladium metal on carbon support catalyst. For both the palladium and the cobalt catalyst studies, a fixed-bed reactor was utilized to allow sample flow rate to be studied. The results of independent variants of flow rate, reaction temperature, and pressure for the Pd/C catalyst studies are presented in FIGS. 15-21. Tables 3 and 4 show the effect of pressure at 70° C. and 100° C. respectively utilizing the Pd/C catalyst. Additional flow reactor studies were conducted utilizing alternative catalysts. Presented herewith are results of flow reactor studies conducted utilizing Pt/SiO2 (FIG. 22), an alternative Co/SiO2 catalyst (FIGS. 23-38), a copper-chromite catalyst (FIGS. 39-42), or Pt/Al2O3 (FIGS. 43-56). The enclosed sets of results for the alternative Co/SiO2 catalyst, Cu-chromite, and Pt/Al2O3 include effects on conversion and product selectivity of varied reaction parameters including gas and liquid flow rates, HMF feed concentration, H2 pressure, and/or temperature. Table 5 shows the effect of pretreatment temperature for the alternative Co/SiO2 catalyst (Engelhard Co-0179). Table 6 shows the effect of pressure for continuous flow reaction utilizing the Pt/Al2O3 catalyst.The impact of various impurities on the hydrogenation of HMF was investigated in both batch-wise and flow reactor studies. Impurities included fructose, ethyl acetate, dimethylacetamide, methyl t-butyl ether, methyl iso-butyl ketone, levulinic acid, formic acid, acetic acid, sodium sulfate, and N-methyl pyrrolidinone. These impurities were found to be non-detrimental to HMF conversion within the accuracy of the experiments. Of particular interest were the results with fructose impurity in batch experiments conducted between 60 and 100° C. and 500 psi for at least 2 h. Both Pt(Ge)/C (Engelhard No.43932) and Co/SiO2 (Sud Chemie G62aRS) catalysts converted HMF to reduced products without reducing fructose to sorbitol or mannitol, even at high HMF conversions. FDM can be formed in high yield. In the absence of HMF, fructose is easily reduced under these reaction conditions, suggesting that HMF either inhibits fructose reduction or is reduced at a faster rate. These results indicate that highly selective reduction of HMF is possible with the HMF precursor fructose present in the feed and that fructose need not be separated from the HMF solution prior to reduction.
	With hydrogen In lithium hydroxide monohydrate at 25℃; for 4h;
	With 5%-palladium/activated carbon; hydrogen In lithium hydroxide monohydrate at 50℃; for 3h;	2 Typical conversion process of fructose for the production of DHMF and DHMTF General procedure: 0.18 g fructose and 0.5 g [BMIm]Cl was charged in an open autoclave and was heated to 130°C for 20 min to afford HMF. About 20 mg samples were withdrawn, weighed, quenched with cold water, and subjected to HPLC analysis. 35 ml cool water and 50 mg metal catalyst were added to the residue reaction mixture. After the solution was mixed uniformly, the hydrogenation reaction was carried out with an initial H2 pressure of 6 MPa (measured at room temperature) at 50°C for set time. After the one-pot transformation, the reaction solution was filtered and the clear filtrate was analyzed by HPLC.
	With 5%-palladium/activated carbon; hydrogen In tetrahydrofuran; lithium hydroxide monohydrate at 80℃; for 20h; Autoclave;
	With hydrogen In 1,4-dioxane at 100℃; for 15h; Sealed tube;
	With hydrogen In lithium hydroxide monohydrate at 30℃; for 12h;
	With hydrogen for 1h;
1: 60 %Chromat. 2: 13 %Chromat.	With hydrogen In lithium hydroxide monohydrate at 90℃; for 8h; Flow reactor;
	With hydrogen In lithium hydroxide monohydrate at 150℃; for 12h; Autoclave;	2.4. Catalytic reactions General procedure: In a typical experimental run, a mixture of furanic aldehydes (10.4 mmol), water (40 mL) and 0.1 g catalyst was stirred in a 100 mL batch autoclave (Anhui Kemi Machinery Technology Co., LTD), then reacted under a specific temperature and H2 pressure. The mixture was periodically sampled and a certain amount of N,N-dimethyl formamide was added as an internal standard substance. Then, the products were extracted by ethyl acetate. The compositions were identified by an Agilent 6890 N GC/5973 MS detector and determined by Trace 1300 gas chromatograph equipped with FID detector and a TG-WAXMS capillary column (30 m × 0.32 mm × 0.25 μm). The reported data were the mean values of three trials with small error bars.
	With NiRe<SUB>0.5</SUB>/TiO<SUB>2</SUB>; hydrogen In lithium hydroxide monohydrate at 40℃; for 4h; Autoclave; Glovebox;
	Multi-step reaction with 2 steps 1: 6 h / 59.84 °C 2: NiRe<SUB>2</SUB>/TiO<SUB>2</SUB>; anhydrous sodium carbonate; hydrogen / lithium hydroxide monohydrate / 4 h / 40 °C / 37503.8 Torr / pH 10.2 / Autoclave; Glovebox
	Multi-step reaction with 2 steps 1: 6 h / 59.84 °C 2: NiRe<SUB>0.5</SUB>/TiO<SUB>2</SUB>; hydrogen / lithium hydroxide monohydrate / 4 h / 40 °C / 37503.8 Torr / pH 7 / Autoclave; Glovebox
	With hydrogen In tetrahydrofuran at 130℃; for 5h;
	With 5 wt% Ru/C; hydrogen In ethanol at 100℃; for 0.5h; Autoclave;

Reference： [1]Mishra, Dinesh Kumar; Lee, Hye Jin; Truong, Cong Chien; Kim, Jinsung; Suh, Young-Wong; Baek, Jayeon; Kim, Yong Jin [Molecular catalysis, 2020, vol. 484]
[2]Perret, Noémie; Grigoropoulos, Alexios; Zanella, Marco; Manning, Troy D.; Claridge, John B.; Rosseinsky, Matthew J. [ChemSusChem, 2016, vol. 9, # 5, p. 521 - 531]
[3]Current Patent Assignee: TOHOKU UNIVERSITY; UBE INDUSTRIES LIMITED - JP6037209, 2016, B2 Location in patent: Paragraph 0086; 0101
[4]Duan, Ying; Zheng, Min; Li, Dongmi; Deng, Dongsheng; Ma, Lu-Fang; Yang, Yanliang [Green Chemistry, 2017, vol. 19, # 21, p. 5103 - 5113]
[5]Current Patent Assignee: BATTELLE MEMORIAL INSTITUTE - US2007/287845, 2007, A1 Location in patent: Page/Page column 6-8
[6]Current Patent Assignee: BATTELLE MEMORIAL INSTITUTE - US2007/287845, 2007, A1 Location in patent: Page/Page column 6-7
[7]Current Patent Assignee: BATTELLE MEMORIAL INSTITUTE - US2007/287845, 2007, A1 Location in patent: Page/Page column 6-7
[8]Current Patent Assignee: BATTELLE MEMORIAL INSTITUTE - US2007/287845, 2007, A1 Location in patent: Page/Page column 6-8
[9]Current Patent Assignee: BATTELLE MEMORIAL INSTITUTE - US2007/287845, 2007, A1 Location in patent: Page/Page column 6-8
[10]Current Patent Assignee: BATTELLE MEMORIAL INSTITUTE - US2007/287845, 2007, A1 Location in patent: Page/Page column 8
[11]Current Patent Assignee: BATTELLE MEMORIAL INSTITUTE - US2007/287845, 2007, A1 Location in patent: Page/Page column 7-8
[12]Current Patent Assignee: BATTELLE MEMORIAL INSTITUTE - US2007/287845, 2007, A1 Location in patent: Page/Page column 7-8
[13]Current Patent Assignee: BATTELLE MEMORIAL INSTITUTE - US2007/287845, 2007, A1 Location in patent: Page/Page column 6-8
[14]Chen, Jiazhi; Lu, Fang; Zhang, Junjie; Yu, Weiqiang; Wang, Feng; Gao, Jin; Xu, Jie [ChemCatChem, 2013, vol. 5, # 10, p. 2822 - 2826]
[15]Cai, Haile; Li, Changzhi; Wang, Aiqin; Zhang, Tao [Catalysis Today, 2014, vol. 234, p. 59 - 65]
[16]Liu, Fei; Audemar, Maite; De Oliveira Vigier, Karine; Clacens, Jean-Marc; De Campo, Floryan; Jerome, Francois [Green Chemistry, 2014, vol. 16, # 9, p. 4110 - 4114]
[17]Kong, Xiao; Zhu, Yifeng; Zheng, Hongyan; Dong, Fang; Zhu, Yulei; Li, Yong-Wang [RSC Advances, 2014, vol. 4, # 105, p. 60467 - 60472]
[18]Chen, Jinzhu; Liu, Ruliang; Guo, Yuanyuan; Chen, Limin; Gao, Hui [ACS Catalysis, 2015, vol. 5, # 2, p. 722 - 733]
[19]Zhu, Yifeng; Kong, Xiao; Zheng, Hongyan; Ding, Guoqiang; Zhu, Yulei; Li, Yong-Wang [Catalysis science and technology, 2015, vol. 5, # 8, p. 4208 - 4217]
[20]Lima, Sérgio; Chadwick, David; Hellgardt, Klaus [RSC Advances, 2017, vol. 7, # 50, p. 31404 - 31407]
[21]Li, Xiang; Deng, Qiang; Zhang, Likang; Wang, Jun; Wang, Rong; Zeng, Zheling; Deng, Shuguang [Applied Catalysis A: General, 2019, vol. 575, p. 152 - 158]
[22]Wiesfeld, Jan J.; Kim, Minjune; Nakajima, Kiyotaka; Hensen, Emiel J. M. [Green Chemistry, 2020, vol. 22, # 4, p. 1229 - 1238]
[23]Wiesfeld, Jan J.; Kim, Minjune; Nakajima, Kiyotaka; Hensen, Emiel J. M. [Green Chemistry, 2020, vol. 22, # 4, p. 1229 - 1238]
[24]Wiesfeld, Jan J.; Kim, Minjune; Nakajima, Kiyotaka; Hensen, Emiel J. M. [Green Chemistry, 2020, vol. 22, # 4, p. 1229 - 1238]
[25]Cerezo-Navarrete, Christian; Corma, Avelino; García-Zaragoza, Adrián; Martínez-Prieto, Luis M.; Mata, Jose A.; Mollar-Cuni, Andrés; Oña-Burgos, Pascual [Catalysis science and technology, 2022, vol. 12, # 4, p. 1257 - 1270]
[26]Antonetti, Claudia; Cavani, Fabrizio; Fulignati, Sara; Raspolli Galletti, Anna Maria; Tabanelli, Tommaso [ChemSusChem, 2022]

13
[ 10551-58-3 ]
[ 1883-75-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium tetrahydroborate In methanol at 20℃; for 0.5h;
91%	Stage #1: 5-acetoxymethyl-2-furaldehyde With sodium tetrahydroborate In ethanol at 0 - 20℃; for 48h; Stage #2: With hydrogenchloride In ethanol at 0℃;

Reference： [1]Kang, Eun-Sil; Hong, Yeon-Woo; Chae, Da Won; Kim, Bora; Kim, Baekjin; Kim, Yong Jin; Cho, Jin Ku; Kim, Young Gyu [ChemSusChem, 2015, vol. 8, # 7, p. 1179 - 1188]
[2]Current Patent Assignee: Gruenenthal Pharma GmbH & Co. Kommanditgesellschaft - WO2006/122772, 2006, A1 Location in patent: Page/Page column 45-46

14
[ 1883-75-6 ]
tetrahydrofuran-2,5-dimethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogen In isopropyl alcohol at 40℃; for 3h; Green chemistry;	59.3 General procedure: The catalyst prepared by loading Pd on the apatite carrier HAP was prepared at 40 ° C, 1 MPa hydrogen, isopropanol solventAnd the reaction was carried out for 3 h to catalyze the hydrogenation of various furan ring derivatives. Specifically include:A catalyst was prepared by adding 100 mg of furan ring starting material (substrate) and 30 mg of Pd supported on an apatite carrier in a 50 mL autoclave, 10 mL of isopropyl alcohol was added, the hydrogen pressure was set to 1 MPa, heated to 40 After the reaction was carried out for 3 hours, the mixture was cooled, deflated and filtered to separate the catalyst from the reaction solution. The reaction solution was diluted with isopropanol and analyzed by gas chromatography. Gas chromatographic conditions are the same as in Example 1, and the results of the gas chromatographic analysis of the three repeats are shown in Table 2 for the experimental results.
97%	With hydrogen In water; isopropyl alcohol at 110℃; for 3h;	5 EXAMPLE 5 Catalytic Hydrogenation Activity Test EXAMPLE 5 Catalytic Hydrogenation Activity Test [0228] All catalysts including comparative example were tested in high throughput mode in a HiP-HOSS reactor (see "High-Throughput Heterogeneous Catalyst Research," Howard W. Turner, Anthony F. Volpe Jr, and W. H. Weinberg, Surface Science 603 (2009) 1763-1769, which is incorporated herein by reference) according to following procedure. 20 mg catalysts have been placed in 1 ml vials, filled with 0.2 ml of 0.4M solution of BHMF (2,5 dimethanol furan) in solvent 90% i-PA + 10 % H20 (v/v). The test was conducted at a temperature of 110°C for 3 hrs under hydrogen pressure 700 psi. Observed products were 2,5 BHMTHF (2,5 dimethanol tetrahydrofuran) and 1,2,6 HTO (1,2,6- hexane triol). The results are provided in Table 1.
95%	With palladium on activated carbon; hydrogen In ethanol at 80 - 130℃; for 12h; Autoclave;	1.1-1.4; 2.1-2.4; 3.1-3.4; 4.1-4.4; 5.1-5.4; 6.1-6.4; 7.1-7.4; 8.1-8.4; 9.1-9.4; 10.1-10.4 Example 10 Add 10g BHMF and 600ml absolute ethanol to the beaker,Stir evenly at room temperature. The concentration of ethanol solution of BHMF is 1.05mM;(2) Transfer the solution prepared in step (1) to a 1000 ml autoclave.Add 0.25g of 5wt% Pd/C to the reactor,At this time, the mass ratio of the substrate BHMF to the catalyst is 40:1;(3) Close the lid of the autoclave and start stirring at 1000 rpm,After three vacuum/nitrogen cycles, the high-pressure reactor was pressurized under 4MpaH2 and the temperature was increased to 80°C. After 2 hours, the hydrogen pressure was increased to 10Mpa,And the temperature rose to 130 . The autoclave continued to be stirred under this condition for 10 hours;(4) After cooling to room temperature, release the pressure,The GC analysis of the contents in the autoclave was performed, and the results are shown in Table 10.

89%	With hydrogen In ethanol at 20℃;
57.3%	With NiRe<SUB>1</SUB>/TiO<SUB>2</SUB>; hydrogen In water at 90℃; for 4h; Autoclave; Glovebox;
	With hydrogen at 110℃;

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; USTC (in: CAS) - CN106967018, 2017, A Location in patent: Paragraph 0099-0101; 0103; 0104
[2]Current Patent Assignee: ARCHER-DANIELS-MIDLAND CO - WO2017/75425, 2017, A1 Location in patent: Paragraph 0228
[3]Current Patent Assignee: ZHEJIANG TANGNENG TECH - CN111233797, 2020, A Location in patent: Paragraph 0055-0131
[4]Current Patent Assignee: Gruenenthal Pharma GmbH & Co. Kommanditgesellschaft - WO2006/122772, 2006, A1 Location in patent: Page/Page column 46-47
[5]Wiesfeld, Jan J.; Kim, Minjune; Nakajima, Kiyotaka; Hensen, Emiel J. M. [Green Chemistry, 2020, vol. 22, # 4, p. 1229 - 1238]
[6]Current Patent Assignee: ROQUETTE FRERES - US2017/121317, 2017, A1 Location in patent: Paragraph 0053

15
[ 1883-75-6 ]
[ 64-17-5 ]
[ 99181-63-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With dual acidic Glu-TsOH-Ti catalyst at 80℃; for 8h;
92.1%	With 2% Sn-ZSM-5 at 130℃; for 4h; Autoclave;	5 Example 5: Preparation of 2,5-furandimethanol diethyl ether Dissolve 0.1188g of SnCl4·5H2O in 2g of methanol, then add 2g of multi-stage pore ZSM-5, after mixing, it was left to stand for 24 hours, dried in an oven at 110 ° C, and then baked at 550 ° C to obtain a multi-stage hole 2% Sn-ZSM-5.Dissolve 5 g of 2,5-furandimethanol in 50 ml of ethanol and pour it into a 100 ml autoclave. Add 0.5 g of multi-stage 2% Sn-ZSM-5. Under the reaction condition of 130 ° C, wait 4 hours for the temperature to drop to room temperature. The catalyst was removed by filtration, and the ethanol in the reaction mixture was distilled off under reduced pressure at 40 ° C. There was obtained pale yellow 2,5-furandimethanol diethyl ether, analysis by high performance liquid chromatography, the conversion of 2,5-furandimethanol and the yield of 2,5-furandimethanol diethyl ether were 99.76% and 92.32%, respectively, and the yield was 92.10%.
81%	With toluene-4-sulfonic acid at 60℃; for 3h;

75%	at 75℃; for 24h;	4 Example 4. Batch experiment with hydrogenation/etherification of 5- ( hy d roxy methyl )f u rf u ra I; In a 7.5 ml batch reactor, 0.06 mmol 5-(hydroxymethyl)furfural (HMF) in 1 mL ethanol and 5 bars of hydrogen was reacted with 3 mol% of a Pt/C catalyst for 2 days at room temperature. The starting material was completely converted in 100% selectivity to 2,5- di(hydroxymethyl)furan. Subsequently, the mixture was heated to 75 0C for 1 day without hydrogen. The 2,5-di(hydroxymethyl)furan was fully converted and 2,5- bis(ethoxymethyl)furan was obtained in 75% yield. 25% Side products are ring opened levulinate derivatives. The experiment was successfully repeated on a 20 gram scale.
74%	With Amberlyst-15 resin at 60℃; for 5h;
69%	With Amberlyst-15 resin at 60℃; for 5h; Sealed tube;
	With Amberlyst 15 at 70.04℃;	2.2. Etherification reactions General procedure: The etherification of furanyl alcohols was typically carried out using 10-100 mM concentrations of the furanyl alcohol, 0.9-35.5 mol% acid, and either ethanol or butanol as the solvent. Reactions below the boiling point of the solvent were performed using magnetic stirring at 600 RPM in sealed scintillation vials on an IKARCT Basic stir plate equipped with an IKA ETS-D5 temperature controller. Reactions at 0 °C were carried out in an ice bath with a thermocouple to monitor solution temperature. Reactions between 0 °C and 25 °C were carried out on a heated stir plate in a refrigerated cold room that was maintained at 4 °C. Etherification reactions for HMF occurred at temperatures above the boiling point of the solvent and were performed in sealed headspace vials equipped with a silicone rubber septum for online sampling. In the cases where online sampling was required, filtration of solid catalysts was performed in situ during sample removal by passage through a packed-cotton filter (see diagram in Supplemental information). Solutions of reactants and inert internal standard were allowed to reach the desired reaction temperature prior to catalyst addition. If less than 4.0 mg of Amberlyst-15 was required or in all cases for HMF etherification, the catalyst was dispensed as a 5.00 mg/mL suspension in the alcohol in which the reaction was carried out. Otherwise, the catalyst was added directly to the reactor as a solid. Samples were removed after a specified reaction time. When soluble acids were used as the catalyst, the reaction mixture was neutralized with NaHCO3 at the end of the reaction period. Heterogeneous catalysts were removed by filtration through a column packed with cotton, silica gel, and NaHCO3 to neutralize protons liberated by ion exchange. Ethyl acetate was then used to wash filtration columns and dilute the solutions to the necessary concentrations for evaluation by gas chromatography.
70 %Chromat.	With Amberyst-15 at 60℃; for 10h;	Etherification of BHMF to BAMF catalyzed by Amberlyst-15 General procedure: BHMF (32 mg, 0.25 mmol) was etherified in various alcohol solvents(1.5 mL) by using Amberyst-15. The reaction proceeded ina glass vial (10 mL) with a magnetic stirring bar. The final productswere analyzed by GC/MS and 1H NMR and the yields werecalculated based on GC analysis.
Ca.74 %Chromat.	With hydrogen at 140℃; for 8h;
	With HZSM-5 (Si/Al=25) zeolites at 80℃; for 2h;

Reference： [1]Gupta, Dinesh; Saha, Basudeb [Catalysis Communications, 2018, vol. 110, p. 46 - 50]
[2]Current Patent Assignee: Ningbo Institute of Material Technology and Engineering (in: CAS); CHINESE ACADEMY OF SCIENCES - CN110343078, 2019, A Location in patent: Paragraph 0047-0049
[3]Kucherov; Galkin; Gordeev; Ananikov [Green Chemistry, 2017, vol. 19, # 20, p. 4858 - 4864]
[4]Current Patent Assignee: AVANTIUM N.V. - WO2009/30509, 2009, A2 Location in patent: Page/Page column 11
[5]Balakrishnan, Madhesan; Sacia, Eric R.; Bell, Alexis T. [Green Chemistry, 2012, vol. 14, # 6, p. 1626 - 1634]
[6]Balakrishnan, Madhesan; Sacia, Eric R.; Bell, Alexis T. [Green Chemistry, 2012, vol. 14, # 6, p. 1626 - 1634]
[7]Sacia, Eric R.; Balakrishnan, Madhesan; Bell, Alexis T. [Journal of Catalysis, 2014, vol. 313, p. 70 - 79]
[8]Han, Jusung; Kim, Yo-Han; Jung, Byeong Yeon; Hwang, Seung Hyun; Jegal, Jonggon; Kim, Jung Won; Lee, Yoon-Sik [Synlett, 2017, vol. 28, # 17, p. 2299 - 2302]
[9]Hu, Hualei; Xue, Tingting; Zhang, Zhenxin; Gan, Jiang; Chen, Liangqi; Zhang, Jian; Qu, Fengzuo; Cai, Weijie; Wang, Lei [ChemCatChem, 2021, vol. 13, # 15, p. 3461 - 3469]
[10]Antonetti, Claudia; Cavani, Fabrizio; Fulignati, Sara; Raspolli Galletti, Anna Maria; Tabanelli, Tommaso [ChemSusChem, 2022]

16
[ 1883-75-6 ]
[ 74-88-4 ]
[ 18801-76-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: 2,5-bis-(hydroxymethyl)furan With sodium hydride In tetrahydrofuran at 20℃; for 0.333333h; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 14h;	1.d d) 2,5-Bis-methoxymethyl-furan To a suspension of sodium hydride (dry, 314 mg, 13.1 mmol) in 2 ML of anh THF under Ar was carefully added a solution of 2,5-bis-hydroxymethylfuran (Pat Applic WO 2006122772 A1) in 10 mL of anh THF. After stirring at RT for 20 min, methyl iodide (672 μL, 10.8 mmol) was added and the mixture stirred for an additional 14 h. Water (15 mL) was added very carefully and the mixture concentrated in vacuo to remove the THF. The remaining aqueous mixture was saturated with solid NaCl and extracted with Et2O (5*15 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to a yellow oil which was purified by silica gel chromatography (5-30% EtOAc/hexane) to give the title compound (688 mg, 94%) as a colorless oil. 1H-NMR (CDCl3; 400 MHz): δ 6.28 (s, 2H) 4.39 (s, 4H) 3.37 (s, 6H).

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2009/105296, 2009, A1 Location in patent: Page/Page column 28

17
[ 67-47-0 ]
[ 1883-75-6 ]
[ 65313-46-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; palladium 10% on activated carbon; hydrogen In water; toluene at 60℃; for 4.05h;
1: 8.1 %Chromat. 2: 61.8 %Chromat.	With [(η⁵-C₅Me₅)Ir(phen)(H₂O)]²⁺; hydrogen In water at 110℃; for 1h;
	With hydrogen In water at 110℃; for 6h; Green chemistry;	2.3. Catalytic experiments and product analysis General procedure: The performance of the catalysts was studied in high pressure100 ml batch stirred reactors (Parr Instrument Co.) A glass linerwas loaded with 45 ml of an aqueous solution of HMF (0.04 M)and 0.06 g of catalyst and placed into the stainless-steel reactor.After sealing the vessel, the reactor was flushed three times withN2 and heated to the required reaction temperature (80-155 °C).Once the targeted temperature was reached, the vessel was pressurisedwith H2 to the respective value (5-60 bar of H2) and stirringwas set to 600 rpm. After the end of the reaction (typically6 h), the identity and distribution of the products were determinedby the combination of 1H and 13C NMR spectroscopy (BrukerAVANCE III HD spectrometer), GC-MS (Agilent 6890 N GC with a5973 MSD detector) and GC (Agilent 7890A GC with an FID). GCand GC-MS were equipped with a DB-WAXetr capillary column(60 m, 0.25 mm i.d., 0.25 lm). Standard reference compoundsused: HMF (Sigma), FDM (Manchester Organics), THFDM (Ambinter)and HXD (Sigma-Aldrich). Details regarding calculations ofconversion, yield and selectivity are provided in the SupportingInformation (SI).

Reference： [1]Location in patent: experimental part Luijkx, Gerard C.A.; Huck, Nina P.M.; Van Rantwijk, Fred; Maat, Leendert; Van Bekkum, Herman [Heterocycles, 2009, vol. 77, # 2, p. 1037 - 1044]
[2]Xu, Zhanwei; Yan, Peifang; Xu, Wenjuan; Liu, Xiumei; Xia, Zhi; Chung, Benjamin; Jia, Songyan; Zhang, Z. Conrad [ACS Catalysis, 2015, vol. 5, # 2, p. 788 - 792]
[3]Ramos, Rubén; Grigoropoulos, Alexios; Griffiths, Ben L.; Katsoulidis, Alexandros P.; Zanella, Marco; Manning, Troy D.; Blanc, Frédéric; Claridge, John B.; Rosseinsky, Matthew J. [Journal of Catalysis, 2019, vol. 375, p. 224 - 233]

18
[ 1883-75-6 ]
[ 625-86-5 ]

Yield	Reaction Conditions	Operation in experiment
97.6%	With tetradecane; hydrogen In ethanol at 200℃; for 15h;	9 Take a special mechanical stirring high pressure reaction kettle, add 500 mg of HMF, 20 ml of ethanol, and 50 mg without returningThe original pretreated Co/rGO catalyst and 200 mg of tetradecane (internal standard, do not participate in the reaction), the reactor was tightened and inspectedSet the air tightness, ensure that the device does not leak, then pass the proposed hydrogen pressure, 500rpm stirring rate, set the specified temperature and reverseTime should be.
	With formic acid; sulfuric acid; palladium on carbon In tetrahydrofuran for 15h; Reflux;
	With formic acid In tetrahydrofuran for 15h; Reflux;	3 This example demonstrates that reduction of BHMF to DMF can be achieved with formic acid and a catalytic amount of base. A solution of BHMF (0.26 g, 2 mmol), formic acid (0.76 mL, 20 mmol), H2SO4 (13.8 μL, 0.26 mmol), THF (10 mL), and Pd/C (0.4 g) were heated at reflux for 15 h. 1H NMR spectroscopy of the solution confirmed a complete conversion of BHMF. Pd/C was removed by filtration (catalyst recovered: 0.38 g).

	Multi-step reaction with 3 steps 1: sulfuric acid / tetrahydrofuran / Reflux 2: sulfuric acid / tetrahydrofuran / 2 h 3: palladium on activated charcoal / tetrahydrofuran / 15 h / Reflux
	With 5% active carbon-supported ruthenium; hydrogen at 189.84℃; for 5h; Inert atmosphere; Sealed tube;
	Multi-step reaction with 3 steps 1: hydrogen; 5% active carbon-supported ruthenium / 15301.5 Torr / Inert atmosphere; Sealed tube 2: hydrogen; 5% active carbon-supported ruthenium / 129.84 °C / 15301.5 Torr / Inert atmosphere; Sealed tube 3: hydrogen; 5% active carbon-supported ruthenium / 15301.5 Torr / Inert atmosphere; Sealed tube
	Multi-step reaction with 3 steps 1: hydrogen; 5% active carbon-supported ruthenium / 159.84 °C / 15301.5 Torr / Inert atmosphere; Sealed tube 2: hydrogen; 5% active carbon-supported ruthenium / 15301.5 Torr / Inert atmosphere; Sealed tube 3: hydrogen; 5% active carbon-supported ruthenium / 15301.5 Torr / Inert atmosphere; Sealed tube
	Multi-step reaction with 2 steps 1: 10% Pd/C; hydrogen / 1 h / 180 °C / 18751.9 Torr 2: 10% Pd/C; hydrogen / 1 h / 180 °C / 18751.9 Torr
	Multi-step reaction with 2 steps 1: hydrogen / ethanol / 3 h / 220 °C / 37503.8 Torr 2: hydrogen / ethanol / 3 h / 220 °C / 37503.8 Torr
	With hydrogen In butan-1-ol at 199.84℃; for 3h; Autoclave;
	Multi-step reaction with 2 steps 1: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave 2: hydrogen / butan-1-ol / 3 h / 199.84 °C / 22502.3 Torr / Autoclave
95.6 %Chromat.	With hydrogen In ethanol at 230℃; for 6h;
	Multi-step reaction with 2 steps 1: hydrogen / ethanol / 4 h / 230 °C / 37503.8 Torr 2: hydrogen / ethanol / 6 h / 230 °C / 37503.8 Torr
81.4 %Chromat.	With hydrogen In butan-1-ol at 240℃; for 12h; Autoclave;
	Multi-step reaction with 2 steps 1: hydrogen / tetrahydrofuran / 12 h / 240 °C / 30003 Torr / Autoclave 2: hydrogen / butan-1-ol / 2 h / 240 °C / 30003 Torr / Autoclave

Reference： [1]Current Patent Assignee: DALIAN UNIVERSITY - CN109384750, 2019, A Location in patent: Paragraph 0029; 0030; 0031; 0032-0039
[2]Thananatthanachon, Todsapon; Rauchfuss, Thomas B. [Angewandte Chemie - International Edition, 2010, vol. 49, # 37, p. 6616 - 6618]
[3]Current Patent Assignee: UNIVERSITY OF ILLINOIS (SYSTEM) - US2011/263880, 2011, A1 Location in patent: Page/Page column 11
[4]Current Patent Assignee: UNIVERSITY OF ILLINOIS (SYSTEM) - US2011/263880, 2011, A1
[5]Jae, Jungho; Zheng, Weiqing; Lobo, Raul F.; Vlachos, Dionisios G. [ChemSusChem, 2013, vol. 6, # 7, p. 1158 - 1162]
[6]Jae, Jungho; Zheng, Weiqing; Lobo, Raul F.; Vlachos, Dionisios G. [ChemSusChem, 2013, vol. 6, # 7, p. 1158 - 1162]
[7]Jae, Jungho; Zheng, Weiqing; Lobo, Raul F.; Vlachos, Dionisios G. [ChemSusChem, 2013, vol. 6, # 7, p. 1158 - 1162]
[8]Scholz, David; Aellig, Christof; Hermans, Ive [ChemSusChem, 2014, vol. 7, # 1, p. 268 - 275]
[9]Kumalaputri, Angela J.; Bottari, Giovanni; Erne, Petra M.; Heeres, Hero J.; Barta, Katalin [ChemSusChem, 2014, vol. 7, # 8, p. 2266 - 2275]
[10]Yu, Lili; He, Le; Chen, Jin; Zheng, Jianwei; Ye, Linmin; Lin, Haiqiang; Yuan, Youzhu [ChemCatChem, 2015, vol. 7, # 11, p. 1701 - 1707]
[11]Yu, Lili; He, Le; Chen, Jin; Zheng, Jianwei; Ye, Linmin; Lin, Haiqiang; Yuan, Youzhu [ChemCatChem, 2015, vol. 7, # 11, p. 1701 - 1707]
[12]Chen, Meng-Yuan; Chen, Chu-Bai; Zada, Bakht; Fu, Yao [Green Chemistry, 2016, vol. 18, # 13, p. 3858 - 3866]
[13]Chen, Meng-Yuan; Chen, Chu-Bai; Zada, Bakht; Fu, Yao [Green Chemistry, 2016, vol. 18, # 13, p. 3858 - 3866]
[14]Li, Jiang; Liu, Jun-Ling; Liu, He-Yang; Xu, Guang-Yue; Zhang, Jun-Jie; Liu, Jia-Xing; Zhou, Guang-Lin; Li, Qin; Xu, Zhi-Hao; Fu, Yao [ChemSusChem, 2017, vol. 10, # 7, p. 1436 - 1447]
[15]Li, Jiang; Liu, Jun-Ling; Liu, He-Yang; Xu, Guang-Yue; Zhang, Jun-Jie; Liu, Jia-Xing; Zhou, Guang-Lin; Li, Qin; Xu, Zhi-Hao; Fu, Yao [ChemSusChem, 2017, vol. 10, # 7, p. 1436 - 1447]

19
[ 98-00-0 ]
[ 50-00-0 ]
[ 1883-75-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With P-SiO₂ In water at 25℃; for 24h;	1.2; 2.3; 3.2 (2) Hydroxymethylation reaction between furfuryl alcohol and formaldehyde Use a pipette to pipette 10 mL of furfuryl alcohol and 20 mL of aqueous formaldehyde solution into the round bottom flask one by one, then weigh 6 g of P-SiO2 into the flask, and react at 25°C for 24 hours. After the reaction is completed, the reaction solution is subjected to a simple filtration operation to obtain 2,5-furandimethanol. Chromatographic analysis results showed that the conversion rate of furan was 100%, and the yield of 2,5-furandimethanol reached 100%.
58%	Stage #1: (2-furyl)methyl alcohol With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.5h; Inert atmosphere; Stage #2: formaldehyd In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere;
	Stage #1: (2-furyl)methyl alcohol With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; Stage #2: formaldehyd In tetrahydrofuran; hexane at -78 - 20℃;

With Fe₂O₃-CoO₂-CuO₂/ZrO₂ supported catalyst In water at 35℃; for 60h; Green chemistry;

1.1; 2.1; 3.1 (1), Fe2O3-CoO2-CuO2 / ZrO2 supported catalyst was added to 50mL of 37% formaldehyde aqueous solution, mixed uniformly, then added 5mL furfuryl alcohol, magnetically stirred oil bath at 35 °C After reacting for 60 h, after cooling to room temperature, the conversion of sterol and the selectivity of 2,5-furan dimethanol were 74% and 63%, respectively, by high performance liquid chromatography (HPLC).The aqueous formaldehyde solution and the unreacted decyl alcohol were distilled off under reduced pressure at 80 °C to obtain a brownish yellow crude 2,5-furan dimethanol liquid.The weight ratio of Fe2O3-CoO2-CuO2/ZrO2 supported catalyst to decyl alcohol is 0.2:1.

Reference： [1]Current Patent Assignee: EAST CHINA NORMAL UNIVERSITY - CN113563289, 2021, A Location in patent: Paragraph 0008; 0023; 0028-0030; 0033; 0038-0040
[2]Yen, Andy; Choo, Ken-Loon; Yazdi, Shabnam K.; Franke, Patrick T.; Webster, Robert; Franzoni, Ivan; Loh, Charles C. J.; Poblador-Bahamonde, Amalia I.; Lautens, Mark [Angewandte Chemie - International Edition, 2017, vol. 56, # 22, p. 6307 - 6311][Angew. Chem., 2017, vol. 129, p. 6404 - 6408,5]
[3]Boyer, Alistair; Lautens, Mark [Angewandte Chemie - International Edition, 2011, vol. 50, # 32, p. 7346 - 7349]
[4]Current Patent Assignee: BEIJING SAIZHI TECH; DONGGUAN UNIVERSITY OF TECHNOLOGY - CN109851597, 2019, A Location in patent: Paragraph 0039; 0040; 0042; 0043; 0045; 0046

20
[ 67-56-1 ]
[ 1883-75-6 ]
[ 4282-32-0 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 7346 - 7349

21
[ 1883-75-6 ]
[ 3238-40-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With oxygen; Sodium hydrogenocarbonate In water monomer at 90℃; for 10h;	2.5. Oxidation of HMF The catalyst (0.039 g) was added into a solution of HMF(0.40 mmol) and NaHCO3 (1.6 mmol) in deionized water (20 mL).The suspension was heated to 90 C under stirring and bubbledwith O2 at a flow rate of 70 mL min-1. An aliquot (50 μL) of thereaction mixture was taken out at given intervals and diluted to5 mL with deionized water in a volumetric flask. The liquid samplewas then syringe-filtered through a 0.2 lm PTFE membrane and analyzed by HPLC. The concentrations of HMF, HMFCA, FFCA, andFDCA in the reaction solutions were measured by HPLC using theexternal standard calibration curve method. To evaluate the relativestandard deviation (RSD) of the reaction results, four parallelexperiments were carried out by using Pt/3DOM-Ce1-xBixO2-δ ascatalyst. The RSD values for yield of HMFCA, FFCA, and FDCA weredetermined as 1.7%, 2.4%, and 2.5%, respectively.
99%	With Au/CeO₂; oxygen In water monomer at 90℃; for 4h; Sealed tube;	1.3; 2.3; 3.3 (3) Oxidation of 2,5-furandimethanol to 2,5-furandicarboxylic acid Add 0.5g of 2,5-furandimethanol, 0.25g of Au-CeO2 and 5mL of water to the small reactor, The reaction kettle was sealed, washed with N2 three times, and then filled with 2.5MPa O2. The reaction kettle was heated to 90°C and reacted for 4 hours. After the reaction is completed, after the kettle body is cooled to room temperature, 2,5-furandicarboxylic acid is obtained after simple filtration and purification operations. The white solid was analyzed by high performance liquid chromatography, and the result showed that the yield of 2,5-furandicarboxylic acid content reached 99%.
93%	With single-walled carbon nanotubes; oxygen; nitric acid; sodium hydroxide at 60℃; Reflux;	4-11; 1 Example 4 (1) Add 70 mL of sodium hydroxide solution (with a concentration of 0.2 M) into the flask, raise the temperature of the oil bath to a reaction temperature of 60° C., and then add 0.2 g of 2,5-furandimethanol raw material. (2) Turn on oxygen, turn on stirring and reflux. (3) Add 0.05g of the 3 catalyst prepared in Example 1,Samples are taken regularly, and the evaluation results are qualitatively and quantitatively evaluated by HPLC. The high-performance liquid chromatogram is shown in Figure 5. (4) The molar yield of 2,5-furandicarboxylic acid is 93% in 1 hour.

93%	With oxygen at 60℃; for 1h;	2.4. Catalytic reaction The oxidation reaction was conducted in a three-neckedflask with a reflux condenser under oxygen bubbling. Typically,a certain amount of BHMF and catalyst were successively addedinto the reactor precharged with water (30 mL) containingNaOH additive at the set reaction temperature under vigorousstirring. The liquid sample was syringe-filtered and analyzed byhigh-performance liquid chromatography (Agilent Technologies1260 Infinity II) equipped with a Ultra-violet absorbanceoptical detector (UV detector) and a Extend-C18 USP L1 column(4.6 mm × 250 mm) using a solution of 90.0% of 5.0 mMammonium formate and 10.0% methanol as mobile phase anda two channels-detection (220 and 265 nm). The absorption forFDCA corresponded to λ = 265 nm while for BHMF to λ = 220nm. Retention times and calibration curves for the startingmaterial (BHMF) and observed products, including HMF,HMFCA, FFCA and FDCA, were obtained by injecting knownconcentration of reference commercial products. The amountof BHMF, FDCA and other intermediates in the liquid productwas determined based on an external standard method.The BHMF conversion, product yield and the carbon balancewere calculated using the following equations.BHMF conversion (%) =(Moles of converted BHMF Moles of initial BHMF) 100 (1)Product yield (%) =(Moles of product formed Moles of initial BHMF) 100 (2)Carbon balance (%) = (Moles of product formed + Moles ofunconverted BHMF) Moles of initial BHMF 100 (3)Catalyst reusability was evaluated for ten consecutive cycles.After the reaction, the catalyst was collected by filtration,washed with water, dried at 60 °C overnight in vacuum, andreused for further recycling test. The spent catalyst after tenrecycles was denoted as Pd/o-CNT-10runs.The purification of FDCA was achieved via the method reportedelsewhere [31,32]. Specifically, at the optimum conditions,the catalyst was firstly separated by filtration after thereaction. The filtrate that contains sodium salts of HMFCA andFDCA was concentrated, and the residue was washed threetimes with methanol/dichloromethane (3:7) to separate thesalt of HMFCA from FDCA. The salt of FDCA was acidified with10% HCl to make pH = 2 and then FDCA was extracted withethyl acetate. After evaporation of ethyl acetate using a rotaryevaporator and vacuum drying overnight, the solid FDCA wasobtained. The formation of FDCA was confirmed by NMR spectroscopy(1H and 13C) and mass spectroscopy.
88%	With C₂₄H₃₃IrN₄O₃; water monomer; anhydrous sodium carbonate for 18h; Reflux;
81%	Stage #1: 2,5-bis-(hydroxymethyl)furan With (4,5-bis(di-isopropylphosphinomethyl)acridine)RuH(CO)Cl; water monomer; sodium hydroxide In 1,4-dioxane at 160℃; for 68h; Inert atmosphere; Glovebox; Schlenk technique; Stage #2: With hydrogenchloride In 1,4-dioxane
4.4%	With recombinant 5-hydroxymethylfurfural oxidase In aq. phosphate buffer at 25℃; for 15h; Enzymatic reaction;
	With potassium permanganate; sodium hydroxide In water monomer at 20℃; for 0.166667h;
	Multi-step reaction with 2 steps 1: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 0.5 h / 25 °C / pH 7 / Enzymatic reaction 2: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 15 h / 25 °C / pH 7 / Enzymatic reaction
	Multi-step reaction with 2 steps 1: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 0.5 h / 25 °C / pH 7 / Enzymatic reaction 2: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 15 h / 25 °C / pH 7 / Enzymatic reaction
	Multi-step reaction with 2 steps 1: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 0.5 h / 25 °C / pH 7 / Enzymatic reaction 2: recombinant 5-hydroxymethylfurfural oxidase; FAD / aq. phosphate buffer / 15 h / 25 °C / pH 7 / Enzymatic reaction
	Multi-step reaction with 2 steps 1: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 1 h / 25 °C / pH 7 / Enzymatic reaction 2: recombinant 5-hydroxymethylfurfural oxidase; FAD / aq. phosphate buffer / 15 h / 25 °C / pH 7 / Enzymatic reaction
	Multi-step reaction with 3 steps 1: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 0.5 h / 25 °C / pH 7 / Enzymatic reaction 2: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 1 h / 25 °C / pH 7 / Enzymatic reaction 3: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 15 h / 25 °C / pH 7 / Enzymatic reaction
	Multi-step reaction with 3 steps 1: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 0.5 h / 25 °C / pH 7 / Enzymatic reaction 2: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 4 h / 25 °C / pH 7 / Enzymatic reaction 3: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 15 h / 25 °C / pH 7 / Enzymatic reaction
	Multi-step reaction with 3 steps 1: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 1 h / 25 °C / pH 7 / Enzymatic reaction 2: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 1 h / 25 °C / pH 7 / Enzymatic reaction 3: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 15 h / 25 °C / pH 7 / Enzymatic reaction
	With oxygen; cobalt(II) diacetate; manganese(II) acetate; glacial acetic acid; sodium bromide at 180℃; for 1h;	58 Example 58: Oxidation of2,5-bis(hydroxymethyl)furan into furandicarboxylicAcid 2,5-bis(hydroxymethyl’)furan (2.5 g), acetic acid (30 ml), cobalt acetate (0.083 g), sodium bromide (0.07 1 g), and manganese acetate (0.084 g) are mixed in a batch reactor and placed under an excess of oxygen at 800 psig with vigorous mixing for 1 hour at 180° C. LC analysis of the total reaction mixture shows conversion of 2,5-bis(hy- droxymethyl)thran to thrandicarboxylic acid.
	Multi-step reaction with 2 steps 1: laccase from Trametes versicolor; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / aq. phosphate buffer / 24 h / 25 °C / pH 6 2: laccase from Trametes versicolor; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / aq. phosphate buffer / 24 h / 25 °C / pH 6

Reference： [1]Yu, Kai; Lei, Da; Feng, Yajun; Yu, Haochen; Chang, Yue; Wang, Yanbing; Liu, Yaqi; Wang, Gui-Chang; Lou, Lan-Lan; Liu, Shuangxi; Zhou, Wuzong [Journal of Catalysis, 2018, vol. 365, p. 292 - 302]
[2]Current Patent Assignee: EAST CHINA NORMAL UNIVERSITY - CN113563289, 2021, A Location in patent: Paragraph 0008; 0023; 0031-0033; 0041-0043; 0051-0052
[3]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Ningbo Institute of Material Technology and Engineering (in: CAS) - CN112898252, 2021, A Location in patent: Paragraph 0125-0169
[4]Chen, Chunlin; Hao, Panpan; Huai, Liyuan; Li, Zhenyu; Wang, Yongzhao; Zhang, Bingsen; Zhang, Jian; Zhao, Xi [Cuihua Xuebao/Chinese Journal of Catalysis, 2022, vol. 43, # 3, p. 793 - 801]
[5]Fujita, Ken-ichi; Toyooka, Genki [ChemSusChem, 2020]
[6]Ben-David, Yehoshoa; Kar, Sayan; Milstein, David; Zhou, Quan-Quan [Journal of the American Chemical Society, 2022, vol. 144, # 3, p. 1288 - 1295]
[7]Dijkman, Willem P.; Groothuis, Daphne E.; Fraaije, Marco W. [Angewandte Chemie - International Edition, 2014, vol. 53, # 25, p. 6515 - 6518][Angew. Chem., 2014, vol. 126, # 25, p. 6633 - 6636,4]
[8]Boyer, Alistair; Lautens, Mark [Angewandte Chemie - International Edition, 2011, vol. 50, # 32, p. 7346 - 7349]
[9]Dijkman, Willem P.; Groothuis, Daphne E.; Fraaije, Marco W. [Angewandte Chemie - International Edition, 2014, vol. 53, # 25, p. 6515 - 6518][Angew. Chem., 2014, vol. 126, # 25, p. 6633 - 6636,4]
[10]Dijkman, Willem P.; Groothuis, Daphne E.; Fraaije, Marco W. [Angewandte Chemie - International Edition, 2014, vol. 53, # 25, p. 6515 - 6518][Angew. Chem., 2014, vol. 126, # 25, p. 6633 - 6636,4]
[11]Dijkman, Willem P.; Groothuis, Daphne E.; Fraaije, Marco W. [Angewandte Chemie - International Edition, 2014, vol. 53, # 25, p. 6515 - 6518][Angew. Chem., 2014, vol. 126, # 25, p. 6633 - 6636,4]
[12]Dijkman, Willem P.; Groothuis, Daphne E.; Fraaije, Marco W. [Angewandte Chemie - International Edition, 2014, vol. 53, # 25, p. 6515 - 6518][Angew. Chem., 2014, vol. 126, # 25, p. 6633 - 6636,4]
[13]Dijkman, Willem P.; Groothuis, Daphne E.; Fraaije, Marco W. [Angewandte Chemie - International Edition, 2014, vol. 53, # 25, p. 6515 - 6518][Angew. Chem., 2014, vol. 126, # 25, p. 6633 - 6636,4]
[14]Dijkman, Willem P.; Groothuis, Daphne E.; Fraaije, Marco W. [Angewandte Chemie - International Edition, 2014, vol. 53, # 25, p. 6515 - 6518][Angew. Chem., 2014, vol. 126, # 25, p. 6633 - 6636,4]
[15]Dijkman, Willem P.; Groothuis, Daphne E.; Fraaije, Marco W. [Angewandte Chemie - International Edition, 2014, vol. 53, # 25, p. 6515 - 6518][Angew. Chem., 2014, vol. 126, # 25, p. 6633 - 6636,4]
[16]Current Patent Assignee: BP P.L.C. - US2018/57897, 2018, A1 Location in patent: Paragraph 0062
[17]Yang, Zi-Yue; Wen, Mao; Zong, Min-Hua; Li, Ning [Catalysis Communications, 2020, vol. 139]

22
[ 67-47-0 ]
[ 1883-75-6 ]
[ 6338-41-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide; at 0 - 20℃;	With reference to Scheme 1 below, 1 ml of 1-ethyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide ([EMIm]TFSI, available from Merck) newly serving as an ionic liquid was placed in a round-bottom flask, 0.126 g (1 mmol) of 5-hydroxymethylfurfural (HMF, Compound I) was dissolved, the reaction temperature was adjusted to 0° C., and then sodium hydroxide powder (0.200 g, 5 mmol) was added thereto. Subsequently, the reaction temperature was increased to room temperature so that the reaction took place. After completion of the reaction, 20 ml of dichloromethane was added, after which the filtrate obtained via filtration, namely, the dichloromethane layer was distilled under reduced pressure, thus recovering the ionic liquid. [0057] The lump of filtered particles resulting from recovering the ionic liquid was dissolved in 2 ml of water, and then neutralized with 1 N HCl, so that the pH of the solution was adjusted to about 78. Extraction using ethyl acetate (3×50 ml) and then concentration under reduced pressure were conducted, yielding 2,5-dihydroxymethylfuran (DHMF, Compound II) as a white solid. [0058] The pH of the remaining water layer was adjusted to about 3, followed by performing extraction using ethyl acetate and then concentration under reduced pressure, yielding 5-hydroxymethylfuranoic acid (HMFA, Compound III) as a light yellow solid. The yields of the products are shown in Table 1 below. [0059] The melting point of the light yellow crystals was 239.5° C., and the light yellow crystals were analyzed to be a target compound using 1H-NMR, 13C-NMR. The analytic data was as follows. [0060] HMFA: 1H NMR (300 MHz, acetone-d6): delta 7.16 (d, J=3.4, 1H), 6.47 (d, J=3.4, 1H), 4.59 (s, 2H) ; 13C NMR (75 MHz, acetone-d6): delta 160.9, 159.5, 144.9, 119.6, 109.6, 57.3. [0061] DHMF: 1H NMR (300 MHz, acetone-d6): delta 6.18 (s, 2H), 4.48 (d, J=5.8, 4H), 4.18 (t, J=5.8, 2H) ; 13C NMR (75 MHz, acetone-d6): delta 155.8, 108.22, 57.2.
	With 1-butyl-3-methylimidazolium Tetrafluoroborate; sodium hydroxide; at 0 - 20℃;	DHMF and HMFA were prepared in the same manner as in Example 1, with the exception that 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIm]BF4, available from C-TRI) was used as the ionic liquid instead of 1-ethyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide ([EMIm]TFSI). [0075] The melting point of the light yellow crystals was 239.5° C., and the light yellow crystals were analyzed to be the target compound using 1H-NMR, 13C-NMR. The analytic data was as follows. [0076] HMFA: 1H NMR (300 MHz, acetone-d6): delta 7.16 (d, J=3.4, 1H), 6.47 (d, J=3.4, 1H), 4.59 (s, 2H) ; 13C NMR (75 MHz, acetone-d6): delta 160.9, 159.5, 144.9, 119.6, 109.6, 57.3. [0077] DHMF: 1H NMR (300 MHz, acetone-d6): delta 6.18 (s, 2H), 4.48 (d, J=5.8, 4H), 4.18 (t, J=5.8, 2H) ; 13C NMR (75 MHz, acetone-d6): delta 155.8, 108.22, 57.2.

Reference： [1]Green Chemistry,2018,vol. 20,p. 5261 - 5265
[2]ChemSusChem,2018,vol. 11,p. 1612 - 1616
[3]ChemCatChem,2017,vol. 9,p. 4244 - 4255
[4]Catalysis Today,2011,vol. 160,p. 55 - 60
[5]Green Chemistry,2012,vol. 14,p. 143 - 147
[6]Patent: US2013/345446,2013,A1 .Location in patent: Paragraph 0056 - 0061
[7]Patent: US2013/345446,2013,A1 .Location in patent: Paragraph 0074 - 0077
[8]Green Chemistry,2017,vol. 19,p. 4544 - 4551

23
[ 57-48-7 ]
[ 1883-75-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: formic acid / dimethyl sulfoxide / 8 h / 150 °C 2: formic acid; Cp*Ir(TsDPEN) / tetrahydrofuran / 2 h / 40 °C
	With hydrogen In N,N-dimethyl-formamide at 100℃; for 3h;	6 EXAMPLE 6; PREPARATION OF TETRAHYDROFURAN DIMETHANOL DERIVATIVES FROM FRUCTOSE; This example illustrates the effect of bifunctional resin on the dehydration of fructose to HMF followed by reduction to give furan dimethanol (FDM). Crystalline fructose (50.21 g) was placed in a 1L reaction vessel with DMF (500 mL) and CH10 resin from Rohm and Haas (10.36 g) and pressurized to 500 psi hydrogen. The solution was heated to 100°C for 3 hours. The reaction was allowed to cool to ambient temperature and filtered to remove the resin. GC/MS confirmed the formation of FDM.
	Multi-step reaction with 2 steps 1: Amberlyst-15 / butan-1-ol / 5 h / 100 °C / Dean-Stark 2: Cu⁽⁵⁰⁾-SiO<SUB>2</SUB>; hydrogen / butan-1-ol / 4 h / 100 °C / 11251.1 Torr

Reference： [1]Thananatthanachon, Todsapon; Rauchfuss, Thomas B. [ChemSusChem, 2010, vol. 3, # 10, p. 1139 - 1141]
[2]Current Patent Assignee: ARCHER-DANIELS-MIDLAND CO - WO2012/82665, 2012, A1 Location in patent: Page/Page column 11
[3]Upare, Pravin P.; Hwang, Young Kyu; Hwang, Dong Won [Green Chemistry, 2018, vol. 20, # 4, p. 879 - 885]

24
[ 1883-75-6 ]
[ 629-11-8 ]

Yield	Reaction Conditions	Operation in experiment
22 %Chromat.	With hydrogen In propan-1-ol at 260℃; for 15h; Inert atmosphere;	21 In a stirred autoclave of 100 ml 0.1g of copper chromite was added to a solution of 0.5 g of THFDM in 30 ml of n-propanol. The lid of the autoclave was closed, stirring was started at 1000 rpm and after three vacuum/nitrogen cycles the autoclave was pressurised at 100 bar H2 and the temperature was raised to 260 °C. The autoclave was kept stirred under these conditions for a further 6 h. After cooling to ambient temperature the pressure was released and the contents of the autoclave were subjected to GC analysis, which shows the presence of 17.3 % of 1,6-hexanediol and 3.7% of 1,2,6-hexanetriol. Other catalysts were tested under similar conditions (Table 3). Table 3: Hydrogenation of THFDM Example Catalyst Conversion Yield 1,6-hexanediol Yield 1,2,6-hexanetriol 16 CuCr 70% 17.3% 3.7% 17 CuZn (JM PR-A) 26% 1.8% 5.4% 18 CuZn (JM PR-B) 71% 2.1% 2.0% 19 CuZn (Sud T-2 130 28% 2.2% 1.1% In the Examples 20-22 the effect of temperature and duration on the hydrogenation of THFDM with CuCr was investigated in experiments which were performed otherwise identical to Example 16. Table 4: Hydrogenation of THFDM with CuCr Example Time Temperature 1,6-hexanediol 1,2,6-hexanetriol 20 6h 260°C 17% 4% 21 15h 260°C 22% 1% 22 6h 320°C 15% 0%
15 %Chromat.	With hydrogen In propan-1-ol at 320℃; for 6h; Inert atmosphere;	22 In a stirred autoclave of 100 ml 0.1g of copper chromite was added to a solution of 0.5 g of THFDM in 30 ml of n-propanol. The lid of the autoclave was closed, stirring was started at 1000 rpm and after three vacuum/nitrogen cycles the autoclave was pressurised at 100 bar H2 and the temperature was raised to 260 °C. The autoclave was kept stirred under these conditions for a further 6 h. After cooling to ambient temperature the pressure was released and the contents of the autoclave were subjected to GC analysis, which shows the presence of 17.3 % of 1,6-hexanediol and 3.7% of 1,2,6-hexanetriol. Other catalysts were tested under similar conditions (Table 3). Table 3: Hydrogenation of THFDM Example Catalyst Conversion Yield 1,6-hexanediol Yield 1,2,6-hexanetriol 16 CuCr 70% 17.3% 3.7% 17 CuZn (JM PR-A) 26% 1.8% 5.4% 18 CuZn (JM PR-B) 71% 2.1% 2.0% 19 CuZn (Sud T-2 130 28% 2.2% 1.1% In the Examples 20-22 the effect of temperature and duration on the hydrogenation of THFDM with CuCr was investigated in experiments which were performed otherwise identical to Example 16. Table 4: Hydrogenation of THFDM with CuCr Example Time Temperature 1,6-hexanediol 1,2,6-hexanetriol 20 6h 260°C 17% 4% 21 15h 260°C 22% 1% 22 6h 320°C 15% 0%
	Multi-step reaction with 2 steps 1: hydrogen / Rh-Re/SiO₂ / water / 5 h / 120 °C / 7500.75 - 60006 Torr / Inert atmosphere 2: hydrogen / copper chromite / propan-1-ol / 6 h / 260 °C / 75007.5 Torr / Inert atmosphere

	Multi-step reaction with 3 steps 1: hydrogen / Rh-Re/SiO₂ / water / 5 h / 120 °C / 7500.75 - 60006 Torr / Inert atmosphere 2: trifluorormethanesulfonic acid / sulfolane / 0.5 h / 125 °C 3: hydrogen / Rh-Re/SiO₂ / water / 4.5 h / 180 °C / 7500.75 - 60006 Torr
	With hydrogen In tetrahydrofuran at 180℃; High pressure;	5 Preparation of 1,6-hexanediol: Put 2.0g of the above-prepared composite catalyst into the continuous tubular reaction, fill it with 4.0MPa hydrogen, raise the temperature to 180, and dissolve 100g of 2,5-furandimethanol in 1000ml In the tetrahydrofuran, use a high-pressure syringe pump to continuously inject the reaction liquid into the reactor at a space velocity of 40g/gh. The reaction liquid is collected in the storage tank of the device, and the reaction liquid is subjected to chromatographic analysis (the filtrate uses Shimadzu 2014C gas chromatography equipped with HP-5 capillary column ). The conversion rate of 2,5-furandimethanol was 97%, and the selectivity of 1,6-hexanediol was 96%.

Reference： [1]Current Patent Assignee: NETHERLANDS ORGANISATION FOR SCIENTIFIC RESEARCH - EP2390247, 2011, A1 Location in patent: Page/Page column 8-9
[2]Current Patent Assignee: NETHERLANDS ORGANISATION FOR SCIENTIFIC RESEARCH - EP2390247, 2011, A1 Location in patent: Page/Page column 8-9
[3]Current Patent Assignee: NETHERLANDS ORGANISATION FOR SCIENTIFIC RESEARCH - EP2390247, 2011, A1
[4]Current Patent Assignee: NETHERLANDS ORGANISATION FOR SCIENTIFIC RESEARCH - EP2390247, 2011, A1
[5]Current Patent Assignee: SUZHOU RES INSTITUTE OF LANZHOU INSTITUTE OF CHEMI; CHINESE ACADEMY OF SCIENCES - CN113024350, 2021, A Location in patent: Paragraph 0006; 0021

25
[ 1883-75-6 ]
[ 106-69-4 ]

Yield	Reaction Conditions	Operation in experiment
25.8 %Chromat.	With hydrogen In water at 120℃; for 5h; Inert atmosphere;	32 In an autoclave of 60 ml, 25 mg of the Rh/Re catalyst prepared according to the procedure above was added to a solution of 100 mg of THFDM in 29 ml of water. The autoclave was closed, stirring was started at 1000 rpm and after 3 vacuum nitrogen cycles the hydrogen pressure was set at 10 bar and the temperature at 120 °C. After 1 h the hydrogen pressure was raised to 80 bar. After 4h the autoclave was allowed to cool to ambient temperature and the pressure was released. Analysis of the contents by GC showed a conversion of THFDM of 16.5%, a yield of 1,2,6-hexanetriol of 7.5% and a yield of 1,2,6-hexanetriol of 0.4%. In the examples 23-32 different catalysts, catalyst mixtures and carrier materials were tested in the hydrogenation of THFDM. These reactions were performed in capped glass vials that contained a stir bar the septum of which had been pierced with a needle to equalise the pressure. Up to 6 of these vials were hydrogenated at the same time in the autoclave. Table 5 Hydrogenation of THFDM to mainly 1,2,6 hexanetriol ExampleCatalyst%-conv%-yield 1,6%-yield 1,2,6%-sel 1,6%-sel 1,2,6 23Rh-Re/SiO2a (2-step)d 16.5 0.4 7.5 2.2 45.7 24Rh-Re/SiO2a (1-step)e 15.3 0.0 6.8 0.0 44.2 25Rh/SiO2 3.1 0.0 0.0 0.0 0.0 26Re/SiO2 3.4 0.0 0.0 0.0 0.0 27Rh-Re/CeO2 (2-step)d 9.5 0.0 2.0 0.0 21.0 28Rh-Re/Al2O3 (2-step)d 4.0 0.0 0.0 0.0 0.0 29Rh/Al2O3 + Re 10.5 0.0 4.4 0.0 42.4 30Rh/Al2O3 2.1 0.0 0.0 0.0 0.0 31Rh-Re/SiO2b (2-step)d 14.1 0.0 10.4 0.0 73.9 32Rh-Re/SiO2c (2-step)d 30.9 1.0 25.8 3.4 83.5a Silica grade 9385 (Aldrich) ; b Silica G-6 5 mikron (Fuji Silysia) ; cSilica G-6 3 mikron (Fuji Silysia); d First impregnation with Rh, followed by impregnation with Re in a second step. eSimultaneous impregnation with Rh and Re in a single step These experiments show it is possible to hydrogenate THFDM with high selectivity to 1,2,6-hexanetriol, when a combination of rhodium and rhenium is used.

Reference： [1]Current Patent Assignee: NETHERLANDS ORGANISATION FOR SCIENTIFIC RESEARCH - EP2390247, 2011, A1 Location in patent: Page/Page column 9

26
[ 67-47-0 ]
[ 1883-75-6 ]
[ 6338-41-6 ]
[ 3128-06-1 ]

Reference： [1]Green Chemistry,2012,vol. 14,p. 143 - 147

27
[ 1883-75-6 ]
[ 88910-22-9 ]
[ 2213-51-6 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia In tetrahydrofuran at 140℃; for 21h; Autoclave; Inert atmosphere;	1 Catalyst complex XIVb (for preparation, see below, weighed out under an inert atmosphere), solvent (such an amount that the total solvent volume is 50 ml) and the alcohol to be reacted were placed under an argon atmosphere in a 160 ml Parr autoclave (stainless steel V4A) having a magnetically coupled inclined blade stirrer (stirring speed: 200-500 revolutions/minute). The indicated amount of ammonia was introduced at room temperature either in precondensed form or directly from the pressurized NH3 gas bottle. If hydrogen was used, this was effected by iterative differential pressure metering. The steel autoclave was electrically heated to the temperature indicated and heated for the time indicated while stirring (500 revolutions/minute) (internal temperature measurement). After cooling to room temperature, venting the autoclave and outgassing the ammonia at atmospheric pressure, the reaction mixture was analyzed by GC (30m RTX5 amine 0.32 mm 1.5 μm). Purification of the particular products can, for example, be carried out by distillation. The results for the amination of 1,4-butanediol (table 1a, 1b), diethylene glycol (table 2) and monoethylene glycol (table 3), 2,5-furandimethanol (table 4), alkyldiols (table 5), 1,4-bis(hydroxymethyl)-cyclohexane (table 6) and aminoalcohols (table 7) are given below.
	With ammonia In <i>tert</i>-butyl alcohol at 140℃; for 3h; Autoclave;	EXAMPLE; General method for the catalytic amination of alcohols by means of ammonia according to the inventionLigand L, metal salt M or catalyst complex XIVb (for preparation, see below, weighed out under an inert atmosphere), solvent and the alcohol to be reacted were placed under an Ar atmosphere in a 160 ml Parr autoclave (stainless steel V4A) having a magnetically coupled inclined blade stirrer (stirring speed: 200-500 revolutions/minute). The indicated amount of ammonia was introduced at room temperature either in precondensed form or directly from the pressurized NH3 gas bottle. If hydrogen was used, this was effected by iterative differential pressure metering. The steel autoclave was electrically heated to the temperature indicated and heated for the time indicated while stirring (500 revolutions/minute) (internal temperature measurement). After cooling to room temperature, venting the autoclave and outgassing the ammonia at atmospheric pressure, the reaction mixture was analyzed by GC (30m RTX5 amine 0.32 mm 1.5 μm). The results for the amination of 1,4-butanediol (tables 1a, 1b and 2), diethylene glycol (tables 3a, 3b and 4), monoethylene glycol (table 5) and diethanolamine (table 6), 1,5-pentanediol, 1,9-nonanediol, 1,6-hexanediol and 1,10-decanediol (table 7) and 2,5-(dimethanol)-furan (table 8) are given below.
	With ammonia In 1,3,5-trimethyl-benzene at 140℃; for 24h; Inert atmosphere;	1 Ligand L, metal salt M, solvent and the stated alcohol were introduced as initial charge under an Ar atmosphere in a 160 ml Parr autoclave (hte, (stainless steel V4A)) with magnetically coupled slanted-blade stirrer (stirring speed: 200-500 revolutions/minute). The stated amount of ammonia was either precondensed at room temperature or directly metered in from the NH3 pressurized-gas bottle. If hydrogen was used, this was carried out by means of iterative differential pressure metering. The steel autoclave was heated electrically up to the stated temperature and heated (internal temperature measurement) for the stated time with stirring (500 revolutions/minute). After cooling to room temperature, decompressing the autoclave and outgassing the ammonia at atmospheric pressure, the reaction mixture was analyzed by means of GC (30 m RTX5 amine 0.32 mm 1.5 μm). Purification of the particular product can be carried out, for example, by distillation. The results for the amination of octanol (Table 1a and 1b), 1,4-butanediol (Table 2), diethylene glycol (Table 3), 1,9-nonanediol, 1,6-hexanediol, 1,10-decandiol (Table 4) and 1,2-dimethanolfuran (Table 5) are given below:

	With chlorocarbonylhydrido[4,5-bis(dicyclohexylphosphinomethyl)acridine]ruthenium(II); ammonia In tetrahydrofuran at 150℃; for 6h; Autoclave; Inert atmosphere;	reaction of 2,5-furandimethanol General procedure: Example General Rules on the catalyst amination of alcohol with ammoniaaccording to the present invention (See below for manufacturing, initialweighed under an inert atmosphere) catalyst complex XIVb and, with the solvent(amount of up to solvent total amount reaches the 50ml), and the alcohol thatthe reaction is, under an argon atmosphere, magnetic coupling type tilt wingsParr autoclave of 160ml equipped with a stirrer (made of special steel V4A)(stirring speed: 200 to 500 rev / min) were charged in. At described the amountof ammonia at room temperature, it has been directly metered from thepreliminary condensed with or NH 3 gas cylinder. If hydrogen is used, this wasdone by repeated differential-pressure volume. Steel autoclave is electricheating heated to the temperature indicated, for a period of time described, ithas been heated under stirring (500 rev / min) (internal temperaturemeasurement). The autoclave was cooled to room temperature, depressurized,after performing outgassing of ammonia at atmospheric pressure, the reactionmixture was analyzed by GC (30m RTX5 Amin 0.32mm, 1.5μm). The desired product,for example, can be isolated by distillation
	With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 140℃; for 24h; Inert atmosphere; Autoclave;	Alcohol amination General procedure: Ligand L, see below for the metal salt M or catalyst complex XIVb (manufacturing, inert atmosphere initial mass below), solvent and an alcohol of the reaction, under an argon atmosphere, a magnetic coupling type Parr autoclave of 160ml equipped with atilt wing stirrer (made of special steel V4A) (Stirring speed: were charged to the 200 to 500 rev / min) in. It described theamount of ammonia at room temperature, It is directly metered from the preliminarycondensed with or NH3 gas cylinder. Hydrogenis used Case, this was done by an iterative difference-pressure amount. Power to the temperature indicated the steel autoclave is NetsuNoboru temperature, for a period of time described, has been heated under stirring (500 rev / min) (internal temperature Measurement). The autoclave was cooled to room temperature, depressurized, row outgassing of ammonia at atmospheric pressure after becoming, the reaction mixture was analyzed by GC (30m RTX5 Amin 0.32mm,1.5μm). The amination of 1,4-butanediol result (the first 1a, 1b and the second table), diethylene glycol of the same result (the first 3a, 3b and Table 4), the resultof monoethylene glycol (Table 5), diethanolamine same result (table 6), 1,5-pentanediol, 1,9-nonanediol, 1,6-hexanediol and 1,10-decanediol same result of (table 7), as well as furan-2,5-dimethanol same result (table 8) are as described below.
	With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); ammonia; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 140℃; for 24h; Autoclave; Inert atmosphere;	1 general procedure for the amination of alcohols with ammonia according General procedure: The ligand L, the metal salt M, the solvent and the alcohol were introduced as an initial feed into a 160 ml Parr autoclave (hte) having a magnetically coupled tilt blade stirrer (stirring rate: 200 to 500 rpm) in an Ar atmosphere , (Stainless steel V4A)). The amount of ammonia is pre-concentrated at room temperature or directly from a cylinder pressurized with NH3. If hydrogen is used, this is done by adding a repeated differential pressure differential. The steel autoclave was electrically heated to the temperature and heated for the time (internal temperature measurement) with stirring (500 revolutions per minute). After cooling to room temperature, the autoclave was decompressed and ammonia was withdrawn at atmospheric pressure, and the reaction mixture (30 m RTX5 amine 0.32 mml. 5 [mu] [pi]) was analyzed by GC. Purification of a specific product can be carried out, for example, by distillation. Octyl alcohol (Table 1), 1,9-nonanediol, 1,6-hexanediol, 1,10_ The amination results of diols (Table 4) and 2,5-dimethanolfuran (Table 5) are given below.

Reference： [1]Current Patent Assignee: BASF SE - US2012/232293, 2012, A1 Location in patent: Page/Page column 12; 15-16
[2]Current Patent Assignee: BASF SE - US2012/232294, 2012, A1 Location in patent: Page/Page column 13-14; 20
[3]Current Patent Assignee: BASF SE - US2012/232292, 2012, A1 Location in patent: Page/Page column 10; 13
[4]Current Patent Assignee: BASF SE - JP5808437, 2015, B2 Location in patent: Paragraph 0099; 01112
[5]Current Patent Assignee: BASF SE - JP2016/27052, 2016, A Location in patent: Paragraph 0088; 0104
[6]Current Patent Assignee: BASF SE - CN103502212, 2016, B Location in patent: Paragraph 0207-0208; 0215

28
[ 1883-75-6 ]
[ 2213-51-6 ]

Yield	Reaction Conditions	Operation in experiment
86%	With ammonia In toluene at 110℃; for 20h;
65%	With carbonylchlorohydrido(4,5-bis((diisopropylphosphino)methyl)acridine)ruthenium(II); ammonia In tert-Amyl alcohol at 150℃; for 7h; Autoclave; Inert atmosphere;
	With ammonia In tert-Amyl alcohol at 150℃; for 18h; Autoclave; Inert atmosphere;	7 Catalyst complex XIVb (for preparation, see below, weighed out under an inert atmosphere), solvent (such an amount that the total solvent volume is 50 ml) and the alcohol to be reacted were placed under an argon atmosphere in a 160 ml Parr autoclave (stainless steel V4A) having a magnetically coupled inclined blade stirrer (stirring speed: 200-500 revolutions/minute). The indicated amount of ammonia was introduced at room temperature either in precondensed form or directly from the pressurized NH3 gas bottle. If hydrogen was used, this was effected by iterative differential pressure metering. The steel autoclave was electrically heated to the temperature indicated and heated for the time indicated while stirring (500 revolutions/minute) (internal temperature measurement). After cooling to room temperature, venting the autoclave and outgassing the ammonia at atmospheric pressure, the reaction mixture was analyzed by GC (30m RTX5 amine 0.32 mm 1.5 μm). Purification of the particular products can, for example, be carried out by distillation. The results for the amination of 1,4-butanediol (table 1a, 1b), diethylene glycol (table 2) and monoethylene glycol (table 3), 2,5-furandimethanol (table 4), alkyldiols (table 5), 1,4-bis(hydroxymethyl)-cyclohexane (table 6) and aminoalcohols (table 7) are given below.

	With chlorocarbonylhydrido[4,5-bis(dicyclohexylphosphinomethyl)acridine]ruthenium(II); ammonia In tert-Amyl alcohol at 150℃; for 18h; Autoclave; Inert atmosphere;	reaction of 2,5-furandimethanol General procedure: Example General Rules on the catalyst amination of alcohol with ammoniaaccording to the present invention (See below for manufacturing, initialweighed under an inert atmosphere) catalyst complex XIVb and, with the solvent(amount of up to solvent total amount reaches the 50ml), and the alcohol thatthe reaction is, under an argon atmosphere, magnetic coupling type tilt wingsParr autoclave of 160ml equipped with a stirrer (made of special steel V4A)(stirring speed: 200 to 500 rev / min) were charged in. At described the amountof ammonia at room temperature, it has been directly metered from thepreliminary condensed with or NH 3 gas cylinder. If hydrogen is used, this wasdone by repeated differential-pressure volume. Steel autoclave is electricheating heated to the temperature indicated, for a period of time described, ithas been heated under stirring (500 rev / min) (internal temperaturemeasurement). The autoclave was cooled to room temperature, depressurized,after performing outgassing of ammonia at atmospheric pressure, the reactionmixture was analyzed by GC (30m RTX5 Amin 0.32mm, 1.5μm). The desired product,for example, can be isolated by distillation
	Multi-step reaction with 3 steps 1.1: hydrogenchloride / dichloromethane; water / 16 h / 20 °C 2.1: sodium azide / N,N-dimethyl-formamide / 16 h / 65 °C / Inert atmosphere 3.1: triphenylphosphine / methanol / 2 h / 20 °C 3.2: 16 h
	With ammonia In water; acetonitrile at 130℃; for 11h; Autoclave; Inert atmosphere;	3 1 mmol of 2,5-dihydroxymethylfuran and a certain amount of supported catalyst was added to 15 mL autoclave, 2 mL of solvent was added, Replace the inside of the kettle with nitrogen for 10 times, pour ammonia into the set pressure, raise the temperature to the set temperature, and keep to the set time, rapid stirring, start the reaction. After completion of the reaction, the stirring was stopped, the reaction mixture was cooled to room temperature, the ammonia gas was evacuated, and the sample was analyzed. The qualitative analysis of the products was carried out by gas chromatography-mass spectrometry and nuclear magnetic resonance spectroscopy. The purification step of the product was: the catalyst was removed by centrifugation, the solvent was distilled off under reduced pressure, and the solid was washed with saturated brine and filtered to give a white solid.Dried in vacuo to give a white solid. The results are shown in Table 2.
	Multi-step reaction with 2 steps 1: diphenylphosphoroamidate; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 20 h / 0 - 20 °C 2: triethylamine; hydrazine hydrate / methanol / 24 h / 0 °C

Reference： [1]Hara, Michikazu; Kamata, Keigo; Kita, Yusuke; Kuwabara, Midori; Yamadera, Satoshi [Chemical Science, 2020, vol. 11, # 36, p. 9884 - 9890]
[2]Pingen, Dennis; Schwaderer, Judith B.; Walter, Justus; Wen, Jiaqi; Murray, George; Vogt, Dieter; Mecking, Stefan [ChemCatChem, 2018, vol. 10, # 14, p. 3027 - 3033]
[3]Current Patent Assignee: BASF SE - US2012/232293, 2012, A1 Location in patent: Page/Page column 12; 15-16
[4]Current Patent Assignee: BASF SE - JP5808437, 2015, B2 Location in patent: Paragraph 0099; 0112
[5]Dunbabin, Alice; Subrizi, Fabiana; Ward, John M.; Sheppard, Tom D.; Hailes, Helen C. [Green Chemistry, 2017, vol. 19, # 2, p. 397 - 404]
[6]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Dalian Institute of Chemical Physics (in: CAS) - CN104277017, 2016, B Location in patent: Paragraph 0026-0029
[7]Current Patent Assignee: SOLVAY - WO2018/113599, 2018, A1

29
[ 1883-75-6 ]
[ 64-17-5 ]
[ 113983-97-4 ]
[ 99181-63-2 ]

Yield	Reaction Conditions	Operation in experiment
90.46%	With hydrogen at 140℃; for 8h; Autoclave;
1: 80% 2: 6%	With Amberlyst-15 resin at 40℃; for 16h;
1: 80.3% 2: 15.4%	With silica-supported nickel phosphide at 150℃; for 3h; Inert atmosphere; Autoclave;	General procedure: For catalytic experiments, a stainless-steel batch reactor of 100mL (Parr Instrument) was charged with a catalyst (100mg), furanyl substrate, and solvent (19mL) in which the substrate concentration was set at 0.21M. The reactor was then purged with inert N2 at 25°C for 1h and heated to a desired temperature (usually, 150°C). The reaction started with stirring at 600rpm and was performed for 3h. After the reaction was complete, the heating and stirring were stopped and cooled to 25°C. From the collected etherification product mixture, a sample (1.5mL) was taken and then mixed with 0.08g of toluene (99.5 %) that is an external standard for GC analysis using an Agilent 7890A GC with a flame ionization detector (FID) and a INNOWAX capillary column (30m × 0.25mm × 0.25μm). While the injector and detector were set at 250 and 300°C, respectively, the oven temperature was programmed as follows: 40°C for 2min, ramping to 160°C at 20°Cmin-1, holding at 160°C for 2min, followed by ramping to 250°C at 10°Cmin-1, and finally holding at 250°C for 5min. The product was confirmed by GC-MS analysis (Agilent INNOWAX column). For quantitative measurement, the experiments were repeated at least three times and the average product compositions were reported in this context. Finally, the conversion of furanyl alcohol and the selectivity and yield of each product were calculated as follows:

1: 30% 2: 43%	With Amberlyst-15 resin at 40℃; for 5h;
	With HZSM-5 (Si/Al=25) zeolites at 60℃; for 4h;

Reference： [1]Hu, Hualei; Hu, Danxin; Jin, Haitao; Zhang, Pilan; Li, Guozheng; Zhou, Hao; Yang, Yong; Chen, Chunlin; Zhang, Jian; Wang, Lei [ChemCatChem, 2019, vol. 11, # 8, p. 2179 - 2186]
[2]Balakrishnan, Madhesan; Sacia, Eric R.; Bell, Alexis T. [Green Chemistry, 2012, vol. 14, # 6, p. 1626 - 1634]
[3]Kim, Jinsung; Shin, Mi; Suh, Young-Woong [Applied Catalysis A: General, 2020, vol. 603]
[4]Balakrishnan, Madhesan; Sacia, Eric R.; Bell, Alexis T. [Green Chemistry, 2012, vol. 14, # 6, p. 1626 - 1634]
[5]Antonetti, Claudia; Cavani, Fabrizio; Fulignati, Sara; Raspolli Galletti, Anna Maria; Tabanelli, Tommaso [ChemSusChem, 2022]

30
[ 1883-75-6 ]
[ 3857-25-8 ]

Yield	Reaction Conditions	Operation in experiment
	With 5% active carbon-supported ruthenium; hydrogen Inert atmosphere; Sealed tube;
	With 10% Pd/C; hydrogen at 180℃; for 1h;
	With hydrogen In water at 35℃; for 6h;

With formic acid In 1,4-dioxane at 160℃; for 5h; Inert atmosphere;

Reference： [1]Jae, Jungho; Zheng, Weiqing; Lobo, Raul F.; Vlachos, Dionisios G. [ChemSusChem, 2013, vol. 6, # 7, p. 1158 - 1162]
[2]Scholz, David; Aellig, Christof; Hermans, Ive [ChemSusChem, 2014, vol. 7, # 1, p. 268 - 275]
[3]Chatterjee, Maya; Ishizaka, Takayuki; Kawanami, Hajime [Green Chemistry, 2014, vol. 16, # 11, p. 4734 - 4739]
[4]Xu, Ling; Nie, Renfeng; Chen, Xujie; Li, Yanchen; Jiang, Yuxi; Lu, Xiuyang [Catalysis science and technology, 2021, vol. 11, # 4, p. 1451 - 1457]

31
[ 67-47-0 ]
[ 620-02-0 ]
[ 1883-75-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 93.01% 2: 6.62%	With hydrogen; 20Cu/Al₂O₃ In methanol at 130℃; for 1h;	3.2.3. Effects of reaction media 3.2.3. Effects of reaction mediaThe reaction medium could significantly influence the selective hydrogenationof 5-HMF to BHMF [18]. In this study, the hydrogenation of5-HMF was carried out in different solvents over the 20CA catalyst underthe so far optimized reaction conditions, and these results are summarizedin Table 2. Initially, the hydrogenation of 5-HMF was conducted inpolar protic solvents like water, methanol, and ethanol. A completeconversion of 5-HMF was achieved in pure water solvent, but the BHMFyield was very low (<35 %). Excellent yields of BHMF (93 % and 90 %)were achieved when the hydrogenation of 5-HMF was carried out inmethanol or ethanol reaction medium, as similarly observed in theliterature [18].In contrast to the previous literature reports [16,18], the polaraprotic solvents such as methyl isobutyl ketone (MIBK), THF, andacetonitrile solvents were also efficient for hydrogenation of 5-HMF,producing 90 %, 74 %, and 89 % of BHMF yields, respectively. SinceMIBK and THF were used as biphasic reaction media to synthesize5-HMF from sugars [73], it would be advantageous to directly convertbiomass-derived sugars into BHMF without isolation of 5-HMF intermediate.On the other hand, low yields of BHMF were reported withnonpolar organic solvents (toluene and hexane) [18]. Therefore, thepolar protic (methanol and ethanol) and polar aprotic (MIBK andacetonitrile) solvents appear to be best for the selective hydrogenation of5-HMF to BHMF over a 20CA catalyst. Since a little higher BHMF yieldwas obtained with the polar protic methanol solvent, methanol was usedas the reaction medium to study the effects of other reaction conditions.
	With water monomer; hydrogen at 160℃; for 4h; Autoclave;
	With hydrogen In ethanol at 100℃; for 6h; Autoclave;

	With hydrogen In methanol at 35℃; for 2h;
	With hydrogen In water monomer at 35℃; for 0.166667h; Autoclave;	1-7 50mL of which will be described later in a stainless steel autoclave solid catalyst 0.03g and hydroxymethyl furfural: put (HMF Aldrich) 0.15g, after further put the water 2mL, was heated container up to a temperature 35 ° C. After reaching sufficient lapse of about 10 minutes 35 ° C, hydrogen was introduced up to a pressure of a predetermined pressure (0.8 MPa), it was allowed to stir initiated reaction with a stirrer. After the predetermined reaction time has elapsed, the reaction vessel was cooled with ice, was returned to normal pressure to remove the hydrogen. Thereafter, the compound remaining in the autoclave was extracted with acetone or chloroform, the catalyst after filtration, the qualitative analysis in GC-MS, was performed quantitative analysis by GC. The catalyst was carried out by changing as shown in Table 2, it was from each Example 1-1 and Example 1-7. The results are shown in Table 2.
1: 79 %Chromat. 2: 8 %Chromat.	With hydrogen In water monomer at 90℃; Flow reactor;
	With isopropanol at 210℃; for 1h; Inert atmosphere;
	With hydrogen In tetrahydrofuran at 100℃; for 4h; Autoclave;	2.4. Catalytic testing General procedure: and solvent were loaded into a 50 mL Teflon-lined stainless steel highpressurereactor. The reactor was sealed, purged with H2, and chargedto the desired pressure, after which it was placed in a furnace at aspecified temperature. Upon completion of the reaction, the reactor wasimmediately cooled with ice water to room temperature. The catalystswere separated by applying a magnetic field.The reactor containing the separated catalysts was purged with H2and refilled with fresh substrate solution for subsequent catalytic cycles.Subsequently, a filter membrane was used to ensure that the liquidproducts were free of solid particles. Gas chromatography (GC) wasperformed using a Nexis GC-2030 instrument (Shimadzu Corp.) equippedwith a flame ionization detector (FID) and a capillary column (SHRtx-1701 30 m × 0.25 mm × 0.25 μm). The products and reactants were further identified by gas chromatography-mass spectroscopy (GC-MS,Shimadzu GCMS-QP2010), and the retention times were compared withthose of the pure chemicals. All compounds were quantified based on theinternal standard method using octane as the internal standard. TheHMF conversion and BHMF selectivity and yield were defined asfollows:

Reference： [1]Hu, Yulin; Rao, Kasanneni Tirumala Venkateswara; Xu, Chunbao Charles; Yuan, Zhongsun; Zhang, Yongsheng [Applied Catalysis A: General, 2021, vol. 609]
[2]Yang, Yanliang; Du, Zhongtian; Huang, Yizheng; Lu, Fang; Wang, Feng; Gao, Jin; Xu, Jie [Green Chemistry, 2013, vol. 15, # 7, p. 1932 - 1940]
[3]Kumalaputri, Angela J.; Bottari, Giovanni; Erne, Petra M.; Heeres, Hero J.; Barta, Katalin [ChemSusChem, 2014, vol. 7, # 8, p. 2266 - 2275]
[4]Chatterjee, Maya; Ishizaka, Takayuki; Kawanami, Hajime [Green Chemistry, 2014, vol. 16, # 11, p. 4734 - 4739]
[5]Current Patent Assignee: UNITIKA LTD; NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY - JP2015/229657, 2015, A Location in patent: Paragraph 0037; 0038; 0039
[6]Lima, Sérgio; Chadwick, David; Hellgardt, Klaus [RSC Advances, 2017, vol. 7, # 50, p. 31404 - 31407]
[7]An, Yadan; Bai, Guoyi; Bian, Gang; Li, Tianming; Niu, Libo; Xia, Zhanghui [Green Chemistry, 2021, vol. 23, # 19, p. 7763 - 7772]
[8]Huang, Zexing; Lei, Jing; Liu, Xianxiang; Xu, Qiong; Yang, Yongjun; Zeng, Zhijuan; Zhao, Wenguang; Zhu, Xiaoting [Molecular catalysis, 2022, vol. 524]

32
[ 67-47-0 ]
[ 625-86-5 ]
[ 1883-75-6 ]
[ 3857-25-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 58.3% 2: 24.9% 3: 5.7%	With hydrogen; nickel In tetrahydrofuran at 180℃; for 4h; Autoclave; Sealed tube;
1: 55% 2: 9.8% 3: 15.1%	With hydrogen In tetrahydrofuran at 220℃; for 1.5h;	5 Example-5 Catalytic Activity Over Ru-Cu [1:3]/NaY for Hydrogenolysis of HMF to DMF Ru-Cu [1:3]/NaY catalyst was prepared by simple ion exchanged method and tested for the selective hydrogenolysis of HMF to DMF under optimum reaction conditions obtained for 2 wt % Ru-NaY catalyst (temperature (220° C.), solvent (THF), H2 pressure (15 bar)) as a function of reaction time and the results are shown in Table 3. It can be seen that DMF yield increases with the progress of reaction, suggesting that intermediates like BHMF, MFA and MF are converting to DMF with prolonged reaction time. After 2.5 h of reaction time, a maximum of 67.5 mol % DMF was obtained (Entry 5, Table 3), which decreased on further increasing reaction time. Overall, activity of Ru-Cu[1:3]/NaY catalyst for DMF formation was found to be lower when compared to 2 wt % Ru-NaY catalyst.
1: 55% 2: 14% 3: 5%	With isopropanol In decane at 160℃; for 8h; Autoclave; Inert atmosphere;	3; 5 Example 3: Hydrogenolysis of HMF or Furfural: General procedure: Example 3: Hydrogenolysis of HMF or Furfural: All the reactions were carried out using 100 mL Parr autoclave (SS316). In a typical experiment, the reactor was charged with 1 mmol HMF (or 5 mmol furfural), hydrogen donor (25 mL), n-decane (0.2 g, internal standard) and required amount of freshly prepared catalyst. The reactor contents were mixed thoroughly and the reactor was sealed, purged 2-3 times with N2 and pressurized to 20 bar N2 pressure. Subsequently, the reaction vessel was heated under stirring at required temperature for a desired duration. Liquid samples were withdrawn periodically during the reaction and analyzed by GC (Agilent 7890A) equipped with a flame ionization detector (FID) having CP Sil 8CB capillary column (30 m length, 0.25 mm diameter). Product identification was done using authentic standards and GC-MS (Varian, Saturn 2200) analysis.

1: 51.1% 2: 19.9% 3: 7.1%	With hydrogen at 160℃; for 2h; chemoselective reaction;
1: 47% 2: 17.2% 3: 14.3%	With hydrogen In tetrahydrofuran at 220℃; for 1h;	5 Example-5 Catalytic Activity Over Ru-Cu [1:3]/NaY for Hydrogenolysis of HMF to DMF Ru-Cu [1:3]/NaY catalyst was prepared by simple ion exchanged method and tested for the selective hydrogenolysis of HMF to DMF under optimum reaction conditions obtained for 2 wt % Ru-NaY catalyst (temperature (220° C.), solvent (THF), H2 pressure (15 bar)) as a function of reaction time and the results are shown in Table 3. It can be seen that DMF yield increases with the progress of reaction, suggesting that intermediates like BHMF, MFA and MF are converting to DMF with prolonged reaction time. After 2.5 h of reaction time, a maximum of 67.5 mol % DMF was obtained (Entry 5, Table 3), which decreased on further increasing reaction time. Overall, activity of Ru-Cu[1:3]/NaY catalyst for DMF formation was found to be lower when compared to 2 wt % Ru-NaY catalyst.
33 %Chromat.	With hydrogen In butan-1-ol at 220℃; for 6h;
1: 64 %Chromat. 2: 27 %Chromat. 3: 6 %Chromat.	With 5% ruthenium on carbon; hydrogen at 240℃; for 100h; Gas phase; Green chemistry;
	With hydrogen In butan-1-ol at 109.84℃; for 18h; Autoclave;
	With hydrogen In butan-1-ol at 199.84℃; for 3h; Autoclave;
	With 2CuO*ZnO; hydrogen at 180℃; for 1h;
1: 15.3 %Chromat. 2: 36.5 %Chromat. 3: 38.5 %Chromat.	With hydrogen In ethanol at 230℃; for 6h;
1: 64.1 %Chromat. 2: 7 %Chromat. 3: 5.8 %Chromat.	With hydrogen In tetrahydrofuran at 180℃; for 16h;
	With hydrogen In butan-1-ol at 120℃; for 1h;
	With copper atom In aq. buffer Electrolysis;
1: 94 %Chromat. 2: 12 %Chromat. 3: 42 %Chromat.	With hydrogen In 1,4-dioxane at 220℃; for 5h; Autoclave;
	With isopropanol at 210℃; for 1h; Inert atmosphere;

Reference： [1]Hou, Yaxin; Hu, Jinbo; Liu, Kai; Liu, Yingxin; Shi, Xiaoyang; Wei, Zuojun; Zeng, Mao [ChemSusChem, 2022]
[2]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - US2016/339414, 2016, A1 Location in patent: Paragraph 0075
[3]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - WO2017/42838, 2017, A1 Location in patent: Page/Page column 17; 21-28
[4]Meng, Ge; Ji, Kaiyue; Zhang, Wei; Kang, Yiran; Wang, Yu; Zhang, Ping; Wang, Yang-Gang; Li, Jun; Cui, Tingting; Sun, Xiaohui; Tan, Tianwei; Wang, Dingsheng; Li, Yadong [Chemical Science, 2021, vol. 12, # 11, p. 4139 - 4146]
[5]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - US2016/339414, 2016, A1 Location in patent: Paragraph 0075
[6]Lucas, Nishita; Kanna, Narasimha Rao; Nagpure, Atul S.; Kokate, Ganesh; Chilukuri, Satyanarayana [Journal of Chemical Sciences, 2014, vol. 126, # 2, p. 403 - 413]
[7]Upare, Pravin P.; Hwang, Dong Won; Hwang, Young Kyu; Lee, U-Hwang; Hong, Do-Young; Chang, Jong-San [Green Chemistry, 2015, vol. 17, # 6, p. 3310 - 3313]
[8]Yu, Lili; He, Le; Chen, Jin; Zheng, Jianwei; Ye, Linmin; Lin, Haiqiang; Yuan, Youzhu [ChemCatChem, 2015, vol. 7, # 11, p. 1701 - 1707]
[9]Yu, Lili; He, Le; Chen, Jin; Zheng, Jianwei; Ye, Linmin; Lin, Haiqiang; Yuan, Youzhu [ChemCatChem, 2015, vol. 7, # 11, p. 1701 - 1707]
[10]Zhu, Yifeng; Kong, Xiao; Zheng, Hongyan; Ding, Guoqiang; Zhu, Yulei; Li, Yong-Wang [Catalysis science and technology, 2015, vol. 5, # 8, p. 4208 - 4217]
[11]Chen, Meng-Yuan; Chen, Chu-Bai; Zada, Bakht; Fu, Yao [Green Chemistry, 2016, vol. 18, # 13, p. 3858 - 3866]
[12]Guo, Weiwei; Liu, Hangyu; Zhang, Suqi; Han, Hongling; Liu, Huizhen; Jiang, Tao; Han, Buxing; Wu, Tianbin [Green Chemistry, 2016, vol. 18, # 23, p. 6222 - 6228]
[13]Yang, Yue; Liu, Qiying; Li, Dan; Tan, Jin; Zhang, Qi; Wang, Chenguang; Ma, Longlong [RSC Advances, 2017, vol. 7, # 27, p. 16311 - 16318]
[14]Zhang, Yan-Ru; Wang, Bing-Xin; Qin, Lei; Li, Qiang; Fan, Yong-Ming [Green Chemistry, 2019, vol. 21, # 5, p. 1108 - 1113]
[15]Brzezińska, Magdalena; Keller, Nicolas; Ruppert, Agnieszka M. [Catalysis science and technology, 2020, vol. 10, # 3, p. 658 - 670]
[16]An, Yadan; Bai, Guoyi; Bian, Gang; Li, Tianming; Niu, Libo; Xia, Zhanghui [Green Chemistry, 2021, vol. 23, # 19, p. 7763 - 7772]

33
[ 67-56-1 ]
[ 1883-75-6 ]
[ 18801-76-8 ]

Yield	Reaction Conditions	Operation in experiment
95.13%	With 2% Sn-ZSM-5 at 120℃; for 6h; Autoclave;	1-4 Example 4: Preparation of 2,5-furan dimethanol dimethyl ether Dissolve 0.1188g of SnCl4·5H2O in 2g of methanol, then add 2g of multi-stage pore ZSM-5, after mixing well, let stand for 24 hours and dry in an oven at 110 ° C. It was then fired at 550 ° C to obtain a multi-stage pore 2% Sn-ZSM-5.Dissolve 10 g of 2,5-furandimethanol in 50 ml of methanol and pour it into a 100 ml autoclave. Add 1 g of multi-stage well 2% Sn-ZSM-5. Under the reaction conditions of 120 ° C, after the reaction for 6 hours, wait for the temperature to drop to room temperature. The catalyst was removed by filtration, and the methanol in the reaction mixture was removed by distillation under reduced pressure at 35 ° C. Obtained pale yellow 2,5-furanedimethanol dimethyl ether, analysis by high performance liquid chromatography, the conversion of 2,5-furandimethanol and the yield of 2,5-furandimethanol dimethyl ether were 100% and 95.13%, respectively, and the yield was 95.13%.
89%	With dual acidic Glu-TsOH-Ti catalyst at 70℃; for 8h;
80.5%	With Hβ (Si/Al=25) at 120℃; for 1h; Inert atmosphere; Autoclave;

	With acidic ZSM-5 zeolite (Si/Al = 25) at 100℃; for 12h; Autoclave;	Typical experimental procedures Etherification of BHMF with methanol was performed in a100 mL autoclave vessel lined with teflon. In a typical reaction,4 g BHMF, 40 mL methanol and 1 g acidic ZSM-5 zeolite (Si/Al = 25)were charged into the vessel, which was heated in an oil bath presetat 100 C with magnetic stirring for 12 h and then cooled down toroom temperature. After removal of the catalyst and methanol byfiltration and vacuum distillation, respectively, the left-over liquidwas dried in vacuum to further remove the volatile componentsand then heated under highly reduced pressure to evaporate theproduct 2,5-bis-methoxymethylfuran (BMMF), which was weighedand then analyzed by NMR and element analysis. The recoveredBMMF diluted with acetone to 5 g/L was further analyzed by highresolutionmass spectrometry.
57 %Chromat.	With Amberyst-15 at 60℃; for 10h;	Etherification of BHMF to BAMF catalyzed by Amberlyst-15 General procedure: BHMF (32 mg, 0.25 mmol) was etherified in various alcohol solvents(1.5 mL) by using Amberyst-15. The reaction proceeded ina glass vial (10 mL) with a magnetic stirring bar. The final productswere analyzed by GC/MS and 1H NMR and the yields werecalculated based on GC analysis.
	With Fe₂O₃-CoO₂-CuO₂/ZrO₂ supported catalyst at 40℃; for 56h; Green chemistry;	2.2; 4; 5; 6; 7 (2) taking 8.5 g of 2,5-furan dimethanol prepared in the above step (1), dissolving with 124 mL of methanol, and then adding Fe2O3-CoO2-CuO2/ZrO2 supported catalyst wherein Fe203-CoO2-CuO2/ZrO2 The weight ratio of supported catalyst to furfuryl alcohol was 0.1:1, and it was reacted in an oil bath with magnetic stirring at 40 ° C for 56 h. After cooling to room temperature, it was analyzed by GC, 2,5-furan.The dimethanol conversion and the 2,5-furandimethanol dimethyl ether selectivity were 86% and 85%, respectively.

Reference： [1]Current Patent Assignee: Ningbo Institute of Material Technology and Engineering (in: CAS); CHINESE ACADEMY OF SCIENCES - CN110343078, 2019, A Location in patent: Paragraph 0038-0046
[2]Gupta, Dinesh; Saha, Basudeb [Catalysis Communications, 2018, vol. 110, p. 46 - 50]
[3]Li, Xing-Long; Zhang, Kun; Chen, Shi-Yan; Li, Chuang; Li, Feng; Xu, Hua-Jian; Fu, Yao [Green Chemistry, 2018, vol. 20, # 5, p. 1095 - 1105]
[4]Cao, Quan; Liang, Wenyuan; Guan, Jing; Wang, Lei; Qu, Qian; Zhang, Xinzhi; Wang, Xicheng; Mu, Xindong [Applied Catalysis A: General, 2014, vol. 481, p. 49 - 53]
[5]Han, Jusung; Kim, Yo-Han; Jung, Byeong Yeon; Hwang, Seung Hyun; Jegal, Jonggon; Kim, Jung Won; Lee, Yoon-Sik [Synlett, 2017, vol. 28, # 17, p. 2299 - 2302]
[6]Current Patent Assignee: BEIJING SAIZHI TECH; DONGGUAN UNIVERSITY OF TECHNOLOGY - CN109851597, 2019, A Location in patent: Paragraph 0042; 0044; 0054-0061

34
[ 1883-75-6 ]
[ 823-82-5 ]
[ 13529-17-4 ]
[ 6338-41-6 ]
[ 3238-40-2 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 6515 - 6518
Angew. Chem.,2014,vol. 126,p. 6633 - 6636,4

35
[ 1883-75-6 ]
[ 13529-17-4 ]
[ 3238-40-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 93% 2: 6%	With oxygen; sodium hydrogencarbonate In water at 90℃; for 10h;	2.5. Oxidation of HMF The catalyst (0.039 g) was added into a solution of HMF(0.40 mmol) and NaHCO3 (1.6 mmol) in deionized water (20 mL).The suspension was heated to 90 C under stirring and bubbledwith O2 at a flow rate of 70 mL min-1. An aliquot (50 μL) of thereaction mixture was taken out at given intervals and diluted to5 mL with deionized water in a volumetric flask. The liquid samplewas then syringe-filtered through a 0.2 lm PTFE membrane and analyzed by HPLC. The concentrations of HMF, HMFCA, FFCA, andFDCA in the reaction solutions were measured by HPLC using theexternal standard calibration curve method. To evaluate the relativestandard deviation (RSD) of the reaction results, four parallelexperiments were carried out by using Pt/3DOM-Ce1-xBixO2-δ ascatalyst. The RSD values for yield of HMFCA, FFCA, and FDCA weredetermined as 1.7%, 2.4%, and 2.5%, respectively.
	Multi-step reaction with 2 steps 1: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 0.5 h / 25 °C / pH 7 / Enzymatic reaction 2: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 1 h / 25 °C / pH 7 / Enzymatic reaction
	Multi-step reaction with 2 steps 1: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 0.5 h / 25 °C / pH 7 / Enzymatic reaction 2: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 4 h / 25 °C / pH 7 / Enzymatic reaction

	Multi-step reaction with 2 steps 1: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 1 h / 25 °C / pH 7 / Enzymatic reaction 2: recombinant 5-hydroxymethylfurfural oxidase / aq. phosphate buffer / 1 h / 25 °C / pH 7 / Enzymatic reaction
	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from Trametes versicolor In aq. phosphate buffer at 25℃; for 24h;

Reference： [1]Yu, Kai; Lei, Da; Feng, Yajun; Yu, Haochen; Chang, Yue; Wang, Yanbing; Liu, Yaqi; Wang, Gui-Chang; Lou, Lan-Lan; Liu, Shuangxi; Zhou, Wuzong [Journal of Catalysis, 2018, vol. 365, p. 292 - 302]
[2]Dijkman, Willem P.; Groothuis, Daphne E.; Fraaije, Marco W. [Angewandte Chemie - International Edition, 2014, vol. 53, # 25, p. 6515 - 6518][Angew. Chem., 2014, vol. 126, # 25, p. 6633 - 6636,4]
[3]Dijkman, Willem P.; Groothuis, Daphne E.; Fraaije, Marco W. [Angewandte Chemie - International Edition, 2014, vol. 53, # 25, p. 6515 - 6518][Angew. Chem., 2014, vol. 126, # 25, p. 6633 - 6636,4]
[4]Dijkman, Willem P.; Groothuis, Daphne E.; Fraaije, Marco W. [Angewandte Chemie - International Edition, 2014, vol. 53, # 25, p. 6515 - 6518][Angew. Chem., 2014, vol. 126, # 25, p. 6633 - 6636,4]
[5]Yang, Zi-Yue; Wen, Mao; Zong, Min-Hua; Li, Ning [Catalysis Communications, 2020, vol. 139]

36
[ 1883-75-6 ]
[ 106-89-8 ]
[ 1269765-69-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water at 0 - 20℃;	2; 6; 7 To a solution of sodium hydroxide solution (1 :2 w/w) was added with furandimethanol (FDM) (10.2 g, 80 mmol) and 10 mol% of tetrabutylammonium hydrogen sulfate (2.7 g, 8.0 mmol). The reaction mixture was cooled to 0°C, epichlorohydrin (32.5 ml_, 400 mmol) was added dropwise over 30 min. The mixture was stirred at room temperature for 16 h. The reaction was quenched by addition of water (50 ml_). The aqueous layer was extracted with pentane (10 ml_) to remove excess epichlorohydrin. Then the aqueous layer was extracted with EtOAc (4*30 ml_). The combined EtOAc extracts were washed with water (30 ml_) and were allowed to pass through a short pad of silica gel. The solvent was evaporated to obtain a pure yellow oil diepoxy product 2,5-bis((oxiran-2-ylmethoxy)methyl)furan in 18.4 g (76 mmol, 95% yield) and characterized by 1 H and 13C NMR.
85%	With tetrabutylammomium bromide; sodium hydroxide at 50℃; for 2h; Inert atmosphere;	Synthesis of glycidyl ethers The formation of glycidyl ethers began by synthesizing a known compound as shown in Scheme 5. Treatment of bishydroxymethylfuran 5 with epichlorohydrin, 50% NaOH, tetra n- butylammonium bromide (TBABr, catalyst) at 50 °C gave the diglycidyl ether 8 in 85% isolated yield. The physical and spectral characteristics of 8 were in complete agreement with those reported in the literature [Shen et al., Ind. Eng. Chem. Res. 2017, 56(38):10929-10938; Ding et al., ACS Sustainable Chem. Eng. 2017, 5(9):7792-7799; Hu et al., Macromolecules 2014, 47(10) :3332-3342] Typical experimental procedure:Compound 8: 1H NMR (400 MHz, CDCI3) d 6.S1 (s, 2H), 4.58 - 4.43 (m, 4H), 3.78 (dd, J = 11.5, 3.1 Hz, 2H), 3.46 (dd, J = 11.5, 5.9 Hz, 2H), 3.17 (ddt, J = 5.8, 4.1, 2.9 Hz, 2H), 2.81 (dd, J = 5.0, 4.2 Hz, 2H), 2.63 (dd, J = 5.0, 2.7 Hz, 2H); 13C NMR (101 MHz, CDCI3) d 151.8, 110.3, 70.7, 65.1, 50.7, 44.3; FTIR (neat) cm -12930, 2871, 1734, 1636, 1457, 1373, 1243, 1090, 929, 855.
60%	Stage #1: 2,5-bis-(hydroxymethyl)furan; epichlorohydrin With tetra(n-butyl)ammonium hydrogensulfate at 60℃; for 4h; Inert atmosphere; Stage #2: With sodium hydroxide In water at 50℃; for 2h;

79.6 %Chromat.

Stage #1: 2,5-bis-(hydroxymethyl)furan; epichlorohydrin at 80℃; for 0.5h; Dean-Stark; Stage #2: With sodium hydroxide In water for 3.58333h;

2.4 Test No. 4 50 g of DHMF (0.39 mol, 1 molar equivalent) and then 361.2 g of epichlorohydrin (3.9 mol, 10 molar equivalents) are introduced into a 1-liter jacketed reactor equipped with a thermostatic bath containing a heat-exchange fluid, equipped with a mechanical blade stirring system, with a system for controlling the temperature of the reaction medium and with an inverse Dean-Stark apparatus surmounted by a reflux condenser. The system is brought to a pressure of 275 mbar relative. The reaction mixture is then heated to 80° C. (boiling point=80° C. at 275 mbar) over 30 minutes before beginning the controlled addition of 125 g of a 50% aqueous sodium hydroxide solution (1.56 mol, 2 molar equivalents). The addition lasts a total of 3 h 35. The water is continuously eliminated by azeotropic distillation. The reaction medium is filtered under vacuum in order to eliminate therefrom the sodium chloride formed over time. The salts are washed with epichlorohydrin which is then eliminated by evaporation under reduced pressure on a rotary evaporator. The composition of furan diglycidyl ether or containing predominantly furan diglycidyl ether is then obtained in the form of a clear liquid (Brookfield viscosity at 25° C. of 139 mPa·s), having an epoxy equivalent of 137 g/equivalent.

Reference： [1]Current Patent Assignee: AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH - WO2019/190409, 2019, A1 Location in patent: Page/Page column 60-61; 66-68
[2]Current Patent Assignee: NDSU RESEARCH FOUNDATION - WO2021/7171, 2021, A1 Location in patent: Paragraph 00042-00044
[3]Hu, Fengshuo; La Scala, John J.; Sadler, Joshua M.; Palmese, Giuseppe R. [Macromolecules, 2014, vol. 47, # 10, p. 3332 - 3342]
[4]Current Patent Assignee: ROQUETTE FRERES - US2017/121317, 2017, A1 Location in patent: Paragraph 0082-0086; 0089

37
[ 67-47-0 ]
tetrahydrofuran-2,5-dimethanol [ No CAS ]
[ 1883-75-6 ]
[ 65313-46-4 ]
[ 110-13-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 31% 2: 12% 3: 13% 4: 17%	With hydrogen In water at 139.84℃; for 2h; Autoclave;
28%	With palladium on activated carbon; water; hydrogen; acetic acid at 89.84℃; for 1h; Autoclave;	3.3. Catalytic Reactions General procedure: A 20 mL stainless-steel autoclave equipped with a glass lining was used for the hydrogenation ofHMF. A magnetic stirring oil bath with a temperature controller was used to control the temperature.For a typical procedure, the magneton, HMF (1 mmol, 126.1 mg), H2O (2.00 g), AcOH (1 mmol, 60.0 mg)and Pd/C were put in the glass lining. Then, the lining was put into the autoclave and the autoclave waspurged with 2 MPa H2 four times to exclude the air before 4 MPa H2 was charged. Then, the autoclavewas put in the oil bath at 393 K. After the reaction, the autoclave was cooled down to room temperature.The internal standard and ethanol were added into the glass lining. The mixture was centrifugatedand the liquid phase was used for analysis. The reaction was repeated at least twice to calculate theconfidence interval with 95% confidence. The solid was washed with water and ethanol for threetimes respectively and dried in a vacuum for the next run. To recover the activity, the solid was thenwashed by tetrahydrofuran at 393 K for 1 h after being washed by water and ethanol. The procedurefor washing by tetrahydrofuran was performed in a 100 mL stainless-steel autoclave (Gongyi YingYu Instrument Factory, Gongyi, China). Before being heated, the air in the autoclave was replaced by1 atm N2 by shlenk technology.
	With 5%-palladium/activated carbon; hydrogen In tetrahydrofuran; water at 80℃; for 15h; Autoclave;

Reference： [1]Duan, Ying; Zheng, Min; Li, Dongmi; Deng, Dongsheng; Ma, Lu-Fang; Yang, Yanliang [Green Chemistry, 2017, vol. 19, # 21, p. 5103 - 5113]
[2]Duan, Ying; Yang, Dexi; Yang, Yanliang; Zhang, Chi; Zheng, Min [Molecules, 2020, vol. 25, # 11]
[3]Liu, Fei; Audemar, Maite; De Oliveira Vigier, Karine; Clacens, Jean-Marc; De Campo, Floryan; Jerome, Francois [Green Chemistry, 2014, vol. 16, # 9, p. 4110 - 4114]

38
[ 67-47-0 ]
tetrahydrofuran-2,5-dimethanol [ No CAS ]
[ 1883-75-6 ]
[ 65313-46-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 33% 2: 28% 3: 7%	With carbon dioxide; hydrogen In water at 120℃; for 15h;
24%	With palladium on activated carbon; water; hydrogen; acetic acid at 79.84℃; for 1h; Autoclave;	3.3. Catalytic Reactions General procedure: A 20 mL stainless-steel autoclave equipped with a glass lining was used for the hydrogenation ofHMF. A magnetic stirring oil bath with a temperature controller was used to control the temperature.For a typical procedure, the magneton, HMF (1 mmol, 126.1 mg), H2O (2.00 g), AcOH (1 mmol, 60.0 mg)and Pd/C were put in the glass lining. Then, the lining was put into the autoclave and the autoclave waspurged with 2 MPa H2 four times to exclude the air before 4 MPa H2 was charged. Then, the autoclavewas put in the oil bath at 393 K. After the reaction, the autoclave was cooled down to room temperature.The internal standard and ethanol were added into the glass lining. The mixture was centrifugatedand the liquid phase was used for analysis. The reaction was repeated at least twice to calculate theconfidence interval with 95% confidence. The solid was washed with water and ethanol for threetimes respectively and dried in a vacuum for the next run. To recover the activity, the solid was thenwashed by tetrahydrofuran at 393 K for 1 h after being washed by water and ethanol. The procedurefor washing by tetrahydrofuran was performed in a 100 mL stainless-steel autoclave (Gongyi YingYu Instrument Factory, Gongyi, China). Before being heated, the air in the autoclave was replaced by1 atm N2 by shlenk technology.
	With 5%-palladium/activated carbon; hydrogen In tetrahydrofuran; water at 80℃; for 15h; Autoclave;

Reference： [1]Liu, Fei; Audemar, Maïté; De Oliveira Vigier, Karine; Clacens, Jean-Marc; De Campo, Floryan; Jérôme, François [ChemSusChem, 2014, vol. 7, # 8, p. 2089 - 2093]
[2]Duan, Ying; Yang, Dexi; Yang, Yanliang; Zhang, Chi; Zheng, Min [Molecules, 2020, vol. 25, # 11]
[3]Liu, Fei; Audemar, Maite; De Oliveira Vigier, Karine; Clacens, Jean-Marc; De Campo, Floryan; Jerome, Francois [Green Chemistry, 2014, vol. 16, # 9, p. 4110 - 4114]

39
[ 67-47-0 ]
[ 1003-38-9 ]
[ 625-86-5 ]
[ 1883-75-6 ]
[ 3857-25-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 40.1% 2: 10.7% 3: 11.5% 4: 12.8%	With hydrogen In tetrahydrofuran at 220℃; for 1h;	3 Catalytic Activity of 2 wt % Ru-NaY Catalyst for Hydrogenolysis of HMF to DMF with all Details and Yield and Selectivity All the catalysts were tested under at optimum reaction conditions obtained for of 2% Ru-NaY catalyst. Six principal products were observed: DMF, DMTHF, BHMF (2,5-bis(hydroxymethyl)furan), MF (5-methyl furfural), MFA (5-methyl furfuryl alcohol) and MFU (2-methyl furan). Other unknown products were also observed. The HMF conversion after 1 h of reaction ranged from 92 mol % for Rh-NaY to 100 mol % for Pt-NaY and Pd-NaY (Table 2). The DMF yield, the desired final product, was highest for Pd-NaY, 49.3 mol %. DMTHF, the hydrogenated compound of DMF was formed in more amount when platinum (4 mol %) and rhodium (10.7 mol %) was used as catalysts, whereas little amount of DMTHF (1.1 mol %) was observed when palladium based catalyst was used. Indicating that at the same weight loading platinum and rhodium catalysts were more active compared to the palladium catalyst for complete hydrogenation of DMF to DMTHF. Higher yield (10 mol %) of MFU was obtained for platinum based catalyst compare to rhodium and palladium as catalysts; shows that platinum catalyze both hydrogenation and carbon-carbon scission reaction. Furthermore, when platinum was used as catalyst, the majority of the HMF was converted to unidentified products. The GC chromatogram of the reaction mixture did not reveal any significant peaks, which may indicate that the undetected carbon is in the form of insoluble polymers, were formed on the catalyst surface. These insoluble polymers can be formed by the loss of formaldehyde from BHMF, followed by furfuryl alcohol polymerization.
	With hydrogen In ethanol at 180℃; for 6h; Autoclave;
	With hydrogen In butan-1-ol at 199.84℃; for 3h; Autoclave;

Reference： [1]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - US2016/339414, 2016, A1 Location in patent: Paragraph 0075
[2]Kumalaputri, Angela J.; Bottari, Giovanni; Erne, Petra M.; Heeres, Hero J.; Barta, Katalin [ChemSusChem, 2014, vol. 7, # 8, p. 2266 - 2275]
[3]Yu, Lili; He, Le; Chen, Jin; Zheng, Jianwei; Ye, Linmin; Lin, Haiqiang; Yuan, Youzhu [ChemCatChem, 2015, vol. 7, # 11, p. 1701 - 1707]

40
[ 67-47-0 ]
tetrahydrofuran-2,5-dimethanol [ No CAS ]
[ 625-86-5 ]
[ 1883-75-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 48% 2: 14% 3: 7%	With carbon dioxide; hydrogen In tetrahydrofuran; water at 150℃; for 30h;
17%	With hydrogen In 1,4-dioxane at 130℃; for 1h; Glovebox;	2.4. Catalytic hydrogenation reactions The hydrogenation reaction of 5-hydroxymethylfurfural (HMF) wasperformed in a SPR multi-reactor (6 mL total volume) fromUnchainedlabs. Prior to the catalytic tests, the catalysts were reduced at550 °C for 2 h (heating ramp of 10 °C min-1) under 5 Vol.% H2 in Arflow (50 mL min-1). For a typical reaction, the reactor was chargedunder the controlled atmosphere of a glove box with 0.030 g of HMF,1.5 mL of 1,4-dioxane as a solvent and 0.021 g of catalyst, sealed andpurged with H2. Then, the reactor was pressurized with 15 bar H2,heated at 130 °C and stirred at a speed of 700 rpm for 1 h. Blank experiment,performed with calcined SBA-15_100 showed 1.5 mol.%conversion of HMF. This conversion could be most probably associatedto an adsorption of HMF on the support surface. The products werecollected and analyzed by GC (Shimadzu 2010 Plus) equipped with ZBWAXPlus capillary column (30.0m×0.25mm×0.25 μm) and a flameionization detector (FID), and by GC-MS (Shimadzu QP2010 Ultra EI)equipped with a ZB-1XT capillary column(15.0m×0.53mm×0.25 μm) and an MS detector.

Reference： [1]Liu, Fei; Audemar, Maïté; De Oliveira Vigier, Karine; Clacens, Jean-Marc; De Campo, Floryan; Jérôme, François [ChemSusChem, 2014, vol. 7, # 8, p. 2089 - 2093]
[2]Chen; Ciotonea; Ungureanu; Dumitriu; Catrinescu; Wojcieszak; Dumeignil; Royer [Catalysis Today, 2019, vol. 334, p. 48 - 58]

41
[ 1883-75-6 ]
[ 65313-46-4 ]

Yield	Reaction Conditions	Operation in experiment
60%	With 2 wt% Pd/C; carbon dioxide; hydrogen In water at 120℃; for 10h;
60%	With carbon dioxide; palladium on activated charcoal; hydrogen In water at 120℃; for 10h; Autoclave;	5 Example 5 Preparation of HMHD from DHMF using CO2/H2O catalyst in the presence of hydrogen and Catalyst (H) Example 5 Preparation of HMHD from DHMF using CO2/H2O catalyst in the presence of hydrogen and Catalyst (H) (0132) To a mixture of deionized water (5 ml) and DHMF (150 mg, 1.17 mmol) was added Pd/C catalyst (3 mg, 1.4 pmol). The resulting composition was then placed inside an autoclave and was flushed with hydrogen, until reaching a hydrogen pressure of 1 bar. Subsequently, CO2 was introduced up to a pressure of 39 bar (i.e. a total gas pressure of 40 bar). Under this gas pressure, the reaction mixture was stirred and heated to 120°C for 10 hours. The reaction mixture was then let cool to room temperature, after which the reactor was vented and opened to release CO2 and hydrogen. A syringe filter was used to remove the solid Pd/C catalyst from the reaction mixture, and the remaining aqueous composition was analysed by GC using biphenyl as the internal standard. The DHMF conversion exceeded 95%, and the yield of HMHD was 60%.
54%	With hydrogen In water at 139.84℃; for 2h; Autoclave;

38.9 %Chromat.

With [(η5-pentamethylcyclopentadienil anion)Ir(2,2'-bipyridine)(H2O)](2+); hydrogen In water at 120℃; for 0.5h;

Reference： [1]Liu, Fei; Audemar, Maïté; De Oliveira Vigier, Karine; Clacens, Jean-Marc; De Campo, Floryan; Jérôme, François [ChemSusChem, 2014, vol. 7, # 8, p. 2089 - 2093]
[2]Current Patent Assignee: SOLVAY - WO2015/127662, 2015, A1 Location in patent: Paragraph 0077
[3]Duan, Ying; Zheng, Min; Li, Dongmi; Deng, Dongsheng; Ma, Lu-Fang; Yang, Yanliang [Green Chemistry, 2017, vol. 19, # 21, p. 5103 - 5113]
[4]Xu, Zhanwei; Yan, Peifang; Xu, Wenjuan; Liu, Xiumei; Xia, Zhi; Chung, Benjamin; Jia, Songyan; Zhang, Z. Conrad [ACS Catalysis, 2015, vol. 5, # 2, p. 788 - 792]

42
[ 1883-75-6 ]
[ 100-46-9 ]
N,N'-(furan-2,5-diylbis(methylene))bis(1-phenylmethaneamine) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With [Cp*Ir(NH₃)3]I₂ In water at 100℃; for 20h; Inert atmosphere; Sealed tube;	4 Example 4: Production of N,N'-bis(benzyl) furan-2,5- diyldimethanamine Example 4: Production of N,N'-bis(benzyl) furan-2,5- diyldimethanamineTo a nitrogen-purged sealed carousel tube was added [Cp*Ir(NH3)3][I]2 (0.04 mol), benzylamine (2.5 mmol), 2,5-bis(hydroxymethyl)furan (1.0 mmol) and deionized water (2 mL). The mixture was heated at 100°C under reflux for 20 h and then extracted with ethyl acetate (2 mL X 3). The product was analyzed by GC-MS and JH NMR using CH3CN as reference. N,N'-bis(benzyl) furan-2,5- diyldimethanamine was obtained in 76% yield with 98% conversion.

Reference： [1]Current Patent Assignee: SOLVAY - WO2014/198057, 2014, A1 Location in patent: Page/Page column 12

43
[ 67-47-0 ]
[ 1883-75-6 ]
[ 6338-41-6 ]
[ 3238-40-2 ]

Reference： [1]Catalysis science and technology,2015,vol. 5,p. 1314 - 1322

44
[ 1883-75-6 ]
[ 917-61-3 ]
furan-2,5-diylbis(methylene) dicarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With trifluoroacetic acid In dichloromethane at 25 - 41℃; for 0.25h;	III.A.1 Example 1 : Synthesis of furan-2,5-diylbis(methylene) dicarbamate, B: Experimental: A two neck, 50 mL round bottomed flask was charged with 1 g of FDM A (7.55 mmol), 1.97 g of sodium cyanate (30.2 mmol) and 20 mL of anhydrous methylene chloride resulting in a suspension. The necks were then stoppered with rubber septa, one with a thermocouple insert that immersed in the solution. While stirring, 2.32 mL of trifluoroacetic acid was added via syringe dropwise over 5 minutes. The temperature of the solution warmed from 25°C to 41°C over 15 minutes and solids disappeared. After about 30 minutes, a white precipitate formed, which was filtered and analyzed as only byproduct sodium trifluoroacetate by13C NMR (D20, 2000 scans) no residual FDM was descried). The supernatant was concentrated in vacuo, affording B as a pale yellow solid that weighed 1.55 g (93% of theoretical).13C NMR (CDC13, 100 MHz) δ (ppm) 151.61, 147.38, 113.57, 61.11 (notable FDM signals at 154.27, 108.79, 57.76 ppm absent).

Reference： [1]Current Patent Assignee: ARCHER-DANIELS-MIDLAND CO - WO2014/200636, 2014, A1 Location in patent: Page/Page column 13; 14

45
[ 10551-58-3 ]
[ 1883-75-6 ]
[ 6338-41-6 ]

Reference： [1]ChemSusChem,2015,vol. 8,p. 1179 - 1188

46
[ 1623-88-7 ]
[ 1883-75-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium dihydrosulfite; hydrogen; calcium carbonate In lithium hydroxide monohydrate at 60℃; for 4h;	1-19 Example 1 General procedure: Weigh 0.103g of RuCl3·3H2O and dissolve it in 30mL of deionized water, then weigh 1g of CuO into the aqueous solution, and stir for 2h. Then NaBH4 solution (0.3 g NaBH4 dissolved in 20 mL deionized water) was added dropwise and stirred for 1 h. After centrifugation, washing (deionized water, 30 mL×3) and freeze-drying, the catalyst Ru/CuO was obtained. The loading of Ru was 5 wt.% Ru relative to the support CuO. 5-chloromethylfurfural (0.1g), catalyst Ru/CuO (0.1g, 5wt.% Ru relative to carrier CuO), calcium carbonate (0.05g), sodium hydrosulfite (0.01g) and 10mL deionized Water was added to the stainless steel closed reactor, filled with 4MPa H2, and heated to 70°C under a stirring speed of 500rpm to carry out the reaction for 2h. After the reaction, solid-liquid separation was carried out with a centrifuge (8000 r/min, 5 min), and quantitative analysis was carried out with a high performance liquid chromatograph (HPLC, Agilent 1260). Qualitative analysis was performed using gas mass spectrometry (GCMS, Thermo Scientific). As a result, the molar yield of 2,5-furandimethanol was 76%.
	Multi-step reaction with 2 steps 1: acetonitrile / 0.17 h / 20 °C 2: sodium tetrahydridoborate / methanol / 0.5 h / 20 °C
	Multi-step reaction with 2 steps 1: acetonitrile / 0.17 h / 20 °C 2: sodium tetrahydridoborate / methanol / 0.5 h / 20 °C

	Multi-step reaction with 2 steps 1: acetonitrile / 0.42 h / 20 °C 2: sodium tetrahydridoborate / methanol / 0.5 h / 20 °C
	Multi-step reaction with 2 steps 1: acetonitrile / 0.42 h / 20 °C 2: sodium tetrahydridoborate / methanol / 0.5 h / 20 °C
	Multi-step reaction with 2 steps 1.1: Amberlite IRA-900 / lithium hydroxide monohydrate / 1 h 1.2: 12 h / 50 °C 2.1: sodium tetrahydridoborate / methanol / 0.5 h / 20 °C
	Multi-step reaction with 2 steps 1: acetonitrile / 0.25 h / 20 °C 2: sodium tetrahydridoborate / methanol / 0.5 h / 20 °C
	Multi-step reaction with 2 steps 1: acetonitrile / 20 °C 2: sodium tetrahydridoborate / methanol / 0.5 h / 20 °C

Reference： [1]- CN114105914, 2022, A Location in patent: Paragraph 0019-0039
[2]Kang, Eun-Sil; Hong, Yeon-Woo; Chae, Da Won; Kim, Bora; Kim, Baekjin; Kim, Yong Jin; Cho, Jin Ku; Kim, Young Gyu [ChemSusChem, 2015, vol. 8, # 7, p. 1179 - 1188]
[3]Kang, Eun-Sil; Hong, Yeon-Woo; Chae, Da Won; Kim, Bora; Kim, Baekjin; Kim, Yong Jin; Cho, Jin Ku; Kim, Young Gyu [ChemSusChem, 2015, vol. 8, # 7, p. 1179 - 1188]
[4]Kang, Eun-Sil; Hong, Yeon-Woo; Chae, Da Won; Kim, Bora; Kim, Baekjin; Kim, Yong Jin; Cho, Jin Ku; Kim, Young Gyu [ChemSusChem, 2015, vol. 8, # 7, p. 1179 - 1188]
[5]Kang, Eun-Sil; Hong, Yeon-Woo; Chae, Da Won; Kim, Bora; Kim, Baekjin; Kim, Yong Jin; Cho, Jin Ku; Kim, Young Gyu [ChemSusChem, 2015, vol. 8, # 7, p. 1179 - 1188]
[6]Kang, Eun-Sil; Hong, Yeon-Woo; Chae, Da Won; Kim, Bora; Kim, Baekjin; Kim, Yong Jin; Cho, Jin Ku; Kim, Young Gyu [ChemSusChem, 2015, vol. 8, # 7, p. 1179 - 1188]
[7]Kang, Eun-Sil; Hong, Yeon-Woo; Chae, Da Won; Kim, Bora; Kim, Baekjin; Kim, Yong Jin; Cho, Jin Ku; Kim, Young Gyu [ChemSusChem, 2015, vol. 8, # 7, p. 1179 - 1188]
[8]Kang, Eun-Sil; Hong, Yeon-Woo; Chae, Da Won; Kim, Bora; Kim, Baekjin; Kim, Yong Jin; Cho, Jin Ku; Kim, Young Gyu [ChemSusChem, 2015, vol. 8, # 7, p. 1179 - 1188]

47
[ 1623-88-7 ]
[ 1883-75-6 ]
[ 6338-41-6 ]

Reference： [1]ChemSusChem,2015,vol. 8,p. 1179 - 1188
[2]ChemSusChem,2015,vol. 8,p. 1179 - 1188
[3]ChemSusChem,2015,vol. 8,p. 1179 - 1188
[4]ChemSusChem,2015,vol. 8,p. 1179 - 1188
[5]ChemSusChem,2015,vol. 8,p. 1179 - 1188
[6]ChemSusChem,2015,vol. 8,p. 1179 - 1188

48
[ 67-47-0 ]
[ 625-86-5 ]
[ 620-02-0 ]
[ 1883-75-6 ]
C₇H₁₀O [ No CAS ]
[ 121709-55-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	With hydrogen In tetrahydrofuran at 130℃; for 24h; Autoclave; High pressure;	A stainless steel autoclave (50 ml) equipped with a magnetic stirring bar was charged with catalyst (0.100 g), HMF (0.252 g), THF (10 ml) and tridecane (0.245 ml, internal standard). The reactor was pressurized with H2 several times to remove air and charged with the desired H2 and heated to the desired temperature. After reaction, the autoclavewas cooled down to room temperature quickly and the solid catalystwas separated from the reaction mixture by filtration. The products inthe filtrate were analyzed by an Agilent7890 GC equipped with a HP-5column and a FID detector, and the further structural characteristics ofthe products were identified by GC-MS.

Reference： [1]Yang, Panpan; Cui, Qiqi; Zu, Yanhong; Liu, Xiaohui; Lu, Guanzhong; Wang, Yanqin [Catalysis Communications, 2015, vol. 66, p. 55 - 59]

49
[ 1883-75-6 ]
[ 111-25-1 ]
[ 139112-82-6 ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: 2,5-bis-(hydroxymethyl)furan With potassium <i>tert</i>-butylate In dimethyl sulfoxide at -10℃; for 0.5h; Stage #2: 1-bromo-hexane In dimethyl sulfoxide at -10 - 20℃; Inert atmosphere;	10 Experimental: An oven dried, single neck 10 mL round bottomed flask equipped with a PTFE coated magnetic stir bar was charged with 100 mg of FDM A (0.780 mmol) and 5 mL of anhydrous DMSO. The flask was then immersed in an ice-brine bath (- 10°C) and, while stirring, 219 mg of potassium i-butoxide (1.95 mmol) added in portions and the mixture stirred for 30 minutes at this temperature. At this time, the neck was stoppered with a rubber septum and an argon gas inlet affixed via a 14" needle. While vigorously stirring and under an argon blanket, 240 μL· of 1 -bromohexane (1.72 mmol) was added via syringe. The mixture was then warmed to room temperature and continued to react overnight. After this time, an aliquot was removed and spotted on a silica gel TLC plate, which exhibited a single band (cerium molybdate stain) after developing in 9:1 hexanes/ethyl acetate. The signature band for FDM A (baseline) was patently absent, suggesting this reagent had fully converted. Here, the mixture was diluted with 5 mL of water and 5 mL of methylene chloride and partitioned and the aqueous layer extracted with 3-5 mL volumes of methylene chloride. The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under vacuum. The oily residue was dissolved in a minimum amount of methylene chloride and added to 20 g of silica gel, which was then dried under vacuum, furnishing product adsorbed silica gel. This material was added to a pre-fabricated silica gel column, where flash chromatography with hexanes to 13% ethyl acetate in hexanes afforded 124 mg of a B as light yellow oil after concentration in vacuo (53% of theoretical). NMR (400 MHz, CDC13) δ (ppm) 6.32 (s, 2H), 4.63 (s, 4H), 3.40- 3.36 (m, 4H), 2.10 (m, 2H), 1.59 (m, 2H), 1.48 (t, J = 6.0 Hz, 4H), 1.42 (m, 4H), 1.35-1.30 (m, 10H), 0.91 (t, J = 7.4 Hz, 6H); 13C NMR (100 MHz, CDCI3) δ (ppm) 152.23, 108.3, 71.6, 68.1, 32.6, 31.4, 29.8, 25.4, 13.3.

Reference： [1]Current Patent Assignee: ARCHER-DANIELS-MIDLAND CO - WO2015/94970, 2015, A1 Location in patent: Page/Page column 34; 35

50
[ 1883-75-6 ]
[ 358-23-6 ]
(5-(hydroxymethyl)furan-2-yl)methyl trifluoromethanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With pyridine In dichloromethane at -10 - 20℃; for 3h; Inert atmosphere;	C.1 Example 1 : Synthesis of (5-(hydroxymethyl)furan-2-yl)methyl trifluoromethanesulfonate B Example 1 : Synthesis of (5-(hydroxymethyl)furan-2-yl)methyl trifluoromethanesulfonate B A B Experimental: An oven dried, 25 mL single-neck round bottomed flask equipped with a 1/2" x 1/8" tapered PTFE coated magnetic stir bar was charged with 250 mg of FDM A (1.95 mmol), 472 μ^ of pyridine (~ 3 eq.) and 10 mL of anhydrous methylene chloride. The neck was capped with a rubber septum and a needle affixed to an argon inlet and the flask immersed in a saturated brine/ice bath (- 10°C). While stirring and under an argon blanket, 328 μ^ of triflic anhydride (1.95 mmol) was added dropwise over a 10 minute period via syringe. After complete addition, the flask was removed from the ice bath, warmed to ambient temperature, and the reaction continued for 3 more hours. After this time, an aliquot was removed and a portion spotted on a silica gel thin-layer chromatography plate abutting a spot from the THF diol starting material for comparison. The plate was developed using a 100% ethyl acetate eluent, and after staining with cerium molybdate, the product mixture revealed three distinct spots manifesting Rfi = 0.63 (FDM di-triflate), Rf2 = 0.30 (FDM mono-triflates), and Rf = 0 (unreacted FDM). The reaction was concluded at this time and residual solution poured directly onto a pre-fabricated silica gel column, where gradient flash chromatography with hexanes/ethyl acetate as the eluent and cerium molybdate visualization produced 182 mg of (5- (hydroxymethyl)furan-2-yl)methyl trifluoromethane-sulfonate B as a light beige solid (36% of theoretical). NMR (400 MHz, CDC13) δ (ppm) 6.38 (d, J= 8.4 Hz, 1H), 6.32 (d, J = 8.4 Hz), 4.77 (s, 2H), 4.48 (s, 2H), 3.70 (broad, 1H); 13C NMR (100 MHz, CDCI3) δ (ppm) 155.0, 152.8, 119.2, 109.4, 108.6, 70.4, 65.2.

Reference： [1]Current Patent Assignee: ARCHER-DANIELS-MIDLAND CO - WO2015/94965, 2015, A1 Location in patent: Page/Page column 19

51
[ 67-47-0 ]
tetrahydrofuran-2,5-dimethanol [ No CAS ]
[ 625-86-5 ]
[ 1883-75-6 ]
[ 3857-25-8 ]

Yield	Reaction Conditions	Operation in experiment
	With Ni/SiO₂ catalyst with Ni loading of 20 wt % In 1,4-dioxane at 180℃; for 3h;
	With Ni/SiO₂ catalyst with Ni loading of 36 wt % In 1,4-dioxane at 150℃; for 3h;
	With 5% active carbon-supported ruthenium; hydrogen In water at 149.84℃; Green chemistry;

Reference： [1]Kong, Xiao; Zhu, Yifeng; Zheng, Hongyan; Li, Xianqing; Zhu, Yulei; Li, Yong-Wang [ACS Catalysis, 2015, vol. 5, # 10, p. 5914 - 5920]
[2]Kong, Xiao; Zhu, Yifeng; Zheng, Hongyan; Li, Xianqing; Zhu, Yulei; Li, Yong-Wang [ACS Catalysis, 2015, vol. 5, # 10, p. 5914 - 5920]
[3]Jain, Anandkumar B.; Vaidya, Prakash D. [International Journal of Chemical Kinetics, 2016, vol. 48, # 6, p. 318 - 328]

52
[ 67-47-0 ]
[ 625-86-5 ]
[ 620-02-0 ]
[ 1883-75-6 ]
[ 3857-25-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In tetrahydrofuran; water monomer at 174.84℃;
1: 21.2 %Chromat. 2: 6.9 %Chromat. 3: 6.5 %Chromat. 4: 5.3 %Chromat.	With hydrogen In tetrahydrofuran at 120℃;
1: 49.8 %Chromat. 2: 7.9 %Chromat. 3: 7.2 %Chromat. 4: 5.4 %Chromat.	With hydrogen In dimethyl sulfoxide at 180℃; for 16h;

	With hydrogen In tetrahydrofuran at 200℃;
	With hydrogen In tetrahydrofuran at 200℃;
1: 7 %Chromat. 2: 26 %Chromat. 3: 10 %Chromat. 4: 43 %Chromat.	With hydrogen In 1,4-dioxane at 220℃; for 5h; Autoclave;
	With hydrogen In tetrahydrofuran at 100℃; for 4h; Autoclave;	2.4. Catalytic testing General procedure: and solvent were loaded into a 50 mL Teflon-lined stainless steel highpressurereactor. The reactor was sealed, purged with H2, and chargedto the desired pressure, after which it was placed in a furnace at aspecified temperature. Upon completion of the reaction, the reactor wasimmediately cooled with ice water to room temperature. The catalystswere separated by applying a magnetic field.The reactor containing the separated catalysts was purged with H2and refilled with fresh substrate solution for subsequent catalytic cycles.Subsequently, a filter membrane was used to ensure that the liquidproducts were free of solid particles. Gas chromatography (GC) wasperformed using a Nexis GC-2030 instrument (Shimadzu Corp.) equippedwith a flame ionization detector (FID) and a capillary column (SHRtx-1701 30 m × 0.25 mm × 0.25 μm). The products and reactants were further identified by gas chromatography-mass spectroscopy (GC-MS,Shimadzu GCMS-QP2010), and the retention times were compared withthose of the pure chemicals. All compounds were quantified based on theinternal standard method using octane as the internal standard. TheHMF conversion and BHMF selectivity and yield were defined asfollows:

Reference： [1]Liu, Yifei; Mellmer, Max A.; Alonso, David Martin; Dumesic, James A. [ChemSusChem, 2015, vol. 8, # 23, p. 3983 - 3986]
[2]Guo, Weiwei; Liu, Hangyu; Zhang, Suqi; Han, Hongling; Liu, Huizhen; Jiang, Tao; Han, Buxing; Wu, Tianbin [Green Chemistry, 2016, vol. 18, # 23, p. 6222 - 6228]
[3]Guo, Weiwei; Liu, Hangyu; Zhang, Suqi; Han, Hongling; Liu, Huizhen; Jiang, Tao; Han, Buxing; Wu, Tianbin [Green Chemistry, 2016, vol. 18, # 23, p. 6222 - 6228]
[4]Srivastava, Sanjay; Jadeja; Parikh, Jigisha [Cuihua Xuebao/Chinese Journal of Catalysis, 2017, vol. 38, # 4, p. 699 - 709]
[5]Srivastava, Sanjay; Jadeja; Parikh, Jigisha [Cuihua Xuebao/Chinese Journal of Catalysis, 2017, vol. 38, # 4, p. 699 - 709]
[6]Brzezińska, Magdalena; Keller, Nicolas; Ruppert, Agnieszka M. [Catalysis science and technology, 2020, vol. 10, # 3, p. 658 - 670]
[7]Huang, Zexing; Lei, Jing; Liu, Xianxiang; Xu, Qiong; Yang, Yongjun; Zeng, Zhijuan; Zhao, Wenguang; Zhu, Xiaoting [Molecular catalysis, 2022, vol. 524]

53
[ 1883-75-6 ]
[ 103-67-3 ]
(5-((benzyl(methyl)amino)methyl)furan-2-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With trimethylamine-N-oxide; tricarbonyl(η⁴-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron In toluene at 20 - 135℃; Schlenk technique; Inert atmosphere; Molecular sieve; Sealed tube;

Reference： [1]Yan, Tao; Feringa, Ben L.; Barta, Katalin [ACS Catalysis, 2016, vol. 6, # 1, p. 381 - 388]

54
[ 67-47-0 ]
[ 1883-75-6 ]
[ 88910-22-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 80% 2: 15%	With ammonia; hydrogen In methanol at 50℃; for 16h; Sealed tube;
1: 86.3 %Chromat. 2: 10.4 %Chromat.	Stage #1: 5-hydroxymethyl-2-furfuraldehyde With 5wt.% Rh on activated alumina; ammonia In water for 1h; Green chemistry; Stage #2: With hydrogen In water at 80℃; for 4h; Green chemistry;
	With ammonium hydroxide; 5% rhodium on activated aluminium oxide; hydrogen at 80℃; for 3h; Autoclave;	8 General procedure: For the synthesis reaction, a 50 mL stainless steel autoclave was used. Into the autoclave, the raw material furfural (0.2 g, 2 mM), the catalyst 5 wt% Rh / Al 2 O 3 (0.002 g, Rh average particle diameter 40 nm), 28 wt% ammonia water (4.0 mL, 66 mM), finally a magnetic stir bar were put and covered, then the temperature was raised while stirring. After about 1 hour, when the vessel reached the reaction temperature of 80 ° C, hydrogen gas (2 MPa) was introduced to start the reaction. After a reaction time of 2 hours, cooled to 5 ° C or less with ice water, then the remaining hydrogen gas was released by opening the valve slowly, and then after filtering with filter paper (No. 1), Qualitative and quantification were carried out using GC-MS (CP-3800 + 1200 L made by Bruker Daltonics Co) or GC (HP6890 manufactured by Agilent Technologies). As a result, the conversion rate of raw material furfural was 100% and disappeared and the target product methyl amino furan was obtained in a yield of 91.7% (based on mol%, same in the following examples also). Other by-products are 8.3% of N, N-bis(furanyl methyl)amine and no other by-products were detected.The reaction was carried out under the same conditions as in Example 1 except that various kinds of raw materials were used instead of furfural as the aromatic compound or furan derivative having an aldehyde group. The results are summarized in Table 2. In all the raw materials, the structure of the aromatic or furan ring was maintained even after the reaction. In the case of having a nitro group as a substituent, it was found that the nitro group was reduced to be converted to an amino group, but otherwise the aldehyde group was converted to a methyl amino group.

Reference： [1]Chandrashekhar, Vishwas G.; Natte, Kishore; Alenad, Asma M.; Alshammari, Ahmad S.; Kreyenschulte, Carsten; Jagadeesh, Rajenahally V. [ChemCatChem, 2022, vol. 14, # 1]
[2]Chatterjee, Maya; Ishizaka, Takayuki; Kawanami, Hajime [Green Chemistry, 2016, vol. 18, # 2, p. 487 - 496]
[3]Current Patent Assignee: UNITIKA LTD; NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY - JP2017/25012, 2017, A Location in patent: Paragraph 0034; 0035

55
[ 67-47-0 ]
[ 1883-75-6 ]
[ 64646-09-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 21% 2: 22%	With Ni_0.53Al_0.47O_1.10H_0.39; hydrogen In water at 139.84℃; for 6h; Autoclave; Inert atmosphere;
	With alumina; C₂₈H₄₀Ir₂N₄O₆⁽⁴⁺⁾*2O₄S^(2-); hydrogen In water at 130℃; for 4h; Autoclave;	2.4. Typical experiment and product analysis General procedure: 5-HMF (25.2 mg, 0.2 mmol), Cp*Ir catalyst (dissolved in H2O,5 mmol L-1, 0.04 mL, 0.1 mol%), γ-Al2O3-1 (10 mg) and H2O (3 mL)were loaded into a 10 mL stainless steel autoclave and stirred at a rateof 1000 rpm. The mixture was heated to 130 °C under 3 MPa H2 for 4 h.The liquid products were diluted with acetonitrile and analyzed by GC.Dimethyl phthalate was used as an internal standard (The typical GCcharts were showed in Supporting information Figs. S2 and S3).
1: 51.6 %Chromat. 2: 25.2 %Chromat.	With Fe#Ni#C; hydrogen In water at 140℃; for 5h; Autoclave;

Reference： [1]Perret, Noémie; Grigoropoulos, Alexios; Zanella, Marco; Manning, Troy D.; Claridge, John B.; Rosseinsky, Matthew J. [ChemSusChem, 2016, vol. 9, # 5, p. 521 - 531]
[2]Xu, Yong-Jian; Shi, Jing; Wu, Wei-Peng; Zhu, Rui; Li, Xing-Long; Deng, Jin; Fu, Yao [Applied Catalysis A: General, 2017, vol. 543, p. 266 - 273]
[3]Zhang, Shujing; Ma, Hong; Sun, Yuxia; Luo, Yang; Liu, Xin; Zhang, Meiyun; Gao, Jin; Xu, Jie [Green Chemistry, 2019, vol. 21, # 7, p. 1702 - 1709]

56
[ 67-47-0 ]
[ 1883-75-6 ]
[ 2144-40-3 ]
trans-2,5-bis-hydroxymethyltetrahydrofurane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrogen In ethanol at 120℃; for 3h; Autoclave;	6 EXAMPLE 6: HMF reduction to FDM EXAMPLE 6: HMF reduction to FDMCopper zinc nanopowder and some commercial catalysts were also tested the hydrogenation of HMF at mild temperature for the achievement of useful diol building blocks (suppliers are indicated in table 6). Table 7. Composition details (and suppliers) of the commercial catalysts used.The vessel was pressurized with 70 bar H2 and subsequently heated to 120 C for 3 hours. In the adopted experimental conditions, all commercial catalysts showed good to excellent activity in the hydrogenation of HMF to FDM (2,5-furandimethanol) and THFDM (2,5-tetrahydrofurandimethanol), which account together for a combined selectivity of >80% (see Scheme 3).Scheme 3. Commercial compositions, such as catalyst D and catalyst G, both based on copper and nickel supported on S1O2 and Si02 Zr02, respectively, showed good selectivity to FDM (Table 8, entry 1 and 2) but no complete conversion of HMF, especially with catalyst G, which is characterized by a lower content of Cu and Ni than catalyst D. Ni Raney alloy showed complete conversion of HMF and high selectivity to THFDM (94%, table 8, entry 3), while Ni supported on ceria and zirconia (table 8, entry 4) led to an approximately equimolar mixture of FDM and THFDM. The strong interaction between nickel and the support might cause a reduced hydrogenation activity. Also the simultaneous presence of copper and nickel centres may attenuate the hydrogenation activity of nickel, which is very active in the reduction of C=C bonds (Table 8, entry 1 and 2 vs. entry 3).Interestingly, Cu-Zn alloy showed quantitative conversion of HMF and excellent selectivity to FDM (94%, table 8, entry 5), with no ring- hydrogenation. With the exception of Pt/C, which also selectively reduced HMF to FDM (table 8, entry 6), other hydrogenation catalysts based on noble metals preferably gave THFDM or a mixture of FDM and THFDM. Interestingly, Pd/A Oe and Pd/C showed high selectivity to THFDM by hydrogenation of both C=0 and C=C bonds (table 8, entry 7 and 8).
1%	With palladium/alumina; hydrogen In ethanol at 120℃; for 3h; Autoclave;	6 EXAMPLE 6: HMF reduction to FDM EXAMPLE 6: HMF reduction to FDMCopper zinc nanopowder and some commercial catalysts were also tested the hydrogenation of HMF at mild temperature for the achievement of useful diol building blocks (suppliers are indicated in table 6). Table 7. Composition details (and suppliers) of the commercial catalysts used.The vessel was pressurized with 70 bar H2 and subsequently heated to 120 C for 3 hours. In the adopted experimental conditions, all commercial catalysts showed good to excellent activity in the hydrogenation of HMF to FDM (2,5-furandimethanol) and THFDM (2,5-tetrahydrofurandimethanol), which account together for a combined selectivity of >80% (see Scheme 3).Scheme 3. Commercial compositions, such as catalyst D and catalyst G, both based on copper and nickel supported on S1O2 and Si02 Zr02, respectively, showed good selectivity to FDM (Table 8, entry 1 and 2) but no complete conversion of HMF, especially with catalyst G, which is characterized by a lower content of Cu and Ni than catalyst D. Ni Raney alloy showed complete conversion of HMF and high selectivity to THFDM (94%, table 8, entry 3), while Ni supported on ceria and zirconia (table 8, entry 4) led to an approximately equimolar mixture of FDM and THFDM. The strong interaction between nickel and the support might cause a reduced hydrogenation activity. Also the simultaneous presence of copper and nickel centres may attenuate the hydrogenation activity of nickel, which is very active in the reduction of C=C bonds (Table 8, entry 1 and 2 vs. entry 3).Interestingly, Cu-Zn alloy showed quantitative conversion of HMF and excellent selectivity to FDM (94%, table 8, entry 5), with no ring- hydrogenation. With the exception of Pt/C, which also selectively reduced HMF to FDM (table 8, entry 6), other hydrogenation catalysts based on noble metals preferably gave THFDM or a mixture of FDM and THFDM. Interestingly, Pd/A Oe and Pd/C showed high selectivity to THFDM by hydrogenation of both C=0 and C=C bonds (table 8, entry 7 and 8).

Reference： [1]Current Patent Assignee: UNIVERSITY OF GRONINGEN - WO2016/43589, 2016, A1 Location in patent: Page/Page column 25; 26; 27
[2]Current Patent Assignee: UNIVERSITY OF GRONINGEN - WO2016/43589, 2016, A1 Location in patent: Page/Page column 25; 26; 27

57
[ 67-47-0 ]
[ 1883-75-6 ]
[ 65313-46-4 ]
[ 110-13-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 67% 2: 6% 3: 8%	With hydrogen In water at 139.84℃; for 2h; Autoclave;
57%	With palladium on activated carbon; water; hydrogen; acetic acid at 89.84℃; for 1h; Autoclave;	3.3. Catalytic Reactions General procedure: A 20 mL stainless-steel autoclave equipped with a glass lining was used for the hydrogenation ofHMF. A magnetic stirring oil bath with a temperature controller was used to control the temperature.For a typical procedure, the magneton, HMF (1 mmol, 126.1 mg), H2O (2.00 g), AcOH (1 mmol, 60.0 mg)and Pd/C were put in the glass lining. Then, the lining was put into the autoclave and the autoclave waspurged with 2 MPa H2 four times to exclude the air before 4 MPa H2 was charged. Then, the autoclavewas put in the oil bath at 393 K. After the reaction, the autoclave was cooled down to room temperature.The internal standard and ethanol were added into the glass lining. The mixture was centrifugatedand the liquid phase was used for analysis. The reaction was repeated at least twice to calculate theconfidence interval with 95% confidence. The solid was washed with water and ethanol for threetimes respectively and dried in a vacuum for the next run. To recover the activity, the solid was thenwashed by tetrahydrofuran at 393 K for 1 h after being washed by water and ethanol. The procedurefor washing by tetrahydrofuran was performed in a 100 mL stainless-steel autoclave (Gongyi YingYu Instrument Factory, Gongyi, China). Before being heated, the air in the autoclave was replaced by1 atm N2 by shlenk technology.
1: 10% 2: 7% 3: 44%	With platinum on activated charcoal; hydrogen In water at 139.84℃; for 2h; Autoclave;

1: 6.32 mmol 2: 1.98 mmol 3: 1.3 mmol

With water In aq. buffer at 20℃; Electrochemical reaction;

Reference： [1]Duan, Ying; Zheng, Min; Li, Dongmi; Deng, Dongsheng; Ma, Lu-Fang; Yang, Yanliang [Green Chemistry, 2017, vol. 19, # 21, p. 5103 - 5113]
[2]Duan, Ying; Yang, Dexi; Yang, Yanliang; Zhang, Chi; Zheng, Min [Molecules, 2020, vol. 25, # 11]
[3]Duan, Ying; Zheng, Min; Li, Dongmi; Deng, Dongsheng; Ma, Lu-Fang; Yang, Yanliang [Green Chemistry, 2017, vol. 19, # 21, p. 5103 - 5113]
[4]Roylance, John J.; Choi, Kyoung-Shin [Green Chemistry, 2016, vol. 18, # 10, p. 2956 - 2960]

58
[ 1883-75-6 ]
[ 625-86-5 ]
[ 3857-25-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 87.2 %Chromat. 2: 10.4 %Chromat.	With hydrogen In ethanol at 230℃; for 4h;
	With formic acid In 1,4-dioxane at 160℃; for 5h;
1: 10.4 %Chromat. 2: 25.8 %Chromat.	With hydrogen In 1,4-dioxane at 230℃; for 6h; Autoclave;

Reference： [1]Chen, Meng-Yuan; Chen, Chu-Bai; Zada, Bakht; Fu, Yao [Green Chemistry, 2016, vol. 18, # 13, p. 3858 - 3866]
[2]Xu, Ling; Nie, Renfeng; Chen, Xujie; Li, Yanchen; Jiang, Yuxi; Lu, Xiuyang [Catalysis science and technology, 2021, vol. 11, # 4, p. 1451 - 1457]
[3]Hu, Xiaohong; Li, Song; Li, Zhijian; Liu, Qiying; Ma, Longlong; Wang, Chenguang; Wang, Haiyong; Xin, Haosheng [ChemSusChem, 2022]

59
[ 67-47-0 ]
[ 620-02-0 ]
[ 1883-75-6 ]
[ 3857-25-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen In water at 35℃; for 0.166667h; Autoclave;	1-2 50mL of which will be described later in a stainless steel autoclave solid catalyst 0.03g and hydroxymethyl furfural: put (HMF Aldrich) 0.15g, after further put the water 2mL, was heated container up to a temperature 35 ° C. After reaching sufficient lapse of about 10 minutes 35 ° C, hydrogen was introduced up to a pressure of a predetermined pressure (0.8 MPa), it was allowed to stir initiated reaction with a stirrer. After the predetermined reaction time has elapsed, the reaction vessel was cooled with ice, was returned to normal pressure to remove the hydrogen. Thereafter, the compound remaining in the autoclave was extracted with acetone or chloroform, the catalyst after filtration, the qualitative analysis in GC-MS, was performed quantitative analysis by GC. The catalyst was carried out by changing as shown in Table 2, it was from each Example 1-1 and Example 1-7. The results are shown in Table 2.
	With isopropyl alcohol at 170℃; for 4h; Inert atmosphere;

Reference： [1]Current Patent Assignee: UNITIKA LTD; NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY - JP2015/229657, 2015, A Location in patent: Paragraph 0037; 0038; 0039
[2]An, Yadan; Bai, Guoyi; Bian, Gang; Li, Tianming; Niu, Libo; Xia, Zhanghui [Green Chemistry, 2021, vol. 23, # 19, p. 7763 - 7772]

60
[ 67-47-0 ]
[ 1883-75-6 ]
[ 3857-25-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 85% 2: 6%	With Cu⁽⁶⁶⁾-ZnO; hydrogen In butan-1-ol at 100℃; for 4h;
	With hydrogen In water at 35℃; for 0.166667h; Autoclave;	1-4 50mL of which will be described later in a stainless steel autoclave solid catalyst 0.03g and hydroxymethyl furfural: put (HMF Aldrich) 0.15g, after further put the water 2mL, was heated container up to a temperature 35 ° C. After reaching sufficient lapse of about 10 minutes 35 ° C, hydrogen was introduced up to a pressure of a predetermined pressure (0.8 MPa), it was allowed to stir initiated reaction with a stirrer. After the predetermined reaction time has elapsed, the reaction vessel was cooled with ice, was returned to normal pressure to remove the hydrogen. Thereafter, the compound remaining in the autoclave was extracted with acetone or chloroform, the catalyst after filtration, the qualitative analysis in GC-MS, was performed quantitative analysis by GC. The catalyst was carried out by changing as shown in Table 2, it was from each Example 1-1 and Example 1-7. The results are shown in Table 2.
1: 81 %Chromat. 2: 10 %Chromat.	With hydrogen In 1,4-dioxane at 220℃; for 5h; Autoclave;

1: 86 %Chromat. 2: 10 %Chromat.

With hydrogen In isopropyl alcohol at 110℃; for 24h; Autoclave; chemoselective reaction;

Reference： [1]Upare, Pravin P.; Hwang, Young Kyu; Hwang, Dong Won [Green Chemistry, 2018, vol. 20, # 4, p. 879 - 885]
[2]Current Patent Assignee: UNITIKA LTD; NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY - JP2015/229657, 2015, A Location in patent: Paragraph 0037; 0038; 0039
[3]Brzezińska, Magdalena; Keller, Nicolas; Ruppert, Agnieszka M. [Catalysis science and technology, 2020, vol. 10, # 3, p. 658 - 670]
[4]Arias, Karen S.; Carceller, Jose M.; Climent, Maria J.; Corma, Avelino; Iborra, Sara [ChemSusChem, 2020, vol. 13, # 7, p. 1864 - 1875]

61
[ 4282-32-0 ]
[ 1883-75-6 ]
[ 36802-01-4 ]

Yield	Reaction Conditions	Operation in experiment
55%; 5%	With diisobutylaluminium hydride; In toluene; at 0℃; for 1.5h;Inert atmosphere;	General procedure: Typical Experimental Procedure for Reduction of Pyrrole Dicaboxylates To a solution of the compound 12a(35.7 mg, 0.098 mmol) in toluene (1 mL) was added DIBAH (1.0 Min toluene, 0.4 mL, 0.39 mmol) at 0C under an argon atmosphere. After being stirred for 45 min, then quenched with saturated aqueous Rochelle salt and extracted with EtOAc for three times. The combined organic layer was dried over Na2SO4and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluted with n-hexane-EtOAc (1 : 1) to give alcohol 13a (27.1 mg, 0.084 mmol, 86%) as reddish solid. Recrystallized from ethyl acetate/ hexane to give colorless crystal.

Reference： [1]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 1262 - 1267

62
[ 1883-75-6 ]
[ 616-38-6 ]
[ 934-93-0 ]
[ 18801-76-8 ]

Yield	Reaction Conditions	Operation in experiment
	With carbon dioxide In methanol at 200℃; for 3h; Sealed tube;	1 Example 1. Experimental conditions (MeOH, DMC, C02, 3h). A 250 cc Hastelloy pressire vessel was charged with 10 g of 2,5-furandimethanol (FDM, 78 mmol), 50 g of dimethyl carbonate (DMC, 555 mmol, 7.11 eq.) and 50 g of MeOH. The vessel was then sealed tightly and affixed to the reactor apparatus, purged x3 with 400 psi of C02, then saturated with CO2 until the pressire remained steady300 psi (methanol absorbs considerably amounts of C02). While stirring at 700 rpm, the vessel washeated to 200°C, where the reaction persisted for 3 h; the maximum pressure attained was 1650 psi at this temperature. After that time, the solution was cooled to ambient temperature, gas released, and stirring halted. The resultant brownish solution was then analyzed by GC/IVIS (70°C initial temp, hold for 4 mm, then 10°C per minute until 300°C, hold for 10 mm), which indicated that most of the FDM had been converted to monoether analog and a significant amount of the diether analog as shown inFigure 2.

Reference： [1]Current Patent Assignee: ARCHER-DANIELS-MIDLAND CO - WO2016/99789, 2016, A1 Location in patent: Paragraph 0047

63
[ 67-56-1 ]
[ 1883-75-6 ]
[ 934-93-0 ]
[ 18801-76-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 63.1% 2: 30.2%	With Hβ (Si/Al=25) at 120℃; for 1h; Inert atmosphere; Autoclave;
	With carbon dioxide In water at 200℃; for 5h; Sealed tube;	3 Comparative Example 3 Experimental conditions (No DMC). A 250 cc Hastelloy pressure vessel was charged with 10 g of 2,5-furandimethanol (FDM, 78 mmol), 100 g of MeOH and 1 g of water. The vessel was then sealed tightly and affixed to the reactor apparatus, pirged x3 with 400 psi of C02, then saturated with CO2 until the pressure remained steady at 400 psi (methanol absorbs considerable amounts of C02). While stirring at 700 rpm, the vessel was heated to 200°C, where the reaction persists for 5 h; themaximum pressire attained is 1605 psi at this temperature. After this time, the solution was cooled to ambient temperature, gas released, and stirring halted. The resulting reddish, transparent solution was then analyzed by GC/MS, using the aforementioned analytical method, and revealing three salient signals at 10.998 mm (residual FDIVI) and 10.3343 (monoether) and 9.764 mm (diether), as shown in Figures 6A, 6B, and 6C.

Reference： [1]Li, Xing-Long; Zhang, Kun; Chen, Shi-Yan; Li, Chuang; Li, Feng; Xu, Hua-Jian; Fu, Yao [Green Chemistry, 2018, vol. 20, # 5, p. 1095 - 1105]
[2]Current Patent Assignee: ARCHER-DANIELS-MIDLAND CO - WO2016/99789, 2016, A1 Location in patent: Paragraph 0051

64
[ 4282-32-0 ]
[ 1883-75-6 ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 15364 - 15368
Angew. Chem.,2016,p. 15590 - 15594,5

65
[ 67-47-0 ]
[ 534-22-5 ]
[ 625-86-5 ]
[ 620-02-0 ]
[ 1883-75-6 ]
[ 3857-25-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 30.4% 2: 7.8% 3: 14% 4: 6.6% 5: 10%	With hydrogen In tetrahydrofuran at 220℃; for 1h;	3 Example-3 Catalytic Activity Over Different Noble Metal for Hydrogenolysis of HMF to DMF All the catalysts were tested under at optimum reaction conditions obtained for of 2% Ru-NaY catalyst. Six principal products were observed: DMF, DMTHF, BHMF (2,5-bis(hydroxymethyl)furan), MF (5-methyl furfural), MFA (5-methyl furfuryl alcohol) and MFU (2-methyl furan). Other unknown products were also observed. The HMF conversion after 1 h of reaction ranged from 92 mol % for Rh-NaY to 100 mol % for Pt-NaY and Pd-NaY (Table 2). The DMF yield, the desired final product, was highest for Pd-NaY, 49.3 mol %. DMTHF, the hydrogenated compound of DMF was formed in more amount when platinum (4 mol %) and rhodium (10.7 mol %) was used as catalysts, whereas little amount of DMTHF (1.1 mol %) was observed when palladium based catalyst was used. Indicating that at the same weight loading platinum and rhodium catalysts were more active compared to the palladium catalyst for complete hydrogenation of DMF to DMTHF. Higher yield (10 mol %) of MFU was obtained for platinum based catalyst compare to rhodium and palladium as catalysts; shows that platinum catalyze both hydrogenation and carbon-carbon scission reaction. Furthermore, when platinum was used as catalyst, the majority of the HMF was converted to unidentified products. The GC chromatogram of the reaction mixture did not reveal any significant peaks, which may indicate that the undetected carbon is in the form of insoluble polymers, were formed on the catalyst surface. These insoluble polymers can be formed by the loss of formaldehyde from BHMF, followed by furfuryl alcohol polymerization.

Reference： [1]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - US2016/339414, 2016, A1 Location in patent: Paragraph 0073

66
[ 1883-75-6 ]
2,5-bis(azidomethyl)furan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With diphenylphosphoroamidate; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 0 - 20℃; for 20h;	1 Example 1 To a 5 L round-bottomed flask equipped with a magnetic stir bar wasadded 2,5-bis(hydroxymethyl)furan (257 g, 2.0 mol) and a solution of diphenyl phosphoryl azide (1.2 kg, 4.4 mol) in toluene (3 L). Under stirring, DBU (732.7 g, 4.8 mol) was added drop-wise to the reaction mixture at 0 °C, then warmed up to ambient temperature and stirred for 20h. The reaction mixture was washedwith water (2 x 4000 ml), HC1 aqueous solution (5%, 4000 ml), and then brine(4000 ml). The organic layer was concentrated and 288 g (81% yield) of 2,5- bis(azidomethyl)furan as brown oil was obtained by distillation under vacuum (90 °C/lOOPa).
13.5%	Stage #1: 2,5-bis-(hydroxymethyl)furan With dmap; 2,2-dimethylpropanoic anhydride In dichloromethane; acetonitrile at 0 - 20℃; for 25h; Stage #2: With sodium azide In acetonitrile Reflux;	General procedure for 2,5-bis(azidomethyl)furan (7)and 2,5-bis(azidomethyl)thiophene (8) General procedure: Compound 6 (0.66 g, 4.58 mmol) and 1.23 g DMAP(10.1 mmol) were placed in a flask. Then 50 cm3 dryCH2Cl2was added and mixed. The reaction flask wascooled to 0 °C and then 1.59 cm3 TFAA (11.4 mmol) dissolvedin 20 cm3 dry CH2Cl2was added dropwise. Afterthe reaction flask was stirred for 1 h at 0 °C, it was stirredat room temperature for 24 h. Water was added drop bydrop to the reaction flask to quench the reaction. Theorganic phase was extracted five times with 100 cm3 water.It was dried with Na2SO4and then the organic phase wasremoved under vacuum. One hundred milliliters of CH3CN and 2.38 g NaN3(36.6 mmol) were added to the residue inflask and refluxed over 24 h. The reaction was monitoredusing TLC and the flask was cooled to room temperature.The organic phase was removed under vacuum. The residuewas dissolved by adding 100 cm3 CH2Cl2and 100 cm3water. The organic phase was extracted twice with 100 cm3water and dried with Na2SO4.The product was purifiedusing column chromatography with n-hexane/EA (20/1)mixture. 2,5-Bis(azidomethyl)furan (7, C6H6N6O)The product wasobtained as a yellow color fluid. Yield: 13.5%; 1H NMR(300 MHz, CDCl3):δ = 6.34 (s, 2H), 4.31 (br s, 4H) ppm;13C NMR (75 MHz, CDCl3):δ = 150.1, 110.4, 47.2 ppm;FT-IR: v= 2085.9 cm-1; HRMS (ESI-TOF): m/z calcd. forC6H7N6O([M + H]+) 179.0681, found 179.0717.
	Multi-step reaction with 2 steps 1: hydrogenchloride / dichloromethane; water / 16 h / 20 °C 2: sodium azide / N,N-dimethyl-formamide / 16 h / 65 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: SOLVAY - WO2018/113599, 2018, A1 Location in patent: Page/Page column 11
[2]Karabulut, H. R. Ferhat; Karatavuk, Ali Osman [Monatshefte fur Chemie, 2020]
[3]Dunbabin, Alice; Subrizi, Fabiana; Ward, John M.; Sheppard, Tom D.; Hailes, Helen C. [Green Chemistry, 2017, vol. 19, # 2, p. 397 - 404]

67
[ 67-47-0 ]
tetrahydrofuran-2,5-dimethanol [ No CAS ]
[ 1883-75-6 ]
[ 69924-30-7 ]

Yield	Reaction Conditions	Operation in experiment
53.8%	With hydrogen In water at 40℃; for 1h; Autoclave;	12 [Synthesis of 2,5-dihydroxymethyltetrahydrofuran] General procedure: 100 mg of "Pd - Mo / SiO 2 catalyst (1)" obtained in Example 1 and 10 ml of 0.5 M 5 - hydroxymethylfurfural aqueous solution were placed in an autoclave having an internal volume of 50 ml equipped with a glass inner tube . Then, the inside of the autoclave was pressurized with hydrogen, and the mixture was stirred at 2 ° C. for 6 hours under a hydrogen atmosphere of 8 MPa. As a result, the reduction reaction shown in the following reaction formula (4) was carried out. After completion of the reduction reaction, the obtained reaction solution was filtered through a syringe equipped with a membrane filter (0.45 μm) to obtain a filtrate. Analysis of this filtrate by gas chromatography revealed that the conversion of 5-hydroxymethylfurfural was 99.7% and the yield of 2,5-dihydroxymethyltetrahydrofuran was 93.5%.The reaction was carried out in the same manner as in Example 8, except that the Pd - Re / SiO 2 catalyst obtained in Example 12 was used in place of the Pd - Rh / SiO 2 catalyst used in Example 8. As a result, the conversion of 5-hydroxymethylfurfural was 99.4% and the yield of 2,5-dihydroxymethyltetrahydrofuran was 53.8%.

Reference： [1]Current Patent Assignee: TOHOKU UNIVERSITY; UBE INDUSTRIES LIMITED - JP6037209, 2016, B2 Location in patent: Paragraph 0086; 0100

68
[ 1883-75-6 ]
tetrahydrofuran-2,5-dimethanol [ No CAS ]
[ 106-69-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 91% 2: 7%	With hydrogen In water; isopropyl alcohol at 110℃; for 3h;	5 EXAMPLE 5 Catalytic Hydrogenation Activity Test EXAMPLE 5 Catalytic Hydrogenation Activity Test [0228] All catalysts including comparative example were tested in high throughput mode in a HiP-HOSS reactor (see "High-Throughput Heterogeneous Catalyst Research," Howard W. Turner, Anthony F. Volpe Jr, and W. H. Weinberg, Surface Science 603 (2009) 1763-1769, which is incorporated herein by reference) according to following procedure. 20 mg catalysts have been placed in 1 ml vials, filled with 0.2 ml of 0.4M solution of BHMF (2,5 dimethanol furan) in solvent 90% i-PA + 10 % H20 (v/v). The test was conducted at a temperature of 110°C for 3 hrs under hydrogen pressure 700 psi. Observed products were 2,5 BHMTHF (2,5 dimethanol tetrahydrofuran) and 1,2,6 HTO (1,2,6- hexane triol). The results are provided in Table 1.

Reference： [1]Current Patent Assignee: ARCHER-DANIELS-MIDLAND CO - WO2017/75425, 2017, A1 Location in patent: Paragraph 0228

69
[ 1883-75-6 ]
[ 106-89-8 ]
[ 1269765-69-6 ]
C₉H₁₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 26.3 %Chromat. 2: 27 %Chromat.	Stage #1: 2,5-bis-(hydroxymethyl)furan; epichlorohydrin at 116℃; for 0.5h; Dean-Stark; Stage #2: With sodium hydroxide In water for 1.66667h;	1.1 Test No. 1 50 g of DHMF (0.39 mol, 1 molar equivalent) and then 361.2 g of epichlorohydrin (3.90 mol, 10 molar equivalents) are introduced into a 1-liter jacketed reactor equipped with a thermostatic bath containing a heat-exchange fluid, with a mechanical blade stirring system, with a system for controlling the temperature of the reaction medium and with an inverse Dean-Stark apparatus surmounted by a reflux condenser. The reaction mixture is then heated to 116° C. (boiling point of epichlorohydrin=116° C. at atmospheric pressure) over 30 minutes. 125 g of a 50% aqueous sodium hydroxide solution (1.56 mol, 2 molar equivalents) are then gradually added. The addition lasts for a total of 1 h 40; the azeotropic distillation continues and the water formed by reaction between the halide (in the case in point the epichlorohydrin) and the DHMF is eliminated. The reaction medium is filtered under vacuum in order to eliminate therefrom the sodium chloride formed over time. The salts are finally washed with epichlorohydrin which is then eliminated by evaporation under reduced pressure on a rotary evaporator. The composition of furan diglycidyl ether or containing predominantly furan diglycidyl ether is then obtained in the form of a liquid (Brookfield viscosity at 25° C. of 442 mPa·s), having an epoxy equivalent of 189 g/equivalent.

Reference： [1]Current Patent Assignee: ROQUETTE FRERES - US2017/121317, 2017, A1 Location in patent: Paragraph 0060-0066; 0091

70
[ 143-07-7 ]
[ 1883-75-6 ]
C₃₀H₅₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With 6CHO₃^(1-)*2Sb⁽³⁺⁾ at 200℃; for 11h; Inert atmosphere;	13 10 mmol of 2,5-furandimethanol, 21 mmol of dodecanoic acid and 0.31 mmol of Sb (OAc) 2 were added to a 50 mL round bottom flask. Heated to 200 ° C; reacted at this temperature for 11 h. And then decompression Distillation gave 2,5-furan dimethyl behenate. The ester was calculated according to the amount of 2,5-furandimethanol Of the isolated molar yield was 98%, the purity was 99.9%

Reference： [1]Current Patent Assignee: Dalian Institute of Chemical Physics (in: CAS); CHINESE ACADEMY OF SCIENCES - CN106146300, 2016, A Location in patent: Paragraph 0028

71
(5-Hydroxymethyl-furan-2-yl)-acetaldehyde [ No CAS ]
tetrahydrofuran-2,5-dimethanol [ No CAS ]
[ 1883-75-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 74.3% 2: 20.1%	With ruthenium-carbon composite; hydrogen; 1-butyl-3-methylimidazolium chloride In water at 50℃; for 6h;	3 Example 3 0.5 g of HMF,2 g of ionic liquid BmimCl and 70 mL of water were charged into a high pressure reactor,While 0.15 g of 5 wt% Ru / C catalyst was added.Closed reactor,H2 was continuously replaced with H2 for 5 times.The H2 pressure was then adjusted to 5 MPa,Heating up to 50 ° C,Rapid stirring (960rpm) reaction 6h,Stop heating, when the kettle temperature dropped to room temperature,Open the vent valve to the kettle pressure down to normal pressure,Discharge.The reaction solution is filtered,Filtrate for analysis,The product was characterized by GC-MS,GC external standard method quantitative analysis,Leg conversion rate of 100%0 leg yield was 74.3%The yield was 20.1%The yield of the two products reached 94.4%.

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Dalian Institute of Chemical Physics (in: CAS) - CN103848802, 2017, B Location in patent: Paragraph 0028-0029

72
[ 67-47-0 ]
[ 62-53-3 ]
[ 1883-75-6 ]
(5-((phenylamino)methyl)furan-2-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogen In ethanol at 70℃; for 16h; Sealed tube;
1: 87 %Chromat. 2: 13 %Chromat.	With rutile titania supported gold; hydrogen In methanol; water at 60℃; for 1.5h; Autoclave; chemoselective reaction;
1: 74 %Spectr. 2: 26 %Spectr.	Stage #1: 5-hydroxymethyl-2-furfuraldehyde; aniline In ethanol at 25℃; for 3h; Stage #2: With (CuAl)O(x); hydrogen In methanol at 100℃; Flow reactor;	3.4. General Procedure for Reductive Amination of Furanic Aldehydes with Primary Amines General procedure: Depending on the nucleophilic properties of the amine, the solution of furanic aldehyde (0.05 M)and primary amine (0.05 M) in methanol was kept at 25 C for 3 or 16 h. Then, the reactionmixture was mixed with H2 and pumped through the flow reactor packed with the CuAlOx material.Catalytic experiments were performed in H-Cube Pro setup (Thalesnano, Budapest, Hungary) equippedwith a 30 mm CatCart cartridge (CatCart30, 0.30 mL empty volume) [11,13]. Before the catalytic run,the catalyst (0.165 g of 250-500 m particles) was reduced by a mixture of hydrogen with methanol at120 C for 1 h (pressure of 10 bar, flow rates of methanol andH2 were 0.5 and 30 mL min1, respectively).Afterwards, the reaction mixture was pumped through the reactor instead of pure solvent, and thispoint in time was chosen as the starting point of the experiment.The reaction was carried out at temperature of 80-120 C, H2 pressure of 10 bar, liquid feed rate of0.5 mL min1 and hydrogen flow rate of 30 mL min1 (inlet H2/substrate molar ratio was 54). The useof a large excess of H2 in the reaction medium is necessary to avoid the influence of external masstransfer on the reaction progress [13]. The performance of the catalyst was evaluated by analysis of thesamples taken in the interval of 30-33 min from the beginning of the experiment. The composition ofthe reaction products was determined using 1H NMR spectroscopy in CDCl3. The error in determiningthe yield is 1%.

Reference： [1]Chandrashekhar, Vishwas G.; Natte, Kishore; Alenad, Asma M.; Alshammari, Ahmad S.; Kreyenschulte, Carsten; Jagadeesh, Rajenahally V. [ChemCatChem, 2022, vol. 14, # 1]
[2]Zhu, Ming-Ming; Tao, Lei; Zhang, Qi; Dong, Jing; Liu, Yong-Mei; He, He-Yong; Cao, Yong [Green Chemistry, 2017, vol. 19, # 16, p. 3880 - 3887]
[3]Bukhtiyarov, Valerii I.; Bukhtiyarova, Marina V.; Nuzhdin, Alexey L. [Molecules, 2020, vol. 25, # 20]

73
[ 1883-75-6 ]
[ 620-02-0 ]
[ 4437-22-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: rhodium contaminated with carbon / 2 h / 150 °C / 60006 Torr / Supercritical conditions 2: rhodium contaminated with carbon; hydrogen / 4 h / 50 °C / Supercritical conditions 3: palladium/alumina / 2 h / 150 °C / 60006 Torr / Supercritical conditions

Reference： [1]Chatterjee, Maya; Ishizaka, Takayuki; Chatterjee, Abhijit; Kawanami, Hajime [Green Chemistry, 2017, vol. 19, # 5, p. 1315 - 1326]

74
[ 1883-75-6 ]
[ 620-02-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: rhodium contaminated with carbon / 2 h / 150 °C / 60006 Torr / Supercritical conditions 2: rhodium contaminated with carbon; hydrogen / 4 h / 50 °C / Supercritical conditions 3: palladium on mesoporous MCM-41 / 2 h / 150 °C / 60006 Torr / Supercritical conditions
72 %Chromat.	With sulfuric acid; sodium iodide In tetrahydrofuran at 180℃; for 10h; Autoclave; Inert atmosphere;

Reference： [1]Chatterjee, Maya; Ishizaka, Takayuki; Chatterjee, Abhijit; Kawanami, Hajime [Green Chemistry, 2017, vol. 19, # 5, p. 1315 - 1326]
[2]Huang, Yang; Jiang, Haiwei; Li, Teng; Peng, Yang; Rong, Nianxin; Shi, Hexian; Yang, Weiran [Green Chemistry, 2021, vol. 23, # 20, p. 8108 - 8115]

75
[ 67-47-0 ]
[ 67-63-0 ]
[ 1883-75-6 ]
2,5-bis[(1-methylethoxy)methyl]furan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 91.4% 2: 6.6%	With ZnO-ZrO₂/USY(Si/Al-7) at 180℃; for 2.5h; Autoclave;	12 A 50 mL autoclave was charged with 2 g of 5-hydroxymethylfurfural and 18 g of isopropanol (10 wt%),Then join separately0.2 g BaO-ZrO 2 / SBA-15,ZnO-ZrO2 / SBA-15As a catalyst,The reaction vessel was sealed, vigorously stirred (500 rpm)Heated to 180 and hold 2.5h,The reaction was cooled to room temperature and sampled,
1: 16.4% 2: 22.8%	With ZrO₂/Beta₁₄₀₁ at 150℃; for 2.5h; Autoclave;	2 To a 50 mL autoclave were added 0.4 g of 5-hydroxymethylfurfural and 19.6 g of isopropanol (2 wt%),And then were added0.2g ZrO2 / MCM-41,ZrO2 / Beta1401,ZrO2 / USY,ZrO2 / SBA-15 (loading of ZrO2 40%)As a catalyst,Sealed reactor,Stirring vigorously (500 rpm),Heated to 150 and hold 2.5h,

Reference： [1]Current Patent Assignee: XIAMEN UNIVERSITY - CN106946820, 2017, A Location in patent: Paragraph 0030-0031; 0037
[2]Current Patent Assignee: XIAMEN UNIVERSITY - CN106946820, 2017, A Location in patent: Paragraph 0024-0025; 0037

76
[ 67-47-0 ]
[ 1883-75-6 ]
3-hydroxymethylcyclopent-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With alumina; C₂₂H₂₉N₂O₃Rh⁽²⁺⁾*O₄S^(2-); hydrogen In water at 130℃; for 4h; Autoclave;	2.4. Typical experiment and product analysis General procedure: 5-HMF (25.2 mg, 0.2 mmol), Cp*Ir catalyst (dissolved in H2O,5 mmol L-1, 0.04 mL, 0.1 mol%), γ-Al2O3-1 (10 mg) and H2O (3 mL)were loaded into a 10 mL stainless steel autoclave and stirred at a rateof 1000 rpm. The mixture was heated to 130 °C under 3 MPa H2 for 4 h.The liquid products were diluted with acetonitrile and analyzed by GC.Dimethyl phthalate was used as an internal standard (The typical GCcharts were showed in Supporting information Figs. S2 and S3).

Reference： [1]Xu, Yong-Jian; Shi, Jing; Wu, Wei-Peng; Zhu, Rui; Li, Xing-Long; Deng, Jin; Fu, Yao [Applied Catalysis A: General, 2017, vol. 543, p. 266 - 273]

77
[ 57-50-1 ]
[ 1883-75-6 ]
[ 6338-41-6 ]

Reference： [1]ChemCatChem,2017,vol. 9,p. 4244 - 4255

78
[ 133-99-3 ]
[ 1883-75-6 ]
[ 6338-41-6 ]

Reference： [1]ChemCatChem,2017,vol. 9,p. 4244 - 4255

79
[ 133-99-3 ]
[ 1883-75-6 ]
[ 6338-41-6 ]

Reference： [1]ChemCatChem,2017,vol. 9,p. 4244 - 4255

80
[ 470-23-5 ]
[ 1883-75-6 ]
[ 6338-41-6 ]

Reference： [1]ChemCatChem,2017,vol. 9,p. 4244 - 4255

81
[ 823-82-5 ]
[ 67-47-0 ]
[ 1883-75-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 76.9% 2: 16.7%	With nickel(II) oxide; isopropyl alcohol In neat (no solvent) at 150℃; for 4h; Sealed tube;
1: 70.6% 2: 23.2%	With isopropyl alcohol at 180℃; for 4h;
1: 70% 2: 5%	With potassium <i>tert</i>-butylate; hydrogen; C₁₈H₂₆Br₂MnN₃P In methanol at 130℃; for 24h; Inert atmosphere; Autoclave; chemoselective reaction;

Reference： [1]He, Jian; Nielsen, Monia Runge; Hansen, Thomas Willum; Yang, Song; Riisager, Anders [Catalysis science and technology, 2019, vol. 9, # 5, p. 1289 - 1300]
[2]He, Jian; Li, Hu; Riisager, Anders; Yang, Song [ChemCatChem, 2018, vol. 10, # 2, p. 430 - 438]
[3]Gholap, Sandeep Suryabhan; Dakhil, Abdullah Al; Chakraborty, Priyanka; Li, Huaifeng; Dutta, Indranil; Das, Pradip K.; Huang, Kuo-Wei [Chemical Communications, 2021, vol. 57, # 89, p. 11815 - 11818]

82
[ 1883-75-6 ]
[ 334-48-5 ]
2,5-furandimethanol didecyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95.04%	With sulfonic acid ionic resin at 100℃;	6-8 Example 7 Mix 0.0125mol (1.60g) 2,5-furandimethanol, 0.25mol decanoic acid, and 5.64mmol sulfonic acid ionic resin, and react at a temperature of 100, and control the stirring speed to 800rpm and the reflux temperature for condensation The temperature is 20°C and the vacuum degree is 0.02MPa. After reacting for 3 hours, the catalyst is filtered, 0.3 mol of acetonitrile is added to precipitate crystals, and the crystallization mother liquor is removed by filtration to obtain white 2,5-furandimethanol didecyl represented by formula (II) The ester crystals were analyzed by high performance liquid chromatography, and the conversion rate of 2,5-furandimethanol and the yield of didecyl 2,5-furandimethanol were 100% and 95.04%, respectively.
	With tin(IV) oxide In toluene for 8h; Reflux;	4 Example 4 6.406 g (0.05 mol) of 2,5-furandimethanol, 29.871g (0.15mol) decanoic acid, 0.3 g of tin oxide and 15 ml of toluene were added to a three-necked flask equipped with a condensation reflux device and a trap. After heating to the first drop of toluene, refluxing is continued for 8 hours. Distillation under reduced pressure then afforded 2,5-furandimethanol dicaprate

Reference： [1]Current Patent Assignee: Ningbo Institute of Material Technology and Engineering (in: CAS); CHINESE ACADEMY OF SCIENCES - CN112209906, 2021, A Location in patent: Paragraph 0061-0068
[2]Current Patent Assignee: Ningbo Institute of Material Technology and Engineering (in: CAS); CHINESE ACADEMY OF SCIENCES - CN107686470, 2018, A Location in patent: Paragraph 0038; 0039

83
[ 6196-57-2 ]
[ 1883-75-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide; acetic acid In water at 60℃; for 4h;	44 Examples 44-55: Dehydration of 3-Deoxyfructoseinto 2,5-bis(hydroxymethyl)furan 10059] 3-deoxy-D-fructose is dissolved in water by placing 10 mg of 3-deoxy-D-fructose in a very small sample vial. To this is added 250 ul of water, and this is mixed to dissolve the 3-deoxy-D-fructose. This stock solution is used for each reaction according to Table 5. In each case, 20 ul of the 3-deoxy-D-fructose solution is added first to a vial along with a mini stir bar. The remaining reagents are added in the order shown in Table 5 (left to right) and mixed by stirring on a stirplate. Each vial is capped and heated to 60° C. with stirring. After the reaction time, the vial contents are cooled and analyzed for 2,5-bis(hydroxymethyl)thran by HPLC analysis. Conversion of 3-deoxy-D-fructose into 2,5 -bis(hydroxymethyl)thran is observed.

Reference： [1]Current Patent Assignee: BP P.L.C. - US2018/57897, 2018, A1 Location in patent: Paragraph 0059

84
[ 57-48-7 ]
[ 1883-75-6 ]
[ 6338-41-6 ]

Reference： [1]ChemSusChem,2018,vol. 11,p. 1612 - 1616

85
[ 67-47-0 ]
[ 1883-75-6 ]
(tetrahydrofüran-2,5-diyl)dimethanol [ No CAS ]
(tetrahydrofüran-2,5-diyl)dimethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With C₅₆H₅₄O₄P₂Ru; hydrogen In toluene at 120℃; Glovebox; Sealed tube; Sonication; Autoclave;	A General procedure 1: Preformed catalyst General procedure: In an Argon-filled glovebox, HMF (typically 100 mg, 1 molar equivalent) and thecatalyst (4.5 mol%) placed in a microwave vial, along with the solvent (10 mL toluene)and sealed. The solution was sonicated to allow full dissolution of the substrate and catalyst (ca. 5-15 mm). The solution was transferred to an N2-purged glass autoclave under a flow of N2. The autoclave was tightly closed, purged with N2, then H2 (typically, 3 times each, 5 bar), and finally pressurized with H2 to the desired pressure (typically10 bar). An oil bath was used to bring the autoclave to the desired temperature (typically 120°C), and was stirred for the specified duration (typically overnight). A sample was collected (while the autoclave was still at the indicated temperature), the solvent was removed fri vacuo, the resulting oil was dissolved in d6-DMSO and analysed by NMR. The ratio of HMF:BHMF:THF-glycol was determined by H1 NMR,and the ratio of c/s.transTHF-glycol was determined by integration of the relevant carbon peaks by 13CNMR, as per literature (G. Bottari, A. J. Kumalaputri, K. K. Krawczyk, B. L. Feringa,H. J. Heeres, K. Barta, ChemSusChem 2015, 8, 1323- 1327).

Reference： [1]Current Patent Assignee: BASF SE - WO2018/87270, 2018, A1 Location in patent: Page/Page column 26; 27; 28

86
[ 1883-75-6 ]
(tetrahydrofüran-2,5-diyl)dimethanol [ No CAS ]
(tetrahydrofüran-2,5-diyl)dimethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With C₅₆H₅₄O₄P₂Ru; hydrogen In toluene at 120℃; Glovebox; Sealed tube; Sonication; Autoclave;	A General procedure 1: Preformed catalyst General procedure: In an Argon-filled glovebox, HMF (typically 100 mg, 1 molar equivalent) and thecatalyst (4.5 mol%) placed in a microwave vial, along with the solvent (10 mL toluene)and sealed. The solution was sonicated to allow full dissolution of the substrate and catalyst (ca. 5-15 mm). The solution was transferred to an N2-purged glass autoclave under a flow of N2. The autoclave was tightly closed, purged with N2, then H2 (typically, 3 times each, 5 bar), and finally pressurized with H2 to the desired pressure (typically10 bar). An oil bath was used to bring the autoclave to the desired temperature (typically 120°C), and was stirred for the specified duration (typically overnight). A sample was collected (while the autoclave was still at the indicated temperature), the solvent was removed fri vacuo, the resulting oil was dissolved in d6-DMSO and analysed by NMR. The ratio of HMF:BHMF:THF-glycol was determined by H1 NMR,and the ratio of c/s.transTHF-glycol was determined by integration of the relevant carbon peaks by 13CNMR, as per literature (G. Bottari, A. J. Kumalaputri, K. K. Krawczyk, B. L. Feringa,H. J. Heeres, K. Barta, ChemSusChem 2015, 8, 1323- 1327).

Reference： [1]Current Patent Assignee: BASF SE - WO2018/87270, 2018, A1 Location in patent: Page/Page column 26; 29

87
[ 1883-75-6 ]
[ 13529-17-4 ]
[ 6338-41-6 ]
[ 3238-40-2 ]

Yield	Reaction Conditions	Operation in experiment
14%; 6%; 76%	With oxygen; sodium hydrogencarbonate; In water; at 90℃; for 10h;Catalytic behavior;	The catalyst (0.039 g) was added into a solution of HMF(0.40 mmol) and NaHCO3 (1.6 mmol) in deionized water (20 mL).The suspension was heated to 90 C under stirring and bubbledwith O2 at a flow rate of 70 mL min-1. An aliquot (50 muL) of thereaction mixture was taken out at given intervals and diluted to5 mL with deionized water in a volumetric flask. The liquid samplewas then syringe-filtered through a 0.2 lm PTFE membrane and analyzed by HPLC. The concentrations of HMF, HMFCA, FFCA, andFDCA in the reaction solutions were measured by HPLC using theexternal standard calibration curve method. To evaluate the relativestandard deviation (RSD) of the reaction results, four parallelexperiments were carried out by using Pt/3DOM-Ce1-xBixO2-delta ascatalyst. The RSD values for yield of HMFCA, FFCA, and FDCA weredetermined as 1.7percent, 2.4percent, and 2.5percent, respectively.

Reference： [1]Journal of Catalysis,2018,vol. 365,p. 292 - 302

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	1883-75-6	MDL No. :	MFCD00003253
Formula :	C₆H₈O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DSLRVRBSNLHVBH-UHFFFAOYSA-N
M.W :	128.13	Pubchem ID :	74663
Synonyms :	5-(Hydroxymethyl)furfuryl Alcohol;NSC 524614;NSC 40737;FaRez 6305;2,5-Dihydroxymethylfurane

Num. heavy atoms :	9
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.33
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	30.96
TPSA :	53.6 Å²

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.59 cm/s

Log Po/w (iLOGP) :	1.28
Log Po/w (XLOGP3) :	-0.71
Log Po/w (WLOGP) :	-0.04
Log Po/w (MLOGP) :	-0.97
Log Po/w (SILICOS-IT) :	0.94
Consensus Log Po/w :	0.1

[ CAS No. 1883-75-6 ] {[proInfo.proName]}

Quality Control of [ 1883-75-6 ]

Related Doc. of [ 1883-75-6 ]

Product Details of [ 1883-75-6 ]

Calculated chemistry of [ 1883-75-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1883-75-6 ]

Application In Synthesis of [ 1883-75-6 ]

[ 1883-75-6 ] Synthesis Path-Downstream 1~87

Related Functional Groups of
[ 1883-75-6 ]

Alcohols

Related Parent Nucleus of
[ 1883-75-6 ]

Furans

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-0.47
Solubility :	43.8 mg/ml ; 0.342 mol/l
Class :	Very soluble
Log S (Ali) :	0.06
Solubility :	147.0 mg/ml ; 1.15 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-1.23
Solubility :	7.53 mg/ml ; 0.0587 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.22

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 1883-75-6 ] {[proInfo.proName]}

Quality Control of [ 1883-75-6 ]

Related Doc. of [ 1883-75-6 ]

Product Details of [ 1883-75-6 ]

Calculated chemistry of [ 1883-75-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1883-75-6 ]

Application In Synthesis of [ 1883-75-6 ]

[ 1883-75-6 ] Synthesis Path-Downstream 1~87

Related Functional Groups of [ 1883-75-6 ]

Alcohols

Related Parent Nucleus of [ 1883-75-6 ]

Furans

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1883-75-6 ]

Related Parent Nucleus of
[ 1883-75-6 ]