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CAS No. : | 6338-41-6 | MDL No. : | MFCD03274472 |
Formula : | C6H6O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PCSKKIUURRTAEM-UHFFFAOYSA-N |
M.W : | 142.11 | Pubchem ID : | 80642 |
Synonyms : |
NSC 40739
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 31.8 |
TPSA : | 70.67 Ų |
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) : | -7.17 cm/s |
Log Po/w (iLOGP) : | 0.81 |
Log Po/w (XLOGP3) : | 0.0 |
Log Po/w (WLOGP) : | 0.32 |
Log Po/w (MLOGP) : | -0.83 |
Log Po/w (SILICOS-IT) : | 0.49 |
Consensus Log Po/w : | 0.16 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -0.96 |
Solubility : | 15.6 mg/ml ; 0.11 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.04 |
Solubility : | 13.1 mg/ml ; 0.0922 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.79 |
Solubility : | 23.1 mg/ml ; 0.163 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.27 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxygen; sodium carbonate; In water; at 95℃; for 7h; | Catalytic Reaction Of HMF To FDCA For this reaction, Na2C03 was used as the base. 1 g of extracted HMF was first dissolved in 5 g of water. The Na2C03 was separately prepared by dissolving Na2C03 in water. The oxidation catalyst was then added follow by the HMF solution at ambient room temperature. With oxygen gas bubbling, the solution was first heated to 50C for 2 hours, and HMF was fully converted to HFCA. After that, the reaction was heat to 95C and kept for 7 hour. The pH of the aqueous solution was then adjusted to 1 and FDCA was precipitated from the solution. The precipitate was filtered and washed with ethanol. | |
With Ru/Pt on active carbon; oxygen; In water; at 90℃; under 1034.32 Torr; for 20h;Alkaline conditions; | This examples shows the oxidation of the FDCA precursor (here FFCA) into FDCA. A series of reactions were prepared as shown in the following Table. All reactions contained 100 mM of commercial FFCA. The reactions were performed in screw capped vials under air (in all reactions with H2O2 and controls runs 11-13) or under oxygen at about 20 psi. All reactions were incubated for 20 h before samples were analyzed by TLC for product formation. All reactions conversions described in the Table above are based on TLC analysis. For example, >90% indicates the result of TLC analysis where FDCA was detected as the only product. ?About? 50% indicates that FFCA and FDCA spots with similar intensity were observed. | |
With oxygen; cobalt(II) acetate; manganese(II) acetate; acetic acid; sodium bromide; at 180℃; under 42133 Torr; for 1h; | 5-hydroxymethyl-2-furoic acid (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 5-hydroxym- ethyl-2-furoic acid to thrandicarboxylic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; acetic anhydride; In dichloromethane; toluene; | (a) 5-Acetoxymethylfuran-2-carboxylic acid A mixture of 5-hydroxymethylfuran-2-carboxylic acid (5.90 g), dry dichloromethane (100 ml), pyridine (6.71 ml), 4-dimethyl-aminopyridine (507 mg), and acetic anhydride (4.21 ml) was stirred for 2 hours at room temperature. The mixture was diluted with ethyl acetate and washed with 5M hydrochloric acid and brine (3 times), dried (MgSO4), and evaporated. The residue was re-evaporated twice from dry toluene to give the title acid as a solid (5.00 g); deltaH [(CD3)2 CO) 2.05 (3 H, s), 5.11 (2 H, s), 6.62 (1 H, d, J 4 Hz), 7.17 (1 H, d, J 4 Hz) and 8.31 (1 H, br s). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19%; 10%; 35%; 20%; 8% | With dihydrogen peroxide;methyltrioxorhenium(VII); In dichloromethane; water; acetonitrile; at 20℃; | Comparative examples 1 to 3: Oxidation of 5-hydroxymethyl furfural in homogeneous conditions; 5-hydroxymethyl furfural (HMF) was oxidized with 10 equivalents of hydrogen peroxide (35percent by weight in aqueous solution) in the presence of methyltrioxo rhenium in an amount of 5percent by weight of HMF, at a temperature about 200C during 24 to 48 hours, until the conversion of furfural was complete, in various solvents. The results of the reactions are summarized in Table 1 below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23%; 6%; 11%; 16%; 29% | With dihydrogen peroxide;methyltrioxorhenium(VII); In ethanol; water; at 20℃; | Comparative examples 1 to 3: Oxidation of 5-hydroxymethyl furfural in homogeneous conditions; 5-hydroxymethyl furfural (HMF) was oxidized with 10 equivalents of hydrogen peroxide (35percent by weight in aqueous solution) in the presence of methyltrioxo rhenium in an amount of 5percent by weight of HMF, at a temperature about 200C during 24 to 48 hours, until the conversion of furfural was complete, in various solvents. The results of the reactions are summarized in Table 1 below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7%; 90% | With bis-acetylacetonyl vanadium (II); In aq. phosphate buffer; at 37 - 80℃; for 16.0833h;pH 7; | HMF (100 mM) was added to KPi buffer (500 mM pH 7.0). GOase M35 (103p1 of3.3mg/mL), PaoABC (ipI of 28.9mg/mL) and a metal complex (see Table 4) were added at 37 00 and the pH was continuously adjusted with NaHCO3 for a period of 16 hours. The reaction was heated to 80 00 for 5 minutes and left to cool. The solution containing denatured protein was centrifuged and the supernatant removed and analysed by RP20 HPLC. |
With sodium carbonate; at 100℃; under 30003 Torr; for 0.1h;pH 10.12; | Experimental Conditions The HMF having 95% purity was supplied by Interchim. The method of the invention was implemented in a discontinuous reactor under pressure in a 300 mL autoclave equipped with magnetically driven gas-inducing agitator. Heating was ensured by a heating collar connected to a PID controller (proportional integral derivative). A sampling gate allowed the taking of a sample from the reaction medium via an immersed tube, allowing the monitoring of the progress of the reaction over time. The samples were analysed by HPLC chromatography with two RID detectors (Refractive Index Detector) and PDA (Photodiode array) (ICE-Coragel 107H column, eluting with 10 mM H2SO4). Total Organic Carbon (TOC) in solution was also analysed using a TOC analyser and the value measured was compared with the mass balance (MB) calculated by HPLC. The reactor was charged with 150 mL of 100 mM aqueous HMF solution (2 g), a weight of catalyst corresponding to a HMF/Pt molar ratio of 100, and the desired amount of base in the form of NaOH (comparative example), NaHCO3, KHCO3, Na2CO3 or K2CO3 expressed as base/HMF molar ratio. Air was added at a pressure of 40 bar and the reactor heated to 100 C. The influence of the Bi/Pt ratio was also examined in the presence of Na2CO3 (Na2CO3/HMF=2). The same trend was observed when comparing a series of bimetallic catalysts having molar ratios varying between 0.07 and 1. The results are grouped together in Tables 11 to 15. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86%; 6.6%; 7.3% | With bis-acetylacetonyl vanadium (II); In aq. phosphate buffer; at 37 - 80℃; for 16.0833h;pH 7; | HMF (100 mM) was added to KPi buffer (500 mM pH 7.0). GOase M35 (103p1 of3.3mg/mL), PaoABC (ipI of 28.9mg/mL) and a metal complex (see Table 4) were added at 37 00 and the pH was continuously adjusted with NaHCO3 for a period of 16 hours. The reaction was heated to 80 00 for 5 minutes and left to cool. The solution containing denatured protein was centrifuged and the supernatant removed and analysed by RP20 HPLC. |
With platinum on carbon; water-d2; oxygen; at 100℃; under 75007.5 Torr; for 4h;Autoclave; | l-b Catalyst screening experiments: Catalyst screening was carried out in a series of single experiments designated "Screen 1 " to "Screen 7". In each single experiment "Screen 1 " to "Screen 7" the organic reactant compound HMF (compound of Formula (II)) was in parts catalytically converted by means of at least one heterogeneous platinum catalyst (see Tables 1 and 2, below) into FDCA (compound of formula (I)). The general experimental procedure for each screening experiment of "Screen 1 " to "Screen 7" was as follows: In a first step, an aqueous reactant mixture was prepared by filling a specific amount of deuterated water (D20, 99,9 atom%, Sigma Aldrich (151882)) and a specific amount of HMF (99+%, Sigma Aldrich (W501808)) into a steel autoclave reactor (inner volume 60 ml or 90 ml, respectively, for exact information see Table 2, below). In case a steel autoclave reactor with an inner volume of 60 ml was used the amounts of HMF and D20 were as follows: D20: 18,0 g, HMF: 2,0 g (corresponding to 15,9 mmol as starting amount of HMF). In case a steel autoclave reactor with an inner volume of 90 ml was used the amounts of HMF and D20 were as follows: D20: 27,0 g, HMF: 3,0 g (corresponding to 23,8 mmol as starting amount of HMF). The starting concentration C0[HMF] of HMF in each aqueous reactant mixture was 10 % by weight, based on the total mass of the aqueous reactant mixture (total mass of deuterated water and HMF). The respective amount of solid heterogeneous catalyst as stated in Table 2 was added to the respective aqueous reactant mixture and, thus, a reaction mixture comprising deuterated water, HMF, and the heterogeneous catalyst was obtained. After adding the specific amount of heterogeneous catalyst the obtained reaction mixture appeared as a deep black slurry, the black color apparently caused by the black solid particles of the heterogeneous catalyst. The molar ratio of substrate to metal of the heterogeneous catalyst (HMF : Pt) was approximately 100 : 1. In a second step, the filled reactor was tightly sealed and pressurized with synthetic air (total pressure 100 bar, Oxygen (as part of the synthetic air) : HMF ratio is approximately 2,25 : 1 ) to obtain conditions for catalytic conversion. The present reaction mixture was heated to a temperature of 100C while stirring at 2000 rpm. After reaching 100C this temperature was maintained for 4 or 20 hours, respectively, (see Table 2 "Reaction time" for exact information) while continuing stirring the heated and pressurized reaction mixture during the reaction time. As a result, a first product suspension comprising FDCA in solid form and the heterogeneous catalyst in solid form was formed. | |
With sodium carbonate; at 100℃; under 30003 Torr; for 0.33h;pH 9.10; | Experimental Conditions The HMF having 95% purity was supplied by Interchim. The method of the invention was implemented in a discontinuous reactor under pressure in a 300 mL autoclave equipped with magnetically driven gas-inducing agitator. Heating was ensured by a heating collar connected to a PID controller (proportional integral derivative). A sampling gate allowed the taking of a sample from the reaction medium via an immersed tube, allowing the monitoring of the progress of the reaction over time. The samples were analysed by HPLC chromatography with two RID detectors (Refractive Index Detector) and PDA (Photodiode array) (ICE-Coragel 107H column, eluting with 10 mM H2SO4). Total Organic Carbon (TOC) in solution was also analysed using a TOC analyser and the value measured was compared with the mass balance (MB) calculated by HPLC. The reactor was charged with 150 mL of 100 mM aqueous HMF solution (2 g), a weight of catalyst corresponding to a HMF/Pt molar ratio of 100, and the desired amount of base in the form of NaOH (comparative example), NaHCO3, KHCO3, Na2CO3 or K2CO3 expressed as base/HMF molar ratio. Air was added at a pressure of 40 bar and the reactor heated to 100 C. The influence of the Bi/Pt ratio was also examined in the presence of Na2CO3 (Na2CO3/HMF=2). The same trend was observed when comparing a series of bimetallic catalysts having molar ratios varying between 0.07 and 1. The results are grouped together in Tables 11 to 15. |
With nicotinamide adenine dinucleotide phosphate; In aq. phosphate buffer; at 37℃; for 2h;pH 7;Enzymatic reaction; | Reaction Conditions: HMF (10mM), KRED (089) (7.5mg), 0.SmL KPi Buffer (pH x), and NOX-1 and NADP as defined in Table 7B were reacted at 37C for 2 hours. A sample was quenched with 1 M HCI, centrifuged and analysed by RP-HPLC. The results from thereaction can be seen in Table 7B.Using lOmol% of NADP (relative to the amount of HMF used) and 5mg NOX-1 provided the highest conversion of HMF to 2,5-FDCA. Reducing the amount of NADP and NOX-1 lead to a lower conversion of HMF to HMFCA. | |
With nicotinamide adenine dinucleotide phosphate; In aq. phosphate buffer; at 37℃; for 2h;pH 7;Enzymatic reaction; | Reaction Conditions: HMF (10mM), KRED (089) (7.5mg), 0.SmL KPi Buffer (pH x), and NOX-1 and NADP as defined in Table 7B were reacted at 37C for 2 hours. A sample was quenched with 1 M HCI, centrifuged and analysed by RP-HPLC. The results from thereaction can be seen in Table 7B.Using lOmol% of NADP (relative to the amount of HMF used) and 5mg NOX-1 provided the highest conversion of HMF to 2,5-FDCA. Reducing the amount of NADP and NOX-1 lead to a lower conversion of HMF to HMFCA. | |
With nicotinamide adenine dinucleotide phosphate; In aq. phosphate buffer; at 37℃; for 2h;pH 7;Enzymatic reaction; | Reaction Conditions: HMF (10mM), KRED (089) (7.5mg), 0.SmL KPi Buffer (pH x), and NOX-1 and NADP as defined in Table 7B were reacted at 37C for 2 hours. A sample was quenched with 1 M HCI, centrifuged and analysed by RP-HPLC. The results from thereaction can be seen in Table 7B.Using lOmol% of NADP (relative to the amount of HMF used) and 5mg NOX-1 provided the highest conversion of HMF to 2,5-FDCA. Reducing the amount of NADP and NOX-1 lead to a lower conversion of HMF to HMFCA. | |
7.67%Chromat.; 18.1%Chromat.; 73.67%Chromat. | With platinum on activated charcoal; sodium hydroxide; In 1-methyl-pyrrolidin-2-one; water; at 80℃; under 16501.7 Torr; for 0.5h;Flow reactor; | 1.) NMP/NaOH/Pt-C/air/22bar/90Ci) Oxidation 1 - inNMP, Pt-c, 17 bar and 80C, NaOHThe starting solution A is prepared by dissolving 5-Hydroxymethylfurfural (99%) in 95gNMP (99,5%, Sigma Aldrich) and 5g deionized water. The starting solution B is a 15%NaOH solution, prepared from 150.41 g NaOH and 850.1 8g deionized water.In a continuous flow plant, solution A and solution B are contacted in a 1/16? t-piece. The flow rate for solution A is 0.08 ml/min, and for solution B 0.06 ml/min. The mixture obtained is directly contacted with 125 ml/min air flow, before the mixture enters the actual reactor. In this case the reactor was a trickle bed reactor using platinum on activated carbon as catalyst. The double jacketed reactor is heated to 80C and provides a residence time of 30 minutes for the given flow rates. The whole system is pressurized to 22 bar with a pressure maintaining valve.The reaction mixture obtained in this step contains no HMF. The oxidation product mixture contains, according to HPLC analysis, FDCA: 73.67%, HMFCA: 18.10%, FFCA: 7.67%, DFF: 0.41% and 0.15% unknown oxidation products. Additionally, a small amount of dark, solid material is yielded using this procedure, leading to a reduced lifetime cycle of the catalyst fixed bed.ii.) Extraction with ethyl acetateThe reaction mixture (20.4m1) collected from the first oxidation step was extracted six times using 20 ml ethyl acetate per cycle to remove NMP. The HPLC chromatogram showed noloss of the acids in the aqueous phase after this procedure. The DFF was transferred completely to the organic phase. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89%; 5% | With sodium hydroxide; In water; at 30℃; under 7500.75 Torr; for 4h; | The Au / Mg (OH)2(1 wt%) catalyst, 2 mmol of 5-hydroxymethylfurfural, NaOH and 10 mL of water were charged into a stainless steel autoclave equipped with a polytetrafluoroethylene liner containing 5-hydroxymethylfurfural: NaOH = 0.01: 1 : 4 (mol: mol: mol).Using automatic temperature control program temperature to the reaction temperature of 30 C, adding 1MPa oxygen, reaction for 4 hours, the reaction process to maintain the same pressure.The reaction product was analyzed by HPLC. |
76%; 12% | With oxygen; potassium hydroxide; In water; at 60℃; under 2250.23 Torr; for 6h;Autoclave; Green chemistry; | Take 0.317 grams of HMF, 2.8 grams of Kappa0Eta (20%), 3 ml of water into the reactor, the reaction vessel containing 10 ml of poly Tetrafluoroethylene-lined high-pressure reactor, take 0.30 g Au / HY (Au2wt%) as a catalyst, the program heated to 60 C, filling 0.3MPa oxygen, the reaction 6 hours, the reaction process continue to add oxygen to ensure that the reaction at constant temperature and constant pressure. reaction product After centrifugation, go to the supernatant and analyze with HPLC. The HMF conversion was 100%, the yield of HMFA was 76% FDA yield of 12%, the reaction results in Table 1. |
26%; 73% | With vanadium(V) oxide; In aq. phosphate buffer; at 37 - 80℃; for 16.0833h;pH 7; | HMF (100 mM) was added to KPi buffer (500 mM pH 7.0). GOase M35 (103p1 of3.3mg/mL), PaoABC (ipI of 28.9mg/mL) and a metal complex (see Table 4) were added at 37 00 and the pH was continuously adjusted with NaHCO3 for a period of 16 hours. The reaction was heated to 80 00 for 5 minutes and left to cool. The solution containing denatured protein was centrifuged and the supernatant removed and analysed by RP20 HPLC. |
60%; 33% | With bis-acetylacetonyl vanadium (II); In aq. phosphate buffer; at 37 - 80℃; for 16.0833h;pH 7; | HMF (100 mM) was added to KPi buffer (500 mM pH 7.0). GOase M35 (103p1 of3.3mg/mL), PaoABC (ipI of 28.9mg/mL) and a metal complex (see Table 4) were added at 37 00 and the pH was continuously adjusted with NaHCO3 for a period of 16 hours. The reaction was heated to 80 00 for 5 minutes and left to cool. The solution containing denatured protein was centrifuged and the supernatant removed and analysed by RP20 HPLC. |
59.4%; 40.6% | With oxygen; sodium hydroxide; In water; at 24.84℃; for 6h; | The HMF oxidation reaction was carried out in a three-neck flask with an attached glass reflux condenser under oxygen flow (Figure 2). In each experiment, the reactor was filled with 1.0mmol of HMF and 5.0mmol of NaOH in 10mL of water. Then, 0.1 g of M/RGO (M = Pd, Rh, Ru, or Pt) was added to the reactor, and oxygen was introduced at a flow rate of 50mL min-1 with stirring under atmosphere pressure. After reaction, the catalyst was filtered off before the high-performance liquid chromatography (HPLC) measurement (AnimexHPX-87H column from Bio-Rad Laboratories Co., Ltd., 0.5mL min-1 flow rate, 10nM H2SO4 solvent, 323 K). The products were analyzed using a refractive index (RI) detector. |
39%; 45% | With oxygen; sodium hydroxide; In water; at 60℃; under 2250.23 Torr; for 6h;Autoclave; Green chemistry; | Take 0.317 grams of HMF, 2 grams of NaOH (20%), 3 ml of water into the reactor, the reaction vessel was equipped with a 10 ml polytetrafluoroethylene lined high pressure reactor, 0.30 g Au / H x Na 1-x Y (Au 2 wt%) as a catalyst, after the program is warmed to 60 C, filled with 0.3MPa oxygen, reaction for 6 hours, during the reaction, oxygen is continuously added, ensure that the reaction is carried out at constant temperature and pressure. The reaction product was centrifuged to the supernatant, analytical using HPLC. after testing, HMF conversion rate of raw materials is 100% HMFA yield of 39%, FDA yield of 45%, the reaction results in Table 1. |
With oxygen; sodium hydroxide; In water; at 60℃; under 7500.75 Torr; for 4h;Autoclave; | The oxidation of 5-hydroxymethyl-2-furfural (HMF) was carriedout using an autoclave (Parr Instruments) reactor of 300 mLcapacity and equipped with a mechanical stirrer (0-1200 rpm) andprovision for measurement of temperature and pressure. The reactorwas charged with an aqueous solution (25 mL distilled water)containing the appropriate amount of 5-hydroxymethyl-2-furfural,base (NaOH) and catalyst (HMF/metal molar ratio = 100). The autoclavewas purged 3 times with O2 (5 bar) and then pressurized at10 bar. If not differently indicated, the temperature was increasedto 60 C and the reaction mixture was stirred at ca. 1000 rpm for4 h. At the end of the reaction, the reactor was cooled to room temperatureand the solution was filtered. Then, 4 mL of water wasadded to an aliquot of the reaction solution (1 mL) before analysiswith an Agilent Infinity 1200 liquid chromatograph equippedwith a Aminex HPX 87-H 300 mm×7.8 mm column using a0.005 M H2SO4 solution as the mobile phase. Identification of compoundswas achieved by calibration using reference commercialsamples. | |
86.39%Chromat.; 9.2%Chromat. | With disodium hydrogenphosphate; copper oxides/alumina; at 90℃; under 13501.4 Torr; for 0.166667h; | i) Oxidation 1 - inNMP, Pt-C, 17 bar and 80C, Na2HPO4The process was carried out in a comparable, scaled up continouos lab-plant setup as used inthe examples above. Starting solution A was prepared by mixing 65.6g HMF and 400.OgNMP; solution B was a 15% solution of sodium phosphate, prepared by mixing 150.OgNa2HPO4 and 850.Og of deionized water.The flow rates used in this trial were 2.86m1/min solution A, 2.14m1/min solution B and 250.Onml/min for air. Further processing parameters were 10 minutes residence time at 90C and 18 bar. The catalyst used was copper oxide on aluminium oxide.The oxidation product mixture obtained from this trial contains, according to HPLC analysis, FDCA: 9.20%, HMFCA: 86.39%, FFCA: 0.13%, DFF: 0.36% and 2.82% of HMF. About 1% are unidentified side products.ii.) Extraction with ethyl acetateNMP extraction was carried out with ethylacetate. 50m1 reaction mixture was extracted six times with 40m1 ethyl acetate in each cycle.FDCA, HMFCA and FFCA remained completely in the water phase. Also a small amount of HMF was found in the water phase (0.5% according to HPLC). DFF completely went into the organic phase and was discarded. |
21%Chromat.; 74%Chromat. | With oxygen; sodium hydrogencarbonate; In water; under 7500.75 Torr;Autoclave; Heating; | HMF (0.2 mmol), NaHCO3 (0.4 mmol), and the catalyst (25 mg) were added to a 12 mL stainless steel autoclave containing 8 mL of deionized water. The autoclave was heated to 80 C and pressurized with O2 (10 bar) under vigorous stirring (900 rpm). During the reaction, 0.1 mL sample was taken at regular intervals of about 0.5-1 hours, filtered with 0.2 mum PTFE filters, diluted with water and analyzed using a high-performance liquid chromatograph (Shimadzu LC-20AD equipped a Bio-Rad Aminex HPX-87H column). Sulfuric acid (5 mM) at 333 Kwith a flow rate of 0.55 mL min-1 was used as an eluent. Each catalyst was tested at least twice to verify the reproducibility. The reproducibility of conversion levels and yields were within 5%. |
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. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With oxygen; In water; at 90℃; under 6000.6 Torr; for 24h;Autoclave;Catalytic behavior; | General procedure: As a general procedure, the oxidation of HMF was performed under a vigorous stirring in a stainless steel autoclave in the presence of molecular O2 (8 bars), 1 mmole of substrate (HMF), 10 mLsolvent, 0.05 g of catalyst and a temperature of 90C for 24 h. All the changes of reaction parameters: temperature, pressure, solvent, amount of the catalysts or reaction time were notified inthe text. After ending the HMF oxidation and filtering off the catalyst, the mother liquor was diluted 5 times and the products were analyzed by high performance liquid chromatography (HPLC), ona Thermo Scientific Accela 600 device equipped with a UV-vis detector and a Rezex-ROA H+column. 5-Hydroxymethyl furfural(HMF), diformyl furan (DFF), 5-hydroxymethyl-2-furancarboxylicacid (HMFCA), 5-formyl-2-furancarboxylic acid (FFCA) and 2,5-furandicarboxylic acid (FDCA) from Sigma-Aldrich were used as standards. The maximum of absorption for FDCA and HMFCA corresponded to = 260 nm while for HMF, FFCA and DFF to = 285 nm. The mobile phase consisted of 0.05 N H2SO4, at a flow rate of 0.5 mL/min, and the analysis was carried out at 40C, using a two channels detection (260 nm and 285 nm) and an injection volume of 3 L. A carbon mass balance of 98-99% was obtained for all the performed reactions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dihydrogen peroxide; In water; at 25℃; under 760.051 Torr; for 24h;Green chemistry; | The catalytic activity performance of the metal Salen complexessupported on SBA-15 (Co/SBA-15, Fe/SBA-15 and Cu Salen/SBA-15) inthe oxidation of HMF were evaluated. The HMF oxidation reaction wascarried out in an aqueous system at neutral pH (the pH was not adjusted)using H2O2 as oxidant agent. The reaction was performed undermild conditions (aqueous media, neutral pH, atmospheric temperatureand pressure). The system consisted of a 125 mL round-bottom flaskwith a refrigerant column to avoid the HMF volatilization. All testswere performed with an initial substrate HMF 0.4 mM [8], 50 mL reactionvolume, H2O2 30 w/Vpercent (100 muL) as oxidant agent and using0.05 g of catalyst. Aliquots of 500 muL were taken during 24 h, fromwhich 75 muL were injected in the chromatograph for their analysis. Thesamples were taken in short periods of time at the early minutes of thereaction, and in a longer period as the reaction advanced in order tohave enough information for the kinetic study. The reaction mixturewas stirred at a constant 500 rpm. Tests were done at low temperatures25, 30 and 40 °C to know how the temperature affects the reaction.Although the catalyst can be used at higher moderate temperatures,40 °C level was selected as the maximum temperature to avoid H2O2degradation. Temperature levels were recorded with thermocouplespreviously connected to a temperature monitoring program using theLabview System Design Software. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With Sn-Beta molecular sieve; In 1,4-dioxane; at 190℃; under 52476.2 Torr; for 12h;High pressure; Autoclave; | A series of experiments were conducted to test the variables related to the conversion of 5-hydroxymethyl-2-furoic acid (HMFA) to 4-hydroxymethylbenzoic acid (HMBA). This transformation is a key intermediate step in the transformation of hydroxymethyl furfural (HMF) to (purified) terephthalic acid (PTA), according to: The results are shown in Tables 8 and FIG. 9. Reaction conditions for FIG. 9 were 1000 psig ethylene at 190° C., 10 g of a 100 mM dioxane solution of HFMA, with 100 mg Sn-Beta catalyst. [TABLE-US-00008] TABLE 8 All reactions were run at 850-1000 psig total pressure, 190° C., 10 g of a 100 mM HFMA solution, 100 mg catalyst. HMFA HMBA HMBA Entry Catalyst Solvent Time (hr) Converson (percent) Yield (percent) Selectivity (percent) 1 Sn-Beta dioxane 0.5 18 4 22 2 Sn-Beta dioxane 2 36 11 31 3 Sn-Beta dioxane 4 57 15 26 4 Sn-Beta dioxane 6 61 19 31 5 Sn-Beta dioxane 12 76 21 28 dioxane/water 6 Sn-Beta 1:1 v/v 0.5 94 0 0 7 Sn-Beta THF+ 0.5 35 2 6 8 Zr-Beta dioxane 6 87 9 10 9 None dioxane 2 5 0 0 10 None dioxane 6 21 0 0 11 Si-Beta dioxane 2 20 0 0 12 Si-Beta dioxane 6 56 13 Si-MFI dioxane 2 25 0 0 |
19% | In 1,4-dioxane; at 20 - 190℃; under 27752.8 - 52505.3 Torr; for 6h;Inert atmosphere; | General procedure: Experiments were carried out in a 50-mL high pressure stainless steel batch reactor (Parr Series 4590) equipped with a magnetic stirrer and heater. The reactor setup allowed for ethylene gas(Matheson, 99.995percent purity) or helium to be charged to the reactor. In a typical experiment, 100 mg of catalyst and 10 g of a 0.1 M diene solution in dioxane (Sigma-Aldrich, 99.8percent) was loaded into the reactor. The magnetic stirrer was operated at 200 rpm and the head space of the reactor was purged with helium gas with a fill/vent cycle (10×). Next, the reactor was pressurized to 37 bar (room temperature) with ethylene gas, the inlet valve was closed, and the reaction was performed in batch operation. The reactor was heated to 190 °C within 15 min while the pressure increased autogenously to 70 bar. At the end of the reaction time, the reactor was allowed to cool to room temperature and the reactor gases were vented. The product was then collected for analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60.26%; 5.9%; 25.45% | With 10% Pt/activated carbon; oxygen; sodium carbonate; In water; at 100℃; under 7500.75 Torr; | General procedure: Oxidation of HMF to obtain FFCA Reactant HMF (5 mg/mL) in wateEach CatCart (70x4 mm) was filled first with 20 mg Celite 545 and then 280 mg 10% Pt/C were added. Fresh CatCart was used every time, when the system pressure was changed. Before each screening series, the entire reaction line was purged with H20 (HPLC Grade), the Teflon frit of the system valve was replaced and ThalesNano X-Cube System Self-Test was performed. The initial system stabilization was always achieved using H20 (HPLC Grade) and when the reaction parameters remained constant, the pumping of the reaction solution began, then the system was allowed to stabilize and equilibrate at the new conditions for 10 min and two samples of 1 mL each were then collected. Then the temperature was increased and the system was again allowed to stabilize (the same procedure was applied for all temperatures within the experimental series). In all the cases 40 bar difference between the system pressure and the external gas pressure was provided for good system stability. At a temperature of 100C, an ideal compromise between substrate conversion and product selectivity regarding the product FFCA was achieved. r.Base additive Na2C03 (2 equiv. based on HMF, premixed with HMF solution) Catalyst 10% Pt/C (280 mg 10% Pt/C + 20 mg Celite 545) Oxidant synthetic air. Reactor System ThalesNano X-Cube, pump flow rate: 0.5mL/min, residence time: 2 min Table 6 below there is set out a summary of the results from HMF-FFCA oxidation screening in flow using the following parameters: 1 mL HMF (5 mg/mL), 2 equiv. Na2C03, H20, 10% Pt/C, 80 bar Air, 60-160C, 0.5 mL/min, 2 min. Table 6 it is evident that under the given conditions a high FFCA yield and a high FFCA selectivity may be achieved. The yield in average is increasing with increasing temperature up to approx. 120C. A temperature yielding FFCA in a range of approx. 45 to 60% related to the starting material HMF is in the range from 60C to 160C, in particular from 80 to 140C, e.g. 100 to 120C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80.65%; 20.15% | With 10% Pt/activated carbon; oxygen; sodium hydroxide; In water; at 120℃; under 60006 Torr; | General procedure: Oxidation of HMF to obtain HMFCA Reactant HMF (5 mg/mL) in water .Catalyst K-OMS-2 (263.4 mg K-OMS-2 + 50 mg Celite 545) prepared according to Angew. Chem. Int. Ed. 2012, 51, 544-547. Oxidant oxygen or synthetic air, Reactor System ThalesNano X-Cube, pump flow rate: 0.5 mL/min, residence time:2/4 min (0108) Each CatCart (70x4 mm) was filled first with 50 mg Celite 545 and then 263.4 mg K-OMS-2 were added. Fresh CatCart was used every time, when the system pressure was changed. Before each screening series, the entire reaction line was purged with H2O (HPLC Grade), the Teflon frit of the system valve was replaced and ThalesNano X-Cube System Self-Test was performed. The initial system stabilization was always achieved using H2O (HPLC Grade) and when the reaction parameters remained constant, the pumping of the reaction solution began, then the system was allowed to stabilize and equilibrate at the new conditions for 10 min and two samples of 1 mL each were then collected. Then the temperature was increased and the system was again allowed to stabilize (the same procedure was applied for all temperatures within the experimental series). In all the cases 40 bar difference between the system pressure and the external gas pressure was provided for good system stability. The experiments were carried out using one or two catalyst cartridges offering ideal reaction conditions to produce DFF in good yield (-70%) requiring only 10 bar of oxygen partial pressure.To reduce the hazardous potential of pure oxygen, the reactions were also performed substituting oxygen with synthetic air. However, to reach similar yields, the pressure had to be increased to 80 bar of compressed air. In Table 2 below there is set out a summary of the results from HMF-DFF oxidation screening in flow using the following parameters:1 mL HMF (5 mg/mL), H20, K-OMS-2/Celite, 10 bar 02, 100-160C, 0.5 mL/min, 2 (using one catalyst cartridge). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With triethylamine; In diethyl ether; at 20℃; for 14h;Cooling with ice; | 15.64 g of HMFCA (104 mmol), 300 mL of ethyl ether, and 20.24 g of triethylamine (NEt3, 0.2 mol) were added into a twin neck bottle (250 mL) and stirred to be completely dissolved. 11.78 mL of acetic anhydride (124.8 mmol) was then slowly added into the twin neck bottle in an ice bath, and the ice bath was then removed after the addition of acetic anhydride for slowly warming up the reaction to room temperature. The reaction was continued at room temperature for 14 hours, and 3M HCl was then added into the twin neck bottle to acidify the solution in the twin neck bottle. The acidified solution was extracted by de-ionized water three times, and the organic phase of the extractions was collected and then dried by anhydrous MgSO4. The organic phase was concentrated to obtain a yellow solid. The yellow solid was washed by n-hexane and then dried to obtain 17.84 g of 5-(acetoxymethyl)-2-furoic acid product (yield=93percent), as shown in Formula 1 with R1 being methyl group. The above reaction is shown in Formula 9. The product of Formula 9 had NMR spectra as below: 1H NMR (400 M Hz, CDCl3): 7.23 (d, 1H, J=3.5 Hz), 6.51 (d, 1H, J=3.5 Hz), 5.07 (s, 2H), 2.07 (s, 3H). 13C NMR (100 M Hz, CDCl3): 170.6, 162.5, 154.4, 144.0, 120.5, 112.5, 57.8, 20.7. The product of Formula 9 had mass spectrum as below: HRMS (EI, m/z): calcd. for C8H8O5 184.15. found 184.11 (M+). |
93% | With triethylamine; In diethyl ether; at 20℃; for 14h;Cooling with ice; | 15.64 g (104 mmol) of HMFCA,300 mL of diethyl ether,Was added with 20.24 g (0.2 mol) of triethylamineAfter the 500 mL double-necked flask,Stirring until complete dissolution.A solution of 11.78 mL (124.8 mmol)Of acetic anhydride (Acetic anhydride) into the double-necked flask,The ice bath was then removed and the reaction temperature was slowly returned to room temperature,Followed by reaction at room temperature for 14 hours.After completion of the reaction, 3M HCl was added to the flask,So that the solution becomes acidic.The acidic solution was then extracted three times with deionized water and the organic layer was taken,The organic layer was again removed with anhydrous magnesium sulfate.Concentration of the organic layer gave a yellow solid,The yellow solid was washed with n-hexane and the solid was dried,To give 17.84 g of the (2-furoic acid-5-hydroxymethyl) acetate product (as in Formula 1, R1 is methyl) in 93percent yield. The above reaction is shown in Formula 9 below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With triethylamine; In dichloromethane; at 20℃; for 16h;Cooling with ice; | 15.64 g of HMFCA (104 mmol), 300 mL of ethyl ether, and 20.24 g of triethylamine (NEt3, 0.2 mol) were added into a twin neck bottle (250 mL) and stirred to be completely dissolved. 11.78 mL of acetic anhydride (124.8 mmol) was then slowly added into the twin neck bottle in an ice bath, and the ice bath was then removed after the addition of acetic anhydride for slowly warming up the reaction to room temperature. The reaction was continued at room temperature for 14 hours, and 3M HCl was then added into the twin neck bottle to acidify the solution in the twin neck bottle. The acidified solution was extracted by de-ionized water three times, and the organic phase of the extractions was collected and then dried by anhydrous MgSO4. The organic phase was concentrated to obtain a yellow solid. The yellow solid was washed by n-hexane and then dried to obtain 17.84 g of 5-(acetoxymethyl)-2-furoic acid product (yield=93percent), as shown in Formula 1 with R1 being methyl group. The above reaction is shown in Formula 9. The product of Formula 9 had NMR spectra as below: 1H NMR (400 M Hz, CDCl3): 7.23 (d, 1H, J=3.5 Hz), 6.51 (d, 1H, J=3.5 Hz), 5.07 (s, 2H), 2.07 (s, 3H). 13C NMR (100 M Hz, CDCl3): 170.6, 162.5, 154.4, 144.0, 120.5, 112.5, 57.8, 20.7. The product of Formula 9 had mass spectrum as below: HRMS (EI, m/z): calcd. for C8H8O5 184.15. found 184.11 (M+). |
76% | With triethylamine; In dichloromethane; at 20℃; for 16h;Cooling with ice; | 9.70 g (69 mmol) of HMFCA,100 mL of dichloromethane,Was added with 10.47 g (0.2 mol) of triethylamineAfter 200 mL double neck flask,Stirring until complete dissolution.10.78 g (82.8 mmol) of Propionic anhydride was slowly added dropwise to the mixture under ice-In a double-necked flask,The ice bath was then removed and the reaction temperature was slowly returned to room temperature,Followed by reaction at room temperature for 16 hours.After completion of the reaction, 3M HCl was added to the flask,So that the solution becomes acidic.The acidic solution was then extracted three times with deionized water and the organic layer was taken,The organic layer was again removed with anhydrous magnesium sulfate.The organic layer was concentrated in vacuo at 80 & lt; 0 &And then placed in a refrigerator overnight to give a yellow solid,The yellow solid was washed with n-hexane and the solid was dried,(2-furoic acid-5-hydroxymethyl) propionic acid ester product (as in formula 1, R1 is ethyl),The yield was 76percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With hydrogen bromide; In water; acetic acid; at 120℃; under 1551.49 Torr; for 0.666667h;Flow reactor; | In this example reactions were performed under flow conditions using a flow reactor system (i.e. as continuous flow reactions). A stock solution of DHG was prepared by dissolving DHG in AcOH/H2O (v/v, 80/20) containing 1.5 M of HBr, to a final concentration of 200 mM. This solution was kept at ambient temperature (about 20° C.) and was passed through the reactor that was heated at either 100° C. or 120° C., at a pressure of 30 psi to keep solvents from evaporating. The reactor consisted of a glass column packed with 3 mL of sand. The flow rate was 0.05 mL/min, thus allowing a residence time in the column of about 40 min. Analysis of various samples at each temperature revealed that the reaction at 120° C. gave 50-70percent yield of HFCA while the reaction at 100° C. produced 25-30percent yield to product in addition to unreacted DHG (15percent). |
With trifluoroacetic acid; at 60℃; for 4h; | 10056] 2-keto-3-deoxygluconic acid was dissolved in water and acetic acid by placing 8.45 mg of 2-keto-3- deoxygluconic acid in a very small sample vial. To this was added 120 ul of water and 120 ul of acetic acid, and this was mixed to dissolve the 2-keto-3-deoxygluconic acid. This stock solution was used for each reaction according to Table 2. In each case, 20 ul of the 2-keto-3-deoxygluconic acid solution was added first to a vial along with a mini stir bar. The remaining reagents were added in the order shown in Table 2 (left to right) and mixed by stirring on a stirplate. Each vial was capped and heated to 60° C. with stirring. Afier the reaction time, the vial contents were cooled and analyzed for 5-hydroxymethyl-2-throic acid by HPLC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; In water; at 80℃; for 18h; | In a separate experiment, 5 mL of an ethanol/water mixture (v/v, 9/1) containing 1.5 M of H2SO4 and 200 mM of purified DHG was placed in two vials. One vial was incubated with stirring at 80 C. and the other at 100 C. for 18 hours. HPLC analysis of the reactions confirmed the formation of HFCA at about 70% molar yield for the 80 C. reaction and about 55% yield for the reaction at 100 C. (and >95% conversion). The previous yield includes both HFCA free acid and the HFCA-ethyl ester (about 1/1 ratio in each reaction). The product identity and quantification was done by comparison with authentic standards by HPLC. |
Tags: 6338-41-6 synthesis path| 6338-41-6 SDS| 6338-41-6 COA| 6338-41-6 purity| 6338-41-6 application| 6338-41-6 NMR| 6338-41-6 COA| 6338-41-6 structure
[ 6270-57-1 ]
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H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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