Name: 5343-92-0|1,2-Pentanediol|98%
Brand: Ambeed
SKU: A101958
Price: 5.0 USD
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1
[ 98-00-0 ]
[ 5343-92-0 ]

Yield	Reaction Conditions	Operation in experiment
41.2%	With hydrogen; at 160℃; under 60006 Torr; for 10h;Autoclave;	General procedure: Example 20 alcohol selected hydrogenolysis reaction under different conditionsFurfuryl alcohol in the hydrogenolysis reaction volume of 100mL autoclave, add 40g of an aqueous solution of a certain concentration of furfuryl alcohol, 0.4 ~ 4.0g activated catalyst 13, three replaced by hydrogen, pressurized to 4 ~ 10MPa, was stirred at 130 ~ 180 reaction 2 ~ 12h. The results are shown in Table 2.
	With hydrogen; at 190℃; under 3000.3 Torr; for 4.91667h;Inert atmosphere; Gas phase;	3 g of a granulated heterogeneous catalyst comprising (i) platinum and (ii) Al2O3 were disposed in the tubular reactor of a continuous gas-phase apparatus. The concentration of (i) platinum is 10 wt. %, based on the total weight of all the constituents of the catalyst. The apparatus comprises a saturator filled with furfuryl alcohol (FA), inlet pipes for hydrogen and an inert gas, gas metering units, a tubular reactor and a condensation unit. [0258] The volume flow of furfuryl alcohol was controlled via the temperature of the saturator and the metering of the hydrogen stream and optionally an additional inert gas stream. The gaseous mixture comprising furfuryl alcohol and hydrogen was passed through the tubular reactor, and organic components as well as water from the product gas stream were converted into the liquid state of aggregation in a condensation unit. Samples were taken at regular intervals and the composition of the condensate was analyzed by means of various analytical methods. The reaction conditions and the conversion X based on furfuryl alcohol and the contents Y (as defined above) of 1-hydroxy-2-pentanone and 1,2-pentanediol in the total amount of the products formed from furfuryl alcohol are given in Table 1.
	With ruthenium on aluminium oxide; hydrogen; sodium carbonate; In water; at 200℃; under 75007.5 Torr; for 0.5h;pH 7.9;Autoclave;	To confirm this pH effect, a further corresponding experiment in which sodium acetate was used as base was carried out (Examples 9 and 10). Specifically, 64.4 ml of water, 1.0 g of the 5% Ru/Al2O3 catalyst A11 and 100 mg of Na2CO3 (Example 9) or 5 g of sodium acetate (Example 10) were placed in the autoclave. The reaction apparatus was closed and a stirring speed of 1000 rpm was set. The reactor was flushed three times with 10 bar of argon and once with 10 bar of hydrogen. The hydrogen pressure was subsequently set so that the pressure expected on reaching the reaction temperature would be 10-20 bar below the reaction pressure of 100 bar. The contents of the reactor were heated to the reaction temperature over a period of 30-60 minutes. The reaction temperature was 200 C. As soon as this had been reached, 40 g of furfuryl alcohol were quickly introduced via the supply tank. Further hydrogen was continually introduced via the gas tank so as to keep the reaction pressure constant. For sampling, the offtake line was flushed beforehand with 1-2 ml of reaction mixture and 0.5-1 ml of sample was then taken. When the hydrogen pressure in the gas tank no longer decreased, which was the case after 30 minutes, the heating jacket was removed and the reactor was cooled in air to room temperature. After the reaction mixture had been taken off, the reactor was thoroughly cleaned and baked at 150 C. under 30 bar of argon for 60 minutes.

With hydrogen; In isopropyl alcohol; at 100℃; under 45004.5 Torr; for 8h;

0.5 g of furfuryl alcohol, 4.5 g of isopropanol,Add 0.25g of 10% Cu/MnCO3 to the 25mL reactor respectively;The reactor was closed, hydrogen was introduced into the reactor, and it was vented.Repeatedly to exchange the air in the kettle,Then, the kettle was filled with hydrogen gas to a pressure of 6 MPa, and the reaction vessel was closed.Turn on magnetic stirring,Warming up to 100 C, 120 C, 140 C, 160 C,180 C and react for 8 h; during the reaction, when the hydrogen pressure is reduced by 0.5 MPa,The reactor was charged with hydrogen gas in time to maintain the reaction pressure constant; after the reaction was completed, the reaction vessel was cooled to room temperature, and the reaction solution was suction filtered to conduct gas chromatography analysis.Sterol conversion rate andThe 1,2-pentanediol selectivity is shown in Table 4.

Reference： [1]Patent: CN104370702,2016,B .Location in patent: Paragraph 0063; 0064; 0065; 0066; 0067
[2]Journal of the American Chemical Society,1949,vol. 71,p. 415,417
[3]Journal of the American Chemical Society,1931,vol. 53,p. 1093
Journal of the American Chemical Society,1932,vol. 54,p. 4680
[4]Green Chemistry,2012,vol. 14,p. 3402 - 3409
[5]Green Chemistry,2012,vol. 14,p. 3402 - 3409
[6]Green Chemistry,2012,vol. 14,p. 3402 - 3409
[7]Patent: US2014/66666,2014,A1 .Location in patent: Paragraph 0257-0259
[8]Patent: US2014/243562,2014,A1 .Location in patent: Paragraph 0226
[9]Patent: CN108911949,2018,A .Location in patent: Paragraph 0065; 0070; 0075; 0076; 0078 0080; 0085; 0086

2
[ 109-67-1 ]
[ 5343-92-0 ]

Yield	Reaction Conditions	Operation in experiment
278.8 g	With tetramethoxytitanium; dihydrogen peroxide; In tetrahydrofuran; water; at 10 - 20℃; for 10.5h;	Add 200 mL of tetrahydrofuran and 3.0 g of tetramethyl titanate to an atmospheric reactor equipped with heating, temperature control, magnetic stirring, constant pressure dropping, and refluxing. Stir it slowly and mix it evenly. Under slow stirring conditions 200 g of n-pentene was added dropwise using a constant pressure dropping funnel; under a constant pressure dropping funnel, 150 g of a 50% strength aqueous hydrogen peroxide solution was slowly added dropwise at a constant pressure dropping separatory funnel at 10 oC for 30 minutes. The reaction was continued for 10 h at 20 oC; then 400 g of water was added to the reactor and then reacted at 50 oC for 15 h; 1 g of manganese dioxide was added to the reactor, and the solvent methanol was distilled to remove water and filtered. Obtained 292.0 g of 1,2 pentanediol crude product with a purity of 98.0 % (standard method for internal standard of gas chromatography, 1,2-propanediol internal standard), and distilled under vacuum to collect about 80 oC at 5 mmHg. The fractions yielded 278.8 g of a 1,2-pentanediol product having a purity of 99.7% (gas chromatographic, internal standard calibration curve for an internal standard of 1,2-propanediol).

Reference： [1]Journal of the American Chemical Society,1954,vol. 76,p. 3472
[2]Bulletin de la Societe Chimique de France,1968,p. 2962 - 2964
[3]Journal of the Chemical Society. Perkin transactions II,1978,p. 839 - 848
[4]Angewandte Chemie - International Edition,2001,vol. 40,p. 586 - 589
[5]Patent: CN104926600,2018,B .Location in patent: Paragraph 0057; 0058; 0059; 0060; 0061; 0062; 0063-0082

3
[ 136185-61-0 ]
[ 5343-92-0 ]
[ 3174-67-2 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 6206 - 6209

4
[ 5343-92-0 ]
[ 58479-61-1 ]
[ 139167-16-1 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 1707 - 1712

5
[ 5343-92-0 ]
[ 2632-10-2 ]
2-bromomethyl-2-(3,4-dichloro-phenyl)-4-propyl-[1,3]dioxolane [ No CAS ]

Reference： [1]Journal of agricultural and food chemistry,2002,vol. 50,p. 3486 - 3490

6
[ 110-87-2 ]
[ 5343-92-0 ]
C₁₅H₂₈O₄ [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 7975 - 7978

7
[ 5343-92-0 ]
[ 165108-64-5 ]

Yield	Reaction Conditions	Operation in experiment
85.1%		Prepare 55g sodium hydrogen (2.3mol) under nitrogen protectionAnd a suspension of 200 ml of tetrahydrofuran,Slowly add <strong>[5343-92-0]1,2-pentanediol</strong> 125g (1.2mol) under micro refluxa mixture with 200 ml of tetrahydrofuran,There is a constant flow of gas to produce a discharge system.No gas is produced after stirring for 10 hours.A sodium salt suspension is obtained for use.After replacing the air in the 2000 mL autoclave with nitrogen,After adding 300 ml of tetrahydrofuran under nitrogen protection,Maintain internal temperature -10 ~ 0 C into the sulfuryl fluoride 151.6g (1.48 mol),The sodium salt suspension was continuously added to the kettle, and the reaction was kept for 2 hours.After the reaction, the nitrogen blowing system removes excess sulfuryl fluoride gas.The reaction solution was filtered and then decomposed to dryness under reduced pressure.The crude product was added with 300 ml of dichloromethane, 15-crown-5 0.1 g,18-crown-6 0.1g, refluxing for 1h,After filtration, the product was dried (162.7 g) (two-step yield 85.1%)
71.9%		In a 1000 mL reaction flask, add 67 g of <strong>[5343-92-0]1,2-pentanediol</strong>, 600 mL of toluene, 149 g of triethylamine, 40 g of calcium oxide, and 4.3 g of tetra-n-butylammonium hydrogen sulfate. Maintain the internal temperature at 0 to 5C, and slowly add the mixture under stirring. Sulfuryl fluoride gas 72g was reacted for 2 hours, nitrogen gas was blown for 1 hour, filtered, and the filtrate was desolvated under reduced pressure to obtain a solid crude product. Toluene 200 mL, 15-crown-5 0.05 g, 18-crown-60.05 g was heated and refluxed to dissolve. Slowly to room temperature, filtration, drying product 77g, yield 71.9%.

Reference： [1]Patent: CN108409708,2018,A .Location in patent: Paragraph 0078; 0079; 0080; 0081
[2]Patent: CN107629032,2018,A .Location in patent: Paragraph 0082; 0083; 0084; 0085
[3]Journal of Medicinal Chemistry,2004,vol. 47,p. 2511 - 2522

8
[ 5343-92-0 ]
[ 105-58-8 ]
4-propyl-1,3-dioxolan-2-one [ No CAS ]

Reference： [1]Chemical Communications,2004,p. 734 - 735

9
[ 617-31-2 ]
[ 5343-92-0 ]

Yield	Reaction Conditions	Operation in experiment
72.1%	With hydrogen;water-moist catalyst (coating: 8percent Ru and 1percent Re); In water; at 190℃; under 187519 Torr; for 14h;Product distribution / selectivity;	A 1 l autoclave was charged with a suspension consisting of 400 g of water and 5.0 g of water-moist catalyst (coating: 8% Ru and 1% Re) and prehydrogenated at 190 C. and 250 bar of hydrogen for the period of 2 hours.Subsequently, after cooling and decompression, 156.0 g of 2-hydroxypentanoic acid-which still contains a proportion of approx. 10% of butyraldehyde cyanohydrin-were added to the catalyst suspension and the reaction mixture was subsequently hydrogenated at a reaction temperature of 190 C. and a hydrogen pressure of 250 bar over the course of 14 hours until the hydrogen uptake had ended.After catalyst removal, the conversion of the hydrogenation was determined to be 96% by acidimetric titration; the further distillative workup of the filtrate was effected analogously to Example 1.This afforded 89.2 g of 1,2-pentanediol with a purity of 98.1%; this corresponds-based on 2-hydroxypentanoic acid used-to a yield of 72.1% of theory.; To this end, a 1 l autoclave was charged with a suspension consisting of 400 g of water and 5.0 g of water-moist catalyst (coating: 8% Ru and 1% Re) and prehydrogenated at 190 C. and 250 bar of hydrogen for a period of 2 hours.Subsequently, after cooling and decompression, the crude 2-hydroxypentanoic acid was added to the catalyst suspension and the reaction mixture was subsequently hydrogenated at a reaction temperature of 190 C. and a hydrogen pressure of 250 bar over the course of 14 hours until the hydrogen uptake had ended.After catalyst removal, the conversion of the hydrogenation was determined to be 96% in the filtrate by acidimetric titration; the further distillative workup of the filtrate was effected analogously to Example 1.This afforded 68.6 g of 1,2-pentanediol with a purity of 98.1%; this corresponds-based on butyraldehyde used-to a yield of 66.0% of theory.
64.6%	With hydrogen;3% Ru 2%Re/C; In water; at 190℃; under 187519 Torr; for 8h;Product distribution / selectivity;	29.5 g (0.25 mol) of the 2-hydroxypentanoic acid thus obtained were dissolved in 470.5 g of water and this mixture, after adding 5.0 of water-moist catalyst on activated carbon (coating: 3% Ru and 2% Re), was hydrogenated exhaustively in a 11 autoclave at a hydrogen pressure of 250 bar and at a reaction temperature of 190 C. within 8 hours. After the end of the reaction and cooling, the catalyst was filtered off and the filtrate was freed of water by distillation under reduced pressure using a rotary evaporator with a column attachment. The resulting residue was then, using a short-path evaporator with a short column, subjected to a fractional high-vacuum distillation. This afforded 16.8 g of 1,2-pentanediol with a GC purity (after silylation) of 98.7%, which corresponds to a yield of 64.6% of theory based on 2-hydroxypentanoic acid used.

Reference： [1]Patent: US2008/64905,2008,A1 .Location in patent: Page/Page column 3-4
[2]Patent: US2008/64905,2008,A1 .Location in patent: Page/Page column 3

10
[ 5699-72-9 ]
[ 5343-92-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;nickel; pyrographite; In ethanol; water;	EXAMPLE 6 40.0 grams (0.4 mole) of butyraldehyde cyanohydrin were dissolved in 250 ml of water and 60 ml of ethanol and there were added 200 ml of an acid ion exchanger (Lewatit S100). After addition of 3 grams of a 10% Pd/activated carbon catalyst hydrogenation was carried out under stirring at 15 C. and a H2 pressure of 1.2 bar until take up of 0.4 mole of hydrogen. Then there were added 3 grams of an activated nickel catalyst and the temperature increased to 50 C. and the hydrogen pressure to 15 bar and hydrogenation continued until the end of the hydrogen take up. Then the catalysts and ion exchanger were filtered off. The 1,2-pentanediol was separated off by distillation. The main part passed over at 53 to 55 C./0.06 mbar. Yield of 1,2-pentanediol: 31.17 grams, corresponding to 77% of theory.
	With hydrogenchloride; hydrogen;pyrographite; In ethanol; water;	EXAMPLE 8 24.8 grams (0.25 mole) of butyraldehyde cyanohydrin were dissolved in 180 ml of water and 20 ml of ethanol and treated with 25 grams of HCl. After addition of 1.25 grams of a 10% Pd/activated carbon catalyst hydrogenation was carried out with stirring at 25 C. and 9 bar hydrogen pressure until take up of 0.25 mole of hydrogen. Then there were added 2.0 grams of an activated Ni catalyst, the temperature increased to 35 C. and the hydrogen pressure increased to 20 bar and hydrogenation continued until the end of hydrogen take up. The solution was concentrated on a rotary evaporator and distilled. The main portion (19.1 grams) passed over at 53 to 55 C./0.06 mbar. Yield of 1,2-pentanediol: 73.3% of theory.
	With hydrogen; In ethanol; water;	EXAMPLE 7 50.0 grams (0.5 mole) of butyraldehyde cyanohydrin were dissolved in 100 ml of ethanol and 350 ml of water and 300 ml of an acid ion exchanger (Lewatit S100) added. After addition of 4 grams of an activated Ni catalyst hydrogenation was carried out under stirring at 15 C. and a hydrogen pressure of 1.2 bar until take up of 0.5 mole of hydrogen. Then the hydrogen pressure was increased to 15 bar and the temperature to 50 C. and hydrogenation continued until the end of the hydrogen taken up. The catalyst and ion exchanger were filtered off. The solution was concentrated on a rotary evaporator, then distilled. The main part passed over at 53 to 55 C. and 0.06 mbar. Yield of 1,2-pentanediol: 35.5 grams, corresponding to 68.2% of theory.

Reference： [1]Patent: US4482760,1984,A
[2]Patent: US4482760,1984,A
[3]Patent: US4482760,1984,A

11
[ 463-71-8 ]
[ 5343-92-0 ]
[ 1051374-79-8 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 6780 - 6783

12
[ 5343-92-0 ]
[ 100-44-7 ]
[ 831-93-6 ]

Yield	Reaction Conditions	Operation in experiment
12.58%	With copper diacetate; at 80℃; for 12h;	A solution of chloromethylbenzene (1 g, 7.90 mmol) in pentane- l,2-diol (8.23 g, 79 mmol) was added diacetoxycopper (1.435 g, 7.90 mmol) and the mixture was stirred at 80 C for 12 hr. Then, mixture was diluted with water (5 mL) and extracted with EtOAc (5 mL x 3). The combined organic layers were washed with brine (10 mL), dried over NaiSOr. fdtered and concentrated to give residue. The residue was purified by prep-HPLC to give 1- (benzyloxy) pentan-2-ol (400 mg, 0.993 mmol, 12.58 % yield) as colorless oil. LCMS (M + H) = 192.

Reference： [1]Monatshefte fur Chemie,2009,vol. 140,p. 181 - 184
[2]Patent: WO2019/244066,2019,A2 .Location in patent: Page/Page column 142

13
[ 5343-92-0 ]
[ 74-88-4 ]
[ 53892-32-3 ]

Reference： [1]Monatshefte fur Chemie,2009,vol. 140,p. 181 - 184

14
[ 5343-92-0 ]
[ 102429-07-2 ]
[ 1259445-79-8 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In toluene; for 5h;Reflux;	1.2 2-(Bromomethyl)-2-(2,4-difluorophenyl)-4-propyl-1 ,3-dioxolaneTo a solution of 2-bromo-1-(2,4-difluorophenyl)ethanone (3.8 g, 16.2 mmol) and pen- tane-1 ,2-diol (21.0 mmol) in toluene (50 ml_), was added PTSA (279 mg, 1.62 mmol). The solution was stirred and heated at reflux with a Dean-Stark trap for 5 h, collecting water to facilitate the ketal formation. The reaction mixture was diluted with EtOAc (ethylacetate; 100 ml.) and washed with brine (2x50 ml_). The organic layer was separated, dried with sodium sulfate, and concentrated in vacuum. The residue was purified by column chromatography (silica gel, eluents: hexanes/EtOAc 4:1 ) to afford the title ketal compound (2.3 g, 44%) as clear oil.

Reference： [1]Patent: WO2010/149758,2010,A1 .Location in patent: Page/Page column 257

15
[ 97-99-4 ]
[ 111-29-5 ]
[ 5343-92-0 ]
[ 71-41-0 ]

Yield	Reaction Conditions	Operation in experiment
	With carbon dioxide; Rh/Al2O3; hydrogen; at 80℃; for 24h;Autoclave;	In this example, screening of the catalyst was carried out. 0.1 g of a catalyst and 0.4 g of tetrahydrofurfuryl alcohol were introduced into a 50 mL stainless steel autoclave, 1 MPa of carbon dioxide was introduced, and then heated to 80 C. Thereafter, hydrogen was introduced for 4 MPa, and finally, carbon dioxide was introduced with a pump to a total of 14 MPa (the total pressure was 18 MPa)After reacting for 24 hours, it was cooled with ice, sufficiently cooled, and pressure was gradually withdrawn. Finally, the reactants remaining in the autoclave were all washed out with acetone, the catalyst was filtered, and the obtained product was measured by gas chromatography or gas chromatography mass spectrometer. The results are shown in Table 1

Reference： [1]Journal of Catalysis,2011,vol. 280,p. 221 - 229
[2]Patent: JP5751625,2015,B2 .Location in patent: Paragraph 0023-0025

16
[ 5343-92-0 ]
[ 7459-33-8 ]
[ 1232870-61-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine;dmap; at 20℃; for 18h;Inert atmosphere;	Linoleoyl chloride (6.7×10-3 mol) and dimethylaminopyridine (DMAP) (0.1 eq) are added, under circulating nitrogen, to a solution of diol (5 eq) in pyridine (20 m1). After vigorous stirring for 18 hours under N2, at room temperature and away from light, the reaction medium is reduced dry.The organic phase is then extracted with AcOEt and then washed with H2O and NH4+Cl-, dried on MgSO4, filtered and concentrated.The crude product is a brown oil which is purified by open column chromatography using silica gel (Ø: 22×3.5 cm) and CHCl3 as solvent.The following product was prepared according to method B with <strong>[5343-92-0]pentylene glycol</strong> as the diol. Purification conditions: CHCl3/AcOEt: 98/2Translucent oilRf (CHCl3/AcOEt: 98/2)=0.54NMR (1H, CDCl3) delta (ppm): 0.9 (m, 6H, CH3 (a, w)) 1.3 (m, 16H, CH2 (o, n, m, l, b, c, d, v)); 1.45 (m, 2H, CH2 (u)); 1.65 (m, 2H, CH2 (p)); 2 (m, 4H, CH2 (k, e)); 2.3 (t, 2H, CH2 (q)); 2.8 (m, 2H, CH2 (h)); 3.8 (m, 1H, CH (t)); 4.1-4.3 (m, 2H, CH2 (s)); 5.4 (m, 4H, CH (f, g, i, j)).NMR (13C, CDCl3) delta (ppm): 14.2 (CH3 (a, w)); 18.6 (CH2 (v)); 22.6 (CH2 (b)); 25 (CH2 (p)); 25.6 (CH2 (h)); 27.2 (CH2 (e, h)); 29 (CH2 (o)); 29.1 (CH2 (n)); 29.3 (CH2 (d)); 29.4 (CH2 (m)); 29.6 (CH2 (l)); 31.4 (CH2 (c)); 34.1 (CH2 (q)); 36.2 (CH2 (u)); 69 (CH2 (s)); 70 (CH (t)); 127.78 (CH (g)); 127.91 (CH (i)); 129.94 (CH (f)); 130.22 (CH (j)); 174.05 (CO (r)).MS: ESI+ [M+H]+=367.3 (100%); [M+Na]+=389.3 (80%)

Reference： [1]Patent: US2011/230557,2011,A1 .Location in patent: Page/Page column 6

17
[ 5343-92-0 ]
[ 95-54-5 ]
[ 81516-60-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	In diethylene glycol dimethyl ether; at 140℃; for 24h;	A generic experiment was as follows. In a two-neck roundbottomflask of 10 mL, 1,2-phenylenediamine (1a, 0.5 mmol),1,2-propyleneglycol (2a, 0.6 mmol), 1.5 mL of diethylene glycol dimethylether (diglyme), and an amount of catalyst were added.Subsequently, the reaction mixture was heated at 140 C in a siliconebath that contains a magnetic stirrer and a temperature controller.

Reference： [1]Journal of Catalysis,2012,vol. 292,p. 118 - 129
[2]ChemCatChem,2018,vol. 10,p. 5627 - 5636

18
[ 98-00-0 ]
[ 97-99-4 ]
[ 5343-92-0 ]

Yield	Reaction Conditions	Operation in experiment
15%; 80%	With 5%PtO2-Al2O3; hydrogen; In ethanol; at 0 - 5℃; under 750.075 Torr; for 5h;	100 g (1.02 mol) of furfuryl alcohol were dissolved in 200 g of ethanol; 10 g of catalyst (5 wt. % platinum dioxide on gamma-aluminum oxide, corresponding to 0.5 g of platinum dioxide) were added, and hydrogenation was carried out at 0 to 5 C. and a hydrogen pressure of 1 bar. After 5 hours, the absorption of hydrogen was complete. The catalyst was filtered off, and the solvent ethanol and finally the product mixture were distilled off. There were obtained 105 g of a distillate having the following composition: [0239] 2% 2-pentanediol [0240] 2% 1-pentanediol [0241] 15% tetrahydrofurfurol [0242] 80% 1,2-pentanediol [0243] 1% 1,5-pentanediol [0244] Yield: 84 g (0.81 mol) of 1,2-pentanediol (corresponding to 80% of the theoretical yield). [0245] The distillates from six hydrogenation batches were combined (630 g in total) and subjected to fractional distillation on a 1 m packed column. 475 g of colorless 1,2-pentanediol having a purity of 99.9% were obtained as the main fraction. [0246] The resulting 1,2-pentanediol was colorless and odorless. [0247] The heterogeneous platinum catalyst used in Example 1 was prepared by dissolving 1.8 g of hexachloroplatinic acid in water and applying the solution to 10 g of the support material gamma-aluminum oxide by means of an incipient-wetness process. The solid so obtained was introduced at a temperature in the range from 310 to 320 C. into a NaNO3 melt, the temperature of the resulting mixture was increased gradually to 500 C., and the mixture was then maintained at 500 C. for one hour.
	With ruthenium on aluminium oxide; hydrogen; sodium carbonate; 1-butyl-3-methylpyridinium dicyanoazanide; In water; at 180℃; under 56255.6 - 67506.8 Torr; for 1.66667h;Autoclave;	A suspension composed of 4 g of FFOH, 6.1 ml of water, 100 mg of the 5% Ru/Al2O3 catalyst A11 and 2.5 mg of sodium dicyanamide (Example 32) or 5 mul of ionic liquid (Example 33: 1-butyl-3-methylimidazolium dicyanamide; Example 34: N-butyl-3-methylpyridinium dicyanamide; Example 35: 1-butyl-1-methylpyrrolidinium dicyanamide) was placed in the reactor. The reactor was closed and connected to the plant. After flushing three times with 30 bar of argon and once with 50 bar of hydrogen, the reactor was pressurized to 85 bar with hydrogen and heated to 180 C. The pressure temporally reached up to 90 bar during heating and towards the end of the reaction dropped to about 75 bar. The experiment is stopped 100 minutes after the reaction temperature has been reached. For this purpose, the pressure line of the reactor was disconnected from the plant and the reactor was cooled to room temperature in a water bath. The reactor was depressurized to ambient pressure by carefully opening the needle valve and the reaction mixture was taken from the reactor. The experimental results are summarized in Table 21.
	With platinum(IV) oxide; hydrogen; In ethanol; at 25℃; for 4.5h;Autoclave;	To examine the influence of the hydrogen pressure, the hydrogenolysis was carried out under a gauge pressure of 5 bar and also under atmospheric pressure at room temperature with addition of 1 ml of 2N hydrochloric acid (Table 27). In contrast to the otherwise usual batch reactor, a glass apparatus was used for carrying out the reaction under atmospheric pressure, with hydrogen being introduced continuously into the reaction solution. A strong dependence of the catalyst activity on the hydrogen pressure was observed. The reaction proceeded so quickly at p(H2)=5 bar that the temperature increased to up to 50 C. due to the heat of reaction. In addition, the increase in pressure led to an improvement in the selectivity to 1,2-PD from 20 to 23%. When the reaction was carried out under atmospheric pressure, a conversion of only 42% was achieved after a reaction time of 270 minutes, but the selectivity to 1,2-PD was 31%.

Reference： [1]Patent: US2014/66666,2014,A1 .Location in patent: Paragraph 0238-0247
[2]Patent: WO2020/57761,2020,A1 .Location in patent: Paragraph 00312-00315
[3]Green Chemistry,2012,vol. 14,p. 3402 - 3409
[4]Patent: US2014/243562,2014,A1 .Location in patent: Paragraph 0253
[5]Patent: US2014/243562,2014,A1 .Location in patent: Paragraph 0261

19
[ 5343-92-0 ]
[ 3778-73-2 ]
[ 1380481-59-3 ]

Yield	Reaction Conditions	Operation in experiment
22%	With N,N,N,N-tetraethylammonium tetrafluoroborate; In acetonitrile;Electrochemical reaction;	IFO therefore was electrochemically oxidized in acetonitrile in the presence of various alcohols with 5 carbon atoms. The reaction was stopped when all the starting material appeared to be consumed as monitored by TLC. At the end of the reaction, sodium bicarbonate (1 Eq.) was added to the medium to neutralize electrogenerated hydrons. The proportions of the various diastereomers were determined on the crude reaction mixture by 31P-NMR before being isolated by ?flash chromatography?.

Reference： [1]Patent: US2013/261088,2013,A1 .Location in patent: Paragraph 0132; 0133

20
[ 64502-89-2 ]
[ 5343-92-0 ]

Yield	Reaction Conditions	Operation in experiment
96%Chromat.	With hydrogen; In ethanol; at 20℃; under 37503.8 Torr; for 6h;	0.5 g of 1-hydroxy-2-pentanone (94%) was reacted for 6 hours at room temperature under 50 bar H2 in 25 ml of ethanol in the presence of a catalyst comprising (i) ruthenium and (ii) Al2O3. The concentration of (i) ruthenium is 5 wt. % based on the total weight of all the constituents of the catalyst and 2 mol % based on the amount of 1-hydroxy-2-pentanone. [0269] The composition of the reaction mixture was determined by means of GC/MS after separation of the catalyst. The conversion X based on 1-hydroxy-2-pentanone and the content Y of 1,2-pentanediol in the total amount of the products formed from 1-hydroxy-2-pentanone are given in Table 3.
	With palladium on activated charcoal; hydrogen; In ethanol; at 45℃; under 7500.75 Torr;	In the first step, the preparation of the intermediate 1-hydroxy-2-pentanone was carried out by adding 1 mol of n-butyraldehyde, 1.1 mol of paraformaldehyde, the reaction solvent methanol, the alkali reagent triethylamine in a closed reactor equipped with a magnetic stirrer, Catalyst 3-ethylbenzothiazole bromide 0.01mol, feeding is completed, the closed reactor placed in a constant temperature water bath, nitrogen protection, 50 constant temperature reaction 5h, 1-hydroxy-2-pentanone;In the second step, the intermediate product 1-hydroxy-2-pentanone, the catalyst Pd / C and the solvent anhydrous ethanol were charged into a reaction kettle equipped with a thermometer and a mechanical stirrer. The vacuum was passed through a certain pressure nitrogen, Empty the reaction kettle in the air, continuous row three times, and then pass a certain pressure of hydrogen, continuous replacement three times, through the hydrogen to high pressure reactor pressure 1.0MPa, stirring speed 350r / min, the reaction temperature control at 45 , And then the reaction is basically finished, the reaction temperature is cooled to room temperature, deflated, replaced with a certain pressure of nitrogen three times, the release of liquid material, filter recovery catalyst, rotary evaporator separation of the solvent in the filtrate anhydrous ethanol and other low boiling point And then distilled under reduced pressure at 20 mmHg to collect a fraction at a top temperature of 95 C to give product 1,2-pentanediol.

Reference： [1]Patent: US2014/66666,2014,A1 .Location in patent: Paragraph 0268-0269
[2]ChemistryOpen,2015,vol. 4,p. 483 - 488
[3]Patent: CN106478366,2017,A .Location in patent: Paragraph 0013

21
[ 98-00-0 ]
[ 5343-92-0 ]
[ 64502-89-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; at 230℃; for 2.05h;Inert atmosphere; Gas phase;	3 g of a granulated heterogeneous catalyst comprising (i) platinum and (ii) Al2O3 were disposed in the tubular reactor of a continuous gas-phase apparatus. The concentration of (i) platinum is 10 wt. %, based on the total weight of all the constituents of the catalyst. The apparatus comprises a saturator filled with furfuryl alcohol (FA), inlet pipes for hydrogen and an inert gas, gas metering units, a tubular reactor and a condensation unit. [0258] The volume flow of furfuryl alcohol was controlled via the temperature of the saturator and the metering of the hydrogen stream and optionally an additional inert gas stream. The gaseous mixture comprising furfuryl alcohol and hydrogen was passed through the tubular reactor, and organic components as well as water from the product gas stream were converted into the liquid state of aggregation in a condensation unit. Samples were taken at regular intervals and the composition of the condensate was analyzed by means of various analytical methods. The reaction conditions and the conversion X based on furfuryl alcohol and the contents Y (as defined above) of 1-hydroxy-2-pentanone and 1,2-pentanediol in the total amount of the products formed from furfuryl alcohol are given in Table 1.
	With hydrogen; at 230℃; under 1500.15 Torr; for 5.05h;Inert atmosphere; Gas phase;	3 g of a granulated heterogeneous catalyst comprising (i) platinum and (ii) Al2O3 were disposed in the tubular reactor of a continuous gas-phase apparatus. The concentration of (i) platinum is 10 wt. %, based on the total weight of all the constituents of the catalyst. The apparatus comprises a saturator filled with furfuryl alcohol (FA), inlet pipes for hydrogen and an inert gas, gas metering units, a tubular reactor and a condensation unit. [0258] The volume flow of furfuryl alcohol was controlled via the temperature of the saturator and the metering of the hydrogen stream and optionally an additional inert gas stream. The gaseous mixture comprising furfuryl alcohol and hydrogen was passed through the tubular reactor, and organic components as well as water from the product gas stream were converted into the liquid state of aggregation in a condensation unit. Samples were taken at regular intervals and the composition of the condensate was analyzed by means of various analytical methods. The reaction conditions and the conversion X based on furfuryl alcohol and the contents Y (as defined above) of 1-hydroxy-2-pentanone and 1,2-pentanediol in the total amount of the products formed from furfuryl alcohol are given in Table 1.

Reference： [1]Patent: US2014/66666,2014,A1 .Location in patent: Paragraph 0257-0259
[2]Patent: US2014/66666,2014,A1 .Location in patent: Paragraph 0257-0259

22
[ 98-00-0 ]
[ 97-99-4 ]
[ 6032-29-7 ]
[ 5343-92-0 ]
[ 71-41-0 ]

Yield	Reaction Conditions	Operation in experiment
20%		In accordance with Journal of American Chemical Society 71, 415 (1949) or the literature reference cited therein Journal of American Chemical Society 67, 272 (1945), 100 g (1.02 mol) of furfuryl alcohol were dissolved in 200 g of acetic acid; 4 g of platinum dioxide (without support material; supplier: Acros) were added, and hydrogenation was carried out at 0 to 5 C. and a hydrogen pressure of 1 bar. After 10 hours, the absorption of hydrogen was complete, the catalyst was filtered off, and the solvent was distilled off. The distillation residue was then taken up in 500 g of methyl tert-butyl ether and stirred with 40 g (0.74 mol) of sodium methylate in order to deacetylate the diols present in the form of mono- or di-acetate. After addition of 50 g of water, the mixture was neutralized with semi-concentrated hydrochloric acid, the phases were separated, and the solvent was removed. After distillation, there were obtained 80 g of an oily liquid having the following composition:26% 2-pentanediol [0250] 10% 1-pentanediol [0251] 35% tetrahydrofurfurol [0252] 26% 1,2-pentanediol [0253] 2% 1,5-pentanediol [0254] Yield: 21 g (0.20 mol) of 1,2-pentanediol (corresponding to 20% of the theoretical yield).

Reference： [1]Patent: US2014/66666,2014,A1 .Location in patent: Paragraph 0248-0254
[2]Patent: WO2020/57761,2020,A1 .Location in patent: Paragraph 00316

23
[ 98-01-1 ]
[ 109-99-9 ]
[ 96-47-9 ]
[ 97-99-4 ]
[ 534-22-5 ]
[ 111-29-5 ]
[ 5343-92-0 ]

Yield	Reaction Conditions	Operation in experiment
41%; 7%; 36%; 6%; 5%; 5%	With 5% Pd/C; hydrogen; In isopropyl alcohol; at 219.84℃; under 25858.1 Torr; for 40h;Inert atmosphere;	Continuous hydrogenation of furfural was carried out in a bench scale, high- pressure, fixed-bed reactor supplied by M/s Geomechanique, France. This reactor set up consisted of a stainless steel single tube of 0.34 m length and 1.5 x 10-2 m inner diameter. The reactor was heated by two tubular furnaces whose zones (TIC1 and TIC2) were independently controlled at the desired bed temperature. The reactor was provided with mass flow controllers, pressure indicator, and controller (PIC) devices and two thermocouples to measure the temperature at two different points. A storage tank was connected to the HPLC pump through a volumetric burette to measure the liquid flow rate. The pump had a maximum capacity of 3 x 10-4 m3/h under a pressure of 100 bar. The gas-liquid separator was connected to other end of the reactor through a condenser. Ten gm of the powder catalyst was charged in to the reactor. The section of 7 x 10-2 m above and 7 x 10-2 m below the catalyst bed was packed with carborandum as an inert packing, and remaining reactor was filled with catalyst powder in four sections, where the sections are separated by carborandoms. Before starting the actual experiment the reactor was flushed thoroughly, first with N2 and then with H2 at room temperature. Then the reactor was pressurized with H2 after attaining the desired temperature. The liquid feed was "switched on" after the reactor reached the operating pressure and was kept at that value for 1 h to obtain the constant liquid flow rate. Liquid samples were withdrawn from time to time. Samples taken during the reaction were analyzed with a Trace GC 700 series GC System (Thermo SCINTIFIC) coupled with FID detector and capillary column (HP-5 capillary column, 30 m length X 0.32 mm id). The following temperature programme method was used for GC analysis: 40 C (3 min)-lC/min-45 C (1 min) -10C/min-60(0 min) -20C/min-250(1 min). Following this procedure, the experiments were carried out at different inlet conditions of liquid and gas flow rates. The reactor was operated in the temperature and pressure ranges of 423-513 K and 20-50 bar, respectively. Steady-state performance of the reactor was observed by analysis of the reactant and products in the exit stream. The conversion and selectivity were calculated and defined as follows; As mentioned above, 3% Pd/C catalyst gives highest selectivity to THF in the batch operation; hence the same catalyst is taken for the continuous process. The continuous hydrogenation reaction was carried out at 493 K temperature and 500 psi H2 pressure. The conversion of FFR was remains 100% as in the continuous process and the THF selectivity was increased from 20% to 41% as compared to batch process and the other ring hydrogenated product were 42% (THFAL 36%, MTHF 7%), the results are shown in fig. 7. Initially the selectivity was 20% at 10 hrs, after 40 hrs the selectivity of THF was 41% and it remains constant up to 74 hrs. The increase in selectivity of THF (41%) is due to lower the contact time of substrate to catalyst as compare to batch process.

Reference： [1]Patent: WO2014/118806,2014,A1 .Location in patent: Page/Page column 10-11; 15-17

24
[ 98-00-0 ]
[ 97-99-4 ]
[ 111-29-5 ]
[ 5343-92-0 ]

Yield	Reaction Conditions	Operation in experiment
	With platinum(IV) oxide; hydrogen; In ethanol; at 50℃; under 1500.15 Torr; for 5h;Autoclave;	[18] An exception was the catalyst Pt-JA-023. Owing to its low activity, hydrogen pressure and reaction temperature were increased to up to 180 C. and 60 bar during the reaction. The experimental results are summarized in Table 23. With the exception of Pt-JA-023, all catalysts achieved high conversions of over 96% within a reaction time of 2-5 h. A broad product spectrum consisting of 1,2-PD, 1,5-PD, THFFOH, 1-POH, 2-MF, 2-MTHF and also further unknown by-products was obtained. This roughly agrees with the reaction products previously reported. [21] Compared to the supported catalysts (Table 11), a significantly higher ratio of 1,5-PD to 1,2-PD was obtained. In the case of the Pt(IV) oxide catalyst from Heraeus, even more 1,5-PD (23% selectivity) than 1,2-PD was formed. The highest selectivity to 1,2-pentanediol of 25% was achieved by the Pt(IV) oxide catalyst from Sigma Aldrich. It is conspicuous that the calculated balance E is significantly below 100% for all catalysts tested. This can presumably be attributed to production of large amounts of unknown by-products for which no GC calibration data were available.
40.2%Chromat.; 21.3%Chromat.; 36.5%Chromat.	With hydrogen; In ethanol; at 150℃; for 4h;	0.1 g of [Pt(0)/HT] (platinum: 0.01 mmol) obtained in Preparation Example 1, furfural (registered trademark) 1 mmol, 2-propanol (2-PrOH) 3.0 mL was added and stirred under a hydrogen atmosphere (30 atm) at 150 C. for 4 hours to obtain 1,2-pentanediol (conversion: 100% : 72.6%, yield: 72.6%). Incidentally, conversion and yield were measured by GC-MS by a standard measurement method.

Reference： [1]Patent: US2014/243562,2014,A1 .Location in patent: Paragraph 0256
[2]Patent: JP6143057,2017,B2 .Location in patent: Paragraph 0044; 0045; 0049; 0050

25
[ 98-00-0 ]
[ 97-99-4 ]
[ 111-29-5 ]
[ 5343-92-0 ]
[ 71-41-0 ]

Yield	Reaction Conditions	Operation in experiment
	With platinum(IV) oxide; hydrogen; In ethanol; at 180℃; under 15001.5 - 45004.5 Torr; for 2h;Autoclave;	[18] An exception was the catalyst Pt-JA-023. Owing to its low activity, hydrogen pressure and reaction temperature were increased to up to 180 C. and 60 bar during the reaction. The experimental results are summarized in Table 23. With the exception of Pt-JA-023, all catalysts achieved high conversions of over 96% within a reaction time of 2-5 h. A broad product spectrum consisting of 1,2-PD, 1,5-PD, THFFOH, 1-POH, 2-MF, 2-MTHF and also further unknown by-products was obtained. This roughly agrees with the reaction products previously reported. [21] Compared to the supported catalysts (Table 11), a significantly higher ratio of 1,5-PD to 1,2-PD was obtained. In the case of the Pt(IV) oxide catalyst from Heraeus, even more 1,5-PD (23% selectivity) than 1,2-PD was formed. The highest selectivity to 1,2-pentanediol of 25% was achieved by the Pt(IV) oxide catalyst from Sigma Aldrich. It is conspicuous that the calculated balance E is significantly below 100% for all catalysts tested. This can presumably be attributed to production of large amounts of unknown by-products for which no GC calibration data were available.

Reference： [1]Patent: US2014/243562,2014,A1 .Location in patent: Paragraph 0256

26
[ 98-00-0 ]
[ 97-99-4 ]
[ 5343-92-0 ]
[ 584-03-2 ]

Yield	Reaction Conditions	Operation in experiment
	With 5% active carbon-supported ruthenium; hydrogen; In water; at 200℃; under 75007.5 Torr; for 0.75h;Autoclave;	The 6 Ru catalysts and 2 Pt catalysts shown in Table 11 were tested in 100 ml of an aqueous solution of furfuryl alcohol at 200 C. and a hydrogen pressure of 100 bar in a batch reactor. Here, 0.5 g of catalyst and the additives indicated were used in each case. The reaction was stopped as soon as complete conversion of furfuryl alcohol had been achieved. Table 11 summarizes the reaction times for complete conversion and the selectivities to the most important reaction products for the 8 catalysts examined.

Reference： [1]Patent: US2014/243562,2014,A1 .Location in patent: Paragraph 0208

27
[ 98-00-0 ]
[ 97-99-4 ]
[ 5343-92-0 ]
[ 96-41-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ruthenium on aluminium oxide; hydrogen; sodium carbonate; In water; at 200℃; under 37503.8 Torr; for 2.33333h;Autoclave;	Specifically, 64.4 ml of water, 100 mg of Na2CO3 and 1.0 g of the 5% Ru/Al2O3 catalyst A11 were placed in the autoclave. The reaction apparatus was closed and a stirring speed of 1000 rpm was set. The reactor was flushed three times with 10 bar of argon and once with 10 bar of hydrogen. The hydrogen pressure was subsequently set so that the pressure expected on reaching the reaction temperature would be 10-20 bar below the respective reaction pressure of 50 bar, 100 bar or 150 bar. The contents of the reactor were heated to the reaction temperature over a period of 30-60 minutes. The reaction temperature was 200 C. As soon as this had been reached, 40 g of furfuryl alcohol were quickly introduced via the supply tank. Further hydrogen was continually introduced via the gas tank so as to keep the reaction pressure constant. For sampling, the offtake line was flushed beforehand with 1-2 ml of reaction mixture and 0.5-1 ml of sample was then taken. When the hydrogen pressure in the gas tank no longer decreased, which was the case after 140 minutes for Example 16, after 30 minutes for Example 17 and was the case after 25 minutes for Example 18, the heating jacket was removed and the reactor was cooled in air to room temperature. After taking off the reaction mixture, the reactor was thoroughly cleaned and baked at 150 C. under 30 bar of argon for 60 minutes.
	With Ru-Pt/Al2O3; hydrogen; sodium carbonate; In water; at 200℃; under 75007.5 Torr; for 3h;Autoclave;	To examine the influence of second metals in the Ru/Al2O3 catalyst, six different bimetallic [n(Ru):n(Me)] Ru-Me/Al2O3 catalysts based on 5% Ru/Al2O3 (A11) with the molar ratio [n(Ru):n(Me)] were prepared as described above (Sections 2.13 to 2.15). Sn, Zn, Fe, Cu, Ni and Pt were used as second metals. While Sn was introduced in situ by addition of Sn(II) chloride, the remaining catalysts were prepared by impregnation with a solution of the metal nitrate. The catalysts were in each case calcined at 200 C. for 1 hour and reduced at 250 C. for 1 hour. Specifically, the hydrogenolysis of furfuryl alcohol was carried out as follows: 0.5 g of the respective bimetallic catalyst (Example 25: 5% Ru/Al2O3 A11; Example 26: [17:2] Ru-Sn/Al2O3; Example 27: [5:2] Ru-Zn/Al2O3; Example 28: [5:2] Ru-Fe/Al2O3; Example 29: [1:2] Ru-Cu/Al2O3; Example 30: [1:2] Ru-Ni/Al2O3; Example 31: [1:2] Ru-Pt/Al2O3) was placed in the autoclave. The reaction apparatus was closed and a stirring speed of 1000 rpm was set. The reactor was flushed three times with 10 bar of argon and once with 10 bar of hydrogen. The hydrogen pressure was subsequently set so that the pressure expected on reaching the reaction temperature would be 10-20 bar below the respective reaction pressure of 100 bar. The contents of the reactor were heated to the reaction temperature over a period of 30-60 minutes. The reaction temperature was 200 C. As soon as this had been reached, 40 g of furfuryl alcohol were quickly introduced via the supply tank. Further hydrogen was continually introduced via the gas tank so as to keep the reaction pressure constant. For sampling, the offtake line was flushed beforehand with 1-2 ml of reaction mixture and 0.5-1 ml of sample was then taken. When the hydrogen pressure in the gas tank no longer decreased, which was the case after 60 minutes for Examples 25 and 30, was the case after 20 minutes for Example 26, was the case after 90 minutes for Examples 27 and 28, was the case after 15 minutes for Example 29 and was the case after 180 minutes for Example 31, the heating jacket was removed and the reactor was cooled in air to room temperature. After taking off the reaction mixture, the reactor was thoroughly cleaned and baked at 150 C. under 30 bar of argon for 60 minutes. The product mixture was analysed and the following selectivities were found for the various catalysts. The experimental results are summarized in Table 20.

Reference： [1]Patent: US2014/243562,2014,A1 .Location in patent: Paragraph 0237
[2]Patent: US2014/243562,2014,A1 .Location in patent: Paragraph 0248

28
[ 98-00-0 ]
[ 96-47-9 ]
[ 97-99-4 ]
[ 5343-92-0 ]
[ 71-41-0 ]

Yield	Reaction Conditions	Operation in experiment
	With platinum(IV) oxide; hydrogen; In ethanol; at 25℃; under 1500.15 Torr; for 2h;Autoclave;	[18] An exception was the catalyst Pt-JA-023. Owing to its low activity, hydrogen pressure and reaction temperature were increased to up to 180 C. and 60 bar during the reaction. The experimental results are summarized in Table 23. With the exception of Pt-JA-023, all catalysts achieved high conversions of over 96% within a reaction time of 2-5 h. A broad product spectrum consisting of 1,2-PD, 1,5-PD, THFFOH, 1-POH, 2-MF, 2-MTHF and also further unknown by-products was obtained. This roughly agrees with the reaction products previously reported. [21] Compared to the supported catalysts (Table 11), a significantly higher ratio of 1,5-PD to 1,2-PD was obtained. In the case of the Pt(IV) oxide catalyst from Heraeus, even more 1,5-PD (23% selectivity) than 1,2-PD was formed. The highest selectivity to 1,2-pentanediol of 25% was achieved by the Pt(IV) oxide catalyst from Sigma Aldrich. It is conspicuous that the calculated balance E is significantly below 100% for all catalysts tested. This can presumably be attributed to production of large amounts of unknown by-products for which no GC calibration data were available.
	With platinum(IV) oxide; hydrogen; In ethanol; at 25℃; under 1500.15 Torr; for 4.5h;Autoclave;	[18] An exception was the catalyst Pt-JA-023. Owing to its low activity, hydrogen pressure and reaction temperature were increased to up to 180 C. and 60 bar during the reaction. The experimental results are summarized in Table 23. With the exception of Pt-JA-023, all catalysts achieved high conversions of over 96% within a reaction time of 2-5 h. A broad product spectrum consisting of 1,2-PD, 1,5-PD, THFFOH, 1-POH, 2-MF, 2-MTHF and also further unknown by-products was obtained. This roughly agrees with the reaction products previously reported. [21] Compared to the supported catalysts (Table 11), a significantly higher ratio of 1,5-PD to 1,2-PD was obtained. In the case of the Pt(IV) oxide catalyst from Heraeus, even more 1,5-PD (23% selectivity) than 1,2-PD was formed. The highest selectivity to 1,2-pentanediol of 25% was achieved by the Pt(IV) oxide catalyst from Sigma Aldrich. It is conspicuous that the calculated balance E is significantly below 100% for all catalysts tested. This can presumably be attributed to production of large amounts of unknown by-products for which no GC calibration data were available.

Reference： [1]Patent: US2014/243562,2014,A1 .Location in patent: Paragraph 0256
[2]Patent: US2014/243562,2014,A1 .Location in patent: Paragraph 0256

29
[ 98-00-0 ]
[ 5343-92-0 ]
[ 96-41-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ruthenium on aluminium oxide; hydrogen; sodium carbonate; In water; at 240℃; under 75007.5 Torr; for 0.25h;pH 7.6;Autoclave;	Specifically, 86.8 ml of water, 0.5 g of the 5% Ru/Al2O3 catalyst A11 and the amount indicated in Table 13 of Na2CO3 (0 mg, 10 mg, 30 mg, 60 mg, 300 mg) were placed in the autoclave. The reaction apparatus was closed and a stirring speed of 1000 rpm was set. The reactor was flushed three times with 10 bar of argon and once with 10 bar of hydrogen. The hydrogen pressure was subsequently set so that the pressure expected on reaching the reaction temperature would be 10-20 bar below the reaction pressure of 100 bar. The contents of the reactor were heated to the reaction temperature over a period of 30-60 minutes. The reaction temperature was 240 C. As soon as this had been reached, 7.46 of furfuryl alcohol in 6.6 ml of water were quickly introduced via the supply tank. Further hydrogen was continually introduced via the gas tank so as to keep the reaction pressure constant. For sampling, the offtake line was flushed beforehand with 1-2 ml of reaction mixture and 0.5-1 ml of sample was then taken. When the hydrogen pressure in the gas tank no longer decreased, which was the case after 15 minutes for Examples 4-7, and was the case after 25 minutes for Example 8, the heating jacket was removed and the reactor was cooled in air to room temperature. After taking off the reaction mixture, the reactor was thoroughly cleaned and baked at 150 C. under 30 bar of argon for 60 minutes.

Reference： [1]Patent: US2014/243562,2014,A1 .Location in patent: Paragraph 0223

30
[ 5343-92-0 ]
[ 15181-14-3 ]

Yield	Reaction Conditions	Operation in experiment
	With [C6H3-2,6-(OP(tBu)2)2]IrH2; trifluorormethanesulfonic acid; hydrogen; In water;Autoclave;	The selectivity trend shown in FIG. 1 may be attributed to both thermodynamic and kinetic factors. Higher water concentration will give lower steady state concentrations of dehydrated species and thus limit formation of byproducts arising from condensation reactions (see Scheme 1). The reversible formation of condensation byproducts, such as ethyl methyl dioxolane, in aqueous solution (>10% water) is apparent in the kinetic trace of the reaction mixture (FIG. 2). It is reasonable to suggest that the relative rate of hydrogenation of propionaldehyde to that of dehydration is much higher at the optimal reaction conditions, leading to lower steady-state concentrations of aldehyde intermediate and minimal competition from subsequent acid-catalyzed conversions. In fact, no propionaldehyde intermediate is observed by NMR spectroscopy in reaction mixtures containing more than 20% water (by volume) and 0.10 equivalents of acid or less. In these cases, the propionaldehyde intermediate is rapidly hydrogenated to n-propanol by the Ir catalyst with excellent overall selectivity. As the acid concentration increases, the acid-catalyzed pathways can become competitive with hydrogenation resulting in significant formation of ether, ester, carboxylic acid, and aromatic byproducts. In the latter case, mesitylene is formed via acid-catalyzed trimerization of the ketone intermediate at high acid concentration. This mechanism was confirmed by an experiment using <strong>[5343-92-0]1,2-pentanediol</strong>, which leads to formation of 1,3,5-tripropylbenzene.

Reference： [1]Patent: US2014/371493,2014,A1 .Location in patent: Paragraph 0092

31
[ 98-00-0 ]
[ 96-47-9 ]
[ 97-99-4 ]
[ 534-22-5 ]
[ 626-95-9 ]
[ 111-29-5 ]
[ 6032-29-7 ]
[ 5343-92-0 ]
[ 71-41-0 ]
[ 539-88-8 ]
[ 109-66-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; In ethanol; at 139.84℃; under 45004.5 Torr; for 0.5h;Autoclave;	General procedure: The FFA hydrogenolysis reactions were carried out in astainless steel autoclave reactor (100 mL) at a stirring speed of800 r/min. Prior to each reaction, the calcined catalyst samplewas reduced at 623 K in 20% H2-80% N2 at a flow of 40mL/min for 3 h. In a typical trial, 40 g of 10 wt% FFA dissolvedin ethanol was added into reactor together with a quantity ofthe reduced catalyst. After flushing with H2, the reactor waspressurized with H2 to 6.0 MPa, and then heated to 413 K overthe course of 0.5 h. The concentrations of the reactant and liquidproducts were analyzed by gas chromatography (Agilent7890A GC) with a PONA capillary column (50 m × 0.20 mm ×0.50 mum). Products were also identified using an Agilent7890A/5975C gas chromatograph-mass spectrometer (GC-MS)with an HP-5MS column. The liquid products identified in thismanner consisted of 1,2-PeD, 1,5-PeD, 1,4-pentanediol,2-methyl furan (2-MF), 2-methyl tetrahydrofuran (2-MTHF),1-pentanol, 2-pentanol, n-pentane and tetrahydrofurfuryl alcohol(THFA). FFA conversions and product selectivities werecalculated on the basis of the following equations.Conversion (%) = (moles of FFA charged - moles ofFFA left)/moles of FFA charged 100%Selectivity (%) = moles of a product generated/(moles of FFA charged - moles of FFA left) 100%

Reference： [1]Cuihua Xuebao/Chinese Journal of Catalysis,2016,vol. 37,p. 700 - 710

32
[ 98-00-0 ]
[ 96-47-9 ]
[ 97-99-4 ]
[ 534-22-5 ]
[ 626-95-9 ]
[ 111-29-5 ]
[ 6032-29-7 ]
[ 5343-92-0 ]
[ 109-66-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; In ethanol; at 139.84℃; under 45004.5 Torr; for 0.5h;Autoclave;	General procedure: The FFA hydrogenolysis reactions were carried out in astainless steel autoclave reactor (100 mL) at a stirring speed of800 r/min. Prior to each reaction, the calcined catalyst samplewas reduced at 623 K in 20% H2-80% N2 at a flow of 40mL/min for 3 h. In a typical trial, 40 g of 10 wt% FFA dissolvedin ethanol was added into reactor together with a quantity ofthe reduced catalyst. After flushing with H2, the reactor waspressurized with H2 to 6.0 MPa, and then heated to 413 K overthe course of 0.5 h. The concentrations of the reactant and liquidproducts were analyzed by gas chromatography (Agilent7890A GC) with a PONA capillary column (50 m × 0.20 mm ×0.50 mum). Products were also identified using an Agilent7890A/5975C gas chromatograph-mass spectrometer (GC-MS)with an HP-5MS column. The liquid products identified in thismanner consisted of 1,2-PeD, 1,5-PeD, 1,4-pentanediol,2-methyl furan (2-MF), 2-methyl tetrahydrofuran (2-MTHF),1-pentanol, 2-pentanol, n-pentane and tetrahydrofurfuryl alcohol(THFA). FFA conversions and product selectivities werecalculated on the basis of the following equations.Conversion (%) = (moles of FFA charged - moles ofFFA left)/moles of FFA charged 100%Selectivity (%) = moles of a product generated/(moles of FFA charged - moles of FFA left) 100%

Reference： [1]Cuihua Xuebao/Chinese Journal of Catalysis,2016,vol. 37,p. 700 - 710

33
[ 5343-92-0 ]
C₁₈H₂₁NO₃ [ No CAS ]
C₂₃H₃₁NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With toluene-4-sulfonic acid; In 5,5-dimethyl-1,3-cyclohexadiene; at 20℃; for 72h;Inert atmosphere; Molecular sieve; Reflux;	Under an argon protective gas, first 0.644g (2mmol) example XIV-1-1 compound was added to 30 ml of xylene, at room temperature by adding 2.083g (20mmol) <strong>[5343-92-0]1,2-pentanediol</strong> and 0.059g (0.29mmol) p-toluenesulfonic acid, adding 0.5g 4 Molecular sieve (powder) and reflux the mixture for three days of stirring under monitoring by thin layer chromatography. After the reaction, the solvent is distilled away. The product is purified by silica gel column chromatography (dichloromethane/acetone = 5:1). Yield: 0.27g( The theoretical yield 35%), melting point: 273 C.

Reference： [1]Patent: CN101160049,2016,B .Location in patent: Paragraph 0991-0995

34
[ 5343-92-0 ]
[ 504-60-9 ]
[ 110-62-3 ]
2-butyl-4-propyl-1,3-dioxolane [ No CAS ]

Reference： [1]Applied Catalysis A: General,2016,vol. 526,p. 164 - 171

35
[ 50-70-4 ]
[ 57-55-6 ]
[ 34557-54-5 ]
[ 64-17-5 ]
[ 5343-92-0 ]
[ 6920-22-5 ]
[ 909878-64-4 ]
[ 69-65-8 ]
[ 584-02-1 ]
[ 124-38-9 ]
[ 107-21-1 ]
[ 56-81-5 ]
[ 78-92-2 ]
[ 504-63-2 ]
[ 513-85-9 ]
[ 584-03-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; sodium hydroxide; In water; at 210℃; under 45004.5 Torr; for 2h;Autoclave;	General procedure: The hydrogenolysis of sorbitol was performed in a 50 mL stainless-steel autoclave with magnetic stirring. After sorbitol aqueous solution, Ru catalyst and an appropriate amount of basewere charged into the reactor, the autoclave was purged with hydrogen four times and then pressurized to the desired pressure at room temperature. Then the reaction was performed atcertain temperature under the stirring speed of 800 r/min. After the reaction, the reactor was cooled down and the used catalystwas separated from the reaction mixture by centrifugation. Thesamples were filtered through 0.22 m-pore-size filters (Mem-brana) prior to analysis. The obtained products such as 1,2-PG,EG and GLY were determined using a gas chromatography (GC,7890A, Agilent, USA) equipped with a CP-Wax 58 (FFAP) capillarycolumn (0.25 mm × 25 m) and a flame ionization detector. Otherproducts like glucose, sugar alcohols were quantified by Anion-Exchange Chromatography (IC, Dionex ICS-3000) equipped with pulsed amperometric detector and an Aminex HPX-87H column(Bio-Rad, 7.8 × 300 mm), using 500 mM NaOH as eluent with a flowrate of 0.4 mL min-1at 30C. The obtained products in resultant solutions were also identified by GC-MS (6890N, Agilent, USA). The conversion of sorbitol and yields of products were calculated on the carbon basis and defined as follows

Reference： [1]Journal of Molecular Catalysis A: Chemical,2017,vol. 426,p. 79 - 87

36
[ 50-70-4 ]
[ 57-55-6 ]
[ 34557-54-5 ]
[ 64-17-5 ]
[ 5343-92-0 ]
[ 6920-22-5 ]
[ 909878-64-4 ]
[ 69-65-8 ]
[ 584-02-1 ]
[ 124-38-9 ]
[ 107-21-1 ]
[ 56-81-5 ]
[ 78-92-2 ]
[ 513-85-9 ]
[ 584-03-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; sodium hydroxide; at 210℃; under 45004.5 Torr; for 2h;	General procedure: The hydrogenolysis of sorbitol was performed in a 50 mL stainless-steel autoclave with magnetic stirring. After sorbitol aqueous solution, Ru catalyst and an appropriate amount of basewere charged into the reactor, the autoclave was purged with hydrogen four times and then pressurized to the desired pressure at room temperature. Then the reaction was performed atcertain temperature under the stirring speed of 800 r/min. After the reaction, the reactor was cooled down and the used catalystwas separated from the reaction mixture by centrifugation. Thesamples were filtered through 0.22 m-pore-size filters (Mem-brana) prior to analysis. The obtained products such as 1,2-PG,EG and GLY were determined using a gas chromatography (GC,7890A, Agilent, USA) equipped with a CP-Wax 58 (FFAP) capillarycolumn (0.25 mm × 25 m) and a flame ionization detector. Otherproducts like glucose, sugar alcohols were quantified by Anion-Exchange Chromatography (IC, Dionex ICS-3000) equipped with pulsed amperometric detector and an Aminex HPX-87H column(Bio-Rad, 7.8 × 300 mm), using 500 mM NaOH as eluent with a flowrate of 0.4 mL min-1at 30C. The obtained products in resultant solutions were also identified by GC-MS (6890N, Agilent, USA). The conversion of sorbitol and yields of products were calculated on the carbon basis and defined as follows

Reference： [1]Journal of Molecular Catalysis A: Chemical,2017,vol. 426,p. 79 - 87

37
[ 108740-82-5 ]
[ 5343-92-0 ]

Yield	Reaction Conditions	Operation in experiment
99.4%	With hydrogen; at 225℃; under 75007.5 Torr;	A 150 g hydrogenation catalyst-alloy catalyst (consisting of 120 g of copper oxide, 15 g of zinc oxide and 15 g of alumina)Was charged in a hydrogenation reactor, the temperature inside the reactor was maintained at 225 C, the hydrogen pressure was maintained at 10 MPa, and hydrogenation was carried out from the lower endThe methyl 2-hydroxyvalerate produced in the above reaction was introduced from the lower end into the hydrogenation reactor, methyl 2-hydroxyvalerate(172.5 g) was controlled at 2 ml / min, and the product of the hydrogenation reaction was withdrawn from the top of the hydrogenation reactor. The effluent was passed throughThe condenser was cooled to 60 C and transferred to a distillation kettle at a distillation temperature of 160 C to give 119.8 g of 1,2-pentanediol,The content of 1,2-pentanediol was 99.4% and the molar yield was 88.15% by gas chromatography.

Reference： [1]Patent: CN106365957,2017,A .Location in patent: Paragraph 0031; 0032; 0036; 0037; 0041; 0042

38
[ 1003-14-1 ]
[ 5343-92-0 ]

Yield	Reaction Conditions	Operation in experiment
91.2%	With water; at 130℃; under 18751.9 Torr;	(1) First, a C2-C16 monoolefin was used as a raw material, and a titanium silicate molecular sieve TS-1 having an MFI structure was used.HTS-1 as a catalyst, with an aqueous hydrogen peroxide solution as an oxidizing agent, according to the process disclosed in CN 104211665A,Oxidation to the corresponding hydrocarbon epoxide;(2) In a 100 ml jacketed stainless steel tubular reactor, 30 ml of a compound represented by the general formula (3)Substituted macroporous polystyrene season scale salt anion exchange resin catalyst, the catalyst bed at the bottom and end filled with inertball. The temperature of the reactor is controlled by an external circulation type heat transfer oil, and the reactor pressure is controlled by a back pressure valve installed on the outlet lineThe reaction material is passed through the bottom of the reactor through the bottom of the reactor and flows through the catalyst bed from the top of the reactor and is cooled by the coolerBut then flows into the reaction product tank. Time sampling, gas chromatography analysis reaction product composition. Study the concentration of reaction raw materials, reactionTemperature, pressure, liquid hourly space velocity and the type of catalyst on the reaction, the reaction materials used in Examples 1 to 10 are shown in Table1, the catalyst used has the general formula (3) structure, wherein Yi, 7, horses, 1? 6,1? 7 groups, resin crosslinking degree, resin alkali exchange capacitySee Table 2, the reaction process conditions and reaction results in Table 3. The catalyst represented by the general formula (3) has an ortho-halogenated styrene,Etine is prepared from the reaction starting material, the reaction equation is as follows:
90.2%	With water; at 130℃; under 18751.9 Torr;	In a 100 ml jacketed stainless steel tubular reactor, 30 ml of a halogen-substituted macroporous polystyrene quaternary ammonium salt type anion exchange resin catalyst having a structure represented by the general formula (3) was charged, and the upper and lower ends of the catalyst bed Filled with inert ceramic ball.The temperature of the reactor is controlled by an external circulation type heat transfer oil, which is controlled by a back pressure valve mounted on the outlet line. The reaction material is fed from the bottom of the reactor through the metering pump and flows through the catalyst bed from the top of the reactor , Cooled by the cooler and flowed into the reaction product tank.Time sampling, gas chromatography analysis reaction product composition.The reaction raw materials used in Examples 1 to 10 are shown in Table 1. The catalyst used has the structure of the general formula (3), wherein X and y are the same as those of the reaction formula, wherein the reaction temperature, pressure, liquid hourly space velocity and catalyst type change affect the reaction. , R5, R6, R7Group, resin crosslinking degree, resin alkali exchange capacity (dry basis) in Table 2, the reaction process conditions and reaction results in Table 3.The catalyst represented by the general formula (3) is prepared by preparing halogenated styrene and diene as reaction materials, and the reaction equation is as follows:
90.0%	With water; at 130℃; under 18751.9 Torr;	General procedure: In a 100 ml jacketed stainless steel tubular reactor, 30 ml of the structure represented by the general formula (3)Halogen meta-substituted macroporous polystyrene-divinylbenzene quaternary ammonium salt anion exchange resin catalyst,The catalyst bed is filled with an inert ceramic ball on the upper and lower ends.The temperature of the reactor is controlled by an external circulation type heat transfer oil,The reactor pressure is controlled by a back pressure valve mounted on the outlet line,The reaction material is fed from the bottom of the reactor through a metering pump,Flowing through the catalyst bed from the top of the reactor,Cooled by the cooler and flowed into the reaction product tank.Timing sampling,Analysis of the reaction product by gas chromatography.To investigate the reaction concentration,Reaction temperature, pressure,Liquid hourly space velocity and catalyst type change on the reaction,The reaction materials used in Examples 1 to 10 are shown in Table 1, and the catalyst used has the structure of the general formula (3), wherein the X, y, R5, R6, R7 groups, the ion exchange resin crosslinking degree, the alkali exchange capacity ) See Table 2, the reaction process conditions and reaction results in Table 3.

With water; at 65℃; for 0.666667h;pH 11.0;

Under the atmospheric pressure, to titanium silicalite molecular sieve as catalyst, in the solvent, under the condition of, to the mass fraction of 25% - 50% of the hydrogen peroxide as the oxidizing agent, is pentene as raw materials epoxidation, hydrolysis synthesis of 1,2-pentanediol. The process conditions of each embodiment are shown in table 1, table 2. Wherein the material and positive pentene than is a quality ratio. Respectively using gas chromatography analysis of the composition of the reaction solution, computing is pentene conversion and 1, the yield of 2-pentanediol, results shown in table 3.

Reference： [1]Patent: CN106478373,2017,A .Location in patent: Paragraph 0024; 0025; 0026; 0028; 0029; 0030-0035
[2]Patent: CN106478374,2017,A .Location in patent: Paragraph 0015; 0031; 0033; 0036
[3]Patent: CN106478375,2017,A .Location in patent: Paragraph 0027; 0029; 0030; 0036
[4]Patent: CN106478371,2017,A .Location in patent: Paragraph 0027-0028; 0032; 0037
[5]Patent: CN105461511,2016,A .Location in patent: Paragraph 0027; 0028
[6]Chemistry - A European Journal,2019,vol. 25,p. 4520 - 4529

39
[ 58-86-6 ]
[ 5343-92-0 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphoric acid; hydrogen; In water; at 160℃; under 30003 Torr; for 4h;	The catalytic reaction was carried out in a 60 ml stainless steel reactor. The reduced catalyst 0.1, 1. 0g xylose, 100.0 mg phosphoric acid (85wt%), 8.9g water was added to a stainless steel reactor equipped with polytetrafluoro lining. After closing the reactor, replace the gas in the reactor with hydrogen four times, the temperature controller was heated to 160 C and charged with hydrogen to 4 MPa. Then started stirring reaction for 4 h. During the reaction, the pressure was kept constant, and the hydrogenation reaction was completed. After cooling and pressure relief, the samples were analyzed by gas chromatography.

Reference： [1]Patent: CN105622347,2016,A .Location in patent: Paragraph 0032; 0033

40
[ 51719-84-7 ]
[ 5343-92-0 ]
4-(4-propyl-1,3-dioxolan-2-yl)-5-phenyl-1,2,3-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With toluene-4-sulfonic acid; In benzene; at 80℃;Dean-Stark;	General procedure: (A) From aldehyde 3. Toluenesulfonic acid (100 mg) was added to a solution of 3.1 g (0.018 mol) aldehyde 3 and 1.5 g (0.024 mol) of ethylene glycol 4a in 20 mL of benzene and the mixture was heated under reflux using a Dean-Stark distilling trap until water evolution ceased. The reaction mixture was cooled, washed with NaHCO3 solution,dried with Na2SO4 and the solvent was removed in a vacuum.

Reference： [1]Doklady Chemistry,2017,vol. 472,p. 3 - 6
Dokl. Akad. Nauk,2017,vol. 472,p. 43 - 46,4

41
[ 5343-92-0 ]
[ 6142-95-6 ]
C₁₄H₁₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In benzene; at 80℃;	General procedure: A solution of 0.05 mol of acetal 1, 0.055 mol of diol 4a-4e, and 100 mg of toluenesulfonic acid in 50 mL of benzene was heated under reflux, while a fraction containing benzene and ethyl alcohol was distilled off. As distillate was distilled off, fresh solvent was added to the boiling solution. The distillation was carried out until the absence of ethanolin distillate according to gas-liquid chromatography.The reaction mixture was cooled, washed with NaHCO3 solution, dried with Na2SO4, benzene was removed, and the residue was distilled in a vacuum.

Reference： [1]Doklady Chemistry,2017,vol. 472,p. 3 - 6
Dokl. Akad. Nauk,2017,vol. 472,p. 43 - 46,4

42
[ 98-01-1 ]
[ 97-99-4 ]
[ 111-29-5 ]
[ 5343-92-0 ]

Yield	Reaction Conditions	Operation in experiment
15.9%Chromat.; 7.9%Chromat.; 72.9%Chromat.	With hydrogen; In isopropyl alcohol; at 150℃; for 4h;	0.1 g of [Pt(0)/HT] (platinum: 0.01 mmol) obtained in Preparation Example 1, furfural (registered trademark) 1 mmol, 2-propanol (2-PrOH) 3.0 mL was added and stirred under a hydrogen atmosphere (30 atm) at 150 C. for 4 hours to obtain 1,2-pentanediol (conversion: 100% : 72.6%, yield: 72.6%). Incidentally, conversion and yield were measured by GC-MS by a standard measurement method.

Reference： [1]Patent: JP6143057,2017,B2 .Location in patent: Paragraph 0044; 0045

43
[ 98-01-1 ]
[ 96-47-9 ]
[ 97-99-4 ]
[ 110-00-9 ]
[ 534-22-5 ]
[ 6032-29-7 ]
[ 5343-92-0 ]
[ 71-41-0 ]
[ 96-41-3 ]
[ 120-92-3 ]
[ 71-36-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; In water; at 199.84℃; under 60006 Torr; for 3h;Autoclave;	Hydrogenation of furfural (99%, Sigma-Aldrich) in aqueous solution (3.5 wt.%, 100 mL) in the presence of PdRu/CNTs (300 mg) was carried out in a periodic mode in a Limbo Liautoclave (Buechi AG) at a temperature of 473 K and overallpressure of 8 MPa with continuous stirring of the reaction mixture (1500 min-1). The duration of any experiment was 3 h.

Reference： [1]Russian Chemical Bulletin,2017,vol. 66,p. 673 - 676
Izv. Akad. Nauk, Ser. Khim.,2017,p. 673 - 676,4

44
[ 2460-44-8 ]
[ 97-99-4 ]
[ 626-95-9 ]
[ 5343-92-0 ]
[ 87-99-0 ]
[ 64502-89-2 ]