CA1202643A - Procede de transformation en deux etapes d'aldoses en polyols - Google Patents

Procede de transformation en deux etapes d'aldoses en polyols

Info

Publication number: CA1202643A
Authority: CA; Canada
Prior art keywords: reaction zone; catalyst; stage; sorbitol; glycerol
Prior art date: 1981-01-21
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000394342A

Other languages

English (en)

Inventor

Amalesh K. Sirkar

James C. Chao

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

HRI Inc

Original Assignee

HRI Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-01-21

Filing date

1982-01-18

Publication date

1986-04-01

1982-01-18 Application filed by HRI Inc filed Critical HRI Inc

1986-04-01 Application granted granted Critical

1986-04-01 Publication of CA1202643A publication Critical patent/CA1202643A/fr

Status Expired legal-status Critical Current

Links

229920005862 polyol Polymers 0.000 title claims abstract description 14
150000003077 polyols Chemical class 0.000 title claims abstract description 14
150000001323 aldoses Chemical class 0.000 title claims abstract description 13
238000000034 method Methods 0.000 title claims description 22
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 108
238000006243 chemical reaction Methods 0.000 claims abstract description 70
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims abstract description 46
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims abstract description 46
239000000600 sorbitol Substances 0.000 claims abstract description 45
239000003054 catalyst Substances 0.000 claims abstract description 40
229920001223 polyethylene glycol Polymers 0.000 claims abstract description 31
150000005846 sugar alcohols Chemical class 0.000 claims abstract description 31
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 29
239000001257 hydrogen Substances 0.000 claims abstract description 26
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 25
239000007788 liquid Substances 0.000 claims abstract description 25
238000010926 purge Methods 0.000 claims abstract description 25
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 15
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims abstract description 15
239000008103 glucose Substances 0.000 claims abstract description 15
230000000694 effects Effects 0.000 claims abstract description 13
150000002334 glycols Chemical class 0.000 claims abstract description 9
239000000463 material Substances 0.000 claims abstract description 8
238000011084 recovery Methods 0.000 claims abstract description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
235000010356 sorbitol Nutrition 0.000 claims description 42
235000011187 glycerol Nutrition 0.000 claims description 34
239000000243 solution Substances 0.000 claims description 15
230000003197 catalytic effect Effects 0.000 claims description 10
238000004821 distillation Methods 0.000 claims description 10
229910052759 nickel Inorganic materials 0.000 claims description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 7
239000002184 metal Substances 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
150000001298 alcohols Chemical class 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
150000002772 monosaccharides Chemical class 0.000 claims description 5
239000002245 particle Substances 0.000 claims description 5
238000004064 recycling Methods 0.000 claims description 5
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
230000008929 regeneration Effects 0.000 claims description 4
238000011069 regeneration method Methods 0.000 claims description 4
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 3
238000006555 catalytic reaction Methods 0.000 claims description 3
238000002386 leaching Methods 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical group OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
229930195725 Mannitol Natural products 0.000 claims description 2
239000012527 feed solution Substances 0.000 claims description 2
239000000594 mannitol Substances 0.000 claims description 2
235000010355 mannitol Nutrition 0.000 claims description 2
238000005406 washing Methods 0.000 claims description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
150000002431 hydrogen Chemical class 0.000 claims 3
150000002314 glycerols Chemical class 0.000 claims 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 2
238000005292 vacuum distillation Methods 0.000 claims 1
239000000047 product Substances 0.000 abstract description 23
235000000346 sugar Nutrition 0.000 abstract description 22
150000008163 sugars Chemical class 0.000 abstract description 21
238000007327 hydrogenolysis reaction Methods 0.000 abstract description 10
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 abstract description 5
239000000920 calcium hydroxide Substances 0.000 abstract description 5
229910001861 calcium hydroxide Inorganic materials 0.000 abstract description 5
239000007795 chemical reaction product Substances 0.000 abstract description 3
229960002920 sorbitol Drugs 0.000 description 36
229960005150 glycerol Drugs 0.000 description 25
238000005984 hydrogenation reaction Methods 0.000 description 9
229920000223 polyglycerol Polymers 0.000 description 7
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
235000011116 calcium hydroxide Nutrition 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
238000005336 cracking Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
SPFMQWBKVUQXJV-BTVCFUMJSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;hydrate Chemical compound O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O SPFMQWBKVUQXJV-BTVCFUMJSA-N 0.000 description 1
HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 description 1
239000004386 Erythritol Substances 0.000 description 1
UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
229930091371 Fructose Natural products 0.000 description 1
239000005715 Fructose Substances 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
238000004523 catalytic cracking Methods 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
235000019414 erythritol Nutrition 0.000 description 1
UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
229940009714 erythritol Drugs 0.000 description 1
HGVHMIAKUYLQLL-UHFFFAOYSA-N ethene;propane-1,2,3-triol Chemical compound C=C.OCC(O)CO HGVHMIAKUYLQLL-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
238000011112 process operation Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000036647 reaction Effects 0.000 description 1
238000012958 reprocessing Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
-1 sorbitol Chemical class 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
239000000811 xylitol Substances 0.000 description 1
235000010447 xylitol Nutrition 0.000 description 1
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
229960002675 xylitol Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by elimination of -OH groups, e.g. by dehydration
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/755—Nickel
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/26—Hexahydroxylic alcohols
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C11/00—Fermentation processes for beer
- C12C11/02—Pitching yeast
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Food Science & Technology (AREA)
Bioinformatics & Cheminformatics (AREA)
Microbiology (AREA)
Mycology (AREA)
Materials Engineering (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000394342A 1981-01-21 1982-01-18 Procede de transformation en deux etapes d'aldoses en polyols Expired CA1202643A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US22699981A	1981-01-21	1981-01-21
US226,999		1981-01-21

Publications (1)

Publication Number	Publication Date
CA1202643A true CA1202643A (fr)	1986-04-01

Family

ID=22851337

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000394342A Expired CA1202643A (fr)	1981-01-21	1982-01-18	Procede de transformation en deux etapes d'aldoses en polyols

Country Status (5)

Country	Link
JP (1)	JPS57159732A (fr)
CA (1)	CA1202643A (fr)
DE (1)	DE3141907A1 (fr)
GB (1)	GB2095231B (fr)
NL (1)	NL8105092A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20070135301A1 (en) *	2005-12-08	2007-06-14	Sud-Chemie Inc.	Catalyst for the production of polyols by hydrogenolysis of carbohydrates
JP6774494B2 (ja) *	2016-02-19	2020-10-21	インターコンチネンタルグレートブランズエルエルシー	バイオマス源から複数の有用なストリームを形成するためのプロセス

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3341609A (en) *		1967-09-12		Process reactor
GB801732A (en) *	1955-07-29	1958-09-17	Melle Usines Sa	Improvements in or relating to a process for producing polyalcohols by hydrogenationof corresponding sugars
DE1129939B (de) *	1958-07-09	1962-05-24	Inventa A G Fuer Forschung	Verfahren zur Herstellung von Glycerin und Glykolen durch Hydrierspaltung von Saccharose
DE1277832B (de) *	1962-07-20	1968-09-19	Atlas Chem Ind	Verfahren zur Herstellung von Glycerin durch kontinuierliche einstufige Hydrogenolyse von reduzierbaren Zuckern
US3471580A (en) *	1968-04-19	1969-10-07	Hydrocarbon Research Inc	Production of glycerol from saccharides
US3965199A (en) *	1972-04-26	1976-06-22	Ici United States Inc.	Hydrogenation and hydrogenolysis of carbohydrates with tungsten oxide promoted supported nickel catalyst

1981
- 1981-10-22 DE DE19813141907 patent/DE3141907A1/de not_active Withdrawn
- 1981-11-10 NL NL8105092A patent/NL8105092A/nl not_active Application Discontinuation
- 1981-12-22 GB GB8138638A patent/GB2095231B/en not_active Expired
1982
- 1982-01-18 CA CA000394342A patent/CA1202643A/fr not_active Expired
- 1982-01-21 JP JP57006900A patent/JPS57159732A/ja active Pending

Also Published As

Publication number	Publication date
NL8105092A (nl)	1982-08-16
GB2095231B (en)	1985-06-12
GB2095231A (en)	1982-09-29
DE3141907A1 (de)	1982-10-14
JPS57159732A (en)	1982-10-01

Legal Events

Date	Code	Title	Description
2003-04-01	MKEX	Expiry

Publication	Publication Date	Title
US4322569A (en)	1982-03-30	Catalytic hydrogenation of glucose to produce sorbitol
US6291725B1 (en)	2001-09-18	Catalysts and process for hydrogenolysis of sugar alcohols to polyols
JP3405420B2 (ja)	2003-05-12	メチル−ｔｅｒｔ−ブチルエーテルの製造・回収方法
US4366332A (en)	1982-12-28	Catalytic hydrogenolysis of alditols to product glycerol and polyols
US4433184A (en)	1984-02-21	Multi-stage catalytic conversion of aldoses to alditols
US4380678A (en)	1983-04-19	Multi-stage aldoses to polyols process
US5030771A (en)	1991-07-09	Method of producing aliphatic and cycloaliphatic diols by catalytic hydrogenation of dicarboxylic acid esters
US4338472A (en)	1982-07-06	Catalytic hydrogenolysis of alditols to produce polyols
EP0581530B1 (fr)	1996-12-11	Elimination catalytique d'impuretés de type peroxid à partir d'une effluent de recyclage d'alcool tert-butylique
US4795733A (en)	1989-01-03	Hydrogenation catalyst and process for its preparation
US4873380A (en)	1989-10-10	Catalyst for removing peroxide contaminants from tertiary butyl alcohol
US6900361B2 (en)	2005-05-31	Process for lactose conversion to polyols
US4742179A (en)	1988-05-03	Catalytic removal of peroxide contaminants from tertiary butyl alcohol
EP0653406A1 (fr)	1995-05-17	Utilisation de catalyseurs de rhodium supportés dans la préparation de l'alcool tertiobutylique de l'hydropéroxide tertiobutylique
EP3551600B1 (fr)	2020-10-14	Procédé de préparation de glycols
EP0653407B1 (fr)	1997-09-10	Préparation simultanée du péroxide ditertiobutylique et de l'alcool tertiobutylique de l'hydropéroxide tertiobutylique
GB2095231A (en)	1982-09-29	Conversion of aldoses to polyols
EP0551022B1 (fr)	1995-09-13	Procédé pour la préparation d'isobutylène
EP0653402B1 (fr)	1997-08-13	Utilisation d'un catalyseur de l'oxyde de plomb dans la préparation de l'alcool tertiobutylique de l'hydropéroxide tertiobutylique
EP0653404B1 (fr)	1997-09-10	Utilisation d'un catalyseur de chrome supporté dans la préparation de l'alcool tertiobutylique de l'hydropéroxide tertiobutylique
EP0653405B1 (fr)	1997-08-13	Utilisation de catalyseurs de palladium/platine supportés dans la préparation de l'alcool tertiobutylique de l'hydropéroxide tertiobutylique
EP0653410A1 (fr)	1995-05-17	Utilisation d'un support d'oxyde d'aluminium ayant une structure pentagonale couché de palladium dans la préparation de l'alcool tert-butylique de l'hydroperoxyde tert-butylique