CA1191871A - Catalytic hydrogenolysis of alditols to produce polyols - Google Patents
Catalytic hydrogenolysis of alditols to produce polyolsInfo
- Publication number
- CA1191871A CA1191871A CA000394311A CA394311A CA1191871A CA 1191871 A CA1191871 A CA 1191871A CA 000394311 A CA000394311 A CA 000394311A CA 394311 A CA394311 A CA 394311A CA 1191871 A CA1191871 A CA 1191871A
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- glycerol
- sorbitol
- reaction zone
- feedstream
- Prior art date
- 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
Links
- 150000005846 sugar alcohols Chemical class 0.000 title claims abstract description 31
- 229920001223 polyethylene glycol Polymers 0.000 title claims abstract description 29
- 238000007327 hydrogenolysis reaction Methods 0.000 title claims abstract description 24
- 230000003197 catalytic effect Effects 0.000 title claims description 12
- 229920005862 polyol Polymers 0.000 title claims description 6
- 150000003077 polyols Chemical class 0.000 title claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 236
- 239000003054 catalyst Substances 0.000 claims abstract description 103
- 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 76
- 239000000600 sorbitol Substances 0.000 claims abstract description 75
- 238000006243 chemical reaction Methods 0.000 claims abstract description 73
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000001257 hydrogen Substances 0.000 claims abstract description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 40
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 33
- 230000008569 process Effects 0.000 claims abstract description 32
- 239000007788 liquid Substances 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000004821 distillation Methods 0.000 claims abstract description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000011069 regeneration method Methods 0.000 claims abstract description 11
- 230000008929 regeneration Effects 0.000 claims abstract description 10
- 230000000694 effects Effects 0.000 claims abstract description 9
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims abstract description 7
- 239000000920 calcium hydroxide Substances 0.000 claims abstract description 6
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims abstract description 6
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 6
- 239000000463 material Substances 0.000 claims abstract description 6
- 238000005406 washing Methods 0.000 claims abstract description 4
- 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 description 74
- 239000000243 solution Substances 0.000 claims description 20
- 229910052759 nickel Inorganic materials 0.000 claims description 14
- 239000002245 particle Substances 0.000 claims description 14
- 150000002334 glycols Chemical class 0.000 claims description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 11
- 150000001298 alcohols Chemical class 0.000 claims description 9
- 239000012527 feed solution Substances 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 3
- 230000008020 evaporation Effects 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 238000007086 side reaction Methods 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 238000005292 vacuum distillation Methods 0.000 claims description 3
- 230000009977 dual effect Effects 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims 2
- 229910052753 mercury Inorganic materials 0.000 claims 2
- 238000004064 recycling Methods 0.000 claims 2
- 230000001172 regenerating effect Effects 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 36
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 229960002920 sorbitol Drugs 0.000 description 67
- 235000010356 sorbitol Nutrition 0.000 description 66
- 235000011187 glycerol Nutrition 0.000 description 64
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 235000000346 sugar Nutrition 0.000 description 5
- 235000011116 calcium hydroxide Nutrition 0.000 description 4
- 229940093476 ethylene glycol Drugs 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 229920000223 polyglycerol Polymers 0.000 description 4
- 150000008163 sugars Chemical class 0.000 description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
- 229930195725 Mannitol Natural products 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 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 3
- 229930006000 Sucrose Natural products 0.000 description 3
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005336 cracking Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 150000002314 glycerols Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000000594 mannitol Substances 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 3
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 239000000811 xylitol Substances 0.000 description 3
- 235000010447 xylitol Nutrition 0.000 description 3
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 3
- 229960002675 xylitol Drugs 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 230000017525 heat dissipation Effects 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 229960001855 mannitol Drugs 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- ZKIRNCACNZXACZ-VFQQELCFSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;propane-1,2,3-triol Chemical compound OCC(O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO ZKIRNCACNZXACZ-VFQQELCFSA-N 0.000 description 1
- KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001323 aldoses Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000039 congener Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 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
- 229940093470 ethylene Drugs 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002052 molecular layer Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 101150008563 spir gene Proteins 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000010301 surface-oxidation reaction Methods 0.000 description 1
- 230000002277 temperature effect Effects 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 238000010518 undesired secondary reaction Methods 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
-
- 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
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US227,000 | 1981-01-21 | ||
| US06/227,000 US4338472A (en) | 1981-01-21 | 1981-01-21 | Catalytic hydrogenolysis of alditols to produce polyols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1191871A true CA1191871A (en) | 1985-08-13 |
Family
ID=22851341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000394311A Expired CA1191871A (en) | 1981-01-21 | 1982-01-18 | Catalytic hydrogenolysis of alditols to produce polyols |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4338472A (enExample) |
| JP (1) | JPS57142932A (enExample) |
| CA (1) | CA1191871A (enExample) |
| DE (1) | DE3141834A1 (enExample) |
| GB (1) | GB2091253B (enExample) |
| NL (1) | NL8105087A (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4476331A (en) * | 1982-02-11 | 1984-10-09 | Ethyl Corporation | Two stage hydrogenolysis of carbohydrate to glycols using sulfide modified ruthenium catalyst in second stage |
| US6291725B1 (en) | 2000-03-03 | 2001-09-18 | Board Of Trustees Operating Michigan State University | Catalysts and process for hydrogenolysis of sugar alcohols to polyols |
| US6479713B1 (en) * | 2001-10-23 | 2002-11-12 | Battelle Memorial Institute | Hydrogenolysis of 5-carbon sugars, sugar alcohols, and other methods and compositions for reactions involving hydrogen |
| US6841085B2 (en) * | 2001-10-23 | 2005-01-11 | Battelle Memorial Institute | Hydrogenolysis of 6-carbon sugars and other organic compounds |
| US20090264686A1 (en) * | 2008-04-16 | 2009-10-22 | Holladay Johnathan E | Hydrogenolysis processes and hydrogenolysis catalyst preparation methods |
| BRPI1008744B1 (pt) * | 2009-08-24 | 2018-06-12 | Phillips 66 Company | Hidrotratamento de carboidratos |
| WO2011078909A1 (en) * | 2009-12-22 | 2011-06-30 | Conocophillips Company | Conversion of carbohydrates to hydrocarbons |
| US8809607B2 (en) | 2010-10-07 | 2014-08-19 | Phillips 66 Company | Co-production of renewable diesel and renewable gasoline |
| USD751535S1 (en) * | 2013-12-17 | 2016-03-15 | World Products, Inc. | Antenna for water meter |
| MX390444B (es) | 2013-12-23 | 2025-03-20 | Archer Daniels Midland Co | Procedimientos mejorados para producir propilenglicol. |
| BR112016018246B1 (pt) | 2014-02-10 | 2021-06-01 | Archer Daniels Midland Company | Processo contínuo para hidrogenação do açúcar em uma alimentação de açúcar em água para um álcool de açúcar correspondente, processo contínuo para hidrogenação do açúcar em uma alimentação de açúcar em água para um álcool de açúcar correspondente, e processo para produção contínua de sorbitol |
| CA2945927C (en) | 2014-04-22 | 2022-07-26 | Archer Daniels Midland Company | Improved process of making bioderived propylene glycol |
| CN109107581A (zh) * | 2017-06-22 | 2019-01-01 | 长春美禾科技发展有限公司 | 一种耐酸合金催化剂 |
| CN118271154A (zh) * | 2024-02-27 | 2024-07-02 | 浙江大学衢州研究院 | 一种制备糖醇的气液逆流连续方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1075582B (de) * | 1960-02-18 | Inventa A.G. für Forschung und Patentverwertung, Luzern (Schweiz) | Verfahren zur Her-,tellung von mehrwertigen Alkoholen aus Hexiten | |
| DD35860A (enExample) * | ||||
| US2852570A (en) * | 1958-09-16 | Process for preparing polyhydric | ||
| US2965679A (en) * | 1960-12-20 | Process for the production of glycerol | ||
| US3278398A (en) * | 1966-10-11 | Recovery op glycerine by plural stage distillation | ||
| CA523789A (en) * | 1956-04-10 | Shell Development Company | Conversion of carbohydrates to polyhydric alcohols | |
| US2004135A (en) * | 1932-12-23 | 1935-06-11 | Du Pont | Production of polyhydric alcohols |
| US2174651A (en) * | 1937-05-17 | 1939-10-03 | Hercules Powder Co Ltd | Hydrogenation process |
| US2456633A (en) * | 1946-11-29 | 1948-12-21 | Universal Oil Prod Co | Catalyst preparation |
| US2549416A (en) * | 1948-02-04 | 1951-04-17 | Du Pont | Preparation of alcohols |
| GB688515A (en) * | 1950-04-06 | 1953-03-11 | Bataafsche Petroleum | Process for preparing polyhydric alcohols by catalytic reduction of carbohydrates |
| US2851390A (en) * | 1955-06-30 | 1958-09-09 | Marc A Chavannes | Fabric and method of manufacture |
| DE1096891B (de) * | 1956-04-12 | 1961-01-12 | Inventa Ag | Verfahren zur Herstellung von mehrwertigen aliphatischen Alkoholen |
| DE1077203B (de) * | 1957-10-29 | 1960-03-10 | Inventa A G Fuer Forschung | Verfahren zur Herstellung von mehrwertigen Alkoholen aus Sorbit |
| DE1077204B (de) * | 1957-11-16 | 1960-03-10 | Inventa A G Fuer Forschung | Verfahren zur Herstellung von Glycerin und Glykolen aus Zuckeralkoholen |
| GB1068712A (en) * | 1962-07-24 | 1967-05-10 | Unilever Ltd | Food products |
| GB1150490A (en) * | 1966-05-28 | 1969-04-30 | Kyowa Chemicals Kabushiki Kais | Separation of Glycerol from other Triols by Distillation |
| US3676364A (en) * | 1970-09-23 | 1972-07-11 | Du Pont | Regeneration of nickel-aluminum catalysts by polycarboxylic acid washing |
-
1981
- 1981-01-21 US US06/227,000 patent/US4338472A/en not_active Expired - Lifetime
- 1981-10-22 DE DE19813141834 patent/DE3141834A1/de not_active Withdrawn
- 1981-11-10 NL NL8105087A patent/NL8105087A/nl not_active Application Discontinuation
- 1981-12-22 GB GB8138640A patent/GB2091253B/en not_active Expired
-
1982
- 1982-01-18 CA CA000394311A patent/CA1191871A/en not_active Expired
- 1982-01-21 JP JP57006899A patent/JPS57142932A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4338472A (en) | 1982-07-06 |
| DE3141834A1 (de) | 1982-08-19 |
| NL8105087A (nl) | 1982-08-16 |
| JPH0331698B2 (enExample) | 1991-05-08 |
| JPS57142932A (en) | 1982-09-03 |
| GB2091253A (en) | 1982-07-28 |
| GB2091253B (en) | 1985-04-03 |
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