GB838766A - A process for the production of polyhydric alcohol mixtures by degradative hydrogenation of sugars - Google Patents
A process for the production of polyhydric alcohol mixtures by degradative hydrogenation of sugarsInfo
- Publication number
- GB838766A GB838766A GB21233/58A GB2123358A GB838766A GB 838766 A GB838766 A GB 838766A GB 21233/58 A GB21233/58 A GB 21233/58A GB 2123358 A GB2123358 A GB 2123358A GB 838766 A GB838766 A GB 838766A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sugars
- glycerin
- acid hydrolysis
- catalytically hydrogenated
- give
- 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
- 235000000346 sugar Nutrition 0.000 title abstract 7
- 150000008163 sugars Chemical class 0.000 title abstract 5
- 239000000203 mixture Substances 0.000 title abstract 4
- 150000005846 sugar alcohols Polymers 0.000 title abstract 2
- 230000003413 degradative effect Effects 0.000 title 1
- 238000005984 hydrogenation reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 4
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 3
- OOJRTGIXWIUBGG-UHFFFAOYSA-N 2-methylpropane-1,2,3-triol Chemical compound OCC(O)(C)CO OOJRTGIXWIUBGG-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- 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 abstract 2
- 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 abstract 2
- 239000004386 Erythritol Substances 0.000 abstract 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 abstract 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 2
- 239000005977 Ethylene Substances 0.000 abstract 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 abstract 2
- 229930195725 Mannitol Natural products 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 235000019414 erythritol Nutrition 0.000 abstract 2
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 abstract 2
- 229940009714 erythritol Drugs 0.000 abstract 2
- 235000011187 glycerol Nutrition 0.000 abstract 2
- 239000000594 mannitol Substances 0.000 abstract 2
- 235000010355 mannitol Nutrition 0.000 abstract 2
- 229960001855 mannitol Drugs 0.000 abstract 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 abstract 2
- 235000013772 propylene glycol Nutrition 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- 239000000600 sorbitol Substances 0.000 abstract 2
- 235000010356 sorbitol Nutrition 0.000 abstract 2
- 229960002920 sorbitol Drugs 0.000 abstract 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 abstract 2
- 239000000811 xylitol Substances 0.000 abstract 2
- 235000010447 xylitol Nutrition 0.000 abstract 2
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 abstract 2
- 229960002675 xylitol Drugs 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 229920002488 Hemicellulose Polymers 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000013543 active substance Substances 0.000 abstract 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000012045 crude solution Substances 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 239000011121 hardwood Substances 0.000 abstract 1
- 150000002402 hexoses Chemical class 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 238000005342 ion exchange Methods 0.000 abstract 1
- 239000000395 magnesium oxide Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- 150000002972 pentoses Chemical class 0.000 abstract 1
- -1 pentoses and hexoses Chemical class 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
Classifications
-
- 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
- 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
-
- 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
-
- 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
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
-
- 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
- C07C31/20—Dihydroxylic alcohols
-
- 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
- C07C31/20—Dihydroxylic alcohols
- C07C31/205—1,3-Propanediol; 1,2-Propanediol
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A crude solution of sugars obtained from the mineral acid hydrolysis of cellulose and/or hemicellulose present in cellulosic material is catalytically hydrogenated at a temperature of 100-160 DEG C. while the solution is maintained at a pH of at least 8 to give polyhydric alcohols having less carbon atoms than the original sugars. Preferably starting solutions are used in which the polymeric sugars have been degraded into monomeric sugars, e.g. pentoses and hexoses, and from which the residual acid has been removed by distillation. Suitable alkalis for maintaining the pH at the required value are lime water, magnesia, sodium carbonate and trimethylamine and these may be added continuously or otherwise. Preferred catalysts are active nickel catalysts precipitated on to active substances, such as active carbon and kieselguhr. The alcohol mixtures obtained may be further purified by ion exchange reactions. In the examples: (a) a sugar mixture obtained by the acid hydrolysis of hardwood is catalytically hydrogenated to give ethylene and propylene glycols, glycerin, methyl glycerin, with sorbitol, mannitol, xylitol and erythritol; and (b) a sugar mixture obtained by the acid hydrolysis of beechwood is catalytically hydrogenated to give ethylene and propylene glycols, glycerin and methyl glycerin along with some sorbitol, mannitol, xylitol and erythritol.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH838766X | 1957-07-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB838766A true GB838766A (en) | 1960-06-22 |
Family
ID=4540997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21233/58A Expired GB838766A (en) | 1957-07-02 | 1958-07-02 | A process for the production of polyhydric alcohol mixtures by degradative hydrogenation of sugars |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB838766A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4127676A (en) * | 1976-03-19 | 1978-11-28 | Farmos-Yhtyma Oy | Fodder additive for ruminants |
| US4292451A (en) | 1978-03-30 | 1981-09-29 | Ici Americas Inc. | High mannitol process (alkaline hydrogenation in presence of alkali metal carbonate) |
| US6440447B1 (en) | 1999-06-22 | 2002-08-27 | Land O'lakes, Inc. | Method and composition for enhancing milk production |
| US6866861B1 (en) | 1999-01-29 | 2005-03-15 | Land O'lakes, Inc. | Method and composition for enhancing milk component concentrations |
| US6982328B2 (en) | 2003-03-03 | 2006-01-03 | Archer Daniels Midland Company | Methods of producing compounds from plant material |
| US8110214B2 (en) | 2003-12-23 | 2012-02-07 | Land O'lakes Purina Feed Llc | Method and composition for enhancing milk production and milk component concentrations |
| US8519008B2 (en) | 2003-01-22 | 2013-08-27 | Purina Animal Nutrition Llc | Method and composition for improving the health of young monogastric mammals |
| US8658199B2 (en) | 2012-02-01 | 2014-02-25 | Purina Animal Nutrition Llc | Systems and methods for feeding sugar alcohol to ruminants during periods of heat stress |
| CN110845303A (en) * | 2019-11-30 | 2020-02-28 | 浙江华康药业股份有限公司 | Method for improving glucose hydrogenation efficiency |
| CN110862298A (en) * | 2019-11-08 | 2020-03-06 | 黑龙江新和成生物科技有限公司 | A kind of preparation method of sorbitol |
| CN114989230A (en) * | 2022-06-20 | 2022-09-02 | 浙江华康药业股份有限公司 | Method for preparing maltitol |
-
1958
- 1958-07-02 GB GB21233/58A patent/GB838766A/en not_active Expired
Cited By (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4127676A (en) * | 1976-03-19 | 1978-11-28 | Farmos-Yhtyma Oy | Fodder additive for ruminants |
| US4292451A (en) | 1978-03-30 | 1981-09-29 | Ici Americas Inc. | High mannitol process (alkaline hydrogenation in presence of alkali metal carbonate) |
| US6866861B1 (en) | 1999-01-29 | 2005-03-15 | Land O'lakes, Inc. | Method and composition for enhancing milk component concentrations |
| US9427414B2 (en) | 1999-06-22 | 2016-08-30 | Land O'lakes, Inc. | Method and composition for enhancing milk production |
| US8980306B2 (en) | 1999-06-22 | 2015-03-17 | Land O'lakes, Inc. | Method and composition for enhancing milk production |
| US7037518B2 (en) | 1999-06-22 | 2006-05-02 | Land O'lakes, Inc. | Method for enhancing milk production |
| US9668983B2 (en) | 1999-06-22 | 2017-06-06 | Land O'lakes, Inc. | Method and composition for enhancing milk production |
| US6440447B1 (en) | 1999-06-22 | 2002-08-27 | Land O'lakes, Inc. | Method and composition for enhancing milk production |
| US8440218B2 (en) | 1999-06-22 | 2013-05-14 | Land O'lakes, Inc. | Method for enhancing milk production |
| US9241914B2 (en) | 1999-06-22 | 2016-01-26 | Land O'lakes, Inc. | Method and composition for enhancing milk production |
| US9889099B2 (en) | 1999-06-22 | 2018-02-13 | Land O'lakes, Inc. | Method and composition for enhancing milk production |
| US11452303B2 (en) | 2003-01-22 | 2022-09-27 | Purina Animal Nutrition Llc | Methods for feeding sows and for improving the health of young piglets |
| US10980250B2 (en) | 2003-01-22 | 2021-04-20 | Purina Animal Nutrition Llc | Methods for feeding sows and for improving the health of young piglets |
| US8519008B2 (en) | 2003-01-22 | 2013-08-27 | Purina Animal Nutrition Llc | Method and composition for improving the health of young monogastric mammals |
| US10172376B2 (en) | 2003-01-22 | 2019-01-08 | Purina Animal Nutrition Llc | Methods for feeding sows and for improving the health of young piglets |
| US6982328B2 (en) | 2003-03-03 | 2006-01-03 | Archer Daniels Midland Company | Methods of producing compounds from plant material |
| US7652131B2 (en) | 2003-03-03 | 2010-01-26 | Battelle Memorial Institute | Methods of producing compounds from plant materials |
| US8591937B2 (en) | 2003-12-23 | 2013-11-26 | Purina Animal Nutrition Llc | Methods of feeding a pre-partum ruminant compositions containing sugar alcohol |
| US9179694B2 (en) | 2003-12-23 | 2015-11-10 | Purina Animal Nutrition Llc | Method and composition for enhancing milk production and milk component concentrations |
| US8110214B2 (en) | 2003-12-23 | 2012-02-07 | Land O'lakes Purina Feed Llc | Method and composition for enhancing milk production and milk component concentrations |
| US10292944B2 (en) | 2012-02-01 | 2019-05-21 | Purina Animal Nutrition Llc | Systems and methods for feeding sugar alcohol to ruminants during periods of heat stress |
| US10052292B2 (en) | 2012-02-01 | 2018-08-21 | Purina Animal Nutrition Llc | Systems and methods for feeding sugar alcohol to ruminants during periods of heat stress |
| US9456622B2 (en) | 2012-02-01 | 2016-10-04 | Purina Animal Nutrition Llc | Systems and methods for feeding sugar alcohol to ruminants during periods of heat stress |
| US9820950B2 (en) | 2012-02-01 | 2017-11-21 | Purina Animal Nutrition Llc | Systems and methods for feeding sugar alcohol to ruminants during periods of heat stress |
| US10588868B2 (en) | 2012-02-01 | 2020-03-17 | Purina Animal Nutrition Llc | Systems and methods for feeding sugar alcohol to ruminants during periods of heat stress |
| US9044041B2 (en) | 2012-02-01 | 2015-06-02 | Purina Animal Nutrition Llc | Systems and methods for feeding sugar alcohol to ruminants during periods of heat stress |
| US11123307B2 (en) | 2012-02-01 | 2021-09-21 | Purina Animal Nutrition Llc | Systems and methods for feeding sugar alcohol to ruminants during periods of heat stress |
| US8658199B2 (en) | 2012-02-01 | 2014-02-25 | Purina Animal Nutrition Llc | Systems and methods for feeding sugar alcohol to ruminants during periods of heat stress |
| US11666541B2 (en) | 2012-02-01 | 2023-06-06 | Purina Animal Nutrition Llc | Systems and methods for feeding sugar alcohol to ruminants during periods of heat stress |
| CN110862298A (en) * | 2019-11-08 | 2020-03-06 | 黑龙江新和成生物科技有限公司 | A kind of preparation method of sorbitol |
| CN110862298B (en) * | 2019-11-08 | 2023-04-11 | 黑龙江新和成生物科技有限公司 | Preparation method of sorbitol |
| CN110845303A (en) * | 2019-11-30 | 2020-02-28 | 浙江华康药业股份有限公司 | Method for improving glucose hydrogenation efficiency |
| CN114989230A (en) * | 2022-06-20 | 2022-09-02 | 浙江华康药业股份有限公司 | Method for preparing maltitol |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4075406A (en) | Process for making xylose | |
| GB838766A (en) | A process for the production of polyhydric alcohol mixtures by degradative hydrogenation of sugars | |
| US2759856A (en) | Preparation of high purity wood sugars | |
| GB1236910A (en) | A process for the manufacture of xylose and xylitol | |
| US3030429A (en) | Process for the direct hydrogenation splitting of | |
| US2775621A (en) | Hydrogenation of formaldehyde condensation products | |
| US3565885A (en) | Preparation of color stable glycosides | |
| US2951775A (en) | Selective saccharification of cellulosic materials | |
| US2325206A (en) | Catalyst and process for the hydrogenation of polyhydroxy compounds | |
| US3085038A (en) | Production of cellulose furfural and fodder from agricultural waste | |
| GB600870A (en) | Improvements relating to the manufacture of the 1:4-3:6-dianhydrides of mannitol andsorbitol | |
| GB490211A (en) | Method of converting aliphatic polyhydric alcohols to alcohols of lower molecular weight | |
| GB801732A (en) | Improvements in or relating to a process for producing polyalcohols by hydrogenationof corresponding sugars | |
| US2110879A (en) | Catalytic hydration of olefines to alcohols | |
| US2894982A (en) | Preparation of diesters of fumaric acid | |
| SU115665A1 (en) | Method for complex processing of vegetable raw materials | |
| US2974067A (en) | Hydrolysis of vegetable cellulosic materials | |
| GB834771A (en) | Improvements relating to the production of glycerol and glycols | |
| SU451685A1 (en) | The method of obtaining 2-medoxy-5-chlorobenzoic acid | |
| Karlivan | New aspects of the production of chemicals from biomass | |
| GB171479A (en) | Improvements in or relating to the preparation of alcohol | |
| GB565774A (en) | Improvements in production of fatty acids, aldehydes, ketones and alcohols from waste cellulose products | |
| KR840000128B1 (en) | Method for producing xylitol using straw fragments | |
| SU132632A1 (en) | The method of chemical processing of plant materials | |
| GB191300400A (en) | Process of Producing Fermentable Sugars. |