GB988316A - Process for the preparation of trans-1,4-dimethylolcyclohexane - Google Patents
Process for the preparation of trans-1,4-dimethylolcyclohexaneInfo
- Publication number
- GB988316A GB988316A GB1750263A GB1750263A GB988316A GB 988316 A GB988316 A GB 988316A GB 1750263 A GB1750263 A GB 1750263A GB 1750263 A GB1750263 A GB 1750263A GB 988316 A GB988316 A GB 988316A
- Authority
- GB
- United Kingdom
- Prior art keywords
- catalyst
- trans
- cis
- oxides
- dimethylolcyclohexane
- 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
- YIMQCDZDWXUDCA-ZKCHVHJHSA-N OC[C@H]1CC[C@H](CO)CC1 Chemical compound OC[C@H]1CC[C@H](CO)CC1 YIMQCDZDWXUDCA-ZKCHVHJHSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 239000003054 catalyst Substances 0.000 abstract 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 abstract 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 2
- 229910052793 cadmium Inorganic materials 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229910052804 chromium Inorganic materials 0.000 abstract 2
- 239000011651 chromium Substances 0.000 abstract 2
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 abstract 2
- -1 hexahydroterephthalic acid ester Chemical class 0.000 abstract 2
- 229910052742 iron Inorganic materials 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 229910044991 metal oxide Inorganic materials 0.000 abstract 2
- 150000004706 metal oxides Chemical class 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 abstract 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 abstract 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052788 barium Inorganic materials 0.000 abstract 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 abstract 1
- 229910001863 barium hydroxide Inorganic materials 0.000 abstract 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 230000008014 freezing Effects 0.000 abstract 1
- 238000007710 freezing Methods 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- RZLVQBNCHSJZPX-UHFFFAOYSA-L zinc sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Zn+2].[O-]S([O-])(=O)=O RZLVQBNCHSJZPX-UHFFFAOYSA-L 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
-
- 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
- B01J23/72—Copper
-
- 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
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/80—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
-
- 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
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/86—Chromium
- B01J23/868—Chromium copper and chromium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED38844A DE1203254B (de) | 1962-05-05 | 1962-05-05 | Kreislaufverfahren zur Herstellung von trans-Dimethylolcyclohexan-(1, 4) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB988316A true GB988316A (en) | 1965-04-07 |
Family
ID=7044359
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1750263A Expired GB988316A (en) | 1962-05-05 | 1963-05-03 | Process for the preparation of trans-1,4-dimethylolcyclohexane |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE631848A (enrdf_load_stackoverflow) |
| CH (1) | CH453340A (enrdf_load_stackoverflow) |
| DE (1) | DE1203254B (enrdf_load_stackoverflow) |
| GB (1) | GB988316A (enrdf_load_stackoverflow) |
| NL (1) | NL292315A (enrdf_load_stackoverflow) |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2334700A1 (fr) * | 1975-12-11 | 1977-07-08 | Eastman Kodak Co | Nouveaux polyesters derivant de composes carbocycliques |
| US4393251A (en) * | 1981-06-17 | 1983-07-12 | Basf Aktiengesellschaft | Preparation of propanediols using a copper-and zinc containing hydrogenation catalyst |
| US4855515A (en) * | 1987-08-12 | 1989-08-08 | Eastman Kodak Company | Process for the production of neopentyl glycol |
| EP0483354A4 (en) * | 1988-12-28 | 1992-01-30 | Mitsubishi Rayon Co | Polyester copolymer. |
| EP0411136A4 (en) * | 1988-12-28 | 1992-03-18 | Mitsubishi Rayon Co., Ltd. | Polyester copolymer |
| US5387752A (en) * | 1993-12-02 | 1995-02-07 | Eastman Chemical Company | Process for the production of cyclohexanedimethanol |
| US5387753A (en) * | 1993-12-02 | 1995-02-07 | Eastman Chemical Company | Process for the preparation of alcohols and diols |
| US5395991A (en) * | 1993-12-02 | 1995-03-07 | Eastman Chemical Company | Process for the production of alcohols and diols |
| US5395987A (en) * | 1993-12-02 | 1995-03-07 | Eastman Chemical Company | Preparation of cyclohexanedimethanol with a particular ratio |
| US5395990A (en) * | 1993-12-02 | 1995-03-07 | Eastman Chemical Company | Process for the production of alcohols and diols |
| US5395986A (en) * | 1993-12-02 | 1995-03-07 | Eastman Chemical Company | Process for the production of cyclohexanedimethanol |
| US5406004A (en) * | 1993-12-02 | 1995-04-11 | Eastman Chemical Company | Hydrogenation process for the preparation of alcohols and diols utilizing gas and liquid phases |
| US5414159A (en) * | 1993-12-02 | 1995-05-09 | Eastman Chemical Company | Process |
| WO2013019440A1 (en) | 2011-07-29 | 2013-02-07 | Eastman Chemical Company | Integrated process for the preparation of 1,4-cyclohexanedimethanol from terephtalic acid |
| WO2013019439A1 (en) | 2011-07-29 | 2013-02-07 | Eastman Chemical Company | Process for the preparation of 1,4-cyclohexanedimethanol |
| WO2013019442A1 (en) | 2011-07-29 | 2013-02-07 | Eastman Chemical Company | Process for the preparation of 1,3-cyclohexanedimethanol from isophthalic acid |
| WO2013019441A1 (en) | 2011-07-29 | 2013-02-07 | Eastman Chemical Company | Process for the preparation of 1,4-cyclohexanedimethanol from terephthalic acid |
| CN112194564A (zh) * | 2020-09-28 | 2021-01-08 | 中国石油化工股份有限公司 | 一种提高环己烷二甲醇反式产物比例的方法 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1190783B (it) * | 1981-04-29 | 1988-02-24 | Davy Mckee Oil & Chem | Processo per l'idrogenolisi di esteri di acidi carbossilici |
| EP0074193B1 (en) * | 1981-08-20 | 1986-10-29 | DAVY McKEE (LONDON) LIMITED | Catalytic hydrogenation |
| FR2521131B1 (fr) * | 1982-02-09 | 1993-01-22 | Mac Kee Oil Chemicals Ltd Davy | Procede d'hydrogenolyse d'esters d'acides carboxyliques |
| EP0104197B1 (en) * | 1982-03-26 | 1986-05-28 | DAVY McKEE (LONDON) LIMITED | Process for the production of ethanol |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1076125B (de) * | 1957-10-09 | 1960-02-25 | Eastman Kodak Co | Verfahren und Vorrichtung zur Herstellung von 1, 4-Dimethylolcyclohexan |
| US2917549A (en) * | 1958-01-07 | 1959-12-15 | Eastman Kodak Co | Preparation of trans-1,4-cyclohexanedimethanol |
-
0
- NL NL292315D patent/NL292315A/xx unknown
-
1962
- 1962-05-05 DE DED38844A patent/DE1203254B/de active Pending
-
1963
- 1963-04-26 CH CH523663A patent/CH453340A/de unknown
- 1963-05-03 BE BE631848A patent/BE631848A/fr unknown
- 1963-05-03 GB GB1750263A patent/GB988316A/en not_active Expired
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2334700A1 (fr) * | 1975-12-11 | 1977-07-08 | Eastman Kodak Co | Nouveaux polyesters derivant de composes carbocycliques |
| US4393251A (en) * | 1981-06-17 | 1983-07-12 | Basf Aktiengesellschaft | Preparation of propanediols using a copper-and zinc containing hydrogenation catalyst |
| US4855515A (en) * | 1987-08-12 | 1989-08-08 | Eastman Kodak Company | Process for the production of neopentyl glycol |
| EP0483354A4 (en) * | 1988-12-28 | 1992-01-30 | Mitsubishi Rayon Co | Polyester copolymer. |
| EP0411136A4 (en) * | 1988-12-28 | 1992-03-18 | Mitsubishi Rayon Co., Ltd. | Polyester copolymer |
| US5387752A (en) * | 1993-12-02 | 1995-02-07 | Eastman Chemical Company | Process for the production of cyclohexanedimethanol |
| US5387753A (en) * | 1993-12-02 | 1995-02-07 | Eastman Chemical Company | Process for the preparation of alcohols and diols |
| US5395991A (en) * | 1993-12-02 | 1995-03-07 | Eastman Chemical Company | Process for the production of alcohols and diols |
| US5395987A (en) * | 1993-12-02 | 1995-03-07 | Eastman Chemical Company | Preparation of cyclohexanedimethanol with a particular ratio |
| US5395990A (en) * | 1993-12-02 | 1995-03-07 | Eastman Chemical Company | Process for the production of alcohols and diols |
| US5395986A (en) * | 1993-12-02 | 1995-03-07 | Eastman Chemical Company | Process for the production of cyclohexanedimethanol |
| US5406004A (en) * | 1993-12-02 | 1995-04-11 | Eastman Chemical Company | Hydrogenation process for the preparation of alcohols and diols utilizing gas and liquid phases |
| US5414159A (en) * | 1993-12-02 | 1995-05-09 | Eastman Chemical Company | Process |
| EP0656334A1 (en) * | 1993-12-02 | 1995-06-07 | Eastman Chemical Company | Process for the production of cydohexanedimethanol, with preponderance of the trans-isomer |
| WO2013019440A1 (en) | 2011-07-29 | 2013-02-07 | Eastman Chemical Company | Integrated process for the preparation of 1,4-cyclohexanedimethanol from terephtalic acid |
| WO2013019439A1 (en) | 2011-07-29 | 2013-02-07 | Eastman Chemical Company | Process for the preparation of 1,4-cyclohexanedimethanol |
| WO2013019442A1 (en) | 2011-07-29 | 2013-02-07 | Eastman Chemical Company | Process for the preparation of 1,3-cyclohexanedimethanol from isophthalic acid |
| WO2013019441A1 (en) | 2011-07-29 | 2013-02-07 | Eastman Chemical Company | Process for the preparation of 1,4-cyclohexanedimethanol from terephthalic acid |
| US8410317B2 (en) | 2011-07-29 | 2013-04-02 | Eastman Chemical Company | Process for the preparation of 1,4-cyclohexanedimethanol |
| US8410318B2 (en) | 2011-07-29 | 2013-04-02 | Eastman Chemical Company | Process for the preparation of 1,4-cyclohexanedimethanol from terephthalic acid |
| US8766017B2 (en) | 2011-07-29 | 2014-07-01 | Eastman Chemical Company | Integrated process for the preparation of 1,4-cyclohexanedimethanol from terephthalic acid |
| US8877984B2 (en) | 2011-07-29 | 2014-11-04 | Eastman Chemical Company | Process for the preparation of 1,3-cyclohexanedimethanol from isophthalic acid |
| CN112194564A (zh) * | 2020-09-28 | 2021-01-08 | 中国石油化工股份有限公司 | 一种提高环己烷二甲醇反式产物比例的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| BE631848A (fr) | 1963-09-02 |
| DE1203254B (de) | 1965-10-21 |
| CH453340A (de) | 1968-06-14 |
| NL292315A (enrdf_load_stackoverflow) |
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