GB988316A - Process for the preparation of trans-1,4-dimethylolcyclohexane - Google Patents

Process for the preparation of trans-1,4-dimethylolcyclohexane

Info

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
Application number
GB1750263A
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.)
DEHYDAG GmbH
Dehydag Deutsche Hydrierwerke GmbH
Original Assignee
DEHYDAG GmbH
Dehydag Deutsche Hydrierwerke GmbH
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.)
Filing date
Publication date
Application filed by DEHYDAG GmbH, Dehydag Deutsche Hydrierwerke GmbH filed Critical DEHYDAG GmbH
Publication of GB988316A publication Critical patent/GB988316A/en
Expired legal-status Critical Current

Links

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)

Abstract

Trans-1,4-dimethylol-cyclohexane is made by treating a mixture of cis- and trans-isomers of hexahydroterephthalic acid ester with hydrogen at elevated pressures and temperatures in the presence of a copper-zinc catalyst, separating the trans form from the cis-trans isomeric mixture of 1,4-dimethylolcyclohexane formed and subjecting the residue to the above treatment again, initial ester being added to replace the separated transform if desired. Before the hydrogen treatment, the addition of 1-3 parts of methanol per part of starting material is advantageous. The catalyst may be a metal catalyst, metal oxide or a mixture thereof. Cd, Fe, Cr and Ba oxides may be added as promoters. Temperatures above 200 DEG C., preferably 240-300 DEG C., and hydrogen pressures of 200-300 atm. are suitable. The process may be continuous. The trans-form may be separated by direct freezing of the trans isomer and subsequent centrifuging, or by crystallizing from solvents, especially ethyl acetate with or without acetone. Detailed examples are given.ALSO:A copper-zinc catalyst, used as metal or metal oxide catalysts for the hydrogenation of cis and trans hexahydroterephthalic acid ester to trans-1,4-dimethylolcyclohexane, is made in an example by dissolving copper sulphate (pentahydrate) and zinc sulphate (heptahydrate) in water, precipitating with calcined soda in water, placing in a reaction furnace in the form of tablets and after complete reduction of the catalyst it was hydrogenated at 250 atm. at 250 DEG C. In another example, a catalyst is made by treating the sulphates with soda solution to precipitate the carbonates and the precipitate is treated with barium hydroxide solution, filtered and dried. The catalyst is charged in the form of tablets to the reaction furnace. The catalyst may also contain cadmium, iron and chromium in the form of oxides as promoters. The optimum range of Cu:Zn lies in the range 1 : 1 to 1 : 4. The catalyst may be supported on silica gel or aluminium oxides.
GB1750263A 1962-05-05 1963-05-03 Process for the preparation of trans-1,4-dimethylolcyclohexane Expired GB988316A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DED38844A DE1203254B (en) 1962-05-05 1962-05-05 Circular process for the production of trans-dimethylolcyclohexane (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 (en)
CH (1) CH453340A (en)
DE (1) DE1203254B (en)
GB (1) GB988316A (en)
NL (1) NL292315A (en)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2334700A1 (en) * 1975-12-11 1977-07-08 Eastman Kodak Co NEW POLYESTERS DERIVED FROM CARBOCYCLIC COMPOUNDS
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
EP0411136A1 (en) * 1988-12-28 1991-02-06 Mitsubishi Rayon Co., Ltd. Polyester copolymer
EP0483354A4 (en) * 1988-12-28 1992-01-30 Mitsubishi Rayon Co 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
US5395990A (en) * 1993-12-02 1995-03-07 Eastman Chemical Company Process for the production 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
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
WO2013019441A1 (en) 2011-07-29 2013-02-07 Eastman Chemical Company Process for the preparation of 1,4-cyclohexanedimethanol from terephthalic acid
WO2013019442A1 (en) 2011-07-29 2013-02-07 Eastman Chemical Company Process for the preparation of 1,3-cyclohexanedimethanol from isophthalic acid
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
CN112194564A (en) * 2020-09-28 2021-01-08 中国石油化工股份有限公司 Method for improving trans-product proportion of cyclohexanedimethanol

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1190783B (en) * 1981-04-29 1988-02-24 Davy Mckee Oil & Chem PROCESS FOR HYDROGENOLYSIS OF ESTERS OF CARBOXYLIC ACIDS
ATE23146T1 (en) * 1981-08-20 1986-11-15 Davy Mckee London CATALYTIC HYDROGENATION.
FR2521131B1 (en) * 1982-02-09 1993-01-22 Mac Kee Oil Chemicals Ltd Davy PROCESS FOR HYDROGENOLYSIS OF CARBOXYLIC ACID ESTERS
JPS59500516A (en) * 1982-03-26 1984-03-29 デイビ−　マツキ−　（ロンドン）　リミテツド How to produce ethanol

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1076125B (en) * 1957-10-09 1960-02-25 Eastman Kodak Co Process and device for the production of 1,4-dimethylolcyclohexane
US2917549A (en) * 1958-01-07 1959-12-15 Eastman Kodak Co Preparation of trans-1,4-cyclohexanedimethanol

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2334700A1 (en) * 1975-12-11 1977-07-08 Eastman Kodak Co NEW POLYESTERS DERIVED FROM CARBOCYCLIC COMPOUNDS
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
EP0411136A1 (en) * 1988-12-28 1991-02-06 Mitsubishi Rayon Co., Ltd. Polyester copolymer
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
EP0483354A1 (en) * 1988-12-28 1992-05-06 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
US5395990A (en) * 1993-12-02 1995-03-07 Eastman Chemical Company Process for the production 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
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
WO2013019441A1 (en) 2011-07-29 2013-02-07 Eastman Chemical Company Process for the preparation of 1,4-cyclohexanedimethanol from terephthalic acid
WO2013019442A1 (en) 2011-07-29 2013-02-07 Eastman Chemical Company Process for the preparation of 1,3-cyclohexanedimethanol from isophthalic acid
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
US8410318B2 (en) 2011-07-29 2013-04-02 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
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 (en) * 2020-09-28 2021-01-08 中国石油化工股份有限公司 Method for improving trans-product proportion of cyclohexanedimethanol

Also Published As

Publication number Publication date
CH453340A (en) 1968-06-14
BE631848A (en) 1963-09-02
NL292315A (en)
DE1203254B (en) 1965-10-21

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