GB879264A - Preparation of 1,4-cyclohexanedimethanol - Google Patents

Preparation of 1,4-cyclohexanedimethanol

Info

Publication number
GB879264A
GB879264A GB32034/58A GB3203458A GB879264A GB 879264 A GB879264 A GB 879264A GB 32034/58 A GB32034/58 A GB 32034/58A GB 3203458 A GB3203458 A GB 3203458A GB 879264 A GB879264 A GB 879264A
Authority
GB
United Kingdom
Prior art keywords
reactor
heat
conduit
reactors
feed
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
GB32034/58A
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.)
Eastman Kodak Co
Original Assignee
Eastman Kodak Co
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 Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of GB879264A publication Critical patent/GB879264A/en
Expired legal-status Critical Current

Links

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
    • C07C29/132—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
    • C07C29/147—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 carboxylic acids or derivatives thereof
    • C07C29/149—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 carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
    • 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
    • C07C31/27—Polyhydroxylic alcohols containing saturated rings
    • C07C31/272—Monocyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
    • C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/75—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Abstract

<FORM:0879264/IV (b)/1> In the production of 1,4-cyclohexanedimethanol by the catalytic hydrogenation of a diester of 1,4-cyclohexane dicarboxylic acid in the liquid phase, wherein the hydrogenation is carried out in two reactors 14, 22 connected in series, each containing catalyst and being maintained at a controlled temperature of 100 DEG -350 DEG C., preferably 200 DEG -300 DEG C., and under a hydrogen-pressure of 50 to 500 atm., part of the partially-reduced ester discharged from the primary reactor 14 is recycled to that reactor, together with fresh diester feed, in order to prevent the formation of injurious "hot spots" in the catalyst due to the exothermic reaction. The mixture of recycled material and fresh feed should have, per part of mixture, a heat of reduction to 1,4-cyclohexanedimethanol equivalent to not more than 0.6 parts of the diester. Copper chromite is a suitable catalyst; and the chromite of zinc, silver or manganese may also be used. Manganese oxide and magnesium oxide may also be used as catalyst. Fresh diester feed is pumped through conduit 11 into conduit 12 where it mixes with recycle material, pumped from reservoir 17. The mixture flows into reactor 14 via heat-exchanger 13. Hydrogen is introduced into reactor 14 via conduit 15. The output from reactor 14 flows into reservoir 17; and a portion of this output flows via conduit and heat-exchange 21 into secondary reactor 22. Heat-exchangers 13 and 21 can serve either to remove excess heat generated in the system or to heat the feed-material to the reactors to the desired temperature. The temperature is controlled by means of the two heat exchangers, and by varying the proportion of reducible ester in the feed material to the reactors, the latter is preferably adjusted so that the temperature rise in the reactors, due to the exothermic reaction, is in the range of 10 DEG to 35 DEG C. The output from reactor 22 flows to gas-liquid separator 24, from which hydrogen is vented through conduit 25, while a mixture of 1,4-cyclohexanedimethanol and by-product alcohol is withdrawn through conduit 26. The by-product alcohol is separated from the 1,4-cyclohexanedimethanol by distillation. Another embodiment is described wherein a gas-liquid separator and a condenser are connected between the two reactors, and part of the by-product alcohol is withdrawn from the system via the condenser.
GB32034/58A 1957-10-09 1958-10-08 Preparation of 1,4-cyclohexanedimethanol Expired GB879264A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US879264XA 1957-10-09 1957-10-09

Publications (1)

Publication Number Publication Date
GB879264A true GB879264A (en) 1961-10-11

Family

ID=22208092

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32034/58A Expired GB879264A (en) 1957-10-09 1958-10-08 Preparation of 1,4-cyclohexanedimethanol

Country Status (1)

Country Link
GB (1) GB879264A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4837367A (en) * 1987-08-03 1989-06-06 Eastman Kodak Company Low pressure catalytic hydrogenation of carbonyl-containing compounds
US4999090A (en) * 1988-04-10 1991-03-12 Towa Chemical Industry Co., Ltd. Process for preparing trans-1,4-cyclohexanedimethanol and powder of the same
US5387753A (en) * 1993-12-02 1995-02-07 Eastman Chemical Company Process for the preparation of alcohols and diols
EP0656339A1 (en) * 1993-12-02 1995-06-07 Eastman Chemical Company Process for the production of cydohexanedimethanol, with preponderance of the trans-isomer
US6187968B1 (en) * 1996-06-28 2001-02-13 Sk Njc Co., Ltd. Process for the preparation of cyclohexanedimethanol

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4837367A (en) * 1987-08-03 1989-06-06 Eastman Kodak Company Low pressure catalytic hydrogenation of carbonyl-containing compounds
US4999090A (en) * 1988-04-10 1991-03-12 Towa Chemical Industry Co., Ltd. Process for preparing trans-1,4-cyclohexanedimethanol and powder of the same
US5387753A (en) * 1993-12-02 1995-02-07 Eastman Chemical Company Process for the preparation of alcohols and diols
EP0656339A1 (en) * 1993-12-02 1995-06-07 Eastman Chemical Company Process for the production of cydohexanedimethanol, with preponderance of the trans-isomer
US6187968B1 (en) * 1996-06-28 2001-02-13 Sk Njc Co., Ltd. Process for the preparation of cyclohexanedimethanol

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