GB744543A - Improvements in and relating to the production of cyclohexa-1,4-diene-1,4-dicarboxylic acid and esters thereof - Google Patents

Improvements in and relating to the production of cyclohexa-1,4-diene-1,4-dicarboxylic acid and esters thereof

Info

Publication number
GB744543A
GB744543A GB12093/53A GB1209353A GB744543A GB 744543 A GB744543 A GB 744543A GB 12093/53 A GB12093/53 A GB 12093/53A GB 1209353 A GB1209353 A GB 1209353A GB 744543 A GB744543 A GB 744543A
Authority
GB
United Kingdom
Prior art keywords
ester
acid
esters
dicarboxylic acid
diol
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
GB12093/53A
Inventor
Peter Smith
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB12093/53A priority Critical patent/GB744543A/en
Publication of GB744543A publication Critical patent/GB744543A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/08—Saturated compounds having a carboxyl group bound to a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
    • 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
    • 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
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Cyclohexa - 1 : 4 - diene - 1 : 4 - dicarboxylic acid or acid esters or di-esters thereof are prepared by heating at a temperature of at least 150 DEG C. cyclohexane - 2 : 5 - diol - 1 : 4-dicarboxylic acid or acid esters or di-esters thereof, containing, in solution, at least 0.01 per cent by weight, based on the amount of acid or acid-ester or di-ester, of a di-alkali metal salt of cyclohexane-2 : 5-diol-1 : 4-dicarboxylic acid. The preferred salt is the di-sodium salt, and in an amount of 1 to 5 per cent. The solution of alkali metal salt may be obtained by addition of the requisite amount of alkali metal hydroxide to the cyclohexane-2 : 5-diol-1 : 4-dicarboxylic acid or ester. The formation of lactones, such as 4-carbomethoxy-2-hydroxy - 6 - oxa - bicyclo - [3 : 2 : 1] - octa-7-one, which is formed when the dimethyl ester is reacted, is diminished by working in a solvent such as water or an aliphatic alcohol containing up to four carbon atoms. The alcohol which corresponds to the ester employed is preferred. When a diester is used as starting material and the process is carried out in the absence of a solvent or in the presence of water, both acid ester and acid are present in the product. The temperature used is below the critical temperature of the solvent if one is employed, and sufficient pressure is applied to maintain the solvent in the liquid phase. In examples (1) a solution of dimethyl cyclohexane - 2:5 - diol - 1:4 - dicarboxylate in methanol containing approximately 0.25 per cent of the disodium salt was heated in an autoclave for 24 hours at 200 DEG C. and the corresponding unsaturated di-ester isolated; (2) as in (1) but using approximately 2.5 per cent of di-sodium salt; (3) the diethyl ester dissolved in ethanol, was reacted with sodium hydroxide and heated as in (1) for 36 hours, the corresponding diethyl ester being obtained. Specification 740,388 is referred to.
GB12093/53A 1953-05-01 1953-05-01 Improvements in and relating to the production of cyclohexa-1,4-diene-1,4-dicarboxylic acid and esters thereof Expired GB744543A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB12093/53A GB744543A (en) 1953-05-01 1953-05-01 Improvements in and relating to the production of cyclohexa-1,4-diene-1,4-dicarboxylic acid and esters thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB12093/53A GB744543A (en) 1953-05-01 1953-05-01 Improvements in and relating to the production of cyclohexa-1,4-diene-1,4-dicarboxylic acid and esters thereof

Publications (1)

Publication Number Publication Date
GB744543A true GB744543A (en) 1956-02-08

Family

ID=9998283

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12093/53A Expired GB744543A (en) 1953-05-01 1953-05-01 Improvements in and relating to the production of cyclohexa-1,4-diene-1,4-dicarboxylic acid and esters thereof

Country Status (1)

Country Link
GB (1) GB744543A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3127413A (en) * 1960-11-22 1964-03-31 Neisler Lab Inc Octahydroisoindoles
US9018408B2 (en) 2011-03-14 2015-04-28 Dow Global Technologies Llc Processes for producing terephthalic acid and terephthalic esters

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3127413A (en) * 1960-11-22 1964-03-31 Neisler Lab Inc Octahydroisoindoles
US9018408B2 (en) 2011-03-14 2015-04-28 Dow Global Technologies Llc Processes for producing terephthalic acid and terephthalic esters

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