GB779052A - Esters and a process for their production - Google Patents

Esters and a process for their production

Info

Publication number
GB779052A
GB779052A GB19516/53A GB1951653A GB779052A GB 779052 A GB779052 A GB 779052A GB 19516/53 A GB19516/53 A GB 19516/53A GB 1951653 A GB1951653 A GB 1951653A GB 779052 A GB779052 A GB 779052A
Authority
GB
United Kingdom
Prior art keywords
tricyclodecane
acid
dimethylol
give
dicarboxylic acid
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
GB19516/53A
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.)
Ruhrchemie AG
Original Assignee
Ruhrchemie AG
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 Ruhrchemie AG filed Critical Ruhrchemie AG
Publication of GB779052A publication Critical patent/GB779052A/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
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
    • C07C69/54—Acrylic acid esters; Methacrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/80—Phthalic acid esters

Landscapes

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

Abstract

The invention comprises polyesters produced by esterifying tricyclodecane-dicarboxylic acid and tricyclodecane-dimethylol with each other or with other polyhydric alcohols and dicarboxylic acids respectively. Suitable polyhydric alcohols are, for example, glycol and glycerol and suitable dicarboxylic acids are phthalic acid and adipic acid. The esterification is carried out by boiling the reactants under reflux in the presence of an esterification catalyst such as p-toluene sulphonic acid. The production of the polymer is preferably carried out at reduced pressure in the absence of oxygen. In the examples, polyesters are obtained by esterifying (a) tricyclodecane-dicarboxylic acid with ethylene glycol; (b) tricyclodecane-dicarboxylic acid with glycerol; (c) tricyclodecane-dicarboxylic acid with tricyclodecane-dimethylol; (d) tricyclodecane-dimethylol with phthalic anhydride; and (e) tricyclodecane-dimethylol with adipic acid.ALSO:The invention comprises esters produced by esterifying tricyclodecane-dicarboxylic acid or tricyclodecane-dimethylol with an alcohol or a carboxylic acid respectively. The esterification is carried out by boiling the esterification mixture comprising tricyclodecane-dicarboxylic acid and an alcohol or tricyclodecane-dimethylol and an acid under reflux in the presence of an esterification catalyst, preferably p-toluene sulphonic acid. The alcohol or acid is preferably present in a quantity which is at least sufficient for the complete esterification of the tricyclodecanedicarboxylic acid or tricyclodecane-dimethylol respectively. In the examples: (a) tricyclodecane-dimethylol is heated with glacial acetic acid in the presence of p-toluene-sulphonic acid to give the tricyclodecane-dimethylol-diacetic acid ester; (b) tricyclodecane-dimethylol is reacted similarly with n-butyric acid to give the dibutyrate; (c) tricyclodecane-dimethylol is reacted similarly with stearic acid to give the distearate; (d) tricyclodecane-dimethylol is reacted similarly with a C15 branched fatty acid to give the corresponding di-ester; (e) tricyclodecane-dicarboxylic acid is reacted with methyl alcohol to give the dimethyl ester; (f) tricyclodecane-dicarboxylic acid is reacted with ethyl alcohol to give the diethyl ester; (g) tricyclodecane-dicarboxylic acid is reacted with n-butyl alcohol to give the di-butyl ester and (h) tricyclodecane dicarboxylic acid is reacted with n-hexyl alcohol to give the di-hexyl ester. The preparation of tricyclodecane-dimethylol-divalerate is also given.
GB19516/53A 1952-08-01 1953-07-14 Esters and a process for their production Expired GB779052A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE779052X 1952-08-01

Publications (1)

Publication Number Publication Date
GB779052A true GB779052A (en) 1957-07-17

Family

ID=6687103

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19516/53A Expired GB779052A (en) 1952-08-01 1953-07-14 Esters and a process for their production

Country Status (1)

Country Link
GB (1) GB779052A (en)

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