GB868890A - Epoxidation - Google Patents

Epoxidation

Info

Publication number
GB868890A
GB868890A GB37463/57A GB3746357A GB868890A GB 868890 A GB868890 A GB 868890A GB 37463/57 A GB37463/57 A GB 37463/57A GB 3746357 A GB3746357 A GB 3746357A GB 868890 A GB868890 A GB 868890A
Authority
GB
United Kingdom
Prior art keywords
acid
reaction
hydrogen peroxide
water
carboxylic 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
GB37463/57A
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.)
Celanese Corp
Original Assignee
Celanese Corp
Celanese Corp of America
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 Celanese Corp, Celanese Corp of America filed Critical Celanese Corp
Publication of GB868890A publication Critical patent/GB868890A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
    • C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof
    • C07D301/16—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof formed in situ, e.g. from carboxylic acids and hydrogen peroxide

Abstract

An epoxy compound is produced by subjecting an olefinic compound to reaction with a carboxylic peracid formed in situ by reaction between the corresponding carboxylic acid and hydrogen peroxide, wherein water is distilled from the reactants during the reaction, preferably by azeotropic distillation using a water-immiscible solvent incorporated into the reaction mixture. The water-solvent azeotrope may be condensed and allowed to separate into two phases and the solvent phase returned to the reaction mixture. Solvents which are inert under the conditions of reaction, e.g. hydrocarbon solvents such as benzene, isoheptane and hexane, are preferred. The olefinic compound may be an olefinic ester such as an ester of an unsaturated aliphatic acid or alcohol, e.g. soya bean or cotton seed oil, the oleic and linoleic esters of 1,2-propylene glycol, 1,3-butylene glycol, ethylene glycol and pentaerythritol, esters of unsaturated fatty acids and oleyl, linoleyl or linolenyl adipates. The carboxylic acid used to form the peracid may be acetic, propionic, formic or a dicarboxylic acid such as adipic acid. When acetic acid is used sulphuric acid or a sulphonic cation exchange resin or similar acid catalyst, may be present. Preferably a 5 to 50% excess of hydrogen peroxide is used, the amount of carboxylic acid being in the range of 0,15 to 1,00 equivalents of acid per mole of hydrogen peroxide.
GB37463/57A 1956-12-06 1957-12-02 Epoxidation Expired GB868890A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US868890XA 1956-12-06 1956-12-06

Publications (1)

Publication Number Publication Date
GB868890A true GB868890A (en) 1961-05-25

Family

ID=22201555

Family Applications (1)

Application Number Title Priority Date Filing Date
GB37463/57A Expired GB868890A (en) 1956-12-06 1957-12-02 Epoxidation

Country Status (1)

Country Link
GB (1) GB868890A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1152415B (en) * 1959-03-25 1963-08-08 Henkel & Cie Gmbh Process for the epoxidation of aliphatic or cycloaliphatic compounds with olefinic double bonds
US4303587A (en) * 1977-02-01 1981-12-01 Produits Chimiques Ugine Kuhlmann Catalytic epoxidation of olefins
US4344887A (en) 1979-12-28 1982-08-17 General Electric Company Method for epoxidizing olefins
US4389529A (en) 1981-05-15 1983-06-21 General Electric Company Method for epoxidizing olefins

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1152415B (en) * 1959-03-25 1963-08-08 Henkel & Cie Gmbh Process for the epoxidation of aliphatic or cycloaliphatic compounds with olefinic double bonds
US4303587A (en) * 1977-02-01 1981-12-01 Produits Chimiques Ugine Kuhlmann Catalytic epoxidation of olefins
US4344887A (en) 1979-12-28 1982-08-17 General Electric Company Method for epoxidizing olefins
US4389529A (en) 1981-05-15 1983-06-21 General Electric Company Method for epoxidizing olefins

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