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GB876125A - Improvements in or modification of the preparation of glycidyl esters - Google Patents

Improvements in or modification of the preparation of glycidyl esters

Info

Publication number
GB876125A
GB876125A GB43815/59A GB4381559A GB876125A GB 876125 A GB876125 A GB 876125A GB 43815/59 A GB43815/59 A GB 43815/59A GB 4381559 A GB4381559 A GB 4381559A GB 876125 A GB876125 A GB 876125A
Authority
GB
United Kingdom
Prior art keywords
acids
epoxy
carboxylic acid
alkaline compound
catalyst
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
GB43815/59A
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of GB876125A publication Critical patent/GB876125A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D303/00Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02Compounds containing oxirane rings
    • C07D303/12Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/16Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/24Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
    • C07C67/26Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D303/00Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02Compounds containing oxirane rings
    • C07D303/38Compounds 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
    • C07D303/40Compounds 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

Landscapes

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

Abstract

An epoxy ester of an organic carboxylic acid is prepared by mixing an organic carboxylic acid with an epoxy halo-substituted compound in which the halogen atom is attached to a carbon atom adjacent to the epoxy group and adding an inorganic alkaline compound thereto. Suitable acids are the soap-forming acids such as fatty acids of 12 to 20 carbon atoms per molecule and dimers and trimers of unsaturated fatty acids or mixtures thereof. Other, aliphatic, cycloaliphatic, aromatic or heterocyclic mono or dicarboxylic acids may be used. The acids may contain alkoxy or ester radicals. Preferred epoxy halo-substituted compounds are of the formula <FORM:0876125/IV (b)/1> in which R is hydrogen or a hydrocarbon radical, preferably an aliphatic radical of not more than 10 carbon atoms. The alkaline compound may be potassium, sodium, lithium, calcium or magnesium hydroxide, as well as magnesium oxide or calcium oxide. As catalyst there may be used a tertiaryamine, those amines having a pH of less than 10 in aqueous solution being preferred. Quaternary salts of the formula [Y.R4]+X-in which Y is nitrogen, phosphorus or arsenic, X is an anion of an inorganic acid, and R is a hydrocarbon radical, may also be used. The catalyst may be used in amounts varying from 0.01% to 5% by weight of the carboxylic acid. The reaction may take place at a temperature of 95 DEG C. to 117 DEG C., preferably at 110 DEG C. The alkaline compound is preferably added over a period varying from 35-145 minutes. Specification 763,559 is referred to.
GB43815/59A 1958-12-29 1959-12-24 Improvements in or modification of the preparation of glycidyl esters Expired GB876125A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US876125XA 1958-12-29 1958-12-29

Publications (1)

Publication Number Publication Date
GB876125A true GB876125A (en) 1961-08-30

Family

ID=22206223

Family Applications (1)

Application Number Title Priority Date Filing Date
GB43815/59A Expired GB876125A (en) 1958-12-29 1959-12-24 Improvements in or modification of the preparation of glycidyl esters

Country Status (1)

Country Link
GB (1) GB876125A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3992432A (en) 1967-04-05 1976-11-16 Continental Oil Company Phase transfer catalysis of heterogeneous reactions by quaternary salts

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3992432A (en) 1967-04-05 1976-11-16 Continental Oil Company Phase transfer catalysis of heterogeneous reactions by quaternary salts

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