GB755778A - Method of epoxidation - Google Patents

Method of epoxidation

Info

Publication number
GB755778A
GB755778A GB16169/54A GB1616954A GB755778A GB 755778 A GB755778 A GB 755778A GB 16169/54 A GB16169/54 A GB 16169/54A GB 1616954 A GB1616954 A GB 1616954A GB 755778 A GB755778 A GB 755778A
Authority
GB
United Kingdom
Prior art keywords
fatty acids
cottonseed
peracetic acid
acids
esters
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
GB16169/54A
Inventor
Frank Philip Greenspan
Ralph Joseph Gall
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.)
FMC Corp
Original Assignee
FMC Corp
Food Machinery and Chemical Corp
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 FMC Corp, Food Machinery and Chemical Corp filed Critical FMC Corp
Priority to GB16169/54A priority Critical patent/GB755778A/en
Publication of GB755778A publication Critical patent/GB755778A/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
    • 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
    • C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/027—Polycondensates containing more than one epoxy group per molecule obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/006—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by oxidation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Inorganic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Epoxy Compounds (AREA)

Abstract

A process for the epoxidation of long chain aliphatic carboxylic acids, carboxylic esters and alcohols having at least 10 carbon atoms in the chain to form oxirane compounds, comprises mixing the acid, ester or alcohol at a temperature below 30 DEG C. with substantially the theoretical amount of an organic peracid required for the epoxidation of the ethylenic bonds, agitating the reaction mixture for some 1 to 3 hours at a temperature below 25 DEG C. and then heating the reaction mixture in the temperature range of 50 DEG to 60 DEG C. for a period of 1/2 to 2 hours. Peracetic acid is the preferred peracid for the reaction-particularly peracetic acid made from 50 or 90 per cent hydrogen peroxide, when the temperature for the initial mixing is advantageously kept below 25 DEG C. The process is applicable to fatty acids, e.g. cotton seed and soybean oil acids, and esters thereof, e.g. esters derived from mono-, di-, tri-and other poly-hydric alcohols such as lower monohydric alcohols and glycerol. In the examples a number of oxirane compounds are prepared by reacting 40 per cent aqueous peracetic acid with methyl, oleyl and butyl oleate, the methyl ester of soy fatty acids and cottonseed fatty acids, the butyl ester of soy fatty acids and cottonseed fatty acids, cottonseed oil, soybean oil, olive oil, oleic acid and oleyl alcohol.
GB16169/54A 1954-06-01 1954-06-01 Method of epoxidation Expired GB755778A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB16169/54A GB755778A (en) 1954-06-01 1954-06-01 Method of epoxidation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB16169/54A GB755778A (en) 1954-06-01 1954-06-01 Method of epoxidation

Publications (1)

Publication Number Publication Date
GB755778A true GB755778A (en) 1956-08-29

Family

ID=10072418

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16169/54A Expired GB755778A (en) 1954-06-01 1954-06-01 Method of epoxidation

Country Status (1)

Country Link
GB (1) GB755778A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1238028B (en) * 1963-04-20 1967-04-06 Basf Ag Process for carrying out the continuous cyanaethylation of mono- or polyhydric alcohols or thiols

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1238028B (en) * 1963-04-20 1967-04-06 Basf Ag Process for carrying out the continuous cyanaethylation of mono- or polyhydric alcohols or thiols

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