GB877632A - Improvements in and relating to epoxidation - Google Patents

Improvements in and relating to epoxidation

Info

Publication number
GB877632A
GB877632A GB41620/59A GB4162059A GB877632A GB 877632 A GB877632 A GB 877632A GB 41620/59 A GB41620/59 A GB 41620/59A GB 4162059 A GB4162059 A GB 4162059A GB 877632 A GB877632 A GB 877632A
Authority
GB
United Kingdom
Prior art keywords
acid
unsaturated compounds
olefines
unsaturation
aliphatic
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
GB41620/59A
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.)
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
Publication of GB877632A publication Critical patent/GB877632A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • 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
    • C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals

Abstract

Ethylenically unsaturated compounds are epoxidized by reacting with a preformed percarboxylic acid having not more than 10 carbon atoms in the molecule in the presence of sufficient acid acceptor to neutralise 15% to 80% of the acid present in the reaction mixture. The reaction is effected at -10 DEG C. to +80 DEG C. for 1/2 to 8 hours and the peracid is employed in an amount sufficient to epoxidize all desired unsaturation. Preferred starting materials are the 4 to 6 carbon aliphatic and cyclo-aliphatic olefines such as pentene and cyclohexene. Olefines which carry alkyl and aromatic hydrocarbon-substituents on carbons alpha to the unsaturation are exemplified by a -methyl styrene, limonene, a -pinene, myrcene, allooccimene, diisobutylene, camphene, polybutadiene, copolymers of butadiene with other unsaturated compounds, tripropylene and tetrapropylene. The unsaturated compounds may also carry hydroxy, carboxyl, sulphonic acid, halogen or aldehyde groups. Thus the process may be used to form epoxides of fatty acid esters. Typical acid acceptors are the alkali and alkaline earth metal hydroxides, carbonates, bicarbonates, acetates, propionates, butyrates, valerates, caproates, caprylates, pelargonates, phosphates, silicates and borates. The preferred percarboxylic acids are performic, peracetic, percyclohexanoic, perpelargonic.
GB41620/59A 1958-12-09 1959-12-08 Improvements in and relating to epoxidation Expired GB877632A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US877632XA 1958-12-09 1958-12-09

Publications (1)

Publication Number Publication Date
GB877632A true GB877632A (en) 1961-09-20

Family

ID=22207099

Family Applications (1)

Application Number Title Priority Date Filing Date
GB41620/59A Expired GB877632A (en) 1958-12-09 1959-12-08 Improvements in and relating to epoxidation

Country Status (1)

Country Link
GB (1) GB877632A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3235568A (en) * 1961-03-20 1966-02-15 Swift & Co Epoxy polyamides
US3979425A (en) 1967-06-15 1976-09-07 Firmenich S.A. Process for the preparation of unsaturated aldehydes
US4882442A (en) * 1980-12-30 1989-11-21 Peroxid-Chemie Gmbh Process for the production of epoxides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3235568A (en) * 1961-03-20 1966-02-15 Swift & Co Epoxy polyamides
US3979425A (en) 1967-06-15 1976-09-07 Firmenich S.A. Process for the preparation of unsaturated aldehydes
US4882442A (en) * 1980-12-30 1989-11-21 Peroxid-Chemie Gmbh Process for the production of epoxides

Similar Documents

Publication Publication Date Title
US2485160A (en) Process for the epoxidation of esters of oleic and linoleic acids
Henbest et al. 40. Aspects of stereochemistry. Part XI. Epoxide formation in the cyclo hexene and bicyclo heptene series
GB880937A (en) New epoxy carbonate esters
US2692271A (en) Method of epoxidation
GB877632A (en) Improvements in and relating to epoxidation
US3130207A (en) Improved epoxidation process with liquid aliphatic peroxy acids
GB873868A (en) Epoxy esters derived from cyclopentadienes
JPS5618973A (en) Manufacture of olefin oxide
GB1198327A (en) Manufacture of Epoxides
GB1136023A (en) Process for the preparation of glycols
GB986155A (en) Modification of polyolefins
GB956115A (en) Improvements in or relating to a process for the preparation of organic peroxides
GB716077A (en) Method of stabilizing a carboxylic peracid
GB922206A (en) Process for the preparation of oxirane derivatives
US2439212A (en) Dithiadecane diester
JPS52211A (en) Process for preparatiopn of epoxides
US2399479A (en) Nitrogenous ester
GB931223A (en) Steroids
GB739175A (en) Steroid compounds
GB739609A (en) Method of epoxidizing organic esters
GB933791A (en) Process for the manufacture of saturated polycyclic halogen-containing epoxides
GB886164A (en) Improvements in the production of epoxides
GB1020866A (en) Epoxidised esters and their uses as plasticisers
GB992861A (en) Composition suitable for dry cleaning
JPS55108864A (en) Tricyclic epoxide