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Reactions of fatty materials with oxygen. VIII. Cis‐trans isomerization during autoxidation of methyl oleate
Author(s) -
Knight H. B.,
Eddy C. Roland,
Swern Daniel
Publication year - 1951
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02646545
Subject(s) - autoxidation , isomerization , chemistry , photochemistry , allylic rearrangement , oxygen , methyl oleate , oleic acid , radical , peroxide , organic chemistry , cis–trans isomerism , catalysis , biochemistry
Summary Methyl oleate irradiated with ultra‐violet light has been autoxidized at 35° and the reaction has been followed by means of the infrared spectrophotometer. During the extremely early stages of autoxidation and continuing up to at least 700 hours, a cis‐trans isomerization induced by oxygen is one of the reactions which occurs. The data suggest that most, if not all, of the peroxides produced during the autoxidation of methyl oleate, at least up to 300 hours, are trans peroxides and not methyl oleate peroxides, as had been previously supposed. A mechanism for the formation of trans peroxides from allylic free radicals is proposed. Mechanisms are also proposed for the formation of non‐peroxidic trans materials during autoxidation. These could explain the formation of trans‐9,10‐epoxystearic acid and high melting 9,10‐dihydroxystearic acid from autoxidizing oleic acid.