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Evidence for hydroperoxide formation in the autoxidation of methyl linolenate
Author(s) -
Privett O. S.,
Nickell Christense,
Tolberg Wesley E.,
Paschke Raymond F.,
Wheeler Donald H.,
Lundberg W. O.
Publication year - 1954
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/bf02544766
Subject(s) - autoxidation , chemistry , linolenate , peroxide , monomer , diene , organic chemistry , distillation , chromatography , polymer , fatty acid , natural rubber
Summary 1. The results of chemical, spectral, and distillation analyses on the isolated oxidized fractions of three samples of methyl linolenate autoxidized at 0°C. to peroxide values from 600 to 760 m.e./kg. indicated that about 60% of the products consisted of cis, transconjugated diene methyl octadecatrienoate‐monohy‐droperoxide. 2. A product was isolated from the reduced peroxide concentrates which consisted of about 90% cis, transconjugated diene methyl monohydroxyoctadecatrienoate. 3. Analytical micromolecular distillation analyses showed that the total oxidized material isolated from samples of autoxidized methyl linolenate contained only about 15% polymeric material under the conditions of autoxidation employed in this study. 4. Linolenate was shown to be similar to linoleate in forming a cis, trans‐conjugated monomeric monohydroperoxide as a major initial product of autoxidation at 0°C.