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Thermal decomposition of individual positional isomers of methyl linoleate hydroperoxide: Evidence of carbon‐oxygen bond scission
Author(s) -
Chan Henry W. S.,
Prescott Frank A. A.,
Swoboda Peter A. T.
Publication year - 1976
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/bf02586311
Subject(s) - chemistry , isomerization , hexanal , bond cleavage , decomposition , oxygen , structural isomer , yield (engineering) , gas chromatography , carbon fibers , cis–trans isomerism , double bond , photochemistry , organic chemistry , medicinal chemistry , catalysis , chromatography , materials science , composite number , metallurgy , composite material
The methyl ester of individual positional isomers of linoleate hydroperoxide were prepared by an enzymic oxidation of linoleate. On injection onto a gas chromatographic column they were thermally decomposed and the resulting volatile components analyzed. The major (67–80% yield on a molar basis) cleavage products were found to be hexanal, methyl octanoate, 2,4‐decadienal isomers, and methyl 9‐oxononanoate. Both the 9 and 13 isomers of linoleate hydroperoxide gave rise to these same four compounds, an observation suggesting carbon‐oxygen scission in their decomposition. This was confirmed by using very pure individual isomers obtained by high performance liquid chromatography. The involvement of an isomerization reaction of the hydroperoxides is discussed.