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The chemistry of polymerized oils. V. The autoxidation of methyl linoleate
Author(s) -
Sephton H. H.,
Sutton Donald A.
Publication year - 1956
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/bf02630858
Subject(s) - autoxidation , chemistry , cis–trans isomerism , conjugated system , peroxide , molecule , double bond , stereochemistry , organic chemistry , medicinal chemistry , polymer
Summary 1. The geometrical forms obtained during autoxidation of methyl linoleate at ordinary temperatures are largely conjugated cis‐trans and trans‐trans as shown by previous workers; there is a possibility that conjugated cis‐cis forms are also produced. 2. The trans‐trans molecules arise partly, at least, by thermal rearrangement of already formed cis‐trans peroxide. 3. Some proportion, at least, of the cis‐trans molecules have their trans double bonds nearest to the hydroperoxide group. 4. A partial separation of the geometrical forms can be accomplished by reversed phase partition chromatography both on methyl linoleate hydroperoxides and on the corresponding mixed hydroxy compounds; isolation of the trans‐trans forms can be accomplished in the latter case by urea complex fractionation. 5. No position isomers except the known 9‐ and 13‐isomers have been positively identified; there is a possibility that very minor amounts of the 2‐isomer are formed; the 9‐ and 13‐isomers are present in about equal amounts; the 11‐isomer was not detected by the methods applied. 6. Various ways in which the linoleate autoxidation problem might be advanced further are suggested.