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Sulfur dichloride diadducts of unsaturated fatty derivatives. I. preparation and oxidation
Author(s) -
Grimm Robert A.
Publication year - 1967
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/bf02901250
Subject(s) - chemistry , sulfur , peracetic acid , organic chemistry , sulfone , stereoselectivity , fatty acid , ethyl ester , catalysis , hydrogen peroxide
Sulfur dichloride diadducts of oleate esters, oleylnitrile, elaidate esters and ethyl linoleate were prepared by addition of the theoretical amount of sulfur dichloride to the fatty derivative. Similar diadducts were also prepared from commercial oleate esters including esters of ADM's monoenoic acid. Several of the resulting β,β' ‐dichlorosulfide diesters were then oxidized with peracetic acid to β,β' ‐dichlorosulfoxide diesters and to β,β' ‐dichlorosulfone diesters. The latter materials were converted to the divinyl sulfone diacids. Cis and trans‐2‐butene were used as model compounds for studying the addition of sulfur dichloride to oleates and elaidates respectively. The results on these systems, which paralleled the results with the fatty materials, indicated that substitution reactions were negligible and that the addition was stereoselective, that is, oleates and elaidates gave stereochemically different products.