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Nonvolatile α‐branched chain fatty acid derivatives: III. Addition of acid chlorides, anhydrides and amides to terminal olefins
Author(s) -
Perlstein T.,
Eisner A.,
Ault W. C.,
De Haven P. A.
Publication year - 1968
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/bf02540170
Subject(s) - stearic acid , chemistry , stearate , yield (engineering) , organic chemistry , acid anhydride , molar ratio , fatty acid , olefin fiber , amide , chloride , catalysis , materials science , epoxy , metallurgy
A t ‐butyl peroxide initiated free radical reaction was employed for the preparation of α‐branched fatty acid chlorides, which were then converted in situ to methyl esters. Similarly prepared were an α‐branched fatty acid amide and an α‐branched acid anhydride. The latter was converted to the methyl ester. The use of the acid chloride and acid anhydride permitted reduction in the molar ratio of reactants to half or less than that used in the addition of esters to terminal olefins without affecting the yield. The resulting increase of α‐branched product concentration in the reaction mixture also made isolation of the product easier. The direct addition of a variety of stearic acid derivatives to 1‐decene under the same conditions (20:4:1.2 molar ratio of reactants at 160 C) gave the following olefin based yield order: stearoyl chloride > stearic anhydride > stearamide and methyl stearate > stearic acid.