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Effect of FA composition on epoxidation kinetics of TAG
Author(s) -
La Scala John,
Wool Richard P.
Publication year - 2002
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/s11746-002-0491-9
Subject(s) - degree of unsaturation , chemistry , reaction rate constant , steric effects , oleic acid , double bond , composition (language) , kinetics , linoleic acid , formic acid , organic chemistry , fatty acid , biochemistry , physics , linguistics , philosophy , quantum mechanics
The rate constants of epoxidation were determined by reacting formic acid with a number of oils, pure TAG, and pure FAME. These results showed that FA composition had a significant effect on the value of the rate constant. In TAG, the double bonds of oleic acid and linoleic acid were equally reactive, and the double bonds of linolenic acid were approximately three times more reactive than oleic and linoleic acids. For FAME, the rate constants of epoxidation increased as the level of unsaturation increased. Furthermore, the rate constants of epoxidation for the FAME were higher than their respective TAG. We conclude that steric and electronic effects caused FA with different levels of unsaturation to have different reactivities. These results were used to derive a model that predicts the epoxidation kinetics of oils from their FA composition. The predictions of the model closely match the experimentally determined rate constants.