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The reaction of ethylene oxide with oleic acid
Author(s) -
Stockburger G. J.,
Brandner J. D.
Publication year - 1966
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/bf02637268
Subject(s) - transesterification , ethylene oxide , ethylene glycol , chemistry , ethylene , oleic acid , oxide , catalysis , inorganic chemistry , alkoxide , organic chemistry , polymer chemistry , copolymer , biochemistry , polymer
The base‐catalyzed reaction of ethylene oxide with oleic acid can be divided into two stages. The first stage consists of a slow reaction of oleic acid with ethylene oxide to form principally ethylene glycol monooleate; other reactions such as esterification, transesterification and polyglycol formation lag behind. In the second stage, after the addition of approximately one mole of ethylene oxide, the reaction accelerates and transesterification equilibrium is rapidly attained. The composition of products containing several molecules or more of ethylene oxide can be calculated satisfactorily on the assumption of random addition of ethylene oxide and random esterification of the hydroxyl groups. The uncatalyzed reaction is much slower and transesterification equilibrium is attained slowly, if at all. A reaction mechanism based on the difference in basicities of the carboxylate and alkoxide ions (and the relative rates of the competitive ethylene oxide reactions) is presented for the base‐cat‐alyzed reaction.