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Direct esterification of sodium cis ‐9,10‐epiminooctadecanoate
Author(s) -
Bilyk A.,
Eisner A.,
Maerker G.
Publication year - 1972
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/bf02609234
Subject(s) - methanesulfonic acid , aziridine , catalysis , chemistry , boron trifluoride , p toluenesulfonic acid , sulfuric acid , nucleophile , polymerization , methanol , organic chemistry , ring (chemistry) , polymer
Compounds containing the aziridine ring are known to have a tendency toward polymerization in the presence of mineral acids. Moreover, with aziridine derivatives of fatty acids, ring opening reactions are possible as a result of nucleophilic attack by generated carboxylic acids groups. It was found that high yields (86–89%) of methyl cis ‐9,10‐epiminooctadecanoate, with a minimum of attendant byproducts could be obtained by heating the corresponding sodium soap with methanol in the presence of certain acid catalysts under carefully controlled conditions. Temperature, duration of the heating period, and catalyst concentration were the variables studied for each catalyst. The catalysts evaluated were: boron trifluoride etherate, methanesulfonic acid, sulfuric acid, fluoboric acid and p ‐toluenesulfonic acid. Of these, for most laboratory preparations, p ‐toluenesulfonic acid is the catalyst of choice.