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High‐yield preparation of methyl stearolate
Author(s) -
Butterfield R. O.,
Dutton H. J.
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/bf02668969
Subject(s) - saponification , chemistry , oleic acid , distillation , organic chemistry , yield (engineering) , chromatography , ethylene glycol , diethyl ether , methanol , materials science , biochemistry , metallurgy
A simplified laboratory procedure for preparing methyl stearolate consists of three steps—bromination, dehydrobromination, and purification. A variety of starting materials was investigated, including oleic acid, olive fatty acids, and triglycerides. Brominations of both fatty acids and triglycerides were conducted in diethyl ether. Dehydrobrominations were carried out in boiling 30% KOH‐ethylene glycol solutions or in 30% KOH‐water solutions under pressure. Saponification of the triglycerides also occurred at this step. After conversion to methyl esters and distillation, the product from olive oil analyzed 79% methyl stearolate. Purification was accomplished by either argentation or acetonitrile‐hexane countercurrent distribution and yielded methyl stearolate of +99% purity. Over‐all recoveries, based upon the amount of oleic acid present in the initial oil, averaged 80%. In addition to the laboratory procedure, possible production operations are outlined.