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Conversion of Methyl Oleate to Branched‐Chain Hydroxy Fatty Acid Derivatives
Author(s) -
Dailey Oliver D.,
Prevost Nicolette T.,
Strahan Gary D.
Publication year - 2009
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/s11746-009-1441-0
Subject(s) - boron trifluoride , methyl oleate , chemistry , organic chemistry , differential scanning calorimetry , oleic acid , fatty acid , reagent , alkyl , transesterification , fatty acid methyl ester , biodiesel , catalysis , biochemistry , thermodynamics , physics
As part of a project to develop new and expanded uses of oilseed products and by‐products (such as biodiesel, fuel additives, and lubricants), studies were conducted on the synthetic conversion of oleic acid (in the ester form) to branched‐chain fatty acid ester derivatives. In these studies, methyl oleate was epoxidized and subsequently treated with four different organocuprate reagents in the presence of boron trifluoride diethyl etherate to produce novel branched‐chain hydroxy acid derivatives. For each reaction, the two distinct isomeric products (methyl 9‐alkyl‐10‐hydroxyoctadecanoate and methyl 9‐hydroxy‐10‐alkyloctadecanoate) were isolated in the pure forms. Details of the synthesis and characterization (GC–MS, NMR, and differential scanning calorimetry) of these compounds will be discussed.