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Conversion of Methyl Oleate to Branched-Chain Hydroxy Fatty Acid Derivatives

Permanent URL:
http://handle.nal.usda.gov/10113/37147
File:
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Abstract:
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.
Author(s):
Dailey, Oliver D. Jr. , Prevost, Nicolette T. , Strahan, Gary D.
Subject(s):
oilseed products , oleic acid , esters , chemical treatment , epoxides , isomers , hydroxy fatty acids , fatty acid esters , gas chromatography , mass spectrometry , nuclear magnetic resonance spectroscopy , differential scanning calorimetry
Format:
p. 1101-1114.
Note:
Includes references
Source:
Journal of the American Oil Chemists' Society 2009 Nov., v. 86, no. 11
Language:
English
Publisher:
Berlin/Heidelberg : Springer-Verlag
Year:
2009
Collection:
Journal Articles, USDA Authors, Peer-Reviewed
Rights:
Works produced by employees of the U.S. Government as part of their official duties are not copyrighted within the U.S. The content of this document is not copyrighted.