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Conversion of Methyl Oleate to Branched-Chain Hydroxy Fatty Acid Derivatives
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.
Dailey, Oliver D. Jr.
Prevost, Nicolette T.
Strahan, Gary D.
hydroxy fatty acids
fatty acid esters
nuclear magnetic resonance spectroscopy
differential scanning calorimetry
Journal of the American Oil Chemists' Society 2009 Nov., v. 86, no. 11
Berlin/Heidelberg : Springer-Verlag
Journal Articles, USDA Authors, Peer-Reviewed
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