Synthesis and Structural Analysis of Branched-Chain Derivatives of Methyl Oleate
2008
Dailey, Oliver D Jr | Prevost, Nicolette T. | Strahan, Gary D.
As part of a project to develop new value-added industrial applications for cottonseed oil (such as biodiesel, fuel additives, and lubricants), studies were conducted on the synthetic conversion of oleic acid to branched-chain fatty acid esters. In these studies, methyl oleate was brominated in the allylic position and subsequently treated with organocuprate reagents to produce novel branched-chain derivatives (methyl, n-butyl, phenyl). Original reaction conditions afforded only the branched methyl derivatives as major products. Modification of reaction conditions (lower temperature, less organocuprate reagent) afforded predominantly the desired n-butyl and phenyl derivatives and minimized products resulting from attack on the ester functionality. Details of the syntheses, characterization (especially by NMR), and the properties of the products (with emphasis on low-temperature properties) are discussed.
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