|Dailey Jr, Oliver|
Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: 10/3/2006
Publication Date: 11/2/2006
Citation: Dailey Jr, O.D., Prevost, N.T. 2006. Synthesis of branched-chain derivatives of methyl oleate. In: Proceedings of the 58th Southeastern Regional Meeting of the American Chemical Society, November 1-4, 2006, Augusta, Georgia. . Meeting Abstract.
Technical Abstract: Oleic acid and linoleic acid are the most abundant fatty acids of cottonseed oil. 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 in the synthetic conversion of oleic acid to branched-chain fatty acids. The conversion of vegetable oils to esters of branched-chain alcohols has been reported to improve low-temperature properties, demonstrated by reduced crystallization onset temperatures. Simple monoalkyl esters containing branched-chain fatty acids could have improved or superior low-temperature properties. 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). Details of the syntheses, characterization, and properties of the products (with emphasis on low-temperature properties) will be discussed.