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United States Department of Agriculture

Agricultural Research Service

Research Project: NEW AND EXPANDED USES OF OILSEED PRODUCTS AND BY-PRODUCTS

Location: Commodity Utilization Research

Title: Synthesis and Characterization of Branched-Chain Derivatives of Methyl Oleate

Authors
item Dailey Jr, Oliver
item Prevost, Nicolette
item Strahan, Gary

Submitted to: Clean (Soil Air Water)
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: May 15, 2008
Publication Date: August 1, 2008
Citation: Dailey Jr, O.D., Prevost, N.T., Strahan, G.D. 2008. Synthesis and characterization of branched-chain derivatives of methyl oleate. Clean (Soil Air Water). 36(8):687-693.

Interpretive Summary: The use of vegetable oils as alternative diesel fuels (biodiesel) has been investigated for over a century. Biodiesel is presently typically obtained by the conversion of vegetable oils or animal fat to simple esters of fatty acids. These products, usually methyl or ethyl esters, can be utilized as alternative fuels or extenders in diesel engines. However, the relatively poor low-temperature properties (freezing in cold climates) of these biodiesel fuels present a problem in their development and commercialization. Oleic acid and linoleic acid are the most abundant fatty acids of many vegetable oils, including cottonseed oil. As part of a project to develop new and expanded uses of cottonseed and other oilseed products and by-products (such as biodiesel, fuel additives, and lubricants), studies were conducted in the synthetic conversion of oleic acid to branched-chain fatty acids. Esters of branched-chain fatty acids should have improved or superior low-temperature properties. In these studies, methyl oleate (a major component of biodiesel) was converted in a series of reactions to branched-chain derivatives. Several of the synthesized products exhibited significantly lower re-crystallization temperatures in comparison with methyl oleate. This research benefits farmers of cotton and other oilseed crops, oil chemists, and the automotive industry in that it demonstrates that biodiesel (using methyl oleate as a model compound) can be converted to branched-chain derivatives exhibiting enhanced low-temperature properties.

Technical Abstract: Oleic acid and linoleic acid are the most abundant fatty acids of many vegetable oils, such as cottonseed oil. 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 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, ethyl, n-butyl, n-hexyl, phenyl). Details of the syntheses, characterization (GC/MS and NMR), and the properties of the products (with emphasis on low-temperature properties) are discussed. Several of the synthesized products exhibited significantly lower re-crystallization temperatures in comparison with methyl oleate and may prove useful as additives to biodiesel for use at low temperatures.

Last Modified: 9/2/2014
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