Synthesis and characterization of branched-chain derivatives of methyll olleate

Oleic acid is one of the most abundant fatty acid components of the triglycerides in 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 (in ester form) 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 (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.