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Synthesis and Characterization of Branched‐Chain Derivatives of Methyl Oleate
Author(s) -
Dailey Oliver D.,
Prevost Nicolette T.,
Strahan Gary D.
Publication year - 2008
Publication title -
clean – soil, air, water
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.444
H-Index - 66
eISSN - 1863-0669
pISSN - 1863-0650
DOI - 10.1002/clen.200800058
Subject(s) - methyl oleate , biodiesel , organic chemistry , oleic acid , chemistry , fatty acid , transesterification , cottonseed oil , crystallization , reagent , allylic rearrangement , glyceride , vegetable oil , catalysis , food science , biochemistry
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.