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Epoxidation ofLesquerella andLimnanthes (Meadowfoam) oils
Authors:Kenneth D Carlson  Robert Kleiman  Marvin O Bagby
Affiliation:(1) New Crops Research, USDA, NCAUR, 1815 N. University, 61604 Peoria, Illinois
Abstract:Lesquerella gordonii (Gray) Wats andLimnanthes alba Benth. (Meadowfoam) are species being studied as new and alternative crops. Triglyceride oil from lesquerella contains 55–60% of the uncommon 14-hydroxy-cis-11-eicosenoic acid. Meadowfoam oil has 95% uncommon acids, includingca. 60%cis-5-eicosenoic acid. Both oils are predominantly unsaturated (3% saturated acids), and have similar iodine values (90–91), from which oxirane values of 5.7% are possible for the fully epoxidized oils. Each oil was epoxidized withm-chloro-peroxybenzoic acid, and oxirane values were 5.0% (lesquerella) and 5.2% (meadowfoam). The epoxy acid composition of each product was examined by gas chromatography of the methyl esters, which showed that epoxidizedL. gordonii oil contained 55% 11,12-epoxy-14-hydroxyeicosanoic acid, and epoxidized meadowfoam oil contained 63% 5,6-epoxyeicosanoic acid, as expected for normal complete epoxidation. Mass spectrometry of trimethylsilyloxy derivatives of polyols, prepared from the epoxidized esters, confirmed the identity of the epoxidation products and the straightforward nature of the epoxidation process. Synthesis and characterization of these interesting epoxy oils and derivatives are discussed.
Keywords:Epoxidation  epoxidized lesquerella oil  epoxidized meadowfoam oil  fatty di-  tri- and tetraols  GC  GC-MS            Lesquerella gordonii                      Limnanthes alba            meadowfoam            m-Cl-peroxybenzoic acid  methyl (5  6  13  14-diepoxy decosanoate  5  6-epoxy docosanoate  13  14-epoxy docosanoate  5  6-epoxy eicosanoate  11  12-epoxy-14-hydroxy eicosanoate diastereomers  TMS derivatives
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