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Rh-based Biphasic Isomerization of Carbon–Carbon Double Bonds in Natural Oils

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Journal of the American Oil Chemists' Society

Abstract

The biphasic conjugation of soybean and other natural oils, as well as the isomerization of various alkenes, was examined using a rhodium catalyst. A maximum yield, of conjugated soybean oil, of 96% was obtained when the reaction was run at 80 °C under argon with ethanol as the polar solvent, using triphenylphosphine monosulfonate sodium salt (tppms) as the ligand, and the surfactant sodium dodecyl sulfate (SDS). The optimized conditions were tested with other substrates, and the products were analyzed by 1H NMR, GC/MS, and ICP-MS.

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Acknowledgments

The authors thank the National Science Foundation (NSF) Engineering Research Center for Biorenewable Chemicals (CBiRC) at Iowa State University for funding this project, and graduate student C. Ebert and Professor R. S. Houk of the Chemistry Department at Iowa State University for help with the ICP-MS analyses.

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Correspondence to Richard C. Larock.

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Quirino, R.L., Larock, R.C. Rh-based Biphasic Isomerization of Carbon–Carbon Double Bonds in Natural Oils. J Am Oil Chem Soc 89, 1113–1124 (2012). https://doi.org/10.1007/s11746-011-1983-9

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  • DOI: https://doi.org/10.1007/s11746-011-1983-9

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