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Conversion of Methyl Oleate to Branched-Chain Hydroxy Fatty Acid Derivatives

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Journal of the American Oil Chemists' Society

Abstract

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 the ester form) to branched-chain fatty acid ester derivatives. In these studies, methyl oleate was epoxidized and subsequently treated with four different organocuprate reagents in the presence of boron trifluoride diethyl etherate to produce novel branched-chain hydroxy acid derivatives. For each reaction, the two distinct isomeric products (methyl 9-alkyl-10-hydroxyoctadecanoate and methyl 9-hydroxy-10-alkyloctadecanoate) were isolated in the pure forms. Details of the synthesis and characterization (GC–MS, NMR, and differential scanning calorimetry) of these compounds will be discussed.

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Acknowledgments

Thanks to Steven Lloyd (SRRC) for conducting the GC–MS studies. Mention of a trademark, proprietary product, or vendor does not constitute a guarantee or warranty of the product by the US Department of Agriculture and does not imply its approval to the exclusion of other products or vendors that may also be suitable.

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Authors and Affiliations

  1. USDA, ARS, Southern Regional Research Center, 1100 Robert E. Lee Blvd., New Orleans, LA, 70124, USA

    Oliver D. Dailey Jr. & Nicolette T. Prevost

  2. USDA, ARS, Eastern Regional Research Center, 600 E. Mermaid Lane, Wyndmoor, PA, 19038, USA

    Gary D. Strahan

Authors
  1. Oliver D. Dailey Jr.
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  2. Nicolette T. Prevost
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  3. Gary D. Strahan
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Correspondence to Oliver D. Dailey Jr..

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Dailey, O.D., Prevost, N.T. & Strahan, G.D. Conversion of Methyl Oleate to Branched-Chain Hydroxy Fatty Acid Derivatives. J Am Oil Chem Soc 86, 1101–1114 (2009). https://doi.org/10.1007/s11746-009-1441-0

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  • DOI: https://doi.org/10.1007/s11746-009-1441-0

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