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2-Fatty Acrylic Acids: New Highly Derivatizable Lipophilic Platform Molecules

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Journal of the American Oil Chemists' Society

Abstract

This paper reports the incorporation of an alpha-methylene unit into fatty acid skeletons. Since the new olefin is conjugated with the carboxylate, it is susceptible to 1,4-(Michael) additions. We have used multifunctional thiols and amines for additions at the methylene. The resulting products possess clusters of functionality grouped at one end of a hydrophobic tail. These structural patterns will be of use in the design of new types of bio-based surfactants and polymers. One particularly promising pattern of functionality that can be obtained through oxidation and reduction chemistry is a 2-fatty 1,2,3-propanetriol, or a lipophilized glycerol moiety.

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Authors and Affiliations

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

    Jonathan A. Zerkowski & Daniel K. Y. Solaiman

Authors
  1. Jonathan A. Zerkowski
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  2. Daniel K. Y. Solaiman
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Correspondence to Jonathan A. Zerkowski.

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Mention of trade names or commercial products in this publication is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the US Department of Agriculture (USDA). USDA is an equal opportunity provider and employer.

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Zerkowski, J.A., Solaiman, D.K.Y. 2-Fatty Acrylic Acids: New Highly Derivatizable Lipophilic Platform Molecules. J Am Oil Chem Soc 91, 1225–1233 (2014). https://doi.org/10.1007/s11746-014-2459-5

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  • DOI: https://doi.org/10.1007/s11746-014-2459-5

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