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Methanesulfonic acid catalyzed addition of aromatic compounds to oleic acid

  • Technical
  • Published:
Journal of the American Oil Chemists’ Society

Abstract

The addition of aromatic compounds to the double bond of oleic acid has been studied using methanesulfonic acid as the acid catalyst. When alkylbenzenes were reacted with oleic acid, the yield of addition product was dependent on the electron density of the benzene ring. For example, a 76% yield of addition product was obtained with toluene, whereas for benzene and monochlorobenzene, the yields of addition products were 60% and 2%. The addition of phenol to oleic acid gave 2 types of addition products, an ethertype (phenylether) product and a ring-substituted product (hydroxy-phenylstearic acid). The ratio of the 2 products varied with the reaction temperature and the amount of methanesulfonic acid. The ring-substituted product predominated at a high molar ratio of methanesulfonic acid to oleic acid (6:1) and elevated reaction temperature (50 C). Thiophenol was found to add to oleic acid to form a thioether derivative exclusively.

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Authors and Affiliations

  1. Eastern Regional Research Center, 19118, Philadelphia, Pennsylvania

    Y. Nakano & T. A. Foglia

Authors
  1. Y. Nakano
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  2. T. A. Foglia
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Additional information

Agricultural Research Service, US Department of Agriculture. Reference to a brand or firm name does not constitute endorsement by the USDA over others of a similar nature that are not mentioned.

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Nakano, Y., Foglia, T.A. Methanesulfonic acid catalyzed addition of aromatic compounds to oleic acid. J Am Oil Chem Soc 61, 569–573 (1984). https://doi.org/10.1007/BF02677034

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  • DOI: https://doi.org/10.1007/BF02677034

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