Journal of the American Oil Chemists' Society

, Volume 86, Issue 7, pp 675–680

Synthesis of Sodium (+)-(12S,13R)-Epoxy-cis-9-octadecenyl Sulfonate from Vernonia Oil

  • Darryl C. Sutton
  • Nikki S. Johnson
  • Caswell Hlongwane
  • Folahan O. Ayorinde
Original Paper

DOI: 10.1007/s11746-009-1377-4

Cite this article as:
Sutton, D.C., Johnson, N.S., Hlongwane, C. et al. J Am Oil Chem Soc (2009) 86: 675. doi:10.1007/s11746-009-1377-4

Abstract

A water-soluble, foaming epoxyalkene sulfonate, sodium (+)-(12S,13R)-epoxy-cis-9-octadecenyl sulfonate, was synthesized from vernonia oil (VO) by a series of simple reactions that include transesterification, metal hydride reduction, tosylation, and SN2 reactions. Conversion of VO into vernonia oil methyl esters (VOME) using sodium methoxide was quantitative. Subsequent reduction of VOME with lithium aluminum hydride yielded (+)-(12S,13R)-epoxy-cis-9-octadecenol (94%), along with minor amounts of hexadecenol, octadecenol, cis-9-octadecenol, and cis-9,12-octadecandienol. The (+)-(12S,13R)-epoxy-cis-9-octadecenol, was tosylated with p-toluenesulfonyl chloride to give (+)-(12S,13R)-epoxy-cis-9-octadecenyl tosylate at 96% yield. Iodination of the tosylate with sodium iodide and subsequent SN2 reaction with sodium sulfite afforded (+)-(12S,13R)-epoxy-cis-9-octadecenyl sulfonate (63% yield). This study demonstrates the ability to produce an epoxyalkenyl sulfonate, belonging to a class of anionic surfactants, from VO without destroying the epoxy functionality in the (+)-(12S,13R)-epoxy-cis-9-octadecenyl moiety of VO. The critical micelle concentration of the synthesized sulfonate was also determined.

Keywords

Fatty acids MALDI-TOF MS Seed oil Sulfonate Surfactant Triacylglycerol Vernonia oil 

Copyright information

© AOCS 2009

Authors and Affiliations

  • Darryl C. Sutton
    • 1
  • Nikki S. Johnson
    • 1
  • Caswell Hlongwane
    • 1
  • Folahan O. Ayorinde
    • 1
  1. 1.Department of ChemistryHoward UniversityWashington, DCUSA

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