, Volume 86, Issue 7, pp 675-680
Date: 23 Apr 2009

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

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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.