Synthesis of hydroxy thio-ether derivatives of vegetable oil

Brajendra K. Sharma, A. Adhvaryu, S. Z. Erhan

Research output: Contribution to journalArticlepeer-review


Bio-based additives are desirable commodities due to their eco-friendly nature. These additives can demonstrate physical and chemical properties comparable to those of conventional mineral oil-based products. Sulfur incorporated triacylglycerol can function as an antiwear/antifriction additive for lubricants. The synthesis of four useful hydroxy thio-ether derivatives of vegetable oils, from commercially available epoxidized soybean oil and common organic thiols, is reported in this paper. The common thiols used herein were 1-butanethiol, 1-decanethiol, 1-octadecanethiol, and cyclohexyl mercaptan. Currently, there is no reported literature describing the synthesis of hydroxy thio-ether derivatives of vegetable oil. The reaction was monitored, and products were confirmed by NMR and FTIR spectroscopies. Experimental conditions involving various thiols, solvent, catalyst amount, time, and temperature were optimized for research quantity and laboratory scale-up. The synthetic process retains the vegetable oil structure, eliminates polyunsaturation in the molecule, and adds polar functional groups on triacylglycerol. These products can be used as agriculturally-based antiwear additives for lubricant applications.

Original languageEnglish (US)
Pages (from-to)9866-9872
Number of pages7
JournalJournal of Agricultural and Food Chemistry
Issue number26
StatePublished - Dec 27 2006
Externally publishedYes


  • Epoxidized soybean oil
  • Epoxy ring opening
  • Thio-ether derivative
  • Thiols
  • Vegetable oil

ASJC Scopus subject areas

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)


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