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Updated: Jun 26, 2026

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
Free radical addition of butanethiol to vegetable oil double bonds
Grigor B Bantchev1, James A Kenar, Girma Biresaw
1Cereal Products and Food Science Research Unit, National Center for Agricultural Utilization Research, Agricultural Research Service, U.S. Department of Agriculture, 1815 North University Street, Peoria, IL 61604, USA. Grigor.Bantchev@ars.usda.gov
Abstract:
Butanethiol was used in ultraviolet-initiated thiol-ene reaction with canola and corn oils to produce sulfide-modified vegetable oils (SMVO). The crude SMVO product was successfully purified by solvent extraction, vacuum evaporation, and silica gel chromatography. The SMVO products were characterized by nuclear magnetic resonance and Fourier transform infrared spectroscopy. Further product characterization and analysis was conducted using GC and GC-MS on the fatty acid methyl esters obtained by the transesterification of the SMVO products. Investigation of the effect of reaction conditions showed that high yield and high conversion of double bonds into thiol were favored at low reaction temperatures and high butanethiol/vegetable oil ratios. Canola and corn oils gave similar double-bond conversions and yields of the desired SMVO product even though they have big differences in the relative numbers of single and multiple double bonds in their structures. Under best reaction conditions, up to 97% of double-bond conversion and 61% isolated yields of the purified SMVO products were attained.
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