Free radical addition of butanethiol to vegetable oil double bonds.
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.
Bantchev
Grigor B
GB
Cereal 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
Kenar
James A
JA
Biresaw
Girma
G
Han
Moon Gyu
MG
D003314:Corn Oil / Q000737:chemistry; D005227:Fatty Acids / Q000032:analysis; D005229:Fatty Acids, Monounsaturated / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010938:Plant Oils / Q000737:chemistry*; D000074262:Rapeseed Oil; D017550:Spectroscopy, Fourier Transform Infrared; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D014466:Ultraviolet Rays
D005227:Fatty Acids; D005229:Fatty Acids, Monounsaturated; D005609:Free Radicals; D010938:Plant Oils; D000074262:Rapeseed Oil; D013438:Sulfhydryl Compounds; C025540:n-butyl mercaptan; D003314:Corn Oil