Free Radical Addition of Butanethiol to Vegetable Oil Double Bonds

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.

Dye conjugation to linseed oil by highly-effective thiol-ene coupling and subsequent esterification reactions

“…2 (a) and (b), respectively. The 1 H NMR spectra produced compare well with spectra obtained in other, related, studies [1,6,39,40,41].…”

“…The reason why the high concentration of 2 yielded high conversions is explained by the fact that thiole-ene reaction involves a rate-determining step where carbon radicals abstract a hydrogen from a thiol compound such as 2 [41]. Higher concentrations of 2 more effectively trap the carbon radicals [40]. In all the experiments performed, washing was required to remove any remaining 2 following the reactions.…”

Fatty Acid Derived Monomers and Related Polymers Via Thiol‐ene (Click) Additions

“…In the same sense, allyl-, acrylate-, as well as vinyl ether derivatives of castor oil were used together with multifunctional thiols for the preparation of UV curable resins. [29] Moreover, Bantchev et al [30] investigated thiol-ene addition reactions of canola and corn oil with butanethiol to yield sulfur-containing compounds with possible applications as lubricants to improve wear and friction properties. Very recently, thiol-ene chemistry was also applied for the preparation of bio-based telechelics [31] and soy-based thiols and enes were formulated with allyl triazine resulting in tack-free coating films after UV curing.…”

Les lipides : une matière première alternative pour la synthèse de polymères de spécialités

“…Les radicaux peuvent être g en er es par action de la lumi ere ou par d ecomposition thermique d'un compos e azoïque tel l'AIBN. Dans le cas o u le thiol utilis e poss ede egalement une fonction alcool (mercapto ethanol par exemple), les polyols ainsi form es pr esentent exclusivement des fonctions alcool primaires (Bantchev et al, 2009 …”