title: Synthesis of hydroxy thio-ether derivatives of vegetable oil.
abstract: 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.
authors.affiliation: Department of Chemical Engineering, Pennsylvania State University, University Park, Pennsylvania 16802, USA.
authors.forename: Brajendra K
authors.initials: BK
authors.lastname: Sharma
authors.forename: A
authors.initials: A
authors.lastname: Adhvaryu
authors.forename: S Z
authors.initials: SZ
authors.lastname: Erhan
mesh_terms: D004852:Epoxy Compounds / Q000737:chemistry; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D010938:Plant Oils / Q000737:chemistry*; D013024:Soybean Oil / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared; D013440:Sulfides / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry; D014280:Triglycerides / Q000737:chemistry
chemical_list: D004852:Epoxy Compounds; D010938:Plant Oils; D013440:Sulfides; D014280:Triglycerides; D013455:Sulfur; D013024:Soybean Oil