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.

Difatty Acyl Urea from Corn Oil: Synthesis and Characterization

“…The disappearance of peaks at 1742 and 1162 cm -1 and appearance of peaks at 3342, 1623 and 1045 cm -1 indicate that fatty acyl urea have been formed 10) . Ethyl fatty esters spectra show the presence of the major absorption bands of corn oil but with no existence of peaks which correspond to amide ( ) 3.1. shows 1 H NMR the spectra of difatty acyl urea.…”

“…Vegetable oils are given considerable attention as they are biodegradable, renewable, non toxic, environmental friendly and easily available. Triglycerides in oils can be converted into their fatty amides via amidation 10,11) . Fatty amides were synthesized from fatty acids with urea instead of amine compounds 12) .…”

Direct acetylation of sunflower oil in the presence of boron trioxide catalyst and the adduct usage as the base stock and lubricant additive

“…The ester linkages deliver inherent lubricity on metallic surfaces because of their adhesive property. Further, vegetable oils have superior solubilizing power for contaminants and additive molecules compared with mineral base fluids [1][2][3][4][5]. Because of existing of bis-allylic protons in the fatty acid chain vegetable oils have poor oxidation stability.…”

Enzymatic Synthesis of Fatty Amides fromPalm Olein

“…Enzymatic synthesis of these compounds from the same starting material has also been reported [8][9][10] . Triglycerides can be converted into their fatty amides via amidation using ammonia or amine compounds 11,12) . Fatty amides were synthesized from fatty acids with urea instead of ammonia or other amidation reactant using Candida antartica lipase (Novozyme 435) as a catalyst at 60 for 48 h and atmospheric pressure 13) .…”