One-pot synthesis of chemically modified vegetable oils

Journal of Agricultural and Food Chemistry
Brajendra K SharmaSevim Z Erhan

Abstract

Vegetable oils are promising candidates as substitutes for petroleum base oils in lubricant applications, such as total loss lubrication, military applications, and outdoor activities. Although vegetable oils have some advantages, they also have poor oxidation and low temperature stability. One of the ways to address these issues is chemical modification of fatty acid chain of triglyceride. We report a one-pot synthesis of a novel class of chemically modified vegetable oils from epoxidized triacylglycerols and various anhydrides. In an anhydrous solvent, boron trifluoride etherate is used as catalyst to simultaneously open the oxirane ring and activate the anhydride. The reaction was monitored and products confirmed by NMR, FTIR, GPC, and TGA analysis. Experimental conditions were optimized for research quantity and laboratory scale-up (up to 4 lbs). The resultant acyl derivatives of vegetable oil, having diester substitution at the sites of unsaturation, have potential in formulation of industrial fluids such as hydraulic fluids, lubricants, and metal working fluids.

References

Aug 15, 2002·Journal of the American Chemical Society·Salah-Eddine StiribaHolger Frey
Nov 24, 2005·Journal of Agricultural and Food Chemistry·Atanu BiswasJulious L Willett
Nov 24, 2005·Journal of Agricultural and Food Chemistry·Kenneth M Doll, Sevim Z Erhan
Mar 16, 2006·Journal of Agricultural and Food Chemistry·Zengshe LiuFranklin E Barton
Dec 21, 2006·Journal of Agricultural and Food Chemistry·Brajendra K SharmaS Z Erhan

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Citations

Sep 22, 2010·Philosophical Transactions. Series A, Mathematical, Physical, and Engineering Sciences·W LiX H Zuo
Aug 20, 2017·Environmental Science and Pollution Research International·Juan Carlos de HaroManuel Carmona
Oct 19, 2017·Toxicological Sciences : an Official Journal of the Society of Toxicology·Anne Kokel, Béla Török
Apr 10, 2019·Polymers·Muhammad IqbalFrancesco Picchioni
Sep 12, 2008·Journal of Agricultural and Food Chemistry·Sevim Z ErhanAtanu Adhvaryu
May 7, 2014·Journal of Agricultural and Food Chemistry·Arukali SammaiahRachapudi B N Prasad

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