Submitted to: Journal of Agricultural and Food Chemistry
Publication Type: Peer reviewed journal
Publication Acceptance Date: 1/20/2008
Publication Date: 6/18/2008
Citation: Sharma, B.K., Liu, Z., Adhvaryu, A., Erhan, S.Z. 2008. One-pot synthesis of chemically modified vegetable oils. Journal of Agricultural and Food Chemistry. 56:3049-3056. Interpretive Summary: The uncertainty in supply of petroleum-based products and their unfavorable impact on the environment has created a demand for eco-friendly lubricants. Vegetable oils are promising candidates for eco-friendly lubricants, because of the advantages like naturally renewable resource, environmentally safe, and good lubricity. Vegetable oils have some shortcomings like poor low temperature flow properties and oxidation stability, which can be improved by chemical modification. This paper presents preparation of chemically modified vegetable oils using acid anhydrides. The reaction monitoring, process optimization and characterization was done using various analytical techniques. These fluids have potential in formulation of industrial fluids such as hydraulic fluids, lubricants, and metal working fluids. This approach will improve the agro-economy of the locally grown renewable resource with the new markets for soybean oil.
Technical Abstract: Vegetable oils are promising candidates as substitutes for petroleum-base oils in lubricants 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, and have potential in formulation of industrial fluids such as hydraulic fluids, lubricants, and metal working fluids.