Oxidation, friction reducing, and low temperature properties of epoxy fatty acid methyl esters

The use of oleochemicals as biobased lubricants is of significant interest. This article presents the oxidative stability of synthesized epoxidized methyl oleate (EMO), epoxidized methyl linoleate (EMLO), and epoxidized methyl linolenate (EMLEN), as well as that of a commercial epoxidized soybean oil, and epoxidized 2-ethylhexyl soyate. The epoxides show increased stability over olefinic oleochemicals by both pressure differential scanning calorimetry (PDSC) and thin film micro oxidation (TFMO). Also reported are the viscosity indices, pour point, and cloud point of the compounds. All of the data indicate that some of these epoxides have significant potential to be used as a fuel additive or lubricating fluid, important areas in the replacement of petrochemicals with environmentally friendly biobased alternatives.