Controlling viscosity in methyl oleate derivatives through functional group design

Abstract

Fatty acid methyl ester (FAME) derivatives have received considerable attention as potential biofuel additives and as sustainable lubricants. One common strategy for the modification of FAMEs, such as methyl oleate, involves epoxidation of the C9–C10 alkene followed by oxirane ring-opening to introduce branches into the FAME backbone. This strategy has been shown to improve cold-flow properties and oxidative stability relative to the parent oleates, and some derivatives have shown promise as lubricants. However, the effect of this strategy on viscosity has not been well established, if at all. Here we present the viscosity properties of methyl oleate derivatives as controlled by rational functional group manipulation with important implications for the preparation of bio-derived lubricants, where viscosity properties must be tightly controlled. The effect of selected derivatives as cold-flow additives in biodiesel is also reported.