Synthesis and physicochemical properties of partially and fully epoxidized methyl linoleate derived from jatropha curcas oil

Partial epoxidation of methyl linoleate was carried out at room temperature (30 °C) using a methyltrioxorhenium catalyst in the presence of pyridine and urea-hydrogen peroxide. Full epoxidation of methyl linoleate was carried out using the Prilezhaev method. The reactions were monitored using the oxirane oxygen content value. The products from partial and full epoxidation were analyzed using GC-FID, FTIR, NMR and GC-MS. Methyl 9,10-epoxy-12Z-octadecenoate and methyl 12,13-epoxy-9Z-octadecenoate were obtained as the major products from partial epoxidation, with a percent yield of 46 %. The product from full epoxidation afforded 97 % yield with methyl 9,10-12,13-diepoxyoctadecanoate as the major component. Physicochemical properties such as kinematic viscosity, viscosity index, crystallization temperature and oxidative stability were examined. Fully epoxidized methyl linoleate exhibits superior kinematic viscosity and oxidative stability due to the complete conversion of double bonds to epoxy groups. Partially epoxidized methyl linoleate exhibits intermediate kinematic viscosity, viscosity index, crystallization temperature and oxidative stability. © 2015 AOCS.