Chemical epoxidation of a natural unsaturated epoxy seed oil fromVernonia galamensis and a look at epoxy oil markets

Abstract

AbstractSince 1963, production of all epoxy esters has ranged from 60 to 150 million lb annually, a steady 7% of the 1 to 2 billion lb of annual plasticizer production. Growth rates in production averaged 4.3% for all plasticizers, 3.8% for all epoxy esters and 5.0% for epoxidized soybean oil (ESBO). ESBO accounted for 70–76% of total epoxy ester production (1963–1982). The natural liquid epoxy oil fromVernonia galamensis seed, with oxirane value (4.1%) and viscosity (100 cps) similar to some commercial epoxy fatty esters but with molecular weight similar to epoxidized vegetable oils, combines some of the properties of both commercial types. Chemical epoxidation ofVernonia oil raises the oxirane content to 8.2, intermediate between ESBO and epoxidized linseed oil (ELSO), while consuming less of the costly epoxidizing reagents. Epoxidation proceeds in stepwise fashion through partially epoxidized products, which are converted to final product. Since the major fatty components ofVernonia oil arecis‐12,13‐epoxy‐9‐octadecenoic (75%) and linoleic (13%) acids, further epoxidation produces fatty acids that are specifically epoxidized at the 9,10‐ and 12,13‐positions, and the major product has 6 epoxy units per triglyceride molecule. The resulting mixture of products has compositional and physical properties distinctly different from commercial samples of ESBO and ELSO.