The epoxidation of canola oil and its derivatives

Abstract

This work explores the epoxidation and subsequent acid catalyzed epoxy ring opening kinetics of canola oil (CanO), canola oil fatty acid methyl esters (CanFAME) and canola oil free fatty acids (CanFFA). Epoxidation reactions were carried out at atmospheric pressure, without any organic solvents and additional catalysts. The formation of epoxide groups and the subsequent acid catalyzed epoxy ring opening reactions and oligomerization were studied over the epoxidation time. An empirical equation describing the in situ epoxidation kinetics including the epoxy ring opening processes is proposed that is applicable to the epoxidation of plant oils and those containing fatty acid derivatives. By comparing the epoxidation kinetics of CanO, CanFAME and CanFFA, it was found that the rates of epoxidation of CanO and CanFAME were similar although the formation of hydroxylated moieties is observed in CanFAME. The epoxidation behaviour of CanFFA was unique since acid groups act as an oxygen carrier (forming peroxy fatty acids with hydrogen peroxide) which leads to extensive epoxide ring opening and formation of oligomeric products. The results of this study have significance in the production of epoxides from plant oils and animal fats, containing FFA and other derivatives.