Epoxidation of Methyl Esters as Valuable Biomolecules: Monitoring of Reaction

The paper is focused on the epoxidation of methyl esters prepared from oil crops with various profiles of higher fatty acids, especially unsaturated, which are mainly contained in the non-edible linseed and Camelina sativa oil (second generation). The novelty consists in the separation and identification of all products with oxirane ring formed through a reaction and in the determination of time course. Through the epoxidation, many intermediates and final products were formed, i.e., epoxides with different number and/or different position of oxirane rings in carbon chain. For the determination, three main methods (infrared spectroscopy, high-pressure liquid chromatography and gas chromatography with mass spectrometry) were applied. Only gas chromatography enables the separation of individual epoxides, which were identified on the base of the mass spectra, molecule ion and time course of products. The determination of intermediates enables: (i) control of the epoxidation process, (ii) determination of the mixture of epoxides in detail and so the calculation of selectivity of each product. Therefore, the epoxidation will be more environmentally friendly especially for advanced applications of non-edible oil crops containing high amounts of unsaturated fatty acids.

Automated summary

This paper investigates the epoxidation of methyl esters derived from oil crops with different profiles of higher fatty acids, particularly unsaturated ones found in non-edible linseed and Camelina sativa oil (second generation). The study focuses on separating and identifying all products with oxirane rings formed during the reaction, as well as determining the time course. Multiple intermediates and final products, including epoxides with varying numbers and positions of oxirane rings in the carbon chain, were formed through the epoxidation process. Three main methods (infrared spectroscopy, high-pressure liquid chromatography, and gas chromatography with mass spectrometry) were used for the determination, with gas chromatography being the only one capable of separating individual epoxides. This method allowed for identification based on mass spectra, molecule ion, and time course. The determination of intermediates provides control over the epoxidation process, detailed analysis of epoxide mixtures, and calculation of selectivity for each product. As a result, epoxidation can be more environmentally friendly, especially for utilizing non-edible oil crops with high levels of unsaturated fatty acids.