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Enzymatic epoxidation of soybean oil in the presence of perbutyric acid

Jingnan Chen, Jinfen Zhou, Wei Liu, Yanlan Bi, and Dan Peng

Henan University of Technology, Zhengzhou, China



Abstract: Enzymatic epoxidation of vegetable oils using a long chain fatty acid as an active oxygen carrier could produce a desirable epoxy oxygen group content (EOC); however, the acid value (AV) of final epoxidized oil is too high. The present study was to investigate the effect of different fatty acids with varying length of carbon chain on EOC and AV of the final epoxidized soybean oil (ESO); finding butyric acid was the choice of active oxygen carrier when hydrogen peroxide was used as an oxygen donor in the presence of lipase Novozyme 435. And in situ IR was used to monitor the epoxidation process, which revealed that the formation of perbutyric acid was the key step in the whole reaction. The epoxidation process was optimized as follows: molar ratio of butyric acid/C=C bonds of 0.19:1, 8% of immobilized lipase Novozyme 435 load (relative to the weight of soybean oil) and molar ratio of H2O2/C=C bonds of 3.5:1, reaction time of 4 h and reaction temperature of 45 °C. Under these conditions, ESO with a high EOC (7.62 ± 0.20%) and a lower AV value (8.53 ± 0.18 mgKOH/g) was obtained. The oxriane conversion degree was up to 97.94%.

Keywords: Epoxidation; Soybean oil; Butyric acid; Lipase; Acid value

Full paper is available at

DOI: 10.1007/s11696-017-0206-8


Chemical Papers 71 (11) 2139–2144 (2017)

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