Preparation of Epoxidized Fatty Acid Methyl Ester with in situ Auto-Catalyzed Generation of Performic Acid and the Influence of Impurities on Epoxidation
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Epoxidized fatty acid methyl ester (EFAME) is a renewable and biodegradable plasticizer that can be produced from various vegetable oils and even waste oils. In this work, refined soybean oil (RSO) was first converted to fatty acid methyl ester (FAME) by enzymatic transesterification, followed by epoxidation with performic acid in situ generated via auto-catalyzed reaction of formic acid with hydrogen peroxide. Effects of several factors on epoxidation of RSO FAME were investigated, and the conditions were optimized by response surface methodology. Impacts of several potential impurities on epoxidation were further investigated. It was found that the effects of triglyceride (RSO), glycerol and free fatty acid could be negligible. However, mineral acid such as sulfuric acid could significantly improve the rate of epoxidation, but the cleavage of epoxy group was also strengthened, resulting in lower epoxy value of the EFAME product. Surfactants showed significant negative effects on epoxidation. The feasibility of producing EFAME from waste cooking oil was further investigated. Compared with RSO, waste oil needed a second-stage epoxidation to epoxidize most of the double bonds, but obtained poorer epoxy value with lower degree and selectivity of epoxidation and EFAME yield.
KeywordsEpoxidized fatty acid methyl ester Epoxidation Performic acid In situ generation Plasticizer
Authors acknowledge the financial support of Dongguan Innovative R&D Team project (No. 201536000100033) to this work.
- 10.Shi, R., Jing, P., Shi, S.: Epoxidized synthesis of nontoxic and environmental-friendly plasticizer from soy acidic oil methyl esters. China Oil Fats 33, 36–39 (2008)Google Scholar
- 11.Yu, L., Nie, Y., Chen, W., Lu, M., Ji, J.: Kinetics of epoxidation and oxirane cleavage of fatty acid methyl ester in formic acid auto catalytic system. Chem. Ind. Times 27, 11–16 (2013)Google Scholar
- 24.Campanella, A., Baltanas, M.A.: Degradation of the oxirane ring of epoxidized vegetable oils in liquid-liquid systems: I. Hydrolysis and attack by H2O2. Lat. Am. Appl. Res. 35, 205–210 (2005)Google Scholar
- 25.Campanella, A., Baltanas, M.A.: Degradation of the oxirane ring of epoxidized vegetable oils in liquid-liquid systems: II. Reactivity with solvated acetic and peracetic acids. Lat. Am. Appl. Res. 35, 211–216 (2005)Google Scholar
- 34.Liu, Q., Cai, B., Yuan, L., Zhou, Y., Huang, J., He, Y.: The clustering analysis of the illegal cooked oil based on high pressure liquid chromatography. J. Food Saf. Qual. 4, 401–409 (2013)Google Scholar