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Preparation of Epoxidized Fatty Acid Methyl Ester with in situ Auto-Catalyzed Generation of Performic Acid and the Influence of Impurities on Epoxidation

  • Junyang Wang
  • Xuebing Zhao
  • Dehua Liu
Original Paper
  • 195 Downloads

Abstract

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.

Keywords

Epoxidized fatty acid methyl ester Epoxidation Performic acid In situ generation Plasticizer 

Notes

Acknowledgements

Authors acknowledge the financial support of Dongguan Innovative R&D Team project (No. 201536000100033) to this work.

Supplementary material

12649_2017_9945_MOESM1_ESM.pdf (211 kb)
Supplementary material 1 (PDF 212 KB)

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Copyright information

© Springer Science+Business Media Dordrecht 2017

Authors and Affiliations

  1. 1.Department of Chemical Engineering, Institute of Applied ChemistryTsinghua UniversityBeijingChina
  2. 2.Tsinghua Innovation Center in DongguanDongguanChina

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