Break | AIChE


In this paper, monomethyl itaconated epoxidized corn oil (MIECO) was synthesized by melt ring-opening esterification of monomethyl itaconate (MI) with epoxidized corn oil (ECO). Downstream corn oil, which obtains as a by-product during production of ethanol, was used to synthesize ECO by reported epoxidation method. The chemical structures of MI, ECO, and MIECO were characterized and confirmed by differential scanning calorimetry (DSC), Fourier-transform infrared spectroscopy (FTIR), and 1H Nuclear Magnetic Resonance spectroscopy. The isothermal thermogravimetric analysis (TGA) at different temperatures (30, 60, and 90 °C) indicated that MI demonstrated tremendously low volatility even at high temperature (90 °C), while acrylic acid showed very fast volatility even at low temperature (30 °C), which indicated that MI is excellent green alternative to acrylic acid. The thermal and mechanical properties of as-synthesized MIECO were compared with commercial acrylated epoxidized soybean oil. The cured pristine MIESO showed similar properties to the pristine acrylated epoxidized soybean oil. Therefore, as-synthesized MIECO provides a fully biobased alternative to commercially available acrylated epoxidized soybean oil, which suffers from invasive odor, corrosive and toxic in nature.

Acknowledgements: The authors would like to thank the following for their financial support: Ontario Ministry of Agriculture, Food and Rural Affairs (OMAFRA)/University of Guelph - Bioeconomy for Industrial Uses Research Program (Project # 030251); and the Ontario Research Fund, Research Excellence Program; Round-7 (ORF-RE07) from the Ontario Ministry of Research, Innovation and Science (MRIS) (Project # 052644 and 052665).