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Abstract
Objective: To obtain acrylated refined rice bran oil (RBO) using a combined functionalization: first, epoxidation with H2O2/Novozym 435 lipase, followed by acrylate group insertion. Design/Methodology/Approach: After being epoxidized with H2O2/Novozym 435, the refined rice bran oil was acrylated via epoxy ring-opening, using triethanolamine as catalyst and 4-methoxyphenol as inhibitor. The experimental conditions of temperature (T100 and 110 °C) and reaction time (t3 and 4 hours), as well as the ratio of g eRBO (epoxidized oil) to g acrylic acid (1.5 and 2.0) were considered for the functionalization. The functionalizations were monitored using iodine value (IV), saponification value (SV), and oxirane oxygen content (OOC), Fourier transform infrared (FTIR), and nuclear magnetic resonance (1 H NMR), which allowed the estimation of the %Acrylation. Results: The 1 H NMR studies indicate that the acrylation of rice bran oil is efficient, which is confirmed with the evolution of IV, SV, and OOC. Using the OOC, the best acrylation condition was identified at T110 °C, t3 hours, and ratio of g eRBO to g acrylic acid1.5, obtaining a %Acrylation of 85.89% via 1 H NMR. Study Limitations/Implications: Partially acrylated rice bran oil may become an intermediate in the biorefining of this oil and be used in the synthesis of crosslinked polymers. Findings/Conclusions: Refined rice bran oil was efficiently acrylated using two consecutive steps: it was initially epoxidized with H2O2/Novozym 435, followed by functionalization with acrylate group.