Aromatic amination of refined rice bran oil previously epoxidized with Novozym 435

Objective: To synthesize aromatically aminated rice bran oil (APA) using a chemo-enzymatic epoxidation based on Novozym 435 followed by p-xylenediamine insertion. Design/methodology/approach: Refined APA was epoxidized using H2O2/Novozym 435. The resulting epoxidized rice bran oil (eAPA) was functionalized with the aromatic diamine p-xylylenediamine via epoxy ring cleavage (X-eAPA), using ZnCl2 as catalyst. Iodine value (IY), saponification value (IS) and oxirane oxygen content (COO) were determined to evaluate structural changes of the oils. APA, eAPA and X-eAPA were identified using FTIR, 1H and 13C NMR. Results: IY, IS and COO values suggested that the synthesis of eAPA and X-eAPA were effective. The increase in molecular weight in eAPA indicates formation of ~6 epoxy rings per original triglyceride. The COO value of X-eAPA was reduced by 22% compared to that of eAPA, implying that an effective aromatic amination was achieved. FTIR, 1H and 13C NMR spectroscopy studies confirmed the epoxidation and amination of APA. Limitations on study/implications: X-eAPA may be a feasible precursor to obtain high added-value products, as polymers or corrosion inhibitors. Findings/conclusions: Refined rice bran oil partially aromatic aminated was synthesized in two steps, under mild conditions. Epoxidized rice bran oil was obtained using H2O2/Novozym 435, to be immediately functionalized with the aromatic diamine p-xylylenediamine. Keywords: Epoxidation, amination, agro-industrial by-products.Objective: To aromatically aminate refined rice bran oil (RBO), a by-product of the rice agro-industry,through a chemical-enzymatic epoxidation based on Novozym 435 and p-xylylenediamine insertion.Design/Methodology/Approach: Refined RBO was epoxidized with H2O2/Novozym 435. The resultingepoxidized rice bran oil (eRBO) was functionalized with the p-xylylenediamine aromatic diamine via epoxyring-opening (X-eRBO), using ZnCl2 as catalyst. Iodine value (IV), saponification value (SV), and oxiraneoxygen content (OOC) were determined to evaluate structural changes in oils. The RBO, the eRBO, and theX-eRBO were identified using FTIR, 1H, and 13C NMR.Results: The IV, the SV, and the OOC suggest that the synthesis of eRBO and X-eRBO were effective. Theincrease of molecular weight in eRBO point to the formation of 6 epoxy rings per original triglyceride. TheOOC value of X-eRBO was 22% lower than the OOC value of eRBO, implying that an effective aromaticamination was achieved. The FTIR, 1H and 13C NMR spectroscopy analysis confirmed the epoxidation andamination of the RBO.Study Limitations/Implications: X-eRBO may be a feasible precursor for value-added products, such ascrosslinked polymers or corrosion inhibitors.Findings/Conclusions: Refined rice bran oil was aromatically aminated after two stages under mild thermal conditions. This result was achieved with an epoxidation sequence with H2O2/Novozym 435, followed byfunctionalization with p-xylylenediamine