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

• Quinto Hernández, Alfredo ^[1] ; Flores Barrera, Esly Damaris ^[1] ; Zúñiga Díaz, Jacqueline ^[1] ; Porcayo Calderón, Jesús ^[2] ; Hernández Campos, Francisco Javier ^[1] ; Salado Huerta, José Elias ^[1] ; Acevedo Quiroz, Macdiel Emilio ^[1]
  1. [1] Tecnológico Nacional de México, Instituto Tecnológico de Zacatepec
  2. [2] Universidad de Sonora
• Localización: Agro Productividad, ISSN-e 2594-0252, Vol. 16, Nº. 12, 1, 2023 (Ejemplar dedicado a: Diciembre), págs. 49-55
• Idioma: inglés
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• Resumen

  • 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.