Effect of surface hydrophobization on the 1,5,9-cyclododecatriene epoxidation process with hydrogen peroxide on silanized Ti-SBA-15 catalyst

This work presents the results of the epoxidation of 1,5,9-cyclododecatriene (CDT) to 1,2-epoxy-5,9-cyclododecadiene (ECDD) with hydrogen peroxide on unmodified and on silanized Ti-SBA-15 catalyst (named as Ti-SBA-15-TMS). Silanization was performed by a simple and quick method using hexamethyl-disilazane. The catalyst was hydrophobic after modification, which was confirmed by FT-IR spectra in which the signals from the surface -OH groups and adsorbed water disappeared. The optimal solvent in terms of selectivity of transformation using H2O2 to ECDD was found to be 90 wt% acetone. From the comparison of the activities of Ti-SBA-15 and Ti-SBA-15-TMS catalysts, it is evident that silanization decreases the rate of the epoxidation reaction but increases the selectivities of transformation of CDT and H2O2 to ECDD. The low selectivity of the transformation of H2O2 to ECDD was a major concern during our studies on conducting this process on the Ti-MCM-41 catalyst. ECDD, due to the high degree of function-alization of the molecule, finds many applications both as a final product (perfume industry) and as an intermediate (epoxy resins and coatings), and can potentially be used as a raw material for the produc-tion of laurolactam. (c) 2023 The Korean Society of Industrial and Engineering Chemistry. Published by Elsevier B.V. All rights reserved.

Automated summary

This study investigates the epoxidation of 1,5,9-cyclododecatriene (CDT) to 1,2-epoxy-5,9-cyclododecadiene (ECDD) using hydrogen peroxide on unmodified and silanized Ti-SBA-15 catalyst (Ti-SBA-15-TMS). Silanization improves the selectivity of the reaction by decreasing the rate of epoxidation but increasing the transformation of CDT and H2O2 to ECDD. The use of 90 wt% acetone as the solvent yields the highest selectivity.