Fabrication of micro-reactors by a self-assembly of cationic surfactants to mediate NHPI/Co catalyzed selective aerobic oxidation of cumene to cumyl hydroperoxide

A highly efficient transformation from cumene to cumyl hydroperoxide (CHP) is pursued industrially. Herein, didodecyl dimethyl ammonium bromide (DDAB) as a phase transfer catalyst was found an outstanding role for aerobic oxidation of cumene to CHP with a conversion of 99.5 % and a selectivity of 83.5 % at near room temperature. The promotion can partially be attributed to the formation of the reversed multilamellar vesicles (MLVs) as micro-reactors via a self-assembly. The vesicles promoted the enrichments of cumene on the outer surface due to their outward hydrophobic chains (didodecyl), and enhanced the concentrations of NHPI and cobaltous ions in the MLVs malls for the inward head groups, leading to close contacts between the catalyst and the substrate and a highly efficient transformation from cumene to CHP. Cumyl, cumyl oxyl, cumyl peroxyl, methyl, phthalimide N-oxyl (PINO) radicals and dicumyl, dicumyl peroxide (DCP) were well confirmed, demonstrating an intact propagation chain of from cumene to CHP.

Automated summary

In this study, didodecyl dimethyl ammonium bromide (DDAB) was found to have a significant promotion effect on the aerobic oxidation of cumene to cumyl hydroperoxide (CHP) at near room temperature. The promotion was attributed to the formation of reversed multilamellar vesicles (MLVs) as micro-reactors.