Hydrolysis of benzoic anhydride mediated by ionenes and micelles

Micelle-mediated catalysis was compared to that of ionene polymers. Hexadecyltrimethylammonium bromide (CTABr) and benzyldimethylhexadecylammonium chloride (BDHA) were the surfactants employed and 2-hydroxy-3-ionene chloride (2-OH-33R) and poly[(dipropyliminium)-1,3-propanediyl bromide], 33R33, the tested ionenes. A modified Michaelis–Menten equation described the kinetics of ionene-mediated hydrolysis. The cationic polymer 2-hydroxy-3-ionene chloride proved to be the most efficient catalyst and a detailed mechanism is proposed for the reaction with benzoic anhydride (Bz2O) based on the kinetic evidence obtained. The catalytic efficiency follows the order 2-OH-33R > BDHA > 33R33 > CTABr.

Micellar catalysis of the hydrolysis of benzoic anhydride by hexadecyltrimethylammonium bromide (CTABr) and benzyldimethylhexadecylammonium chloride (BDHA) was compared with the ionene polymers, 2-hydroxy-3-ionene chloride (2-OH-33R) and poly[(dipropyliminium)-1,3-propanediyl bromide], 33R33. The ionene 2-OH-33R proved to be the most efficient catalyst and the catalytic efficiency follows the order 2-OH–33R > BDHA>33R33 > CTABr.Figure optionsDownload as PowerPoint slide