Multifunctional hydrolytic catalyses. xi. the hydrolysis of p-nitrophenyl acetate by a polysoap-bound bifunctional catalyst

The catalytic hydrolysis of p-nitrophenyl acetate was studied in water at 30°C in the presence of a polysoap-bound bifunctional (LIMHA) catalyst. The polysoaps used were poly(vinylimidazole) quaternized with dodecyl and ethyl groups and poly(ethylenimine) partly quaternized with methyl and higher alkyl (C, C, C) groups. The catalysis proceeded via the acetyl transfer to the dissociated hydroxamate unit of the bifunctional catalyst and the subsequent decomposition of the intermediate by the neighboring imidazole. Catalysis was promoted well in the hydrophobic domain of the polysoap, but was less than that in the conventional cationic micelle of hexadecyltrimethylammonium bromide. The efficiency of the polysoap-bound bifunctional catalyst was ca. 1000 times greater than that of imidazole.