Reactivity of functional detergents with a pyridine ring and an α-nucleophile fragment in the head group

Abstract

Functional detergents (FD) based on pyridine and containing aldoximate, ketoximate, and hydroxamate groups were synthesized. Their reactivity in FD/CTAB comicelles toward 4-nitrophenyl 4-toluenesulfonate (NPTS), diethyl phosphate (NPDEP), and diethylphosphonate (NPDEPS) in weakly alkaline media was investigated. Functional detergents based on pyridine are effective in the decomposition of ecotoxicants; the half-lives for the transformation of the substrates into the reaction products in the presence of a functional detergent containing, for example, a ketoximate group amounts to ∼40 s (NPTS), ∼120 s (NPDEP), and ∼5 s (NPDEPS). By analyzing the results it was possible to establish the paths to further modification of the head group of the surfactant, i.e., by varying the structure of the oximate group at various positions of the pyridinium ring aimed at the production of low-basicity functional detergents.