EFFECT OF CYCLIC ACETAL-TYPE CATIONIC SURFACTANTS ON THE BASIC DEHYDROBROMINATION REACTION

Article abstract of DOI:10.1002/poc.610071110

The reaction of 2-(p-nitrophenyl)ethyl bromide with hydroxide ion was studied at 50 and 25 deg C in the presence of cationic chemodegradable surfactants, i.e. <2-alkyl(1,3-dioxolan-4-yl)methyl>trimethylammonium bromides Ia-c (alkyl: a = n-C9H19, b = n-C11H23, c = n-C13H27).The kinetic data were interpreted with the pseudo-phase ion-exchange (PIE) formalzm at both temperatures.The results indicate that the major source of rate enhancement is the increased reactant concentration in the small micellar reaction volume.The surfactant stability in micellar conditions was probed by means of a hydrolysis reaction of the surfactant 1,3-dioxolane ring.The kinetics of acid hydrolysis of Ia-c micelles, as a result of specific hydronium ion concentration, is one order of magnitude smaller than that of unaggregated systems.