Unusual Hofmann elimination under mild conditions in polymerizable cationic surfactant systems

Abstract

Hofmann elimination and nucleophilic substitution reactions have been simultaneously observed at relatively low temperatures in a family of polymerizable alkyltrimethylammonium methacrylate surfactants, as well as in dodecyltrimethylammonium hydroxide. In concentrated aqueous solutions of the latter surfactant, Hofmann elimination occurs at room temperature. These reactions have been verified by IR, 1H NMR, and 13C NMR spectroscopies; differential scanning calorimetry; gas chromatography coupled to mass spectroscopy; and other techniques. A possible explanation of this phenomenon is provided.