The reaction of ozone with a number of pyridinium salts containing 1-alkoxymethyl and 1-alkylthiomethyl substituents was determined at a total substrate concentration of 2 g/L. Ozonation of pyridinium salts was strongly dependent on the kinds and positions of the substituents in the pyridine ring. The most favorable were the third position and the substituents including hydroxyl or dimethylamino groups. In an aqueous solution, 1-(alkoxymethyl)-3-hydroxypyridinium, 1-(alkylthiomethyl)-3-hydroxypyridinium, and 1-(alkoxymethyl)-3-(dimethylamino)pyridinium salts reacted with ozone. The reaction was fast, and pyridinium salts were quantitatively removed. 1-(Alkoxymethyl)- and 1-(alkylthiomethyl)pyridinium chlorides were obtained by the Menschutkin reaction. In general, the procedure was simple and the reaction was productive and short. During the course of this study, we synthesized a new generation of cationic surfactants that were extremely reactive with ozone in an aqueous solution.