Reactivity of two models of non-ionic surfactants with ozone

The ozonation of ethylene glycol and diethylene glycol mono-n-octylether (models of non-ionic surfactants) has been performed in aqueous solution at pH 4 and pH 9.5. The experiments at acidic pH show that the methylene groups adjacent to the ethereal oxygens are transformed into carbonyl groups. At alkaline pH the aliphatic chain is cleaved. Kinetic experiments allow to suggest a reaction mechanisms.