The effect of 1- and 2-(1-hydroperoxy-1-methylethyl)naphthalenes on the liquid-phase oxidation of alkylaromatic hydrocarbons

The properties of 1- and 2-(1-hydroperoxy-1-methylethyl)-naphthalenes as initiators were studied in the liquid-phase free-radical oxidation of hydrocarbons with oxygen. 2-(1-Hydroperoxy-1-methylethyl)naphthalene was found to initiate the reaction, whereas unexpectedly, 1-(1-hydroperoxy-1-methylethyl)naphthalene was found to inhibit the reaction. The products of decomposition of the studied hydroperoxides were found to exhibit essential differences. Thermal decomposition of 1-(1-hydroperoxy-1-methylethyl)naphthalene was found to yield hydroxyaromatic compounds active as oxidation inhibitors. This fact explains the oft-reported lack of reaction in long-term oxidation of 1-isopropylnaphthalene and its disfavourable effect on the oxidation of 2-isopropylnaphthalene.