Reactions of stabilizer compounds. III. Oxidative reactions of some 2′-hydroxy-2-phenylbenzotriazole light stabilizers in the AIBN-initiated autoxidation of cumene

Oxidative decay of number of commercially important 2′-hydroxy-2-phenylbenzotriazole light stabilizers during the AIBN-initiated autoxidation of cumene at 65°C is described. The reactivity of the hydroxyphenylbenzotriazoles studied increased in the order 2-(2′-hydroxy-5′-methyl)phenylbenzotriazole (Ia) < 2-(2′-hydroxy-3′,5′ -di-tert-pentyl)phenylbenzotriazole (Ie) < 5-chloro-2-(3′,5′-di-tert-butyl-2′-hydroxy)phenylbenzotriazole (Ic) < 5-chloro-2-(3′-tert-butyl-2′-hydroxy-5′-methyl)phenylbenzotriazole (Ib). The major product from the reaction of Ib was identified as the cumylperoxycyclohexa-2,5-dienone (III). The possible occurrence of these reactions during the degradation of stabilized polymers is discussed.