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

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Abstract
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.

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