Author:
Brownlie I. T.,Ingold K. U.
Abstract
The inhibition of the oxidation of styrene by the stable aliphatic nitroxide radical, 2,2,6,6-tetramethyl-4-piperidone nitroxide (I), and two stable aromatic nitroxide radicals, 4,4′-dimethoxydiphenyl nitroxide (II) and 4,4′-dinitrodiphenyl nitroxide (III), has been studied. The aromatic nitroxides react with both alkyl (R·) and peroxy (RO2·) radicals, but the aliphatic nitroxide only reacts with alkyl radicals. The hydroxylamines derived from I and II react only with peroxy radicals. They are quite effective oxidation inhibitors, exhibiting a deuterium kinetic isotope effect kH/kD ~ 2−3. The hydroxylamine from III inhibits the oxidation of styrene for a short time and then becomes an extremely powerful oxidation catalyst. It is suggested that a product from this hydroxylamine undergoes a rapid chain-branching reaction with styrene.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
145 articles.
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