ɤ-Radiation-induced N-phenylation of aniline using chlorobenzene: a novel route for diphenylamine formation

Abstract

A novel route of diphenylamine (DPA) formation via ɤ-radiation-induced N-phenylation of aniline by chlorobenzene in oxygen-free condition is reported. A capillary gas chromatography-mass spectrometry method was developed for DPA identification and quantification. The effects of the reactants molar ratio, absorbed radiation dose, and dose rate on the yield of DPA were investigated in ɤ-irradiated aniline/chlorobenzene samples. The yield of DPA was found to be maximum at aniline: chlorobenzene molar ratio of about 1:1. Generally, the yield of DPA increases as absorbed dose increases. The G (DPA) was determined to be 11.6 μM/J. The DPA yield was found to increase linearly as dose rate increases. This observation can be attributed to the formation of DPA via spur reactions. A reaction mechanism was suggested for the DPA formation in the ɤ-irradiated aniline/chlorobenzene samples.