Reactions of chlorination with tert ‐butyl hypochlorite ( T BuOCl)

The chlorination reactions of nitrogenous organic compounds (2,2,2‐trifluoroethylamine, benzylamine, glycine, and dimethylamine) by tert ‐butyl hypochlorite ( t BuOCl) were studied at 25 °C, ionic strength 0.5 M and under isolation conditions. The kinetic results obtained in the formation processes of the corresponding N ‐chloramines in acid medium (pH = 5–7) are summarized in this paper. Kinetic studies showed a first order with respect to t BuOCl concentration. The chlorination reactions involving benzylamine, glycine and dimethylamine were all first order with respect to nitrogenous compound concentration and approximately −1 order with respect to proton concentration. The reaction with 2,2,2‐trifluoroethylamine was more complex, and the order of reaction with respect to the amine varied with pH. Copyright © 2014 John Wiley & Sons, Ltd.