Kinetics and mechanisms of hypochlorite oxidation of alpha-amino acids during disinfection of water

To obtain information on the stability of the chlorinated compounds produced during chlorination of natural waters or swimming pool water, the authors examined the decomposition of 2 chlorination products over a range of hypochlorite to amino acid ratios and pH values. Oxidation of simple amino acids with hypochlorite in the dark led to rapid formation of (N-chloro)amino acid and (N,N-dichloro)amino acid, which then decomposed spontaneously by first-order kinetics to give a mixture of aldehyde and nitrile. The mechanisms involved are discussed. The rate of decomposition of the chloro-amino acids was temperature-dependent, but was relatively independent of pH over the range found in most natural waters. (Full translation 90 pounds sterling).