N-CHLOROALDIMINES .3. CHLORINATION OF PHENYLALANINE IN MODEL SOLUTIONS AND IN A WASTE-WATER

The chlorination reactions of phenylalanine in water and wastewater were studied. At the lower CI/N molar ratios N-chlorophenylalanine and phenylacetaldehyde were identified as the main products while phenylacetonitrile and N-chlorophenylacetaldimine were the major products at Cl/N ratios of 2.0 and beyond. The concentration of phenylalanine in a primary municipal wastewater effluent was determined, and the chlorination products were found to be the same as those in model solutions. N-Chlorophenylacetaldimine decomposes slowly (t1/2 = 35 h) in water (pH 7.0 and 8.0) and in wastewater (pH 7.0, estimated t1/2 of 58 h). The distribution of chlorination products in the wastewater supports the theory that monochlorinated organic amino nitrogen compounds may represent a disproportionately high fraction of the chlorine-containing oxidants present in marginally chlorinated primary effluent.