A review of the significance and formation of chlorinated N-organic compounds in water supplies including preliminary studies on the chlorination of alanine, tryptophan, tyrosine, cytosine, and syringic acid

Abstract Nitrogenous organic compounds are of environmental significance because of their potential as both trihalomethane (THM) and nonpurgeable organic halide (NPOX) precursors. They additionally lead to falsely positive tests for free available chlorine (FAC) and are components in the reaction of chlorine to form dihaloacetonitriles (DHANs). A large number of naturally occurring nitrogenous compounds additionally react readily with aqueous chlorine exerting significant chlorine demand. Such reactions generally involve the substitution of chlorine for hydrogen on a nitrogen atom. Additionally, N-chloroorganic materials may be produced even when the precursor concentration is low owing to the rapid specific rate of formation. While previous attention has been largely focused on nonpolar chlorinated organic contaminants such as THMs, the wide distribution of N-organic compounds in water, as well as their general reactivity towards aqueous chlorine, warrant further attention and study to this group of materials. Preliminary studies on the chlorination of several N-organic compounds at a few chlorine-to-compound molar ratios at pH 7 and 4.7 over several reaction intervals are presented. NPOX formation was quite rapid and comprised the greatest proportion of the total organic halide formed for the conditions studied.