Chlorination of Amino Acids: Reaction Pathways and Reaction Rates
Access Status
Authors
Date
2017Type
Metadata
Show full item recordCitation
Source Title
ISSN
School
Funding and Sponsorship
Collection
Abstract
Chlorination of amino acids can result in the formation of organic monochloramines or organic dichloramines, depending on the chlorine to amino acid ratio (Cl:AA). After formation, organic chloramines degrade into aldehydes, nitriles and N-chloraldimines. In this paper, the formation of organic chloramines from chlorination of lysine, tyrosine and valine were investigated. Chlorination of tyrosine and lysine demonstrated that the presence of a reactive secondary group can increase the Cl:AA ratio required for the formation of N,N-dichloramines, and potentially alter the reaction pathways between chlorine and amino acids, resulting in the formation of unexpected by-products. In a detailed investigation, we report rate constants for all reactions in the chlorination of valine, for the first time, using experimental results and modelling. At Cl:AA = 2.8, the chlorine was found to first react quickly with valine (5.4x104 M-1 s-1) to form N-monochlorovaline, with a slower subsequent reaction with N-monochlorovaline to form N,N-dichlorovaline (4.9x102 M-1 s-1), although some N-monochlorovaline degraded into isobutyraldehyde (1.0x10-4 s-1). The N,N-dichlorovaline then competitively degraded into isobutyronitrile (1.3x10-4 s-1) and N-chloroisobutyraldimine (1.2x10-4 s-1). In conventional drinking water disinfection, N-chloroisobutyraldimine can potentially be formed in concentrations higher than its odour threshold concentration, resulting in aesthetic challenges and an unknown health risk.
Related items
Showing items related by title, author, creator and subject.
-
Allpike, Bradley (2008)Natural organic matter (NOM), ubiquitous in natural water sources, is generated by biogeochemical processes in both the water body and in the surrounding watershed, as well as from the contribution of organic compounds ...
-
Nihemaiti, M.; Roux, J.; Croue, Jean-Philippe (2015)The aim of this work was to study the formation of haloacetamides (HAcAms) and other DBPs during chlorination and chloramination of algal organic matter (AlOM). The HAcAms formation potentials of different precursors ...
-
How, Zuo Tong; Linge, Kathryn; Busetti, Francesco; Joll, Cynthia (2016)© 2016 Elsevier Ltd. Although organic chloramines are known to form during the disinfection of drinking water with chlorine, little information is currently available on their occurrence or toxicity. In a recent in vitro ...