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    Chlorination of Amino Acids: Reaction Pathways and Reaction Rates

    250586.pdf (457.2Kb)
    Access Status
    Open access
    Authors
    How, Zuo Tong
    Linge, Kathryn
    Busetti, Francesco
    Joll, Cynthia
    Date
    2017
    Type
    Journal Article
    
    Metadata
    Show full item record
    Citation
    How, Z. and Linge, K. and Busetti, F. and Joll, C. 2017. Chlorination of Amino Acids: Reaction Pathways and Reaction Rates. Environmental Science & Technology. 51 (9): pp. 4870-4876.
    Source Title
    Environmental Science & Technology
    DOI
    10.1021/acs.est.6b04440
    ISSN
    1520-5851
    School
    Department of Chemistry
    Funding and Sponsorship
    http://purl.org/au-research/grants/arc/LP110100548
    http://purl.org/au-research/grants/arc/LP130100602
    URI
    http://hdl.handle.net/20.500.11937/51516
    Collection
    • Curtin Research Publications
    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.

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