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    Formation and reactivity of inorganic and organic chloramines and bromamines during oxidative water treatment

    Access Status
    Fulltext not available
    Authors
    Heeb, M.
    Kristiana, Ina
    Trogolo, D.
    Arey, J.
    von Gunten, U.
    Date
    2017
    Type
    Journal Article
    
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    Citation
    Heeb, M. and Kristiana, I. and Trogolo, D. and Arey, J. and von Gunten, U. 2017. Formation and reactivity of inorganic and organic chloramines and bromamines during oxidative water treatment. Water Research. 110: pp. 91-101.
    Source Title
    Water Research
    DOI
    10.1016/j.watres.2016.11.065
    ISSN
    0043-1354
    School
    Curtin Water Quality Research Centre
    URI
    http://hdl.handle.net/20.500.11937/21223
    Collection
    • Curtin Research Publications
    Abstract

    The formation and further reactions of halamines during oxidative water treatment can be relevant for water quality. In this study, we investigated the formation and reactivity of several inorganic and organic halamines (monochloramine, N-chloromethylamine, N-chlorodimethylamine, monobromamine, dibromamine, N-bromomethylamine, N,N-dibromomethylamine, and N-bromodimethylamine) by kinetic experiments, transformation product analysis, and quantum chemical computations. Kinetic model simulations were conducted to evaluate the relevance of halamines for various water treatment scenarios. Halamines were quickly formed from the reaction of chlorine and bromine with ammonia or organic amines. Species-specific second-order rate constants for the reaction of chlorine and bromine with ammonia, methyl- and dimethylamine were in the order of 106-108 M-1s-1. The formed halamines were found to be reactive towards phenolic compounds, forming halogenated phenols via electrophilic aromatic substitution (phenol and resorcinol) or quinones via electron transfer (catechol and hydroquinone). At near neutral pH, apparent second-order rate constants for these reactions were in the order of 10-4-10-1 M-1s-1 for chloramines and 101-102 M-1s-1 for bromamines. Quantum chemical computations were used to determine previously unknown aqueous pKa values, gas phase bond dissociation energies (BDE) and partial atomic charges of the halamines, allowing a better understanding of their reactivities. Kinetic model simulations, based on the results of this study, showed that during chlorination inorganic and organic chloramines are the main halamines formed. However, their further reactions with organic matter are outcompeted kinetically by chlorine. During ozonation, mainly inorganic bromamines are formed, since ozone quickly oxidizes organic amines. The further reactions of bromamine are typically outcompeted by ozone and thus generally of minor importance. The use of peracetic acid for saline ballast water treatment can result in the formation of substantial amounts of bromamines, which can react with dissolved organic matter and contribute to the formation of brominated products.

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