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    NDMA formation mechanism by chloramination of tertiary amines

    Access Status
    Fulltext not available
    Authors
    Le Roux, J.
    Gallard, H.
    Croue, Jean-Philippe
    Papot, S.
    Deborde, M.
    Date
    2012
    Type
    Conference Paper
    
    Metadata
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    Citation
    Le Roux, J. and Gallard, H. and Croue, J. and Papot, S. and Deborde, M. 2012. NDMA formation mechanism by chloramination of tertiary amines.
    Source Title
    Water Quality Technology Conference and Exposition 2012
    ISBN
    9781622767878
    School
    Curtin Water Quality Research Centre
    URI
    http://hdl.handle.net/20.500.11937/51337
    Collection
    • Curtin Research Publications
    Abstract

    Chloramination is used to reduce the formation of regulated disinfection by-products (i.e. trihalomethanes and haloacetic acids), or to avoid biofouling of membranes during wastewater reclamation processes. However, chloramination favors the formation of N-nitrosodimethylamine (NDMA), a human carcinogen. Proposed NDMA formation mechanisms used dimethylamine as a model precursor, but some anthropogenic tertiary amines presenting dimethylamine (DMA) functional groups have been demonstrated to lead to important amounts of NDMA (e.g. the pharmaceutical ranitidine). In this study, the mechanisms of NDMA formation by chloramination of tertiary amines (including model compounds presenting aromatic or heterocyclic rings, e.g. (dimethylaminomethyl)furfuryl alcohol (DFUR) or ranitidine) were studied. Compounds presenting heterocyclic rings substituted with DMA functions (e.g. DFUR, ranitidine) show much higher conversion rates to NDMA than other tertiary amines or DMA. A mechanism is proposed to explain the high yields of NDMA obtained from the decomposition of these tertiary amines during chloramination. This mechanism is based on the production of a carbocation intermediate formed from the methylated aromatic moieties present in the compounds, favouring the release of NDMA. © 2012 American Water Works Association AWWA WQTC Conference Proceedings.

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    • Formation of NDMA by chloramination of nitrogenous contaminants: Potential role of bromide and dissolved oxygen
      Le Roux, J.; Gallard, H.; Croue, Jean-Philippe (2011)
      Disinfection with monochloramine is known to significantly reduce the formation of regulated disinfection by-products (i.e. trihalomethanes and haloacetic acids) as compared to chlorination. Moreover, monochloramine can ...
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      Disinfection with chloramines is often used to reduce the production of regulated disinfection by-products (DBPs) such as trihalomethanes (THMs) and haloacetic acids (HAAs). However, chloramination can lead to the formation ...
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      Le Roux, J.; Gallard, H.; Croué, Jean-Philippe (2012)
      The formation of NDMA and other DBPs (including THMs, HANs, and HKs) has been investigated by chloramination of several tertiary amines in the absence and presence of bromide ion. NDMA formation from the most reactive ...
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