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    NDMA formation by chloramination of ranitidine: Kinetics and mechanism

    Access Status
    Fulltext not available
    Authors
    Roux, J.
    Gallard, H.
    Croué, Jean-Philippe
    Papot, S.
    Deborde, M.
    Date
    2012
    Type
    Journal Article
    
    Metadata
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    Citation
    Roux, J. and Gallard, H. and Croué, J. and Papot, S. and Deborde, M. 2012. NDMA formation by chloramination of ranitidine: Kinetics and mechanism. Environmental Science and Technology. 46 (20): pp. 11095-11103.
    Source Title
    Environmental Science and Technology
    DOI
    10.1021/es3023094
    ISSN
    0013-936X
    School
    Curtin Water Quality Research Centre
    URI
    http://hdl.handle.net/20.500.11937/50189
    Collection
    • Curtin Research Publications
    Abstract

    The kinetics of decomposition of the pharmaceutical ranitidine (a major precursor of NDMA) during chloramination was investigated and some decomposition byproducts were identified by using high performance liquid chromatography coupled with mass spectrometry (HPLC-MS). The reaction between monochloramine and ranitidine followed second order kinetics and was acid-catalyzed. Decomposition of ranitidine formed different byproducts depending on the applied monochloramine concentration. Most identified products were chlorinated and hydroxylated analogues of ranitidine. In excess of monochloramine, nucleophilic substitution between ranitidine and monochloramine led to byproducts that are critical intermediates involved in the formation of NDMA, for example, a carbocation formed from the decomposition of the methylfuran moiety of ranitidine. A complete mechanism is proposed to explain the high formation yield of NDMA from chloramination of ranitidine. These results are of great importance to understand the formation of NDMA by chloramination of tertiary amines.

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