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    Electrochemical Reduction of 2,4-Dinitrotoluene in Room Temperature Ionic Liquids: A Mechanistic Investigation

    Access Status
    Fulltext not available
    Authors
    Lee, Wade
    Hay, C.
    Silvester, Debbie
    Date
    2018
    Type
    Journal Article
    
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    Citation
    Lee, W. and Hay, C. and Silvester, D. 2018. Electrochemical Reduction of 2,4-Dinitrotoluene in Room Temperature Ionic Liquids: A Mechanistic Investigation. Australian Journal of Chemistry. 71 (10): pp. 818-825.
    Source Title
    Australian Journal of Chemistry
    DOI
    10.1071/CH18315
    ISSN
    0004-9425
    School
    Nanochemistry Research Institute
    URI
    http://hdl.handle.net/20.500.11937/71458
    Collection
    • Curtin Research Publications
    Abstract

    © 2018 CSIRO. The reduction mechanism of 2,4-dinitrotoluene (DNT) has been studied in eight room temperature ionic liquids (RTILs) using cyclic voltammetry (CV), square wave voltammetry (SWV), chronoamperometry, and digital simulation. Two distinctive peaks are observed in the voltammetry, corresponding to the stepwise reduction of the two nitro groups on the aromatic ring. Diffusion coefficients (D) and electron counts (n) were calculated from chronoamperometric transients, revealing an electron count of one in most RTILs, and a linear relationship between D and the inverse of viscosity. Focusing on the first reduction only, the peak appears to be chemically reversible at low concentrations. However, as the concentration increases, the current of the reverse peak diminishes, suggesting that one or more chemical steps occur after the electrochemical step. The results from digital simulation of the CVs in one of the RTILs reveal that the most likely mechanism involves a deprotonation of the methyl group of a parent DNT molecule by the electrogenerated radical anion and/or a dimerisation of two electrogenerated radical anions. Elucidation of the reduction mechanism of DNT (and other explosives) is vital if electrochemical techniques are to be employed to detect these types of compounds in the field.

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