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

被引:9
|
作者
Lee, Unqiao [1 ,2 ]
Hay, Catherine E. [1 ,2 ]
Silvester, Debbie S. [1 ,2 ]
机构
[1] Curtin Univ, Curtin Inst Funct Mol & Interfaces, GPO Box U1987, Perth, WA 6845, Australia
[2] Curtin Univ, Sch Mol & Life Sci, GPO Box U1987, Perth, WA 6845, Australia
基金
澳大利亚研究理事会;
关键词
TRANSFER KINETICS; GUNSHOT RESIDUE; EXPLOSIVES; FERROCENE; OXYGEN; 2,4,6-TRINITROTOLUENE; ELECTROREDUCTION; VOLTAMMETRY; ELECTRODES; PLATINUM;
D O I
10.1071/CH18315
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:818 / 825
页数:8
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