Environmental transformation products of 2,4,6-trinitrotoluene

Sequential Electrolytic Degradation of Energetic Compounds in Groundwater

“…The pathway resulting in the formation of this compound may be through the amino-dinitrotoluene isomers (Junk and Catallo, 1998) or through diamino-mononitro toluene compounds (Rodgers and Bunce, 2001) although the diamino-mononitro toluene intermediates were not observed in this study.…”

“…This compound has been identified in the cathode chamber of the batch experiments and in the effluent of the flow-through reactor. This compound is hypothesized to be an azoxynitrotoluene compound, although the molecular weight is low relative to the MW 406 reported by others (Junk and Catallo, 1998). It is not clear what fraction of the original TNT forms the MW 393 compound or if adsorption of this compound to the mineral surfaces is responsible for the TNT removal observed in the Phase 1 (proof-of concept) studies.…”

Quantum mechanical and experimental analyses of TNT metabolite 2-hydroxylamino-4,6-dinitrotoluene

“…It was also agreed that an understanding of the chemical properties of these initial TNT reduction products may provide insight into their reductive pathways and environmental fates [15]. Unfortunately, as pointed out by Junk, Catallo, and Maeda, limited access to various TNT degradation products remains a significant barrier in collecting experimental data from those materials and performing experimental analysis [11,13]. Quantum mechanical simulation can be an advanced and alternative method to evaluate their thermo-chemical properties.…”

“…It was found that initial products of TNT reductive degradation are 2-hydroxylamino-4,6-dinitrotoluene (2-HADNT) and its isomer 4-hydroxylamino-2, 6-dinitrotoluene (4-HADNT), as shown in Fig. 1 [11][12][13]. Homma-Takeda et al found that 4-HADNT damages DNA, prompts the generation of 8-oxodG, and causes cleavage of DNA at sites with consecutive guanines [14].…”

“…However, the extensive application of TNT resulted in significant environmental contaminations through carcinogenic TNT and its metabolites, and environmental remediation is therefore highly wanted [4,5]. It is well known that TNT mineralizes slowly, mostly follows reductive pathways and gives rise to toxic intermediates including 2-hydroxylamino-4,6-dinitrotoluene [6][7][8][9][10][11]. In order to effectively implement environmental remediation, analytical and toxicological evaluations of contaminated sites are required and therefore a thorough knowledge of the properties of the reduction http://dx.doi.org/10.1016/j.molstruc.2014.09.058 0022-2860/Ó 2014 Elsevier B.V. All rights reserved.…”