Sediment-Mediated Reduction of 2,4,6-Trinitrotoluene and Fate of the Resulting Aromatic (Poly)amines

2,4,6-Trinitrotoluene is a major surface and subsurface contaminant found at numerous munitions production and storage facilities. The reductive transformation of 2,4,6-trinitrotoluene (TNT) to aromatic (poly)amines and the consequent fate of these products were studied in anaerobic and aerobic sediment−water systems. Reduction of TNT was rapid under both anaerobic and aerobic conditions. Nitro-reduction was regioselective, leading to the preferential formation of 4-amino-2,6-dinitrotoluene (4-ADNT) and 2,4-diamino-6-nitrotoluene (2,4-DANT). Subsequent sorption of 2,4-DANT was rapid under aerobic conditions and resulted in nearly complete, irreversible retention by the sediment phase. Under anaerobic conditions, the rapidly formed 2,4-DANT displayed little affinity for the sediment phase. Instead, 2,4-DANT was further transformed to products that remained in the aqueous phase. Sorption studies in nontransforming sediments indicated increased irreversible sorption with replacement of nitro groups with amino groups. Covalent binding of the DANTs was partially inhibited under anoxic conditions, but sorption of TNT and the ADNTs was unaffected by changes in redox conditions.