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Title: Sediment-mediated reduction of 2,4,6-trinitrotoluene and fate of the resulting aromatic (poly)amines

Abstract

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.

Authors:
 [1];  [2]
  1. Environmental Protection Agency, Cincinnati, OH (United States)
  2. Environmental Protection Agency, Athens, GA (United States)
Publication Date:
OSTI Identifier:
6428635
Resource Type:
Journal Article
Journal Name:
Environmental Science and Technology
Additional Journal Information:
Journal Volume: 33:15; Journal ID: ISSN 0013-936X
Country of Publication:
United States
Language:
English
Subject:
54 ENVIRONMENTAL SCIENCES; 45 MILITARY TECHNOLOGY, WEAPONRY, AND NATIONAL DEFENSE; BIODEGRADATION; PHASE STUDIES; REMEDIAL ACTION; SEDIMENTS; SORPTION; TNT; CHEMICAL EXPLOSIVES; CHEMICAL REACTIONS; DECOMPOSITION; EXPLOSIVES; NITRO COMPOUNDS; ORGANIC COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; 540220* - Environment, Terrestrial- Chemicals Monitoring & Transport- (1990-); 540320 - Environment, Aquatic- Chemicals Monitoring & Transport- (1990-); 450100 - Military Technology, Weaponry, & National Defense- Chemical Explosions & Explosives

Citation Formats

Elovitz, M S, and Weber, E J. Sediment-mediated reduction of 2,4,6-trinitrotoluene and fate of the resulting aromatic (poly)amines. United States: N. p., 1999. Web. doi:10.1021/es980980b.
Elovitz, M S, & Weber, E J. Sediment-mediated reduction of 2,4,6-trinitrotoluene and fate of the resulting aromatic (poly)amines. United States. doi:10.1021/es980980b.
Elovitz, M S, and Weber, E J. Sun . "Sediment-mediated reduction of 2,4,6-trinitrotoluene and fate of the resulting aromatic (poly)amines". United States. doi:10.1021/es980980b.
@article{osti_6428635,
title = {Sediment-mediated reduction of 2,4,6-trinitrotoluene and fate of the resulting aromatic (poly)amines},
author = {Elovitz, M S and Weber, E J},
abstractNote = {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.},
doi = {10.1021/es980980b},
journal = {Environmental Science and Technology},
issn = {0013-936X},
number = ,
volume = 33:15,
place = {United States},
year = {1999},
month = {8}
}