Environmental fate of 2,4-dinitroanisole (DNAN) and its reduced products

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DOIResolve DOI: http://doi.org/10.1016/j.chemosphere.2014.05.047
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TypeArticle
Journal titleChemosphere
ISSN0045-6535
Volume119
Pages1623; # of pages: 8
Subject2,4-Dinitroanisole; 2,4-Diaminoanisole; Regioselectivity; Insensitive munition
AbstractSeveral defense departments intend to replace 2,4,6-trinitrotoluene (TNT) in munitions formulations by the less sensitive 2,4-dinitroanisole (DNAN). To help understand environmental behavior and ecological risk associated with DNAN we investigated its key initial abiotic and biotic reaction routes and determined relevant physicochemical parameters (pKa, log Kow, aqueous solubility (Sw), partition coefficient (Kd)) for the chemical and its products. Reduction of DNAN with either zero valent iron or bacteria regioselectively produced 2-amino-4-nitroanisole (2-ANAN) which, under strict anaerobic conditions, gave 2,4-diaminoanisole (DAAN). Hydrolysis under environmental conditions was insignificant whereas photolysis gave photodegradable intermediates 2-hydroxy-4-nitroanisole and 2,4-dinitrophenol. Physicochemical properties of DNAN and its amino products drastically depended on the type and position of substituent(s) on the aromatic ring. Sw followed the order (TNT < DNAN < 2-ANAN < 4-ANAN < DAAN) whereas log Kow followed the order (DAAN < 4-ANAN < 2-ANAN < DNAN < TNT). In soil, successive replacement of single bondNO2 by single bondNH2 in DNAN enhanced irreversible sorption and reduced bioavailability under oxic conditions. Although DNAN is more soluble than TNT, its lower hydrophobicity and its tendency to form aminoderivatives that sorb irreversibly to soil contribute to make it less toxic than the traditional explosive TNT.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada; Aquatic and Crop Resource Development; Energy, Mining and Environment
Peer reviewedYes
NPARC number21274171
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Record identifierd6a641b9-7037-43bb-9313-f163405c8acb
Record created2015-02-20
Record modified2016-05-09
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