US EPA

2835947 

Journal Article 

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

Hawari, J; Monteil-Rivera, F; Perreault, NN; Halasz, A; Paquet, L; Radovic-Hrapovic, Z; Deschamps, S; Thiboutot, S; Ampleman, G 

2015 

Yes 

Chemosphere
ISSN: 0045-6535
EISSN: 1879-1298 

PERGAMON-ELSEVIER SCIENCE LTD 

OXFORD 

119 

16-23 

English 

25460743 

10.1016/j.chemosphere.2014.05.047 

WOS:000347739600003 

https://linkinghub.elsevier.com/retrieve/pii/S0045653514006894
Exit
 

Several 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, logKow, 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 logKow followed the order (DAAN<4-ANAN<2-ANAN<DNAN<TNT). In soil, successive replacement of -NO2 by -NH2 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. 

2,4-Dinitroanisole; 2,4-Diaminoanisole; Regioselectivity; Insensitive munition