2,4,6-trinitrotoluene transformation

Explosive residues containing 2,4,6-trinitrotoluene transformation products have been examined (Kleibohmer et al. 1993), and a range of explosives including TNT and related compounds, and nitra-mines analyzed using amperometric detection with a silver-on-gold electrode (Hilmi et al. 1999). 

Felt DR, Larson SL, and Hansen LD, Kinetics of Base-Induced 2,4,6-Trinitrotoluene Transformation, Technical Report ERDC/EL TR-01-17, US Army Engineer Research and Development Center, Vicksburg, MS, 2001. 

Jain, M. R., Zinjarde, S. S., Deobagkar, D. D., Deobagkar, D. N. 2,4,6-trinitrotoluene transformation by a tropical marine yeast Yarrowia lipolytica NCIM 3589. Marine Pollution Bulletin 2004, 49(9-10), 783-788. 

Kutty R and Bennett GN, Biochemical characterization of trinitrotoluene transforming oxygen-insensitive nitroreductases from Clostridium acetobutylicum ATCC 824, Arch. 

Pavlostathis SG, KK Comstock, ME Jacobson, FM Saunders (1998) Transformation of 2,4,6-trinitrotoluene by the aquatic plant Myriophyllum spicatum. Environ Toxicol Chem 17 2266-2273. 

Lewis TA, S Goszczynski, RL Crawford, RA Korns, W Adamassn (1996) Prodncts of anaerobic 2,4,6-trinitrotoluene (TNT) transformation by Clostridium bifermentans. Appl Environ Microbiol 62 4669-4674. 

Pak JW, K1 Knoke, DR Noguera, BG Fox, GH Chambliss (2000) Transformation of 2,4,6-trinitrotoluene by purified xenobiotic reductase B from Pseudomonas fluorescens 1-C. Appl Environ Microbiol 66 4742-4750. 

Preuss A, J Fimpel, G Diekert (1993) Anaerobic transformation of 2,4,6-trinitrotoluene (TNT). Arch Microbiol 159 345-353. 

McCormick NG, Feeherry FE, Levinson HS. 1976. Microbial transformation of 2,4,6-trinitrotoluene and other nitroaromatic compounds. AppI Environ Microbiol 31 949-958. 

An example of a xenobiotic compound reduced through the actions of such flavoproteins is TNT (trinitrotoluene). This compound is transformed by oxygen-insensitive nitroreductases (referred to as type I) that convert aromatic nitro groups sequentially to nitroso- and then hydroxylamino- moieties (Somerville et al., 1995 Vorbeck et al., 1998 Pak et al., 2000) ... 

Explosives and related compounds have become widely recognized as serious environmental contaminants. Among the nitrosubstituted aromatic compounds causing particular concern are 2,4,6-trinitrotoluene (TNT), 2,4,6-trinitrophenol (picric acid), and many nitro- and/or amino-substituted aromatics that result from the manufacture and transformation of explosives. The threat posed by the presence of these compounds in soil and water is the result of their toxicity and is compounded by their recalcitrance to biodegradation. 

Schmelling, D. and Gray, K., Photocatalytic transformation and mineralization of 2,4,6-trinitrotoluene in Ti02 slurries, Water Res., 29, 2651, 1995. 

Tertiary nitro compounds, of course, do not undergo tautomeric transformation, and they might be expected to be resistant to alkalis. Nevertheless aromatic nitro compounds, and polynitro-ones in particular, are very sensitive to alkalis, and undergo transformation when treated with them. For example, sym-trinitrobcnzcnc and also a- trinitrotoluene, when reacted with potassium hydroxide in methyl alcohol solution, form dark addition products (see also p. 202). Under certain conditions the nitro group can break off to form high molecular compounds. 

Further studies (Hantzsch and Picton [85]) showed, that inorganic acids, e.g. sulphuric, decompose these salts, with the evolution of nitrogen oxides. Products of a drastic transformation of trinitrotoluene are precipitated simultaneously, among them stilbene derivatives, products of oxidation of the methyl group. 

Copisarow [86] tried to express the changes which trinitrotoluene undergoes under the action of alcoholates or alkali metal hydroxides by the following scheme, in which he postulated the formation of nitro-nitroso derivatives of dibenzyl (III), and stilbene (IV), followed by the formation of an azoxy compound (V), which might be transformed into more complex azoxy compounds ... 

According to Oddo [97] and Lodati [98], under the influence of radiation trinitrotoluene partly loses nitrogen and is transformed into a compound of acidic character. 

At higher temperatures, however, the a- trinitrotoluene undergoes a more drastic transformation. This is the result of both the action of Na2S03 and of the high pH of the solutions one N02 group is substituted by an S03Na group. Thus the reaction proceeds in essentially the same way as in the case of the unsymmetrical isomers. 

Dinitrobenzisothiazole derivatives and salts were prepared in the course of utilization of explosive 2,4,6-trinitrotoluene [539-541], 3-Cloro-4,6-dinitrobenzisothiazole was prepared on using 2,4,6-trinitrotoluene, which can easily be transformed to 2,4,6-trinitrobenzonitrile (TNBN) by treatment with nitrosyl chloride [539], The reaction of TNBN in the presence of K2C03 led to both ortho and meta isomers, the products of substitution of N02 groups by a PhCH2S unit, with the ratio of isomers being dependent on the solvent polarity (Scheme 2.91). 

Aryl-4,6-dinitrobenzisothiazoles, 3-substituted 4,6-dinitrobenzisothiazoles, and their salts and oxides prepared by the utilization of 2,4,6,-trinitrotoluene or the transformation of 4,6-dinitrobenzamides have been investigated with help of mass spectrometry [784, 803-806],... 

Flash photolysis of aromatic nitro compounds was carried out by a number of authors Wetiermark 40). Suryanarayanan. Capellos. Porter and co-workers [41-43], Among various findings the latter authors came to the conclusion that 2,4,6-trinitrotoluene under Hash photolysis is transformed into aci-quinoid isomer (I) with an absorption maximum at 460 nm. 

An unusual reaction involving reductive elimination of nitrite has been observed in cultures of a Pseudomonas sp. that can use 2,4,6-trinitrotoluene as N-source (Duque et al. 1993). The substrate is transformed by successive reductive loss of nitro groups with the formation of toluene although this product cannot be metabolized by this strain, it can be degraded by a transconjugant containing the TOL plasmid from P. putida. 

Lewis, T.A., S. Goszczynski, R.L. Crawford, R.A. Korns, and W. Admassu, 1996. Products of anaerobic 2,4,6-trinitrotoluene TNT transformation by Clostridium bifermentans. Appl. Environ. Microbiol. 62 4669-6774. 

Oh S-Y et al., Effect of adsorption to elemental iron on the transformation of 2,4,6-trinitrotoluene and hexahydro-l,3,5-trinitro-l,3,5-triazine in solution, Environ. Toxicol. Chem., 21, 1384, 2002. 

Fiorella PD and Spain JC, Transformation of 2,4,6-trinitrotoluene by Pseudomonas pseudoalcaligenes JS52, Appl. Environ. Microbiol., 63, 2007, 1997. 

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