Photochemical generation of the 2,4,6-trinitrobenzyl anion

Burlinson, N. E.; Sitzman, M. E.; Kaplan, Leonard; Kayser, Eleonore G.

doi:10.1021/jo01335a016

Cited by 35 publications

(16 citation statements)

References 6 publications

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“…These compound can easily decarboxylate to trinitrobenzene (Burlinson et al 1979;Martinetz and Rippen 1990), an intermediate that is even more difficult to oxidize than TNT. In accordance with this, in the absence of H 2 O 2 no mineralization can be detected (data not shown).…”

Section: Tnt Mineralization Experiments With Uv-h 2 Omentioning

confidence: 99%

Combined biological–chemical procedure for the mineralization of TNT

Kröger

Fels

2006

Biodegradation

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Contamination of ground and surface water with 2,4,6-trinitrotoluene (TNT) and its biological and chemical transformation products are a persisting problem at former TNT production sites. We have investigated the photochemical degradation of TNT and its aminodinitro-(ADNT) and diaminonitrotoluene (DANT) metabolites using OH-radical generating systems like Fenton and hydrogen peroxide irradiated with UV, in order to compare the degradation and mineralization rate of ADNT- and DANT-isomers with TNT itself. As a result, we find that the aminoderivatives were mineralized much faster than TNT. Consequently, as ADNTs and DANTs are the known dead-end products of biological TNT degradations, we have combined our photochemical procedure with a preceding biological treatment of TNT by a mixed culture from sludge of a sewage plant. This consecutive degradation procedure, however, shows a reduced mineralization rate of the ADNTa and DANTs in the biologically derived supernatant as compared to the pure substances, suggesting that during the biological TNT treatment by sludge competing substrates are released into the solution, and that a more defined biological procedure would be necessary in order to achieve an effective, ecologically and economically acceptable mineralization of TNT from aqueous systems.

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Section: Tnt Mineralization Experiments With Uv-h 2 Omentioning

confidence: 99%

Combined biological–chemical procedure for the mineralization of TNT

Kröger

Fels

2006

Biodegradation

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“…Similar to experiment 4, fo ur major reaction intennediates were fonned and quantified, also shown in Figure 12. Two of the intermediates were identified, similar to experiment 4, as 4-amino,2,6-dinitrotoluene (ADNT) and 2,2',6,4'azoxytoluene (TNAzT), eluting at 20 and 27 minutes, respectively. Spectral matches were conclusive for ADNT and inconclusive for TNAzT, due to noise.…”

Section: �mentioning

confidence: 62%

“…Four reaction intermediates were formed and quantified. Two of the intermediates, eluting at approximately 20 and 27 minutes, were identified as 4-amino,2,6-dinitrotoluene (ADNT) and 2,2',6,4'azoxytoluene (TNAzT), respectively, based on UV-vis spectral analysis from the diode arr ay. Spectral analyses and library match confirmation are shown in Figures 10 and 11.…”

Section: Tnt Photocatalysis Degradation Product Identification Experimentioning

confidence: 99%

“…Additionally a condensation product 2,2',6,4'azoxytoluene (TNAzT) was identified in experiments where pH became alkaline during the course of the experiment. Other isomers of the three reduction products were suspected to have occurre d along with other azoxytoluenes, based on mass spectrometry results, however positive identification was not made.…”

Section: It Photocatalysis Of Tnt and Amino-dinitrotoluene (Adnt)mentioning

confidence: 99%

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Photocatalytic oxidation and reduction chemistry and a new process for treatment of pink water and related contaminated water

Blake¹,

Wolfrum²,

Boulter³

et al. 1996

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“…67 The literature provides data on TNT behaviour under photonitrosation conditions. 68 The photolysis of TNT water solutions with certain pH (a nitrite buffer) leads to the trinitrobenzyl anion leading to a number of products, among which 4,6-dinitrobenzo[d]isoxazole 63 was identified.…”

Section: Synthesis Of Benzannelated Five-membered Heterocycles With Tmentioning

confidence: 99%

Synthesis of benzannelated five-membered heteroaromatic compounds from 2,4,6-trinitrotoluene

Bastrakov¹,

Старосотников²,

Шевелев

2008

Arkivoc

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Methods for the synthesis of five-membered benzannelated heterocyclic compounds from the military explosive 2,4,6-trinitrotoluene (TNT) are summarised. The general approach concerns the transformation of the TNT methyl group followed by either intramolecular substitution of the ortho-nitro group or regioselective substitution of the ortho-nitro group by an appropriate nucleophile and subsequent cyclization.

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Photochemical generation of the 2,4,6-trinitrobenzyl anion

Cited by 35 publications

References 6 publications

Combined biological–chemical procedure for the mineralization of TNT

Combined biological–chemical procedure for the mineralization of TNT

Photocatalytic oxidation and reduction chemistry and a new process for treatment of pink water and related contaminated water

Synthesis of benzannelated five-membered heteroaromatic compounds from 2,4,6-trinitrotoluene

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