Degradation Mechanism of 2,4-Dinitrotoluene in Aqueous Solution (Photooxidation Studies).
Abstract
The synergistic effect of hydrogen peroxide (H2O2) and UV radiation from a medium-pressure mercury vapor lamp on the decomposition of 2,4-dinitrotoluene (DNT) in aqueous solution was studied. The most effective conditions for degradation of aqueous DNT solutions were found to consist of a molar ratio of H2O2/DNT in the range of 26 to 52 in the presence of unfiltered UV radiation. Under these conditions, the intermediates found after short reaction times (2 to 14 minutes), were 2,4-dinitrobenzyl alcohol, 2,4-dinitrobenzaldehyde, 2,4-dinitrobenzoic acid (dominant), 1,3-dinitrobenzene, 3-nitrophenol, 2,4-dinitrophenol, maletic acid derivatives, oxalic acid, glyoxal, and glyoxylic acid. This finding suggests that the degradation pathways of DNT in aqueous solution in the presence of H2O2 and UV light are: (1) sidechain oxidation, which converts DNT to 2,4-dinitrobenzoic acid, followed by decarboxylation to form, 1,3-dinitrobenzene; (2) hydroxylation, which converts 1,3-dinitrobenzene to mono-, di, and trihydroxynitrobenzenes; (3) benzene ring cleavage of these hydroxynitrobenzenes, which produces 2- and 4-carbon caroxylic acids and aldehydes; and (4) further photooxidation, which eventually converts the 2- and 4-carbon carboxylic acids and aldehydes to CO2, H2O, and HNO3. Originator supplied keywords include: Dinitrololuene, Nitroaromatics, Photolysis, Oxidation, Detoxification, Photoxidation.
Document Details
- Document Type
- Technical Report
- Publication Date
- Nov 01, 1984
- Accession Number
- ADA150956
Entities
People
- P. C. Ho
Organizations
- Oak Ridge National Laboratory