Oxidation of Aminodinitrotoluenes with Ozone: Products and Pathways
An investigation of the products from the reaction of ozone with aminodinitrotoluenes (ADNTs) provides information about the oxidation pathway. Studies conducted at low conversions of 2- and 4-ADNT show 2:1 ozone/ADNT stoichiometries, prompt formation of glyoxylic and pyruvic acids, and NO2 - and NO...
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| Veröffentlicht in: | Environmental science & technology 2000-02, Vol.34 (3), p.497-504 |
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| creator | Spanggord, Ronald J Yao, C. David Mill, Theodore |
| description | An investigation of the products from the reaction of ozone with aminodinitrotoluenes (ADNTs) provides information about the oxidation pathway. Studies conducted at low conversions of 2- and 4-ADNT show 2:1 ozone/ADNT stoichiometries, prompt formation of glyoxylic and pyruvic acids, and NO2 - and NO3 - (NO x ) ions. Reaction schemes to account for these results involve a 1,3-dipolar cycloaddition of ozone to selected double bonds of the aromatic ring, leading to ring cleavage. 15N-Labeling experiments indicate that the amino function is not involved in the initial ozone oxidation and eventually is incorporated into pyruvamide (2-ADNT) and oxamic acid (4-ADNT) before being oxidized to nitrate. |
| doi_str_mv | 10.1021/es990190h |
| format | Article |
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Reaction schemes to account for these results involve a 1,3-dipolar cycloaddition of ozone to selected double bonds of the aromatic ring, leading to ring cleavage. 15N-Labeling experiments indicate that the amino function is not involved in the initial ozone oxidation and eventually is incorporated into pyruvamide (2-ADNT) and oxamic acid (4-ADNT) before being oxidized to nitrate.</description><identifier>ISSN: 0013-936X</identifier><identifier>EISSN: 1520-5851</identifier><identifier>DOI: 10.1021/es990190h</identifier><identifier>CODEN: ESTHAG</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Applied sciences ; BIODEGRADATION ; Biological and physicochemical phenomena ; Chemical reactions ; Decontamination. Miscellaneous ; Earth sciences ; Earth, ocean, space ; Engineering and environment geology. 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| subjects | Applied sciences BIODEGRADATION Biological and physicochemical phenomena Chemical reactions Decontamination. Miscellaneous Earth sciences Earth, ocean, space Engineering and environment geology. Geothermics ENVIRONMENTAL SCIENCES Exact sciences and technology MILITARY TECHNOLOGY, WEAPONRY, AND NATIONAL DEFENSE Natural water pollution NITRO COMPOUNDS OXIDATION OZONE Pollution Pollution, environment geology REMEDIAL ACTION Soil and sediments pollution SOIL CHEMISTRY TNT Water treatment and pollution |
| title | Oxidation of Aminodinitrotoluenes with Ozone: Products and Pathways |
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