Oxidation of Aminodinitrotoluenes with Ozone:  Products and Pathways

• Published in: Environmental science & technology Vol. 34; no. 3; pp. 497 - 504
• Main Authors: Spanggord, Ronald J, Yao, C. David, Mill, Theodore
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01.02.2000
• 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; Decontamination; Reaction product; Reaction mechanism; Ozone; Oxidation; Water pollution; Toluene derivatives; Soil pollution; Organic compounds
• ISSN: 0013-936X; 1520-5851
• DOI: 10.1021/es990190h

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.