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 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.