Molecular Weight Distribution of the Final Products of TNT-Hydroxide Reaction

Abstract

Explosives contamination of groundwater, surface water and soil has occurred at military sites throughout the world. Base-catalyzed transformation of 2,4,6-Trinitrotoluene (TNT) could potentially be used as part of a rapid, low-cost, and minimally resource-intensive technology for detoxifying explosives in soil and water. In order to identify the chemical properties of the final products of the TNT- hydroxide reaction and indicate possible reaction mechanisms, radiolabeled (14C) TNT was challenged with hydroxide and the reaction was allowed to proceed to completion. 14C labeled final products were separated by solvent/solvent extraction and acid/base chemistry. 14C TNT-hydroxide reaction final products were analyzed by scintillation counting to identify the final products of the TNT-hydroxide reaction, their distribution in the final reaction mixture, and their molecular weight fractions. Most (98 percent) of the final products of the TNT-hydroxide reaction are polar compounds that vary in molecular weight from 3,000-6,000 Daltons (Da) to <100 Da. Organic acids with pKa of>8 account for 8.4 percent of polar transformation products of the TNT-hydroxide reaction. The majority (66.5 percent) of the non-polar products were in the small (<100) molecular weight range. The results from this study could give insight into the chemistry of the TNT-hydroxide reaction.