Removal of 2,4,6‐trinitrotoluene (TNT) and 1,3,5‐trinitro‐1,3,5‐triazacyclohexane (RDX) from aqueous solutions with surfactants

Abstract

2,4,6‐Trinitrotoluene (TNT) was found to react in aqueous solution with surfactants containing amino and quaternary ammonium groups at pH 10–11 at ambient temperature. The surfactants investigated included N‐tallow 1,3‐diaminopropane, trimethyl N‐tallow ammonium chloride and N,N,N′,N′,N′‐pentamethyl N‐tallow 1,3‐propane diammonium dichloride. The reaction products were insoluble in water and readily separated through filtration. The dried solids were not explosive and the solids burned without explosion. The results showed that TNT can be reduced to less than 0.1 ppm from the initial concentration of 110 ppm in 2–3 hours. The wastewater of Composition B contains TNT and 1,3,5‐trinitro‐1,3,5‐triazacyclohexane (RDX). Treatment of the wastewater with the ammonium cationic surfactants showed that TNT was removed quantitatively by precipitation and RDX was simultaneously hydrolyzed. The mechanism of this treatment is discussed.

Alkaline hydrolysis of trinitrotoluene, TNT

“…[8][9][10][11][12][13] There appear to be few studies on the alkaline hydrolysis of TNT in water, despite its recognized significance as a promising route for the removal of TNT from contaminated environments. 3,[14][15][16] From the results of the studies of TNT hydrolysis that have been carried out in non-aqueous and aqueous media the reaction pathway appears strongly influenced by the medium in which the reaction takes place. 3,[14][15][16] An excellent example of this is provided by the work of Bernasconi 10 in which he reports that the initial product of TNT hydrolysis in ethanol, methanol and a 50 : 50 dioxane-water solution is the 2,4,6-trinitrobenzyl anion (TNT À ) with an absorption maximum around 510 nm, whereas, in a 10 : 90 dioxane-water mixture the initial hydrolysis product has a completely different absorption spectrum, l max ¼ 450 nm.…”

“…3,[14][15][16] From the results of the studies of TNT hydrolysis that have been carried out in non-aqueous and aqueous media the reaction pathway appears strongly influenced by the medium in which the reaction takes place. 3,[14][15][16] An excellent example of this is provided by the work of Bernasconi 10 in which he reports that the initial product of TNT hydrolysis in ethanol, methanol and a 50 : 50 dioxane-water solution is the 2,4,6-trinitrobenzyl anion (TNT À ) with an absorption maximum around 510 nm, whereas, in a 10 : 90 dioxane-water mixture the initial hydrolysis product has a completely different absorption spectrum, l max ¼ 450 nm. Bernasconi attributes the latter to an unidentified radical species, 10 although, from the work of others, 14,17,18 it appears more likely to be a Meisenheimer complex (MC)…”

Alkaline Hydrolysis of TNT in Micellar System

“…Results obtained with the aqueous surfactant-TNT systems indicated initial formation of a TNT addition complex (Janovsky reaction) with a subsequent precipitation from solution of a surfactant-TNT complex salt. [11] Likewise cationic surfactants are found to cause hydrolysis for explosives. For example, hexadecyltrimethylammonium bromide has been used to catalyze the hydrolysis of RDX and TNT in water.…”

Molten-State Nitration of Substituted Imidazoles: New Synthetic Approaches to the Novel Melt-Cast Energetic Material, 1-Methyl-2,4,5-trinitroimidazole

“…1 Furthermore, the 2,4,6-trinitrotoluene manufacturing process produces environmentally undesirable 'pink water'. 2 Due to these issues, defense agencies continue to search for high energy, high density materials that would either replace 2,4,6-trinitrotoluene or find application in melt-cast formulations. It is with this background, and as part of our ongoing program aimed at fulfilling the needs of the U.S. Department of Defense, that we have been working on the synthesis and development of high nitrogen-containing materials for energetic applications for the past several years.…”

“…5 Later, other groups, essentially following the original procedure, revisited the preparation of 1 and established unambiguously its structure via single crystal X-ray crystallography. 6 All the approaches involved synthesis and transformation of a key intermediate potassium salt of 2,4,5-trinitroimidazole (2) into 1 by employing diazomethane as a methylating agent in the final step. Literature reports suggest that 1 has both good thermal stability and impact insensitivity, while possessing a low melting point.…”