4-ADNT

     4-ADNT, an acronym for 4-amino-2,6-dinitrotoluene, is a high explosive derivative of TNT. Other names include aminodinitrotoluene; para-toluidine; 2,6-dinitro-4-aminotoluene; 2,6-dinitro-4-methylaniline; and 2,6-dinitro-p-toluidine. Aminodinitrotoluene is often found in soil or groundwater contaminated with TNT as it is a biodegradation product of TNT. Aminodinitrotoluene is typically used as a precursor for TATB or TNPG, although it has found a use in some propellant compositions.

CHEMICALS	APPARATUS
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     Prepare a solution of 25 g of TNT and 1 mL of concentrated ammonium hydroxide in 50 mL of p-dioxane. Using a bubbler pass a steady stream of hydrogen sulfide gas into the solution for 30 minutes while keeping the temperature below 40 C. Filter the solution to remove any sulfur that has precipitated and add the filtrate to 200 mL of ice water. The bright yellow solid that precipitates is filtered to collect it and washed with 100 mL of water. This solid contains a rather significant amount of a byproduct, 2,6-dinitro-4-hydroxylaminotoluene. The aminodinitrotoluene may be purified by recrystallizing from methyl alcohol. Yield is around 60-70%. Optionally the 2,6-dinitro-4-hydroxylaminotoluene byproduct can be converted into aminodinitrotoluene instead of recrystallizing. Mix the precipitate with enough 3 N HCl to create a suspension and add 7 g of potassium iodide. Heat the solution under reflux until no more vapors of iodine are given off. Allow the solution to cool to room temperature and filter to collect the crystals. Yield of aminodinitrotoluene is around 21 g or 96%.

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