Synthesis of 4,4'-Dimethyl-3,3',5,5'-Tetranitroazoxybenzene by Selective Reduction of Trinitrotolune

Selective reduction of trinitrotoluene in dioxane solution by H/sub 2/S/NH/sub 3/ yields a mixture containing 4-amino-2,6-dinitrotoluene, 4-hydroxylamino-2,6-dinitrotoluene and 4,4'-dimethyl- 3,3',5,5'-tetranitroazoxybenzene. Treatment of crude mixture with KI/HCl converts 4-hydroxylamino-2,6-dinitrotoluene into 4-amino-2,6-dinitrotoluene as well as increases the percentage of 4,4'-dimethyl-3,3,5,5'-tetranitroazoxybenzene. The resulting compound 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) was isolated and characterised by IR, NMR and elemental analysis. Its thermal decomposition as well as explosive properties have been studied. The data indicate that TATB is stable up to 294 °c and is also insensitive to impact and friction.