Synthesis, characterization and thermolysis studies on new derivatives of 2,4,5-trinitroimidazoles: Potential insensitive high energy materials

Abstract

This paper reports the synthesis of three new derivatives of 2,4,5-trinitroimidazole namely, 1-methyl-2,4,5-trinitroimidazole ( III), 1-carboethoxy-2,4,5-trinitroimidazole ( V) and 1-picryl-2,4,5-trinitroimidazole ( VII). The title compounds ( III) and ( V) were synthesized by the nitration of 1-methyl-/1-carboethoxy-(2,4,5-triiodoimidazole) ( II and IV) with fuming nitric acid at 0 °C and ( VII) was synthesized by condensation of 2,4,5-triiodoimidazole ( I) with picryl chloride to obtain 1-picryl-2,4,5-triiodoimidazole ( VI) followed by its nitration with fuming nitric acid at 0 °C. The synthesized compounds have been characterized by elemental analysis, spectral and thermal techniques. The thermolysis studies using TG-DTA revealed exothermic decomposition of the nitroimidazoles ( III, V and VII) with T max in the temperature range of 196–225 °C. The energy of activation obtained for these compounds was in the range 150–170 kJ/mol. The sensitivity data obtained for the newly synthesized compounds ( III, V and VII) indicated their safe nature towards external stimuli ( h 50% > 100 cm; friction > 36 kg) and could be potential candidates for low vulnerable applications in the futuristic systems. The theoretically predicted performance parameters suggest that 1-methyl-2,4,5-trinitroimidazole ( III), exhibits higher velocity of detonation (VOD: 8.8 km/s) compared to compounds V and VII (VOD: 7.6 and 8.41 km/s, respectively).