Synthesis, characterization and thermolysis studies on new derivatives of 2,4,5-trinitroimidazoles: potential insensitive high energy materials.
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 degrees 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 degrees 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 degrees 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).
Jadhav
H S
HS
Department of Chemistry, University of Pune, Pune 411 007, India.
Talawar
M B
MB
Sivabalan
R
R
Dhavale
D D
DD
Asthana
S N
SN
Krishnamurthy
V N
VN
D002152:Calorimetry, Differential Scanning; D004735:Energy Transfer; D007093:Imidazoles / Q000138:chemical synthesis*; D009574:Nitro Compounds / Q000138:chemical synthesis*; D009593:Nitroimidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared
D007093:Imidazoles; D009574:Nitro Compounds; D009593:Nitroimidazoles