A Study of the Detonation Properties, Propellant Impulses, Impact Sensitivities and Synthesis of Nitrated ANTA and NTO Derivatives

Nitrated derivatives of 5-amino-3-nitro-1,2,4-triazole (ANTA) and 3-nitro-1,2,4-triazol-5-one (NTO) were theoretically characterized with respect to their performance as high explosives and rocket propellants. The detonation velocity and the detonation pressure of the derivatives, calculated with EXPLO5 software, were at the same level or slightly above the performance of 1,3,5-trinitroperhydro-1,3,5-triazine (RDX). The results showed that compositions of 1,3,4-trinitro-1,2,4-triazol-5-one and glycidyl azide polymer (GAP) could give specific impulses just above 2600 m/s in rocket propellants. The sensitivities of the derivatives were evaluated using their heats of detonation, CHNO-ratios, free space in the crystal lattice and N−NO2 bond dissociation energy. The stability and sensitivity of several of the derivatives could be poor due to the low N−NO2 bond dissociation energies. The N−NO2 bond dissociation energies in the derivatives were calculated to be between 41 and 296 kJ/mol when the M06-2X/6-311+G(2d,p) functional was used. Synthetic routes for the most stable derivatives were proposed. In addition, preliminary studies of the chloride-assisted nitrolysis of NTO were performed. The infrared spectrum of the NTO derivative indicated that N−NO2 bonds were formed.