Trinitromethyl-Substituted 5-Nitro- or 3-Azo-1,2,4-triazoles: Synthesis, Characterization, and Energetic Properties

Abstract

Various new polynitro-1,2,4-triazoles containing a trinitromethyl group were synthesized by straightforward routes. These high nitrogen and oxygen-rich compounds were fully characterized using IR and multinuclear NMR spectroscopy, elemental analysis, natural bonding orbital (NBO) analysis, and differential scanning calorimetry (DSC) and, in the case of 12, with single crystal X-ray structuring. The heats of formation for all compounds were calculated with Gaussian 03 (revision D.01) and then combined with experimentally determined densities to determine detonation pressures (P) and velocities (D) of the energetic materials (Cheetah 5.0). They exhibit high density, good thermal stability, acceptable oxygen balance, positive heat of formation, and excellent detonation properties, which, in some cases, are superior to those of TNT, RDX, and HMX.

Computational design of tetrazolone‐based high‐energy density energetic materials: Property prediction and decomposition mechanism

“…[7] Desirable characteristics for new HEDMs include high density, positive heat of formation (HOF), high detonation performance, good thermal stability, low sensitivity, and eco-friendly. [8] However, low sensitivity and high performance are contradictory making the development of new HEDMs an interesting but challenging problem. [9] Nitrogen-rich heterocycles represent a unique class of energetic frameworks featuring a large number of energetic NN bonds, planar structures with electronic delocalization, and releasing environmentally friendly N 2 when decomposition or degradation.…”

Thermal hazard assessment of 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazaisowutrzitane (TEX) by accelerating rate calorimeter (ARC)

“…Currently, explosives with superior detonation characteristics and/or decreased sensitivity to exterior stimuli [1][2][3][4][5][6][7][8][9][10][11][12] are of great concern. 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazaisowutrzitane, also called as TEX (Fig.…”

Synthesis and Property of 1,4-Diamino-3,6-dinitropyrazolo[4,3-c]pyrazole and Its Derivatives

“…The large amount of nitrogen gas generated as an end product of the nitrogen-rich compounds listed above is highly favored both for the enhancement of energy output and the avoiding of environmental pollution [3,7]. In order to develop environmentally friendly explosives, a number of heterocyclic-based energetic compounds have been developed and extensively used as high-energy explosives and ingredients of propellants [1,2,4,10]. 1,4-Diamino-3,6-dinitropyrazolo [4,3-c]pyrazole (DADNP) is a nitrogen-rich energetic compound.…”