Tricyclic nitrogen-rich explosives with a planar backbone: bis(1,2,4-triazolyl)-1,2,3-triazoles as potential stable green gas generants†
Abstract
Two tricyclic nitrogen-rich compounds, 4,5-bis(5-nitro-1H-1,2,4-triazol-3-yl)-2H-1,2,3-triazole (4) and 4,5-bis(5-nitramino-1,2,4-triazole-3-yl)-2H-1,2,3-triazole (5), were obtained based on the combination of two different triazole heterocycles. The metal-free energetic salts (6–16) were synthesized with positive heat of formation and good thermal stability. Among these salts, dicarbohydrazide salt 9 and triaminoguanidine salt 16 exhibit the relevant high detonation velocities (9: D = 8720 m s−1 and 16: D = 8748 m s−1) which are comparable to that of RDX (8795 m s−1). Besides, the impact and friction sensitivities of compounds 4–16 (IS: 28–40 J, FS: 324–360 N) indicate that they have low sensitivities to mechanical stimulations. The planar structure of crystal 4·3H2O was confirmed by single crystal X-ray analysis. In order to evaluate their gas production capacities, constant-volume combustion experiments were conducted on 9 and 16 with high gas production volume (≥840 dm3 kg−1). The maximum gas-production pressures of 9 (Pmax = 16.20 MPa) and 16 (Pmax = 11.21 MPa) are much higher than that of commonly used gas generant guanidine nitrate (GN: Pmax = 4.20 MPa).