4,4'-Dinitrimino-5,5'-diamino-3,3'-azo-bis-1,2,4-triazole: A High-Performing Zwitterionic Energetic Material.

Abstract

Mixed acid nitration of electrochemically generated 4,4',5,5'-tetraamino-3,3'-azo-bis-1,2,4-triazole (TAABT) generated the novel energetic material 4,4'-dinitrimino-5,5'-diamino-3,3'-azo-bis-1,2,4-triazole (DNDAABT). Various energetic salts of DNDAABT were also prepared and characterized to confirm their structures and determine their explosive sensitivities and performances. The free acid of DNDAABT exists as a zwitterionic molecule that leads to a high-density material with predicted detonation parameters comparable to those of TKX-50 (bis(hydroxylammonium) 5,5'-bis(tetrazolate-1 N-oxide). Due to the insensitive nature of TAABT, it was predicted that DNDAABT would demonstrate remarkably low sensitivities for a primary N-nitramine. However, it was found that DNDAABT and all salts produced have primary explosive sensitivities, albeit with relatively high thermal stabilities for primary N-nitramines.