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

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.

Automated summary

The novel energetic material DNDAABT was synthesized via mixed acid nitration of electrochemically generated TAABT, with various energetic salts also prepared and characterized. Despite predictions of low sensitivities, DNDAABT and its salts showed primary explosive sensitivities with relatively high thermal stabilities for primary N-nitramines.