Stability of Dihydroxylammonium 5,5’‐Bistetrazole‐1,1’‐Diolate (TKX‐50) in Solvents

• Published in: Propellants, explosives, pyrotechnics Vol. 44; no. 8; pp. 989 - 999
• Main Authors: Jia, Jianhui, Xu, Jinjiang, Cao, Xiong, Li, Shichun, Huang, Shiliang, Liu, Yu, Li, Jinshan
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 01.08.2019
• Subjects: Acetone; Acetonitrile; Deionization; Dimethyl sulfoxide; Ethanol; Ethyl acetate; Methanol; Reaction mechanisms; Single crystals; solvent; Solvents; stability; Thermal stability; TKX-50
• DOI: 10.1002/prep.201800379
• ISSN: 0721-3115

The stability of solid TKX‐50 has attracted considerable attention. However, the stability of TKX‐50 in solvents has not been investigated sufficiently yet. Herein, the stability of TKX‐50 in various solvents, including N, N‐dimethylformamide (DMF), dimethyl sulfoxide (DMSO), acetone, deionized water, ethyl acetate, acetonitrile, methanol, ethanol, petroleum ether, hexane, DMF/acetone (mixture of DMF and acetone) and DMF/DMSO (mixture of DMF and DMSO), has been studied. The results show that TKX‐50 remains stable in DMSO, deionized water, ethyl acetate, acetonitrile, methanol, ethanol, petroleum ether and hexane. It is remarkable that TKX‐50 can react with DMF in different ways under different conditions, such as a wide temperature range from 25 °C to 150 °C. The products in reactions between TKX‐50 and DMF were dimethylammonium 5, 5’‐bistetrazole‐1‐hydroxy‐1’‐oxygen (DMA‐BTO), dimethylamine 5, 5’‐bistetrazole‐1, 1’‐diolate (2DMA‐BTO) and diammonium 5,5’‐bistetrazole‐1,1’‐diolate (ABTOX), which were confirmed by single crystal diffraction, respectively. Moreover, the thermal stability of the products and the interconversion pathways between TKX‐50 and products were determined. Subsequently, the reaction mechanism of TKX‐50 in DMF solvent has been inferred.