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

Abstract

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.

An Overview on Synthesis, Explosion, Catalysis, Modification, and Application of Dihydroxylammonium 5,5′-Bistetrazole-1,1′-diolate (TKX-50)

“…Research on the solubility of TKX-50 shows that TKX-50 is insoluble in a wide range of organic solvents, with the solubility not as high in partially soluble reagents. 64−67 Liu et al 68 first studied the properties of TKX-50 in DMF, dimethyl sulfoxide (DMSO), acetone, deionized water, acetic acid, ethyl acetate, acetonitrile, methanol, ethanol, petroleum ether, n-hexane, DMF/acetone (a mixture of DMF and acetone), and DMF/DMSO (a mixture of DMF and DMSO), investigating the stability of the compound in different solvents to identify in which solvents TKX-50 is soluble. As shown in Table 7, TKX-50 remained stable and insoluble in DMSO, deionized water, ethyl acetate, acetonitrile, methanol, ethanol, petroleum ether, and n-hexane but dissolved slowly in acetone and quickly in DMF, DMF/ acetone, and DMF/DMSO solvents.…”

Thermal Decomposition Characteristics and Thermal Safety of Dihydroxylammonium 5,5′-Bistetrazole-1,1′-diolate Based on Microcalorimetric Experiment and Decoupling Method

“…In recent years, it has been an important research direction in the field of explosives to seek a kind of energetic material with high power and insensitive nature. As a typical tetrazole derivative, nitrogen rich high energy density compound TKX-50 contains a large amount of N–N bonds, C–N bonds, and a large ring tension compared with traditional nitramine and nitro energetic materials. , A large number of literatures indicate that − the detonation velocity of TKX-50 (9698.0 m s –1 ) is higher than that of 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazaisowurtzitane (CL-20, 9455.0 m s –1 ) and 1,3,5-trinitro-1,3,5-triazinane (RDX, 8983.0 m s –1 ). Its detonation pressure (42.4 GPa) is also higher than that of 2,4,6-trinitrobenzene (TNT, 23.5 GPa), RDX (38.0 GPa) and 1,3,5,7-tetranitro-1,3,5,7-tetrazocane (β-HMX, 41.5 GPa).…”