Derivatives of 5-nitro-1,2,3-2H-triazole – high performance energetic materials

Zhang, Yanqiang; Parrish, Damon A.; Shreeve, Jean’ne M.

doi:10.1039/c2ta00136e

Cited by 127 publications

(80 citation statements)

References 26 publications

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“…Five-membered heterocyclic rings (pyrozole, imidazole, triazole, tetrazole) are one kind of important structural units of nitrogen-rich energetic materials [3][4][5][6][7]. Among them, the tetrazole ring possesses the highest nitrogen content, which in turn leads to the highest positive heat of formation and best detonation performance.…”

Section: Introductionmentioning

confidence: 99%

Thermal characterization of the promising energetic material TKX-50

Huang

Shi

Yang

2015

J Therm Anal Calorim

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The thermal behavior of dihydroxylammonium 5,5 0 -bistetrazole-1,1 0 -diolate (TKX-50) was measured by differential scanning calorimetry (DSC), thermal gravimetric analysis-Fourier transform infrared spectroscopy (TG-FTIR) and thermal gravimetric analysisdifferential scanning calorimetry-mass spectrometry (TG-DSC-MS). The critical temperature of thermal explosion (T b ) and the initial decomposition temperature (T p0 ) were determined to be 523.39 and 513.80 K, respectively. The apparent activation energy (E) and preexponential factor (A) of the exothermic decomposition reaction, and activation entropy (DS = ), activation enthalpy (DH = ), activation Gibbs free energy (DG = ) at T P0 of the reaction and the critical temperature of thermal explosion (T b ) were calculated: E K = 237.59 kJ mol -1 , E O = 234.11 kJ mol -1 , DS = = 209.83 J K -1 mol -1 , DH = = 233.32 kJ mol -1 , DG = = 126.53 kJ mol -1 . TG-DSC-FTIR/MS analysis of thermal decomposition products of TKX-50 reveals that the main decomposition products are N 2 , H 2 O, NH 3 , NH 2 , N 2 O and NO.

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Section: Introductionmentioning

confidence: 99%

Thermal characterization of the promising energetic material TKX-50

Huang

Shi

Yang

2015

J Therm Anal Calorim

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“…The corresponding salts of 3 and 5 have the similar densities, and are higher than those of salts of 4, which is in agreement with their molecular precursors. 12 Hydroxylammonium salts possess the highest density as 1.86 (3b) and 1.85 g/cm 3 (5b) in their corresponding series.…”

Section: Properties Of Energetic Saltsmentioning

confidence: 99%

Nitrogen-rich energetic 4-R-5-nitro-1,2,3-triazolate salts (R = –CH₃, –NH₂, –N₃, –NO₂ and –NHNO₂) as high performance energetic materials

Liu

Zhang

et al. 2015

J. Mater. Chem. A

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Table of Contents:4-R-5-nitro-1,2,3-triazolate salts (R = -CH3, -NH2, -NO2, -N3, and -NHNO2) were systematically synthesized with nitrogen-rich cations. Among the energetic salts, hydroxylaminium 4,5-dinitro-1,2,3-triazolate and dihydroxylaminium 4-nitramino-5-nitro-1,2,3-triazolate exhibit excellent energetic performances (38.0 GPa, 9302 m/s, 256.1 s; 38.8 GPa, 9464 m/s, 251.1 s).A series of 4-R-5-nitro-1,2,3-triazolate salts (R = -CH 3 , -NH 2 , -NO 2 , -N 3 , and -NHNO 2 )were synthesized with cations of ammonium, hydroxylammonium, hydrazinium, guanidinium, aminoguanidinium, diaminoguanidinium, and triaminoguanidinium, respectively. The resulting energetic salts were characterized with 1 H and 13 C NMR, IR spectroscopy, elemental analysis, and some with single crystal X-Ray diffraction. Their key properties were measured or calculated such as melting and decomposition temperatures, density, detonation pressure and velocity, and impact and friction sensitivities. The results show that guanidinium salts possess the highest thermal stability in each group with decomposition temperatures as 265, 251, 221, 142, and 216 o C, respectively. Hydroxylammonium 4,5-dinitro-1,2,3-triazolate and dihydroxylammonium 4-nitramino-5-nitro-1,2,3-triazolate exhibit much higher detonation performances (38.0 GPa, 9302 m/s; 38.8 GPa, 9464 m/s) than cyclotrimethylenetrinitramine (34.9 GPa, 8748 m/s). Moreover, the high specific impulses (256.1 and 251.1 s) from the formula calculations based on the two salts further support their application prospects.

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“…Energetic triazole compounds [10][11][12][13][14] are promising candidates of insensitive high explosives because of their positive heats of formation, good thermal stability, and low sensitivity. However, most of them have moderate explosive properties, which would limit their further applications.…”

Section: Introductionmentioning

confidence: 99%

Quantum chemical studies on three novel 1,2,4-triazole N-oxides as potential insensitive high explosives

Zhu

Xiao

2014

J Mol Model

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Three novel explosives were designed by introducing N-oxides into 1,2,4-triazole: 1-amino-3,5-dinitro-1,2,4-triazole-2 N-oxide (ADT2NO), 1-amino-2,5-dinitro-1,2,4-triazole-3 N-oxide (ADT3NO), and 1-amino-3,5-dinitro-1,2,4-triazole-4 N-oxide (ADT4NO). Their detonation performance and sensitivity were estimated by using density functional theory and compared with some famous explosives like 1,3,5,7-tetranitro-1,3,5,7-tetrazocane (HMX) and 1-methyl-2,4,6-trinitrobenzene (TNT). All three designed molecules are more powerful than HMX and less sensitive than TNT, indicating that ADT2NO, ADT3NO, and ADT4NO have high detonation performance as HMX and low sensitivity as TNT, making them being very valuable and may be considered as the potential candidates of insensitive high explosives. Properly introducing N-oxides into the energetic triazole derivatives can generate some superior energetic compounds with both high explosive performance and reduced sensitivity.

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Derivatives of 5-nitro-1,2,3-2H-triazole – high performance energetic materials

Cited by 127 publications

References 26 publications

Thermal characterization of the promising energetic material TKX-50

Thermal characterization of the promising energetic material TKX-50

Nitrogen-rich energetic 4-R-5-nitro-1,2,3-triazolate salts (R = –CH₃, –NH₂, –N₃, –NO₂ and –NHNO₂) as high performance energetic materials

Quantum chemical studies on three novel 1,2,4-triazole N-oxides as potential insensitive high explosives

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Derivatives of 5-nitro-1,2,3-2H-triazole – high performance energetic materials

Cited by 127 publications

References 26 publications

Thermal characterization of the promising energetic material TKX-50

Thermal characterization of the promising energetic material TKX-50

Nitrogen-rich energetic 4-R-5-nitro-1,2,3-triazolate salts (R = –CH3, –NH2, –N3, –NO2 and –NHNO2) as high performance energetic materials

Quantum chemical studies on three novel 1,2,4-triazole N-oxides as potential insensitive high explosives

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Nitrogen-rich energetic 4-R-5-nitro-1,2,3-triazolate salts (R = –CH₃, –NH₂, –N₃, –NO₂ and –NHNO₂) as high performance energetic materials