Synthesis, crystal structure and thermal properties of an unsymmetrical 1,2,4,5-tetrazine energetic derivative

Chen, Xiang; Zhang, Cong; Bai, Yang; Guo, Zhaoqi; Yao, Yan-Ru; Song, Jirong; Ma, Hua

doi:10.1107/s2053229618006617

Cited by 9 publications

(3 citation statements)

References 32 publications

(29 reference statements)

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“…(3‐(3,5‐dimethylpyrazole)‐6‐hydrazino‐1,2,4,5‐tetrazine (DPHT) and 3,6‐dihydrazino‐1,2,4,5‐tetrazine (DHT) were synthesized according to the literature method [21, 22].…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Thermal Behavior and Energy Performance of Nitroguanidyl‐Functionalized Energetic Materials

Bai

Yao²,

Xiao³

et al. 2021

Propellants Explo Pyrotec

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Six nitroguanidyl‐functionalized nitrogen‐rich compounds were synthesized and characterized by EA, FT‐IR, and NMR. In addition, the crystal structures of ANPTz, CABNG, and FANG were further determined by X‐ray single‐crystal diffractometer. The thermal decomposition behaviours were studied by the DSC‐TG‐FTIR‐MS coupling technique and the results showed that all the compounds had good thermal stability, among which ANPTz had the best thermal stability (Td=211.03 °C). Also, HCN, CO2, H2O, and NO2 were released during thermal decomposition process. The self‐accelerating decomposition temperature (TSADT) and thermal explosion critical temperature (Tb) were calculated to evaluate thermal safety, and the relative order was as follows: FANG (TSADT=198.68 °C, Tb=209.97 °C)> ANPTz (TSADT=194.12 °C, Tb=208.63 °C)> BANTz (TSADT=182.52 °C, Tb=207.54 °C)> AANG (TSADT=180.04 °C, Tb=188.35 °C)> CABNG (TSADT=176.80 °C, Tb=187.32 °C)> MABNG (TSADT=173.61 °C, Tb=184.29 °C). The results indicated that FANG had the acceptable sensitivity (IS=7.84 J), good detonation performance (D=8551 m⋅s−1, P=32.33 GPa), and the significant catalytic effect (the decomposition temperature of RDX decreased by 8.31 °C).

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“…(3‐(3,5‐dimethylpyrazole)‐6‐hydrazino‐1,2,4,5‐tetrazine (DPHT) and 3,6‐dihydrazino‐1,2,4,5‐tetrazine (DHT) were synthesized according to the literature method [21, 22].…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Thermal Behavior and Energy Performance of Nitroguanidyl‐Functionalized Energetic Materials

Bai

Yao²,

Xiao³

et al. 2021

Propellants Explo Pyrotec

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“…[ 8–12 ] Other than them, tetazine derivatives are also the excellent EMs that have an impressive high‐nitrogen content (68.3%) and favorable thermal stability. [ 13–16 ] Considering that the main goal of designing superb EMs is balancing the contradiction between energetic performances and stability, tetrazine skeleton can provide an achievable path due to its relatively high reactivity, low sensitivity, and high thermal stability. [ 17–20 ] Recently, many of the tetrazine compounds, which possess application prospects, have been fabricated.…”

Section: Introductionmentioning

confidence: 99%

Alkaline earth metal salts of 3,6‐bis‐nitroguanyl‐1,2,4,5‐tetrazine: Promising perchlorate‐free environmentally friendly pyrotechnic components

Chen

Wang

Chen

et al. 2021

Applied Organom Chemis

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Alkaline earth metal salts (magnesium, 2; calcium, 3; strontium, 4; barium, 5) with nitrogen‐rich 3,6‐bis‐nitroguanyl‐1,2,4,5‐tetrazine anion (DNGTz2−) were prepared and characterized by elemental analysis, infrared, and multinuclear NMR spectroscopy. All new compounds were further characterized by single‐crystal X‐ray diffraction measurements. Full analysis of the crystal structures and graph sets of hydrogen bonds were conducted out. The results revealed a large‐scale conjugation effect of DNGTz anion in all four salts and a middle to high densities ranging from 1.751 (2) to 2.296 (5) g·cm−3. Both 3 and 4 were one‐dimensional coordination polymers and show zig‐zag chain, whereas 5 crystalized in a two‐dimensional sql topological network. Differential scanning calorimetry (DSC) and thermogravimetric (TG) analysis revealed the good thermal stability of all the new salts. Meanwhile, their specific heat capacities are in inverse proportion to atomic number of the metal cations. The constant‐volume combustion energy of 2–5 was determined experimentally, and the standard molar enthalpy of formation was backcalculated to evaluate their energetic performance. Impact sensitivity test disclosed that all the four metal salts were insensitive towards impact with a value higher than 40 J. Flame burning test supports their potential application as the environmentally friendly perchlorate‐free pyrotechnic components.

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“…Energetic materials (EMs), including explosives, propellants, and pyrotechnics, are a significant class of compounds containing large amounts of stored chemical energy, which can liberate heat and exert high pressure under some stimuli, like impact, shock, or thermal effect [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 ]. With the development of science and technology, more and more attention has been paid to the high energy density materials (HEDMs) used for energy and as explosives or propellants [ 9 ].…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Synthesis and Properties of Nitrated-Pyrazoles Based Energetic Compounds

et al. 2020

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Nitrated-pyrazole-based energetic compounds have attracted wide publicity in the field of energetic materials (EMs) due to their high heat of formation, high density, tailored thermal stability, and detonation performance. Many nitrated-pyrazole-based energetic compounds have been developed to meet the increasing demands of high power, low sensitivity, and eco-friendly environment, and they have good applications in explosives, propellants, and pyrotechnics. Continuous and growing efforts have been committed to promote the rapid development of nitrated-pyrazole-based EMs in the last decade, especially through large amounts of Chinese research. Some of the ultimate aims of nitrated-pyrazole-based materials are to develop potential candidates of castable explosives, explore novel insensitive high energy materials, search for low cost synthesis strategies, high efficiency, and green environmental protection, and further widen the applications of EMs. This review article aims to present the recent processes in the synthesis and physical and explosive performances of the nitrated-pyrazole-based Ems, including monopyrazoles with nitro, bispyrazoles with nitro, nitropyrazolo[4,3-c]pyrazoles, and their derivatives, and to comb the development trend of these compounds. This review intends to prompt fresh concepts for designing prominent high-performance nitropyrazole-based EMs.

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Synthesis, crystal structure and thermal properties of an unsymmetrical 1,2,4,5-tetrazine energetic derivative

Cited by 9 publications

References 32 publications

Synthesis, Thermal Behavior and Energy Performance of Nitroguanidyl‐Functionalized Energetic Materials

Synthesis, Thermal Behavior and Energy Performance of Nitroguanidyl‐Functionalized Energetic Materials

Alkaline earth metal salts of 3,6‐bis‐nitroguanyl‐1,2,4,5‐tetrazine: Promising perchlorate‐free environmentally friendly pyrotechnic components

Recent Advances in Synthesis and Properties of Nitrated-Pyrazoles Based Energetic Compounds

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