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Aza-linked energetic compound based on triazole and synthesis method of aza-linked energetic compound

A synthetic method and technology of triazoles, applied in the field of energetic compounds based on triazole nitrogen-heterobicyclic rings and their synthesis, can solve complex and time-consuming synthetic methods, poor modifiability, and low thermal stability of pentazole ion salts and other problems, to achieve the effect of safe and controllable synthesis process, high thermal decomposition temperature, and simple synthesis method

Inactive Publication Date: 2021-12-24
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The enthalpy of formation of imidazole is as low as 14.0kcal·mol -1 , although tetrazole and pentazole have high formation enthalpy, they are poorly modifiable. At present, pentazole only exists in the form of ionic salt, and the thermal stability of pentazole ionic salt is generally low.
There are two isomers of triazoles including 1,2,3-triazole and 1,2,4-triazole. The nitrogen structure in the 1,2,3-triazole molecule makes it higher than 1,2,4 -The formation enthalpy of triazole, but its N-H acidity is strong, in fact, it cannot be directly applied in the field of energetic materials
[0003] In 1974, S. Polanc first reported the synthesis of carbon-carbon bridged pyrazole-linked 1,2,4-triazole skeleton compounds, but the synthesis method was complicated and time-consuming

Method used

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  • Aza-linked energetic compound based on triazole and synthesis method of aza-linked energetic compound
  • Aza-linked energetic compound based on triazole and synthesis method of aza-linked energetic compound

Examples

Experimental program
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Embodiment 1

[0021] a) Synthesis of intermediate 3,5-dimethyl-4-nitro-1H-pyrazole:

[0022] Add 9.6g (0.10mol) of 3,5-dimethyl-1H-pyrazole in batches to the mixture of 20mL concentrated sulfuric acid and 5mL fuming nitric acid at low temperature, keep the temperature below 20°C, and add After completion, slowly raise the temperature to 60°C for 10 hours, cool to room temperature, pour the reaction solution into ice water to quench, a large amount of white solid precipitates, filter, wash with ice water three times, dry and weigh to obtain a white solid 3,5-dimethyl Base-4-nitro-1H-pyrazole 12.40g, yield 87.9%.

[0023] b) Synthesis of 4-nitro-1H-pyrazole-3,5-dicarboxylic acid:

[0024] At 70°C, weigh 14.10 g (0.10 mol) of 3,5-dimethyl-4-nitro-1H-pyrazole and dissolve it in 100 mL of water, then slowly add 120.0 (0.50 mol) of KMnO 4 Solid, control the feeding temperature to maintain at 90-95°C, continue to react for 12h, filter while hot after the reaction is completed, adjust the pH of t...

Embodiment 2

[0029] The difference between this example and Example 1 is that the ratio of the amount of substances in the mixed system of 4-nitro-1H-pyrazole-3,5-dicarboxylic acid and phosphorus pentoxide orthophosphoric acid is 1:10, 1:12, 1:14, 1:16, 1:18, and the ratio of the amount of phosphorus pentoxide to orthophosphoric acid is 1:4, 4-nitro-1H-pyrazole-3,5-di The ratio of the amount of formic acid and diaminoguanidine hydrochloride is 1:12. 4-nitro-1H-pyrazole-3,5-dicarboxylic acid is dropped into diaminoguanidine hydrochloride under acidic conditions, and the reaction temperature The temperature is 120°C, the reaction time is 12 hours, and the post-reaction treatment operation is the same as the above-mentioned experimental procedure. The results show that the ratio of the amount of substances in the mixed system of 4-nitro-1H-pyrazole-3,5-dicarboxylic acid and phosphorus pentoxide orthophosphoric acid is 1:12, 1:14, and 1:16. The reaction yields are respectively 77.8%, 82.4%, 8...

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Abstract

The invention discloses an aza-linked energetic compound based on triazole and a synthesis method of the aza-linked energetic compound. The energetic compound is 4-nitro-3, 5-bis (3, 4-diamino-1, 2, 4-triazole-5-yl) 1H-pyrazole. According to the aza-linked energetic compound based on triazole synthesized by the synthesis method disclosed by the invention, the actually measured impact sensitivity is greater than 40J, the friction sensitivity is greater than 360N, the calculated detonation velocity is 8197m / s, the detonation pressure is 24.2 Gpa, the thermal decomposition temperature is 318.6 DEG C, the performance is superior to that of TNT, the thermal decomposition temperature and sensitivity are superior to that of RDX, the aza-linked energetic compound is stable at room temperature, the synthesis method is simple, the synthesis process is safe and controllable, mass production can be realized, and the compound has high thermal decomposition temperature and has application prospects in the fields of heat-resistant explosives and the like.

Description

technical field [0001] The invention belongs to the technical field of organic energetic materials, and relates to a triazole-based nitrogen-heterobicyclic energetic compound and a synthesis method thereof. Background technique [0002] Energetic materials are the key material basis for the development of advanced weapons and equipment. They are the power energy for the launch of guns and projectiles and the propulsion of rockets and missiles. They are the powerful energy for the destruction of warheads. The power energy of capital adjustment and separation device. Modern high energy density materials (HEDMs) have been widely used in civilian and military applications. Nitrogen-rich azole energetic compounds are a focus of research in the field of energetic materials. Their basic structural units include nitrogen-rich heterocyclic rings such as imidazole, triazole, tetrazole, and pentazole. The enthalpy of formation increases with the increase of nitrogen content, but is st...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C06B25/34
CPCC07D403/14C06B25/34
Inventor 程广斌聂新羽杨红伟
Owner NANJING UNIV OF SCI & TECH