Fluorine-containing [1,2,4]triazole[4, 3-b][1,2,4,5]tetrazine ammonium nitrate and preparation method thereof

A 3-b, nitroamine-based technology, applied in attack equipment, nitrated acyclic/alicyclic/heterocyclic amine explosive compositions, organic chemistry, etc., can solve problems such as unsatisfactory detonation performance, and achieve reaction conversion The effect of high rate and yield, mild reaction conditions and strong operability

Active Publication Date: 2021-09-17
SICHUAN UNIVERSITY OF SCIENCE AND ENGINEERING
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Problems solved by technology

[0010]In 2007, Shreeve's research group synthesized pentafluorosulfanyl azole energetic derivatives by click chemistry method. The res

Method used

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  • Fluorine-containing [1,2,4]triazole[4, 3-b][1,2,4,5]tetrazine ammonium nitrate and preparation method thereof
  • Fluorine-containing [1,2,4]triazole[4, 3-b][1,2,4,5]tetrazine ammonium nitrate and preparation method thereof
  • Fluorine-containing [1,2,4]triazole[4, 3-b][1,2,4,5]tetrazine ammonium nitrate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1 Preparation of compound 3-trifluoromethyl-6-amino-[1,2,4]triazol[4,3-b][1,2,4,5]tetrazine (2):

[0046]

[0047] Add compound 1 (2.84 g, 10 mmol) and about 50 mL of solvent NMP into a 250 mL dry three-necked flask equipped with a magnetic stirrer, and bubble ammonia gas for half an hour under stirring. Subsequently, the reaction flask was placed in an oil bath at 50° C. for 2 h of thorough stirring. After confirming the end point of the reaction by thin-layer chromatography, cool the reaction bottle to room temperature, add an appropriate amount of aqueous solution to quench the reaction, then add ethyl acetate to extract the aqueous phase, combine the organic phase, wash the organic phase with saturated NaCl aqueous solution, and dry over anhydrous sodium sulfate , filtered, and the solvent was recovered by rotary evaporation. After the residue was columned, 1.7 g of yellow solid (2) was obtained with a yield of 83%.

[0048] Td 219°C; 1 H NMR (600MHz, D...

Embodiment 2

[0049] Example 2 Preparation of compound 3-trifluoromethyl-6-nitroamino-[1,2,4]triazol[4,3-b][1,2,4,5]tetrazine (3):

[0050]

[0051] Add 30mL of concentrated sulfuric acid to a reaction tube protected by dry oxygen-free nitrogen, and the reaction bottle is cooled to 0°C in a cryogenic tank, and 15mL of pure nitric acid is added dropwise thereto, followed by the compound 2 (2g, 10mmol ) are slowly added. After reacting for 3 h, the reaction solution was poured into ice water and filtered to obtain the solid product 3 with a yield of 77%.

[0052] Td 113℃; 1H NMR (600MHz, DMSO-d6) δ6.47(s,1H),2.60(s,3H),2.32(s,3H). 13 CNMR(151MHz,DMSO-d6)δ158.94,149.87,135.71(d,J=41.2Hz),120.30(d,J=289.8Hz).IR(KBr) max 3127,2980,1636,1539,1472,1307,1243,1164,1061,1024,758,665cm -1 ; elemental analysis (%) for C 4 HF 3 N 8 o 2 (250.1): calcd C, 19.21; H, 0.40; F, 22.79; N, 44.80; O, 12.79. Found: C 19.27; H 0.53; N 46.02.

Embodiment 3

[0053] Example 3 Compound 3-trifluoromethyl-[1,2,4]triazol[4,3-b][1,2,4,5]tetrazine-6-nitramide ammonium salt (4) preparation:

[0054]

[0055] Add compound 3 (2.5g, 10mmol) and 20mL of absolute ethanol to an anhydrous single-necked flask, 25% ammonia water (1.4g, 20mmol) was added dropwise to the reaction flask, continue stirring at 50°C for 2h, and then filter to obtain 2.27g of a yellow solid , the yield of the product 3-trifluoromethyl-[1,2,4]triazol[4,3-b][1,2,4,5]tetrazine-6-nitroaminated ammonium salt (4) was 86%.

[0056] Adopt differential scanning calorimeter (DSC) to carry out thermal decomposition temperature test to compound 4 and show that the thermal decomposition temperature of compound is 194 ℃, adopt the density meter to measure the density of compound to be (1.7832g / cm -3 ), the impact sensitivity and friction sensitivity of the compound measured by the impact sensitivity instrument and the friction sensitivity instrument were >40J, >360N, respectively...

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Abstract

The invention belongs to the technical field of synthesis of nitrogen-rich energetic materials, and particularly discloses fluorine-containing [1,2,4]triazole[4, 3-b][1,2,4,5]tetrazine ammonium nitrate and a preparation method thereof. According to the method, starting from easily available 3-trifluoromethyl-6-(3, 5-dimethylpyrazole)-[1,2,4]triazole[4,3-beta][1,2,4,5]tetrazine, a corresponding neutral nitramine energetic material can be obtained through a two-step reaction, and then a corresponding energetic ionic salt is obtained through a reaction of the neutral nitramine energetic material and neutral nitrogen-containing small molecules. Based on the compound density, thermal decomposition temperature and impact and friction sensitivity test, the product is an energetic material with high density (p is greater than 1.75), good thermal stability (the highest temperature reaches 220 DEG C) and insensitivity to external stimulation (IS is greater than 40J, and FS is greater than 360N).

Description

technical field [0001] The invention relates to the field of synthesis of nitrogen-rich energetic materials, in particular to a class of fluorine-containing [1,2,4]triazol[4,3-b][1,2,4,5]tetrazine ammonium nitrate and a preparation method thereof . Background technique [0002] Energetic materials (commonly known as explosives) are substances that can undergo intense redox reactions and release a large amount of energy under certain external stimuli. In military affairs, energetic materials are the energy source of weapons and ammunition, and the magnitude of their energy determines the damage effect of weapons. In the civil industry, energetic materials are widely used in fireworks, automobile airbags, deep-sea drilling and other fields. Based on this, the research on energetic materials has attracted the attention of countries all over the world. The research history of energetic materials can be traced back to black powder in ancient China and nitroglycerin invented by...

Claims

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Application Information

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IPC IPC(8): C07D487/04C06B49/00C06B25/34
CPCC07D487/04C06B49/00C06B25/34
Inventor 刘应乐董宇婷白豪
Owner SICHUAN UNIVERSITY OF SCIENCE AND ENGINEERING
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