3, 6-dinitramine triazolo triazole, ionic salt thereof, preparation method and application

A technology of triazolo and dinitroamine, which is applied in the field of new high-energy energetic compounds to achieve the effects of reducing friction sensitivity, enhancing π-π interaction, and improving thermal stability and sensitivity

Pending Publication Date: 2021-12-10
ZHONGBEI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This is the first synthetic route of this compound, which has not been reported before

Method used

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  • 3, 6-dinitramine triazolo triazole, ionic salt thereof, preparation method and application
  • 3, 6-dinitramine triazolo triazole, ionic salt thereof, preparation method and application
  • 3, 6-dinitramine triazolo triazole, ionic salt thereof, preparation method and application

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preparation example Construction

[0038] The present invention provides a specific embodiment of the preparation method of 3,6-dinitroamine[1,2,4]triazolo[4,3-b][1,2,4]triazole, comprising the following steps: Dissolve 3,6-diamino[1,2,4]triazolo[4,3-b][1,2,4]triazole in sulfuric acid, add nitric acid dropwise, and react for 2-4 hours, and the reaction solution Quenched by adding to crushed ice, filtered with suction to obtain a yellow solid, dried to obtain 3,6-dinitroamine[1,2,4]triazolo[4,3-b][1,2,4]triazole .

[0039] In a specific application, the system temperature is kept below 0° C. during the whole preparation process.

[0040] In the present invention, the sulfuric acid is concentrated sulfuric acid with a mass fraction of 98% or oleum with a mass fraction of 20%, and the nitric acid is fuming nitric acid or anhydrous nitric acid.

[0041] In the present invention, when the above-mentioned types of sulfuric acid and nitric acid are used, the volume ratio of sulfuric acid to nitric acid is 3:1˜4:1. ...

Embodiment 1 2

[0056] The synthesis of embodiment 1 dinitramine triazolotriazole (1)

[0057] Add 1.39g of 3,6-diamino[1,2,4]triazolo[4,3-b][1,2,4]triazole (10mmol) that was ground and pulverized in advance to 15g of oleum, and wait After ultrasonic dissolution is complete, then keep the temperature not exceeding -5°C, and slowly add 4mL of fuming nitric acid. Reacted for 3.5h, keeping the temperature at -5°C. It was then quenched with 40 g of crushed ice and filtered to obtain a yellow solid that was dissolved in CaCl 2 After drying in medium overnight, the product was obtained (yield 78%).

[0058] In the present invention, the 3,6-diamino[1,2,4]triazolo[4,3-b][1,2,4]triazole is self-made in the laboratory, and the specific preparation method can be found in C. Bian, Q. Lei, J. Zhang, et al, Polyhedron, 2021, 201, 115158.

[0059] Product structure identification:

[0060] Decomposition temperature: 121°C (DSC, the melting point and decomposition temperature mentioned below are peak t...

Embodiment 2 2

[0066] The synthesis of embodiment 2 dinitramine triazolotriazoles (1)

[0067] Add 1.98g of 3,6-diamino[1,2,4]triazolo[4,3-b][1,2,4]triazole (14.2mmol) that was pulverized in advance to 17.1g of concentrated sulfuric acid, After the ultrasonic solution is completely dissolved, then keep the temperature not exceeding -2°C, slowly add 3.8mL of anhydrous nitric acid, react for 2.5h, and keep the temperature at -5°C. Then quenched with 56g of crushed ice, filtered and compacted to obtain a yellow solid, which was dissolved in CaCl 2 Dry overnight in medium, then wash with appropriate amount of acetonitrile, filter, and put the obtained filter cake into an oven for 2 hours at 50° C. to vacuum-dry to obtain 2.73 g of dinitramine triazolotriazole (yield: 84%).

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Abstract

The invention relates to 3, 6-dinitramine [1, 2, 4] triazolo [4, 3-b] [1, 2, 4] triazole as well as an ionic salt, a preparation method and application thereof, wherein the 3, 6-dinitramine [1, 2, 4] triazolo [4, 3-b] [1, 2, 4] triazole has a better application prospect in high-energy explosives. According to the molecular sturcutre of 3, 6-dinitramine [1, 2, 4] triazolo [4, 3-b] [1, 2, 4] triazole, a nitramine group perpendicular to the N5 position of a fused ring skeleton is removed from the molecular structure of 3, 6-dinitramine [1, 2, 4] triazolo [4, 3-b] [1, 2, 4] triazole, so that when the 3, 6-dinitramine [1, 2, 4] triazolo [4, 3-b] [1, 2, 4] triazole is converted into anions, a completely planar large conjugated system is formed, the pi-pi interaction between layers is enhanced, and the thermal stability and sensitivity of the dinitramine triazolo triazole energetic ionic salt are improved. According to the invention, the energetic ion salt is tested by a BAM impact sensitivity instrument, and the impact sensitivity is 7-10 J; a BAM friction sensitivity instrument is used for testing to find that the friction sensitivity is 140-220 N. In combination with detonation performance and sensitivity, the detonation performance of the hydrazinium salt is equivalent to that of RDX, the sensitivity is superior to that of RDX, and the comprehensive performance is optimal.

Description

technical field [0001] The invention relates to the field of energetic materials, in particular to a class of novel high-energy energetic compounds, especially 3,6-dinitroamine[1,2,4]triazolo[4,3-b][1,2,4 ] Triazole and ionic salt thereof and preparation method and application, the present invention has better application prospect in high-energy explosives. Background technique [0002] Nitramine explosives usually have excellent detonation performance, such as the traditional monocyclic nitramine explosive cyclotrimethylene trinitramine (commonly known as RDX) and cyclotetramethylene tetranitramine (commonly known as Octojin , HMX), their detonation performance is about 1.5-1.8 times that of 2,4,6-trinitrotoluene (TNT) of the same mass. [0003] The energy of traditional monocyclic or bicyclic nitramine explosives almost comes from the oxidation of carbon skeleton. Nitramine explosives with nitrogen-rich fused rings also have another source of energy, that is, the high po...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C06B25/34
CPCC07D487/04C06B25/34
Inventor 卞成明朱娜吴晓青
Owner ZHONGBEI UNIV
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