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3,6,7-triamino-1,2,4-triazolocycle ionic type nitroazole compound and preparation method thereof

A technology for nitroazoles and cyclic compounds, applied in the direction of organic chemistry and the like, can solve the problems of low mechanical sensitivity of detonation performance, and achieve the effects of non-toxic by-products, mild conditions and simple preparation method

Active Publication Date: 2016-01-20
INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no use of the above-mentioned cationic 3,6,7-triamino-1,2,4-triazolo ring compound and nitroazole-1H compound for compound synthesis to obtain more stable, higher detonation performance, Reports on compounds with lower mechanical sensitivity

Method used

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  • 3,6,7-triamino-1,2,4-triazolocycle ionic type nitroazole compound and preparation method thereof
  • 3,6,7-triamino-1,2,4-triazolocycle ionic type nitroazole compound and preparation method thereof
  • 3,6,7-triamino-1,2,4-triazolocycle ionic type nitroazole compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The structure of 3,6,7-triamino-1,2,4-triazolocyclo-2,4-dinitroimidazole is as follows:

[0034]

[0035] Its preparation method is as follows:

[0036] Add 158 mg (1 mmol) of 2,4-dinitroimidazole-1H to 10 mL (0.5 mol) of aqueous solution, and add 154 mg of 3,6,7-triamino-1,2,4-triazolocyclic compound under stirring ( 1mmol), heated to 80°C, the solution turned into a light yellow transparent solution, continued to stir, reacted for 1h and then stood still. After the temperature dropped to room temperature, yellow crystals were precipitated, filtered out and washed with water, and dried to obtain the target compound 3,6,7-tri Amino-1,2,4-triazolocyclo-2,4-dinitroimidazole 280 mg, yield 89.7%.

[0037] 3,6,7-triaminotriazolocyclo-2,4-dinitroimidazole 1 H NMR (DMSO, δ, ppm): 8.18(2H), 7.30(1H), 7.24(2H), 5.78(2H); 13 C NMR such as figure 2 Shown (DMSO, δ, ppm): 160.61, 156.83, 147.91, 141.61, 98.83; Infrared (KBr, cm -1 ): 3420(s), 3357(m), 3255(s), 1679(s), 1650...

Embodiment 2

[0039] The conditions were the same as in Example 1, but the reaction temperature was changed to 90°C and the reaction time was changed to 0.5h to obtain 295 mg of the target compound 3,6,7-triaminotriazolocyclo-2,4-dinitroimidazole, with a yield of 94.5 %.

Embodiment 3

[0041] The structure of 3,6,7-triamino-1,2,4-triazolocyclo-4,5-dinitroimidazole is as follows:

[0042]

[0043] Its preparation method is as follows:

[0044]Add 158 mg (1 mmol) of 4,5-dinitroimidazole-1H to 10 mL (0.5 mol) of aqueous solution, and add 154 mg of 3,6,7-triamino-1,2,4-triazolocyclic compound under stirring ( 1mmol), heated to 85°C, the solution turned into a light yellow transparent solution, continued to stir, reacted for 0.5h and then stood still. After the temperature dropped to room temperature, yellow crystals were precipitated, filtered out, washed with water, and dried to obtain the target compound 3,6,7- Triaminotriazolocyclo-4,5-dinitroimidazole 290 mg, yield 92.9%.

[0045] After recrystallization, a single crystal of 3,6,7-triaminotriazolocyclo-4,5-dinitroimidazole monohydrate was obtained, the crystal structure of which is image 3 As shown, the space group is P-1, the unit cell parameters are α=79.688(5)°, β=74.117(6)°, γ=80.828(5)°, and the c...

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Abstract

The invention discloses a 3,6,7-triamino-1,2,4-triazolocycle ionic type nitroazole compound and a preparation method thereof. The preparation method of the 3,6,7-triamino-1,2,4-triazolocycle ionic type nitroazole compound comprises the following steps: dispersing a 3,6,7-triamino-1,2,4-triazolocycle compound and a nitroazole type-1H compound in right amount of deionized water, heating, reacting, then standing, filtering out a solid after temperature is reduced to normal temperature, washing the solid, and drying, so that the 3,6,7-triamino-1,2,4-triazolocycle ionic type nitroazole compound is obtained, wherein the nitroazole type-1H compound is one of 2,4-dinitroimidazole-1H, 4,5-dinitroimidazole-1H, 3,5-dinitroparazole-1H, 3-amino-5-nitro-1,2,4-triazole-1H, 3-nitro-1,2,4-triazole-5-one and 5,5'-dinitro-3,3'-bi-triazole-1H,1'H. The preparation method of the 3,6,7-triamino-1,2,4-triazolocycle ionic type nitroazole compound is simple, no toxic substance or byproduct is produced, conditions are mild, yield is high, and detonation velocity, through quantum chemistry calculation, of the obtained product is 8500-9200m / s.

Description

technical field [0001] Embodiments of the present invention relate to the field of organic chemistry, more specifically, embodiments of the present invention relate to 3,6,7-triamino-1,2,4-triazolocyclic ionic nitroazole compounds and their preparation methods . Background technique [0002] Ionic energetic materials are a class of energetic compounds with high nitrogen content and high heat of formation, which have attracted much attention in the field of explosive synthesis in recent years. Most of its decomposition products are dinitrogen tetroxide with high density and low vapor pressure, so it is more environmentally friendly than traditional simple explosives. Because of its excellent detonation performance, low mechanical sensitivity, high heat of formation, and excellent thermal stability, it can be used as a high-energy component in military, aerospace, and civil blasting fields. Nitrogen-enriched azole compounds are a good carrier of ionic energetic materials, an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D233/92C07D231/16C07D249/14
CPCC07D231/16C07D233/92C07D249/14C07D487/04
Inventor 马卿屈延阳黄靖伦王军卢欢唱刘雨季
Owner INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS
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