Energetic compound 3,3'-diamido-2,2'-2(2,2,2-trinitroethyl)-5,5'-linked triazole-diamine and preparation method and intermediate thereof

A technology of trinitroethyl and diamino is applied in the directions of nitrated acyclic/alicyclic/heterocyclic amine explosive compositions, organic chemistry, etc., and achieves the effects of good application prospects, mild reaction conditions and low cost

Active Publication Date: 2015-03-25
INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS
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  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

[0006] After literature and patent searches, the important intermediate 3,3',4,4'-tetraamino-5,5'-bitriazole and the target compound 3,3'-diamino-2,2 None of '-bis(2,2,2-trinitroethyl)-5,5'-triazole-diamine has been reported

Method used

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  • Energetic compound 3,3'-diamido-2,2'-2(2,2,2-trinitroethyl)-5,5'-linked triazole-diamine and preparation method and intermediate thereof
  • Energetic compound 3,3'-diamido-2,2'-2(2,2,2-trinitroethyl)-5,5'-linked triazole-diamine and preparation method and intermediate thereof
  • Energetic compound 3,3'-diamido-2,2'-2(2,2,2-trinitroethyl)-5,5'-linked triazole-diamine and preparation method and intermediate thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Add 30mL water to a 100mL three-necked flask, add 1g 6mmol of 3,3'-diamino-5,5'-bis(1H-1,2,4-triazole), add 0.67g 12mmol potassium hydroxide under stirring, Heat to 50°C to react for 0.5h, filter off the residue, spin dry the filtrate at a vacuum of 55mbar and a temperature of 60°C to obtain a light yellow solid, and obtain 3,3'-diamino-5,5'-bitriazole after vacuum drying -4,4'-dipotassium 1.33g, yield 91.7%, melting point 381.4°C.

[0035] In an ice-salt bath, add 1 g of 3,3'-diamino-5,5'-bitriazole-4,4'-dipotassium to 2,4,6-trimethylbenzenesulfonyl with a mass concentration of 82.4% Hydroxylamine in methanol solution, stirred for 6 hours, returned to room temperature, filtered under reduced pressure, washed with water, and dried in vacuum at 50°C to obtain the intermediate 3,3',4,4'-tetraamino-5,5'- Bitriazole 0.64g, yield 81%. Water recrystallization is dark yellow crystal, melting point 78.1 ℃.

[0036] 3,3’,4,4’-tetraamino-5,5’-bitriazole 1 H NMR spectrum such ...

Embodiment 2

[0042] Add 20mL water into a 100mL three-necked flask, add 1g 6mmol of 3,3'-diamino-5,5'-bis(1H-1,2,4-triazole), add 0.67g 12mmol potassium hydroxide under stirring, Heat to 50°C for 1 hour, filter off the residue, spin dry the filtrate at a vacuum of 60mbar and a temperature of 45°C to obtain a white solid, and obtain 3,3'-diamino-5,5'-bitriazole-4 after vacuum drying ,4'-dipotassium 1.58g, yield 94.3%, melting point 357.0°C.

[0043] At 5°C, add 1 g of 3,3'-diamino-5,5'-bitriazole-4,4'-dipotassium to 90% mass concentration of 2,4,6-trimethylbenzenesulfonyl Hydroxylamine in methanol solution, stirred for 5 hours, returned to room temperature, filtered under reduced pressure, washed with water, and dried in vacuo at 45°C to obtain the intermediate 3,3',4,4'-tetraamino-5,5'- Bitriazole 0.69g, yield 86%. Water recrystallization is dark yellow crystal, melting point 78.0 ℃.

[0044] At room temperature, add 1 g of 3,3',4,4'-tetraamino-5,5'-bitriazole into a 38% mass concentrat...

Embodiment 3

[0046] Add 20mL water into a 100mL three-necked flask, add 1g 6mmol of 3,3'-diamino-5,5'-bis(1H-1,2,4-triazole), add 0.67g 12mmol potassium hydroxide under stirring, Heat to 50°C for 1 hour, filter off the residue, spin dry the filtrate at a vacuum of 60mbar and a temperature of 45°C to obtain a white solid, and obtain 3,3'-diamino-5,5'-bitriazole-4 after vacuum drying , 4'-dipotassium, the yield is 94.3%, and the melting point is 357.0°C.

[0047] At a temperature of 5°C, add 1 g of 3,3'-diamino-5,5'-bitriazole-4,4'-dipotassium to 2,4,6-trimethylbenzenesulfonyl with a mass concentration of 80% Hydroxylamine in methanol solution, stirred for 8 hours, returned to room temperature, filtered under reduced pressure, washed with water, and dried under vacuum at 45°C to obtain the intermediate 3,3',4,4'-tetraamino-5,5'- Bitriazole 0.67g, yield 85%. Water recrystallization is dark yellow crystal, melting point 78.1 ℃.

[0048] At room temperature, add 1 g of 3,3',4,4'-tetraamino-5...

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Abstract

The invention discloses an energetic material compound 3,3'-diamido-2,2'-2(2,2,2-trinitroethyl)-5,5'-linked triazole-diamine and a preparation method and intermediate of the energetic material compound 3,3'-diamido-2,2'-2(2,2,2-trinitroethyl)-5,5'-linked triazole-diamine. Firstly, 3,3'-diamido-5,5'-2(1H-1,2,4-triazole) is adopted as raw materials, and synthesized into 3,3',4,4'-tetramino-5,5'-linked triazole through nitrogenation and ammoniation of nucleophilic animation reagent 2,4,6-trimethylbenzene sulfonyl hydroxylamine, then hydroxylation is carried out through formaldehyde solutions, and finally a condensation reaction is carried out on the 3,3'-diamido-5,5'-2(1H-1,2,4-triazole) and trinitromethane to generate a target product. Solvents adopted in the preparation method are low in price. The raw materials are prepared easily, reaction steps are few, and productivity is high. The detonation energy of the target product can be equivalent to that of HMX, sensitivity is lower than that of RDX, intramolecular oxygen balance is high, and the energetic material compound 3,3'-diamido-2,2'-2(2,2,2-trinitroethyl)-5,5'-linked triazole-diamine is a high-energy explosive with the good application prospect.

Description

technical field [0001] Embodiments of the present invention relate to the field of preparation of energetic materials, more specifically, embodiments of the present invention relate to an energetic compound 3,3'-diamino-2,2'-bis(2,2,2-tri Nitroethyl)-5,5'-bitriazole-diamine and its preparation method, and the intermediate 3,3',4,4'-tetraamino-5,5'-bistriazole of the energetic compound azole. Background technique [0002] Energetic materials have a wide range of applications in many fields such as weapons, aerospace, and civilian explosives. Constantly looking for high-safety, high-energy energetic materials has become the goal pursued by research institutions at home and abroad. Nitrate-based explosives have attracted wide attention in the field of energetic materials in recent years. Its oxygen content and heat of formation are high, and its instantaneous work ability is strong, but it is sensitive to mechanical and thermal stimuli; azole molecules are a kind of electrosta...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/14C06B25/34
CPCC06B25/34C07D249/14
Inventor 马卿王军黄靖伦范桂娟刘永刚蒋涛屈延阳
Owner INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS
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