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Synthetic method of 3,3'-binitro-5,5'-di-1,2,4-triazole

A synthesis method, dinitro technology, applied in the direction of organic chemistry, can solve the problems of increased side reactions, difficult operation, and high consumption of sodium nitrite, and achieve less reaction by-products, high reaction yield, and simple post-treatment process Effect

Inactive Publication Date: 2014-08-06
XIAN MODERN CHEM RES INST
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] This method has the following disadvantages: 1) 5,5'-diamino-3,3'-bi-1,2,4-triazole is insoluble in inorganic acids, and it is injected into the reaction system in batches in the form of suspension during operation. 2) The reaction needs to be fed at a higher temperature of 40°C, which leads to an increase in the side reactions of sodium nitrite decomposed by acid, and requires more sodium nitrite consumption. The reported molar ratio of 5,5'-diamino-3,3'-bi-1,2,4-triazole to sodium nitrite is 1:20; 3) The crude product needs to be dissolved in boiling water and hot filtered to remove some Impurities; 4) This reaction belongs to the diazotization-nitro substitution reaction with higher selectivity, and there is still room for improvement in the yield

Method used

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  • Synthetic method of 3,3'-binitro-5,5'-di-1,2,4-triazole
  • Synthetic method of 3,3'-binitro-5,5'-di-1,2,4-triazole
  • Synthetic method of 3,3'-binitro-5,5'-di-1,2,4-triazole

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Experimental program
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Effect test

Embodiment 1

[0023] Dissolve 4.0 g of 5,5'-diamino-3,3'-bi-1,2,4-triazole in 32.0 g of methanesulfonic acid to prepare a salt solution for use. Add 50mL aqueous solution containing 11.6g of sodium nitrite to a reaction flask equipped with stirring. Add the above-mentioned salt solution dropwise to the reaction flask at a temperature of 20°C. Control the dropping time to 30min. After the salt solution is added dropwise, The water bath is heated to 40°C. At this time, a large amount of gas is released in the system. After stirring for 60 minutes, the gas is released completely. Cool to a temperature of 20°C and filter. The filter cake obtained is washed and dried to obtain 3,3'-dinitro-5. ,5'-Bi-1,2,4-triazole dihydrate 5.85g, purity 98.8%, yield 92.1%.

[0024] Structure Identification:

[0025] Proton nuclear magnetic resonance spectrum: (DMSO-d 6 , 500MHz, δ, ppm): 5.14 (s, br, 2H, NH); carbon nuclear magnetic resonance spectrum: (DMSO-d 6 , 125MHz): 146.6(C-C), 163.0(C-NO 2 )

[0026] Infrare...

Embodiment 2

[0033] Dissolve 4.0 g of 5,5'-diamino-3,3'-bi-1,2,4-triazole in 32.0 g of methanesulfonic acid to prepare a salt solution for use. Add 50mL aqueous solution containing 8.3g of sodium nitrite to a reaction flask equipped with stirring. Add the above-mentioned salt solution dropwise to the reaction flask at a temperature of 20°C. Control the dropping time to 30min. After the salt solution is added dropwise, The water bath is heated to 40°C. At this time, a large amount of gas is released in the system. After stirring for 60 minutes, the gas is released completely. Cool to a temperature of 20°C and filter. The filter cake obtained is washed and dried to obtain 3,3'-dinitro-5. ,5'-Bi-1,2,4-triazole dihydrate 5.36g, purity 98.2%, yield 84.4%.

Embodiment 3

[0035] Dissolve 4.0 g of 5,5'-diamino-3,3'-bi-1,2,4-triazole in 32.0 g of methanesulfonic acid to prepare a salt solution for use. Add a 50mL aqueous solution containing 16.6g of sodium nitrite to a reaction flask equipped with stirring. Add the above-mentioned salt solution dropwise to the reaction flask at a temperature of 20°C. Control the dropping time to 30min. After the salt solution is added dropwise, The water bath is heated to 40°C. At this time, a large amount of gas is released in the system. After stirring for 60 minutes, the gas is released completely. Cool to a temperature of 20°C and filter. The filter cake obtained is washed and dried to obtain 3,3'-dinitro-5. ,5'-Bi-1,2,4-triazole dihydrate 5.77g, purity 98.5%, yield 90.8%.

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Abstract

The invention discloses a synthetic method of 3,3'-binitro-5,5'-di-1,2,4-triazole. The structural formula of 3,3'-binitro-5,5'-di-1,2,4-triazole is as follows: as shown in the description. The synthetic method disclosed by the invention comprises the following steps: taking 5,5'-diamido-3,3'-di-1,2,4-triazole as a raw material, dissolving 5,5'-diamido-3,3'-di-1,2,4-triazole in organic sulfonic acid to prepare a salt solution, at normal temperature, dripping the salt solution in a sodium nitride aqueous solution, heating in water bath, when the gas is released completely, cooling to the room temperature, filtering, washing with water and drying the solution to obtain the target product 3,3'-binitro-5,5'-di-1,2,4-triazole. The synthetic method disclosed by the invention is easy in operation, few in side reactions and high in reaction yield, and can be mainly applied to synthesis of 3,3'-binitro-5,5'-di-1,2,4-triazole.

Description

Technical field [0001] The present invention relates to a method for synthesizing 1,2,4-triazole derivatives, in particular to the synthesis of 3,3'-dinitro-5,5'-bi-1,2,4-triazole method. Background technique [0002] 1,2,4-triazole compounds, which contain C-N, N-N, and N=N bonds in their structure, have the characteristics of high nitrogen content, high enthalpy of formation, large gas production, and clean detonation products. At the same time, since the atoms in the triazole ring all adopt sp2 heterocycles when forming bonds, a planar molecular structure with a delocalized conjugated system is formed, which improves the thermal stability and reduces the mechanical sensitivity and electrostatic sensitivity of the molecule. [0003] Bi1,2,4-triazole compounds with symmetrical structure have smaller dipole moment and tighter molecular space arrangement than monotriazole derivatives, thus having excellent detonation performance. 3,3-Dinitro-5,5-bi-1,2,4-triazole is a representati...

Claims

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Application Information

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IPC IPC(8): C07D249/14
CPCC07D249/14
Inventor 王子俊郭涛刘敏黄晓川葛忠学邱少君唐望姜俊秦明娜石强李洪丽吕英迪郑晓东陈志强姚冰洁
Owner XIAN MODERN CHEM RES INST
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