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5,5'-bistetrazole-1,1'-dioxide metal salt and synthesis method thereof

A technology of metal dioxide and synthesis methods, applied in the fields of nitration explosive components, compressed gas generation, organic chemistry, etc., can solve the problems of unfavorable industrial preparation and low purity, reduce the characteristic signal of propellant, increase energy output, and synthesize The effect of short process route

Inactive Publication Date: 2015-08-12
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

About 5,5'-tetrazole-1,1'-dioxometallic salt, only 5,5'-tetrazole-1,1'-dioxyl sodium salt (Huang Haifeng, Yang Jun, Yang Pu .Synthesis, crystal structure and properties of 1,1′-dihydroxy-5,5′-bitetrazolium tetrahydrate sodium salt. Energetic Materials, 2014, 22(4):462-446), 5 prepared by this method ,The yield of 5′-bistetrazole-1,1′-dioxysodium salt is only 42.2%, and the purity is not high, which requires recrystallization for purification, which is not conducive to industrial production. Except for 5,5′-bistetrazole- The preparation of other kinds of metal salts has not been seen except 1,1'-dioxosodium salt

Method used

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  • 5,5'-bistetrazole-1,1'-dioxide metal salt and synthesis method thereof
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  • 5,5'-bistetrazole-1,1'-dioxide metal salt and synthesis method thereof

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Experimental program
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Embodiment 1

[0024] Synthesis of 5,5'-bitetrazole-1,1'-dihydroxy dihydrate

[0025] (1) Add 10 g of glyoxime to 100 mL of N-N-dimethylformamide system, slowly add 30 g of N-chlorosuccinimide (NCS) in batches at room temperature, and wait until N-chlorosuccinyl After the imine (NCS) was completely dissolved, it was stirred and kept at room temperature for 8 hours. The temperature of the reaction system was lowered to 0°C, and 16 g of sodium azide was slowly added in batches. Keep warm at 0-5°C for 60 minutes. The reaction solution was poured into 100mL of water, precipitated and filtered. The filter cake was washed once more with 200 mL of water to obtain 25 g of a wet product of diazideglyoxime, which was then dried to obtain 17.5 g.

[0026] (2) Add 4.25 g of the wet product diazideglyoxime into 65 mL of ether system, and mix the feed liquid completely and evenly. When the temperature is lowered to 0-5°C, HCI gas is introduced until the ether solution is saturated. Warm up to room te...

Embodiment 2

[0028] Synthesis of 5,5'-bitetrazole-1,1'-dihydroxy dihydrate

[0029] (1) Add 10 g of glyoxime to 150 mL of N-N-dimethylformamide system, slowly add 30 g of N-chlorosuccinimide (NCS) in batches at room temperature, and wait until N-chlorosuccinyl After the imine (NCS) was completely dissolved, it was stirred and kept at room temperature for 12 hours. The temperature of the reaction system was lowered to 0°C, and 16 g of sodium azide was slowly added in batches. 0-5 ℃ insulation 90min. The reaction solution was poured into 150mL of water, precipitated and filtered. The filter cake was washed once with 200 mL of water to obtain 25.6 g of a wet product of diazideglyoxime, which was then dried to obtain 17.9 g.

[0030] (2) Add 4.25 g of the wet product diazideglyoxime into 85 mL of ether system, and mix the feed liquid completely and evenly. When the temperature is lowered to 0-5°C, HCI gas is introduced until the ether solution is saturated. Warm up to room temperature and...

Embodiment 3

[0032] Synthesis of 5,5'-bistetrazole-1,1'-dioxodipotassium

[0033] Add 4 g of 5,5′-bitetrazole-1,1′-dihydroxy dihydrate into 100 mL of water system, start stirring, and raise the temperature to 40°C to make the liquid completely dissolved and transparent. Add 2.64 g of potassium hydroxide, keep warm for 60 min, slowly cool down to room temperature, filter, and wash the filter cake with cold water. Naturally air-dried to obtain 3.72 g of colorless 5,5′-bistetrazole-1,1′-dioxypotassium salt crystals, with a yield of 78%.

[0034] Structure Identification:

[0035] Infrared (KBr, υ / cm -1 ) 2166, 1667, 1510, 1408, 1356, 1233, 1164, 1058, 997, 732, 502.

[0036] Elemental Analysis: C 2 N 8 o 2 K 2

[0037] Theoretical value: C (9.756%), N (45.3%);

[0038] Found values: C (9.859%), N (46.51%).

[0039] Thermal decomposition temperature: Tp=383℃.

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Abstract

The present invention relates to a 5,5'-bistetrazole-1,1'-dioxide metal salt and a synthesis method thereof, and belongs to the high-energy nitrogen-rich compound synthesis in the energy-containing material field. According to the present invention, glyoxime is adopted as a raw material, N-chlorosuccinimide chlorination, sodium azide azidization and ring formation are performed to obtain a skeleton 5,5'-bistetrazole-1,1'-dihydroxy dehydrate, and the 5,5'-bistetrazole-1,1'-dihydroxy dehydrate reacts with a water-soluble metal ion compound in a water medium to obtain the different types of the 5,5'-bistetrazole-1,1'-dioxide metal salts; and the method has characteristics of less synthesis steps, simple process, and high product yield.

Description

technical field [0001] The invention relates to a 5,5'-bistetrazole-1,1'-dioxide metal salt and a synthesis method thereof, belonging to the synthesis of high-energy nitrogen-rich compounds in the field of energetic materials. Background technique [0002] Azole compounds are an important class of energetic materials, which have a series of advantages such as high nitrogen content, high enthalpy of formation, high gas production, and clean detonation products. They are currently a hot frontier in the research of energetic materials. The C-C atoms in the tetrazole molecule adopt sp2 hybridization when forming bonds, which can form a delocalized large л bond and have a planar molecular structure of a conjugated system, so that the tetrazole molecule can improve thermal stability while reducing Mechanical sensitivity and electrostatic sensitivity. [0003] At present, the methods for preparing 5,5′-bitetrazolium-1,1′-dihydroxyl at home and abroad all use glyoxime as raw materi...

Claims

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Application Information

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IPC IPC(8): C07D257/04C06B25/00C06D5/00
CPCC07D257/04C06B25/00C06D5/00
Inventor 王小军束庆海金韶华张晓鹏张春园王俊峰王霞尚凤琴李京霖鲁志艳李丽洁陈树森
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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