4-nitro-3-(5-tetrazole) furoxan energetic ionic salt and preparation method thereof

A technology for oxidizing furoxan and ionic salts, which is applied in chemical instruments and methods, preparation of organic compounds, nitrated acyclic/alicyclic/heterocyclic amine explosive compositions, etc., can solve the problems that cannot be used as anions of energetic ionic salts, etc. , to achieve the effect of high yield, environmental friendliness and simple synthesis method

Inactive Publication Date: 2013-04-24
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the furoxan ring does not have an acidic proton hydrogen

Method used

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  • 4-nitro-3-(5-tetrazole) furoxan energetic ionic salt and preparation method thereof
  • 4-nitro-3-(5-tetrazole) furoxan energetic ionic salt and preparation method thereof
  • 4-nitro-3-(5-tetrazole) furoxan energetic ionic salt and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1 Preparation of 4-amino-3-(5-tetrazole)furoxan (2)

[0025] Its structural formula is as follows:

[0026]

[0027] Dissolve (1.000g, 7.9mmol) 4-amino-3-cyanofuroxan in 10mL water in a 25mL single-necked flask, and then add 0.619g (9.5mmol) NaN 3 and 1.786g (7.9mmol) ZnBr 2 . The resulting reaction mixture was stirred at room temperature for 3 hours, then cooled to room temperature, adjusted to pH=1-2 with 2% hydrochloric acid, filtered, washed with water to obtain a crude product, and recrystallized with ethanol to obtain white crystals. Yield: 83%.

[0028] Decomposition temperature: 182°C (DSC). 1 H NMR ([D 6 ]DMSO,400MHz,25°C,TMS):δ=6.784(br.s,2H,NH 2 ) ppm. 13 C NMR ([D 6 ]DMSO,100MHz,25°C):δ=155.8,144.9,101.9ppm.IR(neat):=3516,3438,3315,1650,1614,1567,1496,1422,1389,1233,1113,1080,1034 ,1012,950,861,762,657cm -1 .MS(ESI):m / z(%):168.3.

Embodiment 2

[0029] Example 2 Preparation of 4-nitro-3-(5-tetrazole)furoxan (3)

[0030] Its structural formula is as follows:

[0031]

[0032] Cool down to -15°C in an ice-salt bath, add 18.000g H 2 o 2 (50%), add 1.980g (6.0mmol) Na under stirring 2 WO 4 , and then slowly add 14 mL of concentrated sulfuric acid dropwise, keeping the temperature below 5°C. After the dropwise addition was completed, remove the ice-salt bath, and when the temperature stabilized at room temperature, start adding 1.000 g (5.9 mmol) of 4-amino-3-cyanofuroxan in batches. into ice water. Extracted with ethyl acetate (50mL×4), dried the organic phase with anhydrous MgSO4, and distilled under reduced pressure to obtain a crude product. The crude product was passed through the column (CH 2 Cl 2 / CH 3 OH=10 / 1) separated and purified to obtain a white solid. Yield: 45%.

[0033] Melting point: 140°C, decomposition temperature: 169°C (DSC). 1 H NMR ([D 6 ]DMSO,400MHz,25°C,TMS):δ=9.285(br.s,1H,NH)ppm. ...

Embodiment 3

[0034] Example 3 Preparation of 4-nitro-3-(5-tetrazole) furazan ammonium oxide salt (4)

[0035] Its structural formula is as follows:

[0036]

[0037] Dissolve 199mg (1.0mmol) of 3 in methanol, add 68mg (1.0mmol) of ammonia water (25%) to it, stir and react at room temperature for 2h, after the reaction solution is concentrated, the crude product is recrystallized with ethanol / dichloromethane to obtain white crystals. Yield: 85%.

[0038] Decomposition temperature: 142°C (DSC). Density is 1.84g cm -3 . 1 H NMR ([D 6 ]DMSO,400MHz,25°C,TMS):δ=7.260(br.s,4H,NH 4 ) ppm. 13 C NMR ([D 6 ]DMSO,100MHz,25°C):δ=158.5,144.8,105.4ppm.IR(neat):=3310,3161,3033,2874,1636,1566,1549,1369,1313,1186,1151,1086,1038 ,988,845,601,470,408cm -1 .Elemental analysis for C 3 h 4 N 8 o 4 (216.12):calcd.C 16.67,H 1.87,N 51.85%;found:C 16.59,H 1.94,N 51.26%.

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Abstract

The invention discloses a 4-nitro-3-(5-tetrazole) furoxan energetic ionic salt and a preparation method thereof, belongs to the technical field of energetic materials. A synthesis method of the 4-nitro-3-(5-tetrazole) furoxan energetic ionic salt is as follows: directly reacting the 4-nitro-3-(5-tetrazole) furoxan with a corresponding cation, and steaming for eliminating a solvent so as to obtain a target product; reacting the 4-nitro-3-(5-tetrazole) furoxan with the sulfate of the equimolar corresponding cation after mixing the 4-nitro-3-(5-tetrazole) furoxan with equimolar Ba(OH)2.8H2O, filtering and precipitating, steaming and eliminating the solvent in the filtrate to obtain the target product. The synthesis method provided by the invention is simple and easy to industrialize. The referred 9 energetic ionic salt has high density (rho: 1.55-1.84g/cm3), wherein the degree of percussion sensitivity of two compounds is more than 40J, and the energetic ionic salt belongs to insensitive explosive. The energetic ionic salt has excellent calculation detonation property and is a potential energetic material.

Description

technical field [0001] The invention relates to 4-nitro-3-(5-tetrazole)furazan oxide, 4-nitro-3-(5-tetrazole)furazan oxide energetic ion salt and a preparation method thereof, which belong to energetic material technology field. Background technique [0002] In recent years, new energetic heterocyclic compounds have been receiving great attention. Studies have included a wide variety of species such as 2,4,5-trinitroimidazole, 3,5-dinitrotriazole, 5-nitrotetrazole, bistetrazole, 3-amino-6-nitroamine tetrazine, 4-amino-3-(5-tetrazole)furoxan and 3-(3,5-dinitropyrazol-4-yl)-4-nitrofurazan etc. Many energetic heterocyclic compounds have been reported in the literature, and they are widely used as components of high-energy explosives and propellants. Among them, furoxan (furoxan) is a unique class of heterocyclic compounds with various interesting properties. They can be used as bioactive compounds and high-energy energetic materials. Previous studies have shown that a seri...

Claims

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Application Information

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IPC IPC(8): C07D413/04C07D249/14C07C279/02C07C277/00C07C277/08C07C281/16C07C279/24C06B25/34
Inventor 周智明梁丽轩卞成明王凯
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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