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Energetic ionic salts of 7-nitryl-4-ketone-4,8-dihydro-[1,2,4] triazole [5,1-d] [1,2,3,5] tetrazine-2-oxide and preparation method of energetic ionic salt

A technology of oxides and ionic salts, applied in the fields of nitrated acyclic/alicyclic/heterocyclic amine explosive composition, organic chemistry, etc., to achieve the effects of mild conditions, high yield and simple synthesis method

Inactive Publication Date: 2015-03-25
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although derivatives of 1,2,3,4-tetrazine and 1,2,3,5-tetrazine have been studied exhaustively, there are no studies on energetic materials of 1,2,3,5-tetrazine to report
So far, 1,2,3,5-tetrazine-2-oxide has not been reported in the literature, let alone its fused ring compounds

Method used

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  • Energetic ionic salts of 7-nitryl-4-ketone-4,8-dihydro-[1,2,4] triazole [5,1-d] [1,2,3,5] tetrazine-2-oxide and preparation method of energetic ionic salt
  • Energetic ionic salts of 7-nitryl-4-ketone-4,8-dihydro-[1,2,4] triazole [5,1-d] [1,2,3,5] tetrazine-2-oxide and preparation method of energetic ionic salt
  • Energetic ionic salts of 7-nitryl-4-ketone-4,8-dihydro-[1,2,4] triazole [5,1-d] [1,2,3,5] tetrazine-2-oxide and preparation method of energetic ionic salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1, the preparation of 3-nitro-1-(2 hydrogen-tetrazol-5-yl)-1 hydrogen-1,2,4-triazole-5-amine (2)

[0026] Its structural formula is as follows:

[0027]

[0028] Add 1.06g (10mmol) cyanogen bromide, 50mL anhydrous acetonitrile, and several grains of 4A molecular sieves to a 250mL single-necked bottle, add 2.6g (40mmol) sodium azide at 0°C, stir for 4h at 0-4°C, and filter , retain the filtrate. An aqueous solution (15 mL) of 5-amino-3-nitro-1,2,4-triazole (1) was added to the filtrate, and stirred at room temperature for 4 h. Rotary steam at room temperature to remove acetonitrile, then add 15 mL of water and adjust to pH = 1 with concentrated hydrochloric acid, continue stirring for 0.5 h, filter, and wash with cold water twice to obtain a yellow solid with a yield of 78%.

[0029] Decomposition temperature: 246°C (DSC). 1 H NMR ([D 6 ]DMSO, 400MHz, 25°C, TMS): δ=7.96(s, 1H), 6.31(brs, 2H)ppm. 13 C NMR ([D 6 ]DMSO,100MHz,25℃):δ=161.8,156.8,154.6ppm....

Embodiment 2

[0030] Example 2, 7-nitro-4-keto-4,8-dihydro-[1,2,4]triazol[5,1-d][1,2,3,5]tetrazine-2- Preparation of sodium salt of oxide (3)

[0031] Its structural formula is as follows:

[0032]

[0033] Add 11 mL of fuming nitric acid to a 100 mL three-necked flask equipped with a thermometer and magnetic stirring, keep the temperature not exceeding 20°C in an ice-salt bath, and add 11 mL of fuming sulfuric acid dropwise thereto. After keeping for 5 min, 4.4 g (22.3 mmol) of compound 2 were added in portions. After the addition, the system temperature generally does not exceed 15°C. After keeping the temperature not exceeding 20°C for half an hour, then remove the ice-salt bath and react at room temperature for 2 hours. After the reaction was detected by TLC, the solution was poured into crushed ice and extracted with ethyl acetate. The obtained organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered and then concentrated. A yellow solid was p...

Embodiment 3

[0035]Example 3, 7-nitro-4-keto-4,8-dihydro-[1,2,4]triazol[5,1-d][1,2,3,5]tetrazine-2- Preparation of silver salt of oxide (4)

[0036] Its structural formula is as follows:

[0037]

[0038] Add 2.21 g of compound 3 (20 mmol) in water (20 mL) to a 100 mL three-neck flask equipped with magnetic stirring, and add 20 mL of silver nitrate solution (1.7 g, 10 mmol) dropwise. Stir in the dark for half an hour, and filter to obtain a tan solid with a yield of 97%. Anal.calcd.for AgC 3 N 7 o 4 : C 11.78, H 0.00, N 32.05%; found: C 11.80, H 0.04, N 32.01%.

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Abstract

The invention discloses energetic ionic salts of a 7-nitryl-4-ketone-4,8-dihydro-[1,2,4] triazole [5,1-d] [1,2,3,5] tetrazine-2-oxide and a preparation method of the energetic ionic salts, and belongs to the technical field of energetic materials. The synthesis method comprises the following steps: reacting a silver salt of the 7-nitryl-4-ketone-4,8-dihydro-[1,2,4] triazole [5,1-d] [1,2,3,5] tetrazine-2-oxide with corresponding hydrochloride of energetic cation; filtering and participating; and evaporating filtrate and removing a solvent, so as to obtain a target product. The energetic ionic salts are simple in synthesis method, and easy to industrialize. The 6 energetic ionic salts disclosed by the invention are relatively high in density (rho is 1.77-1.97g / cm<3>); the impact sensitivity is greater than 40J; the friction sensitivity is greater than or equal to 324N; the energetic ionic salts belong to insensitive explosives; and all energetic ionic salts are excellent in calculating detonation performance, and are energetic materials with potential.

Description

technical field [0001] The present invention relates to 7-nitro-4-keto-4,8-dihydro-[1,2,4]triazol[5,1-d][1,2,3,5]tetrazine-2-oxidation The invention discloses an energetic ion salt of a substance and a preparation method thereof, belonging to the technical field of energetic materials. Background technique [0002] In recent years, research on thermally stable and low-sensitivity high-energy-density materials (HEDMs) has attracted the attention of research teams from various countries. However, high performance and low sensitivity are usually opposite, which is a big challenge for the research of high energy density materials. Modern HEDMs are also required to have a high nitrogen content, and their detonation ability comes not only from the oxidation exotherm of the carbon skeleton structure, but also additionally from ring strain, a large number of N-N, C-N and N-O bond energies, and positive enthalpy of formation. [0003] In the pursuit of HEDMs with higher energy and ...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D249/14C06B25/34
CPCC07D487/04C06B25/34C07D249/14
Inventor 周智明卞成明
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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