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Nitroimidazole energetic compound substituted by polynitrobenzene and preparation method thereof

The technology of nitroimidazole and compound is applied in the field of nitroimidazole energetic compound substituted by polynitrobenzene of novel high-energy insensitive explosive and its preparation field, and achieves the effects of simple reaction steps, little environmental harm, and safe and reliable production.

Inactive Publication Date: 2016-01-13
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, researchers at home and abroad rarely report on the synthesis of this class of compounds, and only a few documents have reported 2-azidoimidazoles, see (HammerlA., KlapmkeM.K., warchholdM., Inorg.Chem. ,2002,41(4),906.), so the energetic compounds of azidonitroimidazoles substituted by polynitrobenzene have also been in the exploration and research

Method used

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  • Nitroimidazole energetic compound substituted by polynitrobenzene and preparation method thereof
  • Nitroimidazole energetic compound substituted by polynitrobenzene and preparation method thereof
  • Nitroimidazole energetic compound substituted by polynitrobenzene and preparation method thereof

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preparation example Construction

[0025] The preparation method of the 2-azido-4-nitroimidazole substituted by polynitrobenzene of the present invention comprises the following steps:

[0026] In the first step, dissolve 2-azido-4-nitroimidazole in isopropanol, add base and tetrabutylammonium bromide at room temperature, and stir for 0.5h.

[0027] In the second step, the substituted trinitrochlorobenzene is added to the above reaction solution and reacted at 75~85°C. After the reaction is completed, it is cooled to room temperature, and the mixed solution is filtered, washed with methanol, washed with water, and dried to obtain the compound (I).

[0028] Wherein, in the first step, the mol ratio of 2-azido-4-nitroimidazole and alkali is 1:1, and the mol ratio of 2-azido-4-nitroimidazole and tetrabutylammonium bromide is 10 :1~20:1, among which KHCO is selected as the base 3 、K 2 CO 3 Or KOH, the reaction time is 0.5~1h.

[0029] The substituted trinitrochlorobenzene in the second step is 2,4,6-trinitroch...

Embodiment 1

[0032] Add 0.15g (1.0mmol) of 2-azido-4-nitroimidazole to 15mL of isopropanol, add 0.10g (1mmol) of potassium bicarbonate and 0.03g (0.1mmol) of tetrabutyl bromide under stirring at room temperature Ammonium, stirred at room temperature for 0.5h. 0.25 g (1.0 mmol) of 2,4,6-trinitrochlorobenzene was added thereto, and the temperature was raised to 85° C. for 4 h. Cool to room temperature, filter, wash with 5 mL of methanol, and wash with a large amount of water to obtain a yellow solid 1-(2',4',6'-trinitrobenzene)-2-azido-4-nitroimidazole with a yield of 68%.

[0033] m.p.99~101℃;

[0034] 1 HNMR (Acetone- d 6 ,500MHz):8.43(s,1H),9.46(s,2H);

[0035] Elemental Analysis: C 9 h 3 N 9 o 8 , Calculated value: C, 29.60; H, 0.83; N, 34.52; Measured value: C, 29.63; H, 0.81; N, 34.51;

[0036] The compound has both nitroimidazole and polynitrobenzene structures, and has potential applications in the field of high-energy insensitive energetic materials. The theoretically calc...

Embodiment 2

[0038] Add 0.15g (1.0mmol) of 2-azido-4-nitroimidazole to 15mL of isopropanol, add 0.10g (1mmol) of potassium bicarbonate and 0.015g (0.05mmol) of tetrabutyl bromide under stirring at room temperature Ammonium, stirred at room temperature for 0.5h. 0.22g (0.9mmol) of 2,4,6-trinitrochlorobenzene was added thereto, and the temperature was raised to 85°C for 6h. Cool to room temperature, filter, wash with 5 mL of methanol, and wash with a large amount of water to obtain a yellow solid with a yield of 60%.

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Abstract

The present invention relates to polynitrobenzene-substituted nitroimidazole energetic compounds of general formula (I), wherein R represents H or NH2. The present invention also relates to the preparation method of the compound. The method is to realize the reaction of substituted polynitrochlorobenzene and 2-azido-4-nitroimidazole at 75-85°C, after the reaction is completed, cool to room temperature, filter, wash with methanol, wash with water, and dry to obtain. The energetic compound synthesized by the invention has novel structure, mild reaction conditions, no special device, simple process, safe and reliable production, simple post-processing of products, little harm to the environment, and meets the basic requirements of industrial scale-up production.

Description

technical field [0001] The invention belongs to the field of explosive synthesis, in particular to a novel high-energy insensitive explosive polynitrobenzene substituted nitroimidazole energetic compound and a preparation method thereof. Background technique [0002] In recent years, imidazole-based high-energy insensitive energetic compounds, especially 2,4-dinitroimidazole and 1-methyl-2,4,5-trinitroimidazole, have attracted much attention and can be widely used in explosives and propellants. The introduction of an azido group into nitroimidazole can greatly increase the nitrogen content, thereby increasing its energy and density. The introduction of polynitrophenyl groups into nitroimidazoles can further improve the explosive and thermal properties of energetic compounds. However, researchers at home and abroad rarely report on the synthesis of this class of compounds, and only a few documents have reported 2-azidoimidazoles, see (HammerlA., KlapmkeM.K., warchholdM., Ino...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/95
Inventor 刘祖亮侯可辉马丛明
Owner NANJING UNIV OF SCI & TECH
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