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Compound containing tetrazine polynitrobenzene and synthesis method thereof

A technology of tetrazine trinitrobenzene and a synthesis method, which is applied to the compound containing tetrazine trinitrobenzene and the synthesis field thereof, can solve the problems of unstable energy-containing groups, difficulty in large-scale synthesis, and high production costs, and achieves the Easy to separate and purify, easy to synthesize in large quantities, and low cost

Inactive Publication Date: 2009-08-26
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The disadvantages of these compounds are that some contain low sensitivity and poor thermal stability, such as very unstable energetic groups such as azide; Difficult to large-scale synthesis, high production cost, difficult to realize application

Method used

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  • Compound containing tetrazine polynitrobenzene and synthesis method thereof
  • Compound containing tetrazine polynitrobenzene and synthesis method thereof
  • Compound containing tetrazine polynitrobenzene and synthesis method thereof

Examples

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Effect test

Embodiment 1

[0030] 3-imino-(2,4,6-trinitrobenzene)-6(3,5-dimethylpyrazole)-1,2,4,5-tetrazine synthesis method, the synthesis route is shown in Figure 1 , Dissolve 1.5mmol chlorotrinitrobenzene and 1mmol 3-amino-6(3,5-dimethylpyrazole)-1,2,4,5-tetrazine in 20mL of acetonitrile, heat at 80°C Reflux for 6 hours, stop the reaction and cool down to 20°C, concentrate by rotary evaporation, and purify by column chromatography to obtain a red precipitate. Dry in a water bath oven at 40 °C for over 1 hour. The product was dissolved in a mixed solvent of ethyl acetate and acetone with a molar ratio of 2, and slowly volatilized to obtain a red single crystal with a yield of 75% (based on chlorotrinitrobenzene). For the characterization, please see the accompanying drawing 2 for the infrared spectrum, the accompanying drawing 3 for the ultraviolet-visible spectrum, and the accompanying drawing 4 for the single crystal structure spectrum.

Embodiment 2

[0032] 3-imino-(2,4,6-trinitrobenzene)-6(3,5-dimethylpyrazole)-1,2,4,5-tetrazine synthesis method, the synthesis route is shown in Figure 1 , Dissolve 1.5mmol bromotrinitrobenzene and 1mmol 3-amino-6(3,5-dimethylpyrazole)-1,2,4,5-tetrazine in 20mL of acetonitrile, heat at 80°C Reflux for 2 hours, stop the reaction and lower the temperature to 20°C, concentrate by rotary evaporation, and purify by column chromatography to obtain a red precipitate. Dry in a water bath oven at 40 °C for over 1 hour. The product was dissolved in a mixed solvent of ethyl acetate and acetone with a molar ratio of 2, and slowly volatilized to obtain a red single crystal with a yield of 85% (based on bromotrinitrobenzene). For the characterization, please see the accompanying drawing 2 for the infrared spectrum, the accompanying drawing 3 for the ultraviolet-visible spectrum, and the accompanying drawing 4 for the single crystal structure spectrum.

Embodiment 3

[0034] 3-imino-(2,4,6-trinitrobenzene)-6(3,5-dimethylpyrazole)-1,2,4,5-tetrazine synthesis method, the synthesis route is shown in Figure 1 , 1.5mmol chlorotrinitrobenzene and 1mmol 3-amino-6(3,5-dimethylpyrazole)-1,2,4,5-tetrazine were dissolved in 20mL of N,N-dimethyl Dimethyl formamide, heated to reflux at 80°C for 4h, cooled to 20°C after stopping the reaction, extracted with ethyl acetate (3×20mL) and water, concentrated by rotary evaporation, and purified by column chromatography to obtain a red precipitate. Dry in a water bath oven at 40 °C for over 1 hour. The product was dissolved in a mixed solvent of ethyl acetate and acetone with a molar ratio of 2, and slowly volatilized to obtain a red single crystal with a yield of 78% (based on chlorotrinitrobenzene). For the characterization, please see the accompanying drawing 2 for the infrared spectrum, the accompanying drawing 3 for the ultraviolet-visible spectrum, and the accompanying drawing 4 for the single crystal st...

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Abstract

The invention relates to a compound containing trinitrobenzene tetrazine and a synthesis method thereof. The nucleophilic substitution reaction between them synthesized a nitrogen-rich compound containing tetrazine trinitrobenzene, and the organic solvent in the liquid phase reaction was acetonitrile, acetone, 2-butanone, dioxane , tetrahydrofuran, nitrogen nitrogen dimethylformamide, ethanol or methanol, the product is a mixed solvent of ethyl acetate and acetone through a solvent with appropriate polarity, and a single crystal is cultivated. The synthesis method is simple and does not need nitrogen protection. It is suitable for many A kind of halogenated nitrobenzene and nitrogen-rich tetrazine molecules are used to synthesize insensitive, high-calorie energetic compounds, which are easy to produce in large quantities, waste liquid can be recycled, save costs, and are beneficial to environmental protection.

Description

technical field [0001] The invention relates to a compound containing tetrazine trinitrobenzene and a synthesis method thereof, belonging to the field of explosive synthesis. Background technique [0002] Traditional organic energetic compounds generally contain nitro groups in their molecular structures, and their enthalpy of formation is generally low, generally negative or close to zero, and the energy released mainly comes from the formation of CO 2 and H 2 O exothermic process. As a class of energetic materials with unique properties, the energy of nitrogen-rich energetic materials mainly depends on the high formation enthalpy of the molecule itself, rather than the oxidative cleavage of C-H bonds. Nitrogen-rich compound molecules contain a large number of N-N and C-N bonds, so they have high positive enthalpy of formation. At the same time, because the carbon and hydrogen content in the compound is relatively low, it shows a double positive effect, which can not only...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/04C06B25/04C07D231/00C07D257/00
Inventor 潘万龙胡长文
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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