Compound containing tetrazine polynitrobenzene and synthesis method thereof

A synthesis method and technology for nitrobenzene are applied in the directions of aromatic nitration compositions, organic chemistry, etc., and can solve the problems of difficult large-scale synthesis, high production cost, poor thermal stability, etc., and achieve easy mass synthesis, low cost, and reduced Sensitivity effect

Inactive Publication Date: 2007-02-28
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Abstract
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  • Claims
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Problems solved by technology

[0004] The disadvantages of these compounds are that some have low sensitivity and poor thermal stability, such as very unstable energetic groups such as azide, or the synthesis method needs to go through multi-step reactions, many side reactions, harsh conditions, quite complicated, difficult to realize, and more Difficult to large-scale synthesis, high production cost, difficult to realize application

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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

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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 of chlorotrinitrobenzene and 1mmol of 3-amino-6(3,5-dimethylpyrazole)-1,2,4,5-tetrazine in 20mL of acetonitrile, heat to reflux at 80°C After 6h, 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 of bromotrinitrobenzene and 1mmol of 3-amino-6(3,5-dimethylpyrazole)-1,2,4,5-tetrazine in 20mL of acetonitrile, heat to reflux at 80°C After 2h, the reaction was stopped and the temperature was lowered to 20°C, 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 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 , Dissolve 1.5mmol of chlorotrinitrobenzene and 1mmol of 3-amino-6(3,5-dimethylpyrazole)-1,2,4,5-tetrazine in 20mL of N,N-dimethyl Formamide was heated at 80°C and refluxed for 4 hours. After the reaction was stopped, the temperature was lowered to 20°C, extracted with ethyl acetate (3×20 mL) 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...

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Abstract

The invention discloses a compound with tetrazine multi-nitrobenzol with molecular structural formula as formula I and synthesizing method, which is characterized by the following: realizing the synthesis of tetrazine molecular with rich nitrogen and multinitrobenzol compound; adopting organic solvent in the liquid phase reaction as large-polarity solvent; culturing monocrystalline through fitful polarity solvent.

Description

technical field [0001] The invention relates to a compound containing tetrazine polynitrobenzene 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 onl...

Claims

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Application Information

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Patent Type & Authority Applications(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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