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Energetic salt based on 2, 4, 6-trinitro-1, 3-di(2', 4', 6'-trinitro-3'-hydroxyl styryl) benzene, synthetic method and application thereof

A technology of hydroxystyrene and synthetic methods, which is applied in the direction of preparation of amino compounds, chemical instruments and methods, aromatic nitration compositions, etc., can solve the problems of poor chemical and physical stability and low energy, and achieve improved heat resistance, Simple operation and high productivity

Active Publication Date: 2014-08-20
NANJING UNIV OF SCI & TECH
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  • Claims
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AI Technical Summary

Problems solved by technology

[0004] At present, there is an urgent need for energetic materials with excellent comprehensive properties such as high energy, insensitivity, stability, and non-toxicity. However, these properties are always contradictory to some extent. Materials with good stability and low sensitivity usually have low energy. When the energy is higher, the chemical and physical stability will become worse

Method used

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  • Energetic salt based on 2, 4, 6-trinitro-1, 3-di(2', 4', 6'-trinitro-3'-hydroxyl styryl) benzene, synthetic method and application thereof
  • Energetic salt based on 2, 4, 6-trinitro-1, 3-di(2', 4', 6'-trinitro-3'-hydroxyl styryl) benzene, synthetic method and application thereof
  • Energetic salt based on 2, 4, 6-trinitro-1, 3-di(2', 4', 6'-trinitro-3'-hydroxyl styryl) benzene, synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Mix and dissolve 2,4,6-trinitro-m-xylene (1.21g, 5.0mmol) and m-hydroxybenzaldehyde (1.28g, 10.5mmol) in 25mL of benzene and 25mL of dioxane, add pyridine (0.08g ) as a catalyst, and install a water separator at the same time. Slowly raise the temperature to reflux, and control the reflux rate to about 100 drops / min. The progress of the reaction was monitored by TLC and stopped when the reaction was almost complete (10 h). Part of the solvent (about 40mL) was removed, and the concentrated solution was separated by column chromatography. The developer ratio (n-hexane / ethyl acetate=5:1) was used to obtain 2.04g of a bright yellow solid with a yield of 91%.

[0059] Bright yellow solid, melting point 194-196°C, IR (v, cm -1 ): 3400, 3095, 1635, 1609, 1586, 1514, 1395, 1323, 972; 1 H NMR (500MHz, DMSO-d 6 ), δ9.60(s, 2H), 9.00(s, 1H), 7.29(d, J=16.60Hz, 2H), 7.23(t, J=7.85Hz, 2H), 6.98(d, J=7.70Hz , 2H), 6.94(s, 2H), 6.81-6.78(dd, J 1 =8.10Hz,J 2 =1.75Hz, 2H), 6.78(d...

Embodiment 2

[0068] Mix and dissolve 2,4,6-trinitro-m-xylene (1.21g, 5.0mmol) and m-hydroxybenzaldehyde (1.28g, 10.5mmol) in 25mL of benzene and 25mL of dioxane, add morpholine (0.08 g) As a catalyst, install a water separator at the same time. Slowly raise the temperature to reflux, and control the reflux rate to about 100 drops / min. The progress of the reaction was monitored by TLC and stopped when the reaction was almost complete (10 h). Part of the solvent (approximately 40 mL) was removed, and the concentrated solution was separated by column chromatography. The developer ratio (n-hexane / ethyl acetate=5:1) was used to obtain 1.84 g of a bright yellow solid with a yield of 84%.

[0069] The following synthesis method follows the steps of Reference Example 1.

Embodiment 3

[0071] Mix and dissolve 2,4,6-trinitro-m-xylene (1.21g, 5.0mmol) and m-hydroxybenzaldehyde (1.28g, 10.5mmol) in 25mL of benzene and 25mL of dioxane, add morpholine (0.08 g) As a catalyst, install a water separator at the same time. Slowly raise the temperature to reflux, and control the reflux rate to about 100 drops / min. The progress of the reaction was monitored by TLC and stopped when the reaction was almost complete (10 h). Part of the solvent (about 40 mL) was removed, and the concentrated solution was separated by column chromatography. The developer ratio (n-hexane / ethyl acetate=5:1) was used to obtain 1.77 g of a bright yellow solid with a yield of 81%.

[0072] The following synthesis method follows the steps of Reference Example 1.

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Abstract

The invention discloses an energetic salt based on a compound 2, 4, 6-trinitro-1, 3-di(2', 4', 6'-trinitro-3'-hydroxyl styryl) benzene, and a synthetic method thereof. The chemical structure of the 2, 4, 6-trinitro-1, 3-di(2', 4', 6'-trinitro-3'-hydroxyl styryl) benzene is characterized in that 3 nitro groups are located on 2, 4 and 6 sites on an intermediate benzene ring of 1, 3-distyryl benzene, a nitro group is respectively connected to 2, 4, 6 sites on benzene rings on both sides of the 1, 3-distyryl benzene, and a hydroxyl is further connected to a meta-position. As the coupling constant of distyryl double bonds in a nuclear magnetic spectrogram is about 16.60Hz, the double bonds are in a trans-structure. As the compound has a structure similar to picric acid, a series of stable energetic salts are generated by hydroxyl functional groups and nitrogenous positive ions. The compound is synthesized by adopting a four-step reaction. The method is simple to operate, mild in reaction condition and relatively high in yield. The compound has good heat-resistant performance and detonation performance and belongs to the field of energetic materials.

Description

technical field [0001] The present invention relates to a series of compounds, preparation methods and applications thereof, in particular to a compound based on 2,4,6-trinitro-1,3-bis(2',4',6'-trinitro-3'- An energetic salt of hydroxystyryl)benzene and a synthesis method thereof, the compound is applied in the field of energetic materials. Background technique [0002] Polynitrostilbenes (Polynitrostilbenes) is a very important chemical intermediate, which can be widely used in the fields of nonlinear optics and high-energy heat-resistant energetic materials. For example, it can be used to synthesize new ligands for nonlinear optical materials and heat-resistant explosives for military and civilian use. Among them, hexanitrostilbene (HNS) with outstanding performance belongs to one of the polynitrostilbene compounds. It is a yellow crystal with a melting point as high as 317°C. It is a heat-resistant explosive with good physical and chemical properties. Stability, low mec...

Claims

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Application Information

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IPC IPC(8): C07C205/24C07C201/12C07C279/02C07C277/00C07C281/16C07C275/02C07C273/02C07C211/04C07C209/00C06B25/04
Inventor 彭新华徐俊辉魏建平高曦
Owner NANJING UNIV OF SCI & TECH
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