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Synthesis method of 2,6-diamido-3,5-dinitropyrazine-1-oxide

A technology of dinitropyrazine and diaminopyrazine, applied in the direction of organic chemistry and the like, can solve the problems of strong solvent volatility, difficult recovery, high price, etc., and achieves the advantages of cheap and environmentally friendly solvents, shortened synthesis process, and reduced manufacturing costs. Effect

Inactive Publication Date: 2015-06-10
INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Four steps are required to synthesize LLM-105, which requires the use of trifluoroacetic acid. The solvent is highly volatile, which is highly corrosive and irritating to the equipment and human body, and it is expensive and difficult to recycle, causing serious environmental pollution.
[0007] Another method uses a relatively large amount of pyromellitic anhydride to catalyze the oxidation of 2,6-diamino-3,5-dinitropyrazine to synthesize LLM-105. The synthesis process uses additional catalyst and a large amount. From the perspective of atom economy and The consideration of production cost is still not ideal, and the problem of catalyst treatment needs to be considered

Method used

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  • Synthesis method of 2,6-diamido-3,5-dinitropyrazine-1-oxide

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Embodiment 1

[0024] Embodiment 1. the synthesis of formula (III) compound 2,6-dichloropyrazine-1-oxide

[0025]

[0026] At 0°C, add 1.5g (10mmol) (II) into 10mL 95% concentrated sulfuric acid and stir, add 0.3g (1.1mmol) of potassium persulfate every 10 minutes, and add 3g (11mmol) of potassium persulfate in total. After the reaction system was raised to room temperature and stirred for 48 h, it was poured into ice, extracted with ethyl acetate (4×50 mL), washed with 10 mL of saturated brine, dried with 1.4 g (10 mmol) of anhydrous sodium sulfate, filtered, and evaporated to dryness to obtain the formula ( III) Compound 2,6-dichloropyrazine-1-oxide, yield 88.0%.

Embodiment 2

[0027] Embodiment 2. the synthesis of formula (III) compound 2,6-dichloropyrazine-1-oxide

[0028] At 0°C, 1.5 g (10 mmol) (II) was added into 10 mL of 95% concentrated sulfuric acid and stirred, and 3 g (11 mmol) of potassium persulfate was added rapidly. After the reaction system was raised to room temperature and stirred for 48 h, it was poured into ice, extracted with ethyl acetate (4×50 mL), washed with 10 mL of saturated brine, dried with 1.4 g (10 mmol) of anhydrous sodium sulfate, filtered, and evaporated to dryness to obtain the formula ( III) Compound 2,6-dichloropyrazine-1-oxide, yield 85.0%.

Embodiment 3

[0029] Embodiment 3. the synthesis of formula (III) compound 2,6-dichloropyrazine-1-oxide

[0030] At 0°C, add 1.5g (10mmol) (II) into 10mL 95% concentrated sulfuric acid and stir, add 0.3g (1.1mmol) of potassium persulfate every 10 minutes, and add 3g (11mmol) of potassium persulfate in total. After the reaction system was raised to room temperature and stirred for 24 hours, 0.6 g (2.2 mmol) of potassium persulfate was added, and the reaction was continued for 24 hours. Poured into ice, extracted with ethyl acetate (4×50mL), washed with 10mL of saturated brine, dried with 1.4g (10mmol) of anhydrous sodium sulfate, filtered, and evaporated to dryness to obtain formula (III) compound 2,6-dichloro Pyrazine-1-oxide, yield 91.0%.

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Abstract

The invention discloses a synthesis method of 2,6-diamido-3,5-dinitropyrazine-1-oxide. 2,6-dichloropyrazine serves as initial raw materials, potassium peroxodisulfate serves as oxidizing agents to carry out oxidizing reaction, the 2,6-dichloropyrazine is oxidized to obtain 2,6-dichloropyrazine1-oxide, then the 2,6-dichloropyrazine1-oxide is reacted in an ammonia solution to obtain 2,6-diamidopyrazine1-oxide, then the 2,6-diamidopyrazine1-oxide is subjected to a nitration reaction in nitro-sulfuric acid, and the 2,6-diamido-3,5-dinitropyrazine-1-oxide is obtained. Compared with an existing synthesis method, only three steps are needed for synthesizing LLM-105, the synthesis process is shortened, trifluoroacetic acid is not needed, solvents are cheap and environmentally friendly, and the manufacturing cost is reduced.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a synthesis method of 2,6-diamino-3,5-dinitropyrazine-1-oxide. Background technique [0002] Modern weapons require energetic materials to be as safe as possible while having as high an energy as possible. Insensitive high-energy materials with energy higher than that of 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) are pursued by people. 2,6-diamino-3,5-dinitropyrazine-4-oxide (LLM-105) is a breakthrough in the field of energetic material research1, its crystal density is high (1.913g / cm3), and its detonation velocity is 8560m˙s-1, the specific impulse is 2212.68N˙s / kg (7MPa), the energy is 20% higher than TATB, and the heat resistance is close to TATB (DSC exothermic peak is 354°C), which is better than most high-energy single-mass explosives , insensitive to impact, sparks, friction, and shock waves, and has good compatibility with copper, aluminum, stainless steel, and RDX. ...

Claims

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Application Information

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IPC IPC(8): C07D241/20
CPCC07D241/20
Inventor 张文全张庆华李金山
Owner INST OF CHEM MATERIAL CHINA ACADEMY OF ENG PHYSICS
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