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A kind of high-energy insensitive energetic compound and its synthesis method

A synthesis method and compound technology, applied in the direction of nitrated acyclic/alicyclic/heterocyclic amine explosive composition, organic chemistry, etc., can solve the problems of high toxicity, complicated preparation steps, safety and environmental protection, etc. Achieve the effect of good thermal stability and simple reaction steps

Active Publication Date: 2020-12-04
NANJING UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] Although the measured sensitivity of the prepared 4-nitro-5-(5-nitro-1,2,4-triazol-3-yl)-1,2,3-2H-triazole is relatively low at 24J, but The preparation steps of its precursor 4-nitro-2H-1,2,4-triazole-5-carboxylate are complex and require the use of highly toxic and explosive NaN 3 , safety and environmental protection are difficult to meet the requirements

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  • A kind of high-energy insensitive energetic compound and its synthesis method
  • A kind of high-energy insensitive energetic compound and its synthesis method
  • A kind of high-energy insensitive energetic compound and its synthesis method

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preparation example Construction

[0031] The preparation steps of target product of the present invention are as follows:

[0032] Ⅰ. Add metal sodium to the anhydrous methanol solution several times at 0°C to prepare the sodium methoxide solution, then slowly add aminoguanidine sulfate in batches, and finally add 4-nitro-1H-pyrazole-3,5- Dimethyl diformate (1) was added to the mixed solution several times, after the addition, the temperature was raised to reflux for reaction, after the reaction was finished, it was cooled and filtered, and the filter cake was washed several times with methanol solution, the combined filtrate was concentrated under reduced pressure and poured into ice water. Adjust the pH to about 5 to have solid precipitation, filter, wash, and dry to obtain orange solid 4-nitro-3,5-bis(1H-1,2,4-triazole-3-amino)-1H-pyrazole ( 2), wherein the molar ratio of sodium metal:aminoguanidine sulfate:4-nitro-1H-pyrazole-3,5-dicarboxylic acid dimethyl ester=5:5:1;

[0033] Ⅱ. At 0°C, slowly add 4-nit...

Embodiment 1

[0035] a) Synthesis of intermediate 4-nitro-3,5-bis(1H-1,2,4-triazole-3-amino)-1H-pyrazole

[0036] Sodium metal (1.20 g, 52.2 mmol) was dissolved in 50 mL of methanol at 0° C., and aminoguanidine sulfate (12.20 g, 50.0 mmol) was slowly added thereto in several portions. After the addition, take dimethyl 4-nitro-1H-pyrazole-3,5-dicarboxylate (2.30g, 10.0mmol) and slowly add it to the solution, heat to reflux for 24-48h, cool to room temperature, filter, and wash with methanol Wash the filter cake several times, combine the filtrate, concentrate under reduced pressure to 20 mL, add 50 mL of ice water to it, add concentrated HCl dropwise to adjust the pH to about 5, filter, and dry to obtain orange-yellow solid 4-nitro-3,5-bis (1H-1,2,4-triazole-3-amino)-1H-pyrazole 2.36g, yield 85.2%.

[0037] Attachment: Intermediate decomposition temperature: 353.6°C; 1 H NMR (300MHz, DMSO-d 6 ): δ=6.26(s,4H), 3.59(br)ppm; 13 C NMR (125MHz, DMSO-d 6 ): δ=161,155,147,137ppm; mass spectrum...

Embodiment 2

[0044] At 0° C., sodium metal (1.40 g, 60.8 mmol) was dissolved in 50 mL of methanol, and aminoguanidine sulfate (15.00 g, 61.2 mmol) was slowly added thereto in several portions. After the addition, dimethyl 4-nitro-1H-pyrazole-3,5-dicarboxylate (2.30g, 100.0mmol) was slowly added to the solution, heated to reflux for 24-48h, cooled to room temperature, filtered, and washed with methanol Wash the filter cake several times, combine the filtrate, concentrate under reduced pressure to 20 mL, add 50 mL of ice water to it, add concentrated HCl dropwise to adjust the pH to about 5, filter, and dry to obtain orange-yellow solid 4-nitro-3,5-bis (1H-1,2,4-triazole-3-amino)-1H-pyrazole 2.25 g, yield 81.2%.

[0045] Take 20mL30%H 2 o 2 Put it into a 50mL three-necked bottle, set the low temperature bath to -20°C, and slowly add 15mL of 98% H 2 SO 4 , the temperature is controlled below 0°C during the dropwise addition. After the dropwise addition is completed, add 4-nitro-3,5-bis(1H...

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Abstract

The invention discloses a high-energy insensitivity energetic compound and a synthesis method thereof. The method comprises the steps 4-nitro-1H-pyrazole-3,5-dicarboxylic acid dimethyl ester is takenas raw material, and an intermediate object is obtained under the catalytic action of metal sodium through a one-pot synthesis method with aminoguanidine hemisulfate salt; the intermediate body is oxidized in an oxidation system to obtain a target product. The method has the advantages that the method is simple, the reaction steps are less, the yield is higher, the separation method is simple, thepractical measuring density of an ultimate product 4-nitro-3,5-bis(1H-1,2,4-triazole-3-nitro)-1H-pyrazole reaches 1.865g cm<3>, the theoretical detonation velocity of the ultimate product predicted by a BKW state equation is 8747m / s, the theoretical detonation pressure is 33.0 GPa, which are close to cyclotrimethylene trinitramine (RDX, detonation velocity:8841 m / s, detonation pressure 34.9 GPa),the testing impacting insensitivity is 30J, which is lower than the RDX (7.4J) and 2, 4, 6-trinitrotoluene TNT (15J), and the compound has wider application prospects in the field of high-energy insensitivity energetic materials.

Description

technical field [0001] The invention relates to the field of organic energetic materials, in particular to a high energy density insensitive energetic compound and a synthesis method thereof. Background technique [0002] Energetic materials are the key material basis for the development of advanced weapons and equipment. They are the power energy for the launch of guns and projectiles and the propulsion of rockets and missiles. They are the powerful energy for the destruction of warheads. The power energy of capital adjustment and separation device. With the rapid development of modern high-performance weapon systems, the safety requirements for energetic material charges under various conditions are becoming increasingly urgent. Although energetic materials have been developed for decades, the contradiction between energy and safety is still a problem waiting to be solved. High-nitrogen energetic compounds contain a large number of C-N, C=N, N-N and N=N bonds in their st...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/14C06B25/34
CPCC06B25/34C07D403/14
Inventor 杨红伟徐旻贤熊华林程广斌
Owner NANJING UNIV OF SCI & TECH
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