5,5'-bis(3,5-dinitropyrazolyl)-2,2'-bi(1,3,4-oxadiazole) and synthetic method thereof

A technology of dinitropyrazolyl and dinitropyrazole, which is applied in the field of 5,5'-bis-2,2'-bis compound and its synthesis, can solve the problem of low HNS density and energy, and unsatisfactory energy density Issues such as the development direction of high-energy materials for energetic materials, to achieve the effect of excellent thermal stability

Active Publication Date: 2019-12-03
XIAN MODERN CHEM RES INST
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Problems solved by technology

[0004]The structural formula of HNS is shown in II. The heat-resistant mixed explosive based on HNS has excellent heat resistance at 210-260°C, but the density and energy of HNS are relatively high. Low, with a density of 1.74g·cm-3 and a detonation velocity of 7600m·s-1, the energy density cannot meet the development direction of high-energy energetic materials

Method used

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  • 5,5'-bis(3,5-dinitropyrazolyl)-2,2'-bi(1,3,4-oxadiazole) and synthetic method thereof
  • 5,5'-bis(3,5-dinitropyrazolyl)-2,2'-bi(1,3,4-oxadiazole) and synthetic method thereof
  • 5,5'-bis(3,5-dinitropyrazolyl)-2,2'-bi(1,3,4-oxadiazole) and synthetic method thereof

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Embodiment 1

[0025] (1) Synthesis of 4-carboxy-3,5-dinitropyrazole

[0026] Add sodium dichromate (17.88g, 0.06mol) to 4-methyl-3,5-dinitropyrazole (5.16g, 0.03mol) in concentrated sulfuric acid solution (98%, 90mL) in batches at room temperature , The reaction solution was stirred at room temperature for 12h. The reaction solution was poured into crushed ice, extracted three times with ethyl acetate, 150 mL each time, and the extract was dried and concentrated to obtain 4.08 g of a white solid, with a yield of 67.3%.

[0027] Characterization data:

[0028] 1 H NMR (400MHz, DMSO-d 6 ):δ11.67(br,1H).

[0029] 13 C NMR (100MHz, DMSO-d 6 ): δ161.2, 148.9, 108.6.

[0030] IR(ATR,cm -1 ):3166,2961,1737,1546,1488,1432,1333,1294,1257,1210,1120,1029,849,826,743.

[0031] MS(ESˉ):201.0[M-1]ˉ.

[0032] Elemental Analysis: C 4 h 2 N 4 o 6 , theoretical value C 23.77, H 1.00, N 27.73; measured value C 23.79, H 1.13, N 26.78.

[0033] The above data prove that the structure of the synth...

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Abstract

The invention discloses a 5,5'-bis(3,5-dinitropyrazolyl)-2,2'-bi(1,3,4-oxadiazole) compound. The compound has a structural formula represented by a formula I shown in the specification. The syntheticprocess comprises the following steps: (1) carrying out an oxidation reaction on 4-methyl-3,5-dinitropyrazole to obtain 4-carboxyl-3,5-dinitropyrazole; (2)reacting the 4-carboxyl-3,5-dinitropyrazole with benzotriazole, carrying out a reaction with thionyl chloride, and carrying out a reaction with hydrazine hydrate to generate 4-hydrazino-3,5-dinitropyrazole; (3) reacting the 4-hydrazino-3,5-dinitropyrazole with oxalyl chloride to generate N,N'-bis(3,5-dinitropyrazolyl)acethydrazide; and (4) carrying out a cyclization reaction on the N,N'-bis(3,5-dinitropyrazolyl)acethydrazide in fuming sulfuric acid to generate the 5,5'-bis(3,5-dinitropyrazolyl)-2,2'-bi(1,3,4-oxadiazole). The 5,5'-bis(3,5-dinitropyrazolyl)-2,2'-bi(1,3,4-oxadiazole) synthesized by the method has excellent thermal stability, and has potential to be used as a heat-resistant explosive.

Description

technical field [0001] The invention relates to a 5,5'-bis(3,5-dinitropyrazolyl)-2,2'-bis(1,3,4-oxadiazole) compound and a synthesis method thereof. The compound can be used as a heat-resistant explosive and belongs to the technical field of energetic materials. Background technique [0002] Heat-resistant explosives refer to a class of energetic materials that can maintain appropriate mechanical sensitivity and detonate reliably after being exposed to high-temperature environments for a long time. They have broad application requirements in the fields of nuclear weapons, space exploration, and deep well blasting. In order to prevent energetic materials from decomposing or detonating prematurely in the high-temperature environment, energetic materials are required to have a high melting point or decomposition temperature, low vapor pressure and good heat resistance. The research on heat-resistant explosives was originally to meet the special needs of space vehicles and spac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14C06B25/34
CPCC07D413/14C06B25/34
Inventor 李辉赵凤起杨燕京张建侃蒋周峰
Owner XIAN MODERN CHEM RES INST
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