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Compound and energetic ion salts thereof

A technology for compounds and ionic salts, applied in the field of compounds and their energetic ionic salts, achieves the effects of good thermal stability, high yield and mild conditions

Active Publication Date: 2018-10-23
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is no acidic hydrogen in the furoxan ring, which makes them unable to be directly used as Bronsted acids, that is, they cannot react with Lewis bases, so they cannot be directly used as anions of energetic ion salts

Method used

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  • Compound and energetic ion salts thereof
  • Compound and energetic ion salts thereof
  • Compound and energetic ion salts thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Preparation of 3,3'-azobis[5-amino-1,2,4-oxadiazol-3-yl-]-1,2,5-oxadiazole, whose structure is as follows:

[0033]

[0034] Compound 1 (4 g, 23.8 mmol) was added to a mixture of acetonitrile (80 ml) and concentrated hydrochloric acid (50 ml) at room temperature. After mixing evenly, slowly add saturated potassium permanganate (3.76g, 23.8mmol) aqueous solution. After the addition, continue stirring for 15min, add water (30ml) for dilution, and slowly add 5% hydrogen peroxide until the solution becomes colorless. After filtering and washing with water, Compound 2 (3.5 g, 10.5 mol) was obtained with a yield of 87.5%.

[0035] Decomposition temperature>250℃. 1 H NMR (500MHz, d6-DMSO): δ8.37ppm. 13 C NMR (500MHz, d6-DMSO): δ173.66, 163.11, 158.33, 142.52ppm.

Embodiment 2

[0037] Preparation of 3,3'-azobis[5-amino-1,2,4-oxadiazol-3-yl-]-1,2,5-oxadiazole, whose structure is as follows:

[0038]

[0039] Compound 2 was oxidized with a mixture of acetic anhydride and 100 wt% nitric acid (mass ratio 2:1) at -20°C-10°C to obtain compound 3.

[0040] 1 H NMR(500MHz,d6-DMSO):δ8.42ppm(s,2H).IR(KBr):υ3450 3280 1770 16701610 1560 1490 1340 1240 1170 1030 973 895 811 764 615 526cm -1 ; Elemental analysis: C 28.83, H 0.92, N 46.26%.

[0041] After differential scanning calorimetry test, the decomposition temperature of compound 3 is 270°C; the measured density is 1.80g / cm -3 Calculated by the equibond equation, the enthalpy of formation is 942.6kJ / mol; calculated by Explo5 software, the detonation velocity is 8419m / s, and the detonation pressure is 29.6GPa; after the sensitivity measurement, the impact sensitivity is 26J, and the friction sensitivity is 240N.

Embodiment 3

[0043] Preparation of 3,3'-azobis[1,2,4-oxadiazol-5-one-3-yl-]-1,2,5-oxadiazole, whose structure is as follows:

[0044]

[0045]At 0°C, 2 (3.32g, 10mmol) was slowly added to a mixture of acetic anhydride (10ml) and 100% nitric acid (5ml). After reacting at 0°C for 30 minutes, the reaction temperature was raised to room temperature, and the reaction was stopped until solid was precipitated with vigorous stirring. The suspension was poured into ice water, and a large amount of insoluble matter precipitated out. After filtering and washing with water, 4 (1.8 g, 5.4 mmol) was obtained with a yield of 53.9%.

[0046] 1 H NMR (500MHz, d6-DMSO): No peak. 13 C NMR (500MHz, D6-DMSO): Δ162.18,159.52,148.26,139.89ppm.ir (KBR): υ2990 2820 2700 1800 1760 1540 1430 1310 12501140 943 906 873 7986868 6186cm 6186cm 6186C -1 .

[0047] After differential scanning calorimetry test, the decomposition temperature of compound 4 is 322°C; the measured density is 1.89g / cm -3 Calculated by t...

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Abstract

The present invention relates to 3,3'-azobis[1,2,4-oxadiazole-5-one-3-yl]-1,2,5-oxadiazole and energetic ion salts thereof, and belongs to the field of synthesis. 4-[5-amino-1,2,4-oxadiazole-3-yl-]-3-amino-1,2,5-oxadiazole is coupled by an aqueous solution of potassium permanganate to obtain 3,3'-azobis[5-amino-1,2,4-oxadiazole-3-yl-]-1,2,5-oxadiazole (compound 2), the compound 2 undergoes an oxidation reaction by a mixed solution of acetic anhydride and 100 wt% nitric acid (with a mass ratio of 2:1) to obtain 3,3'-azobis[1,2,4-oxadiazole-5-one-3-yl-]-1,2,5-oxadiazole, and the 3,3'-azobis[1,2,4-oxadiazole-5-one-3-yl-]-1,2,5-oxadiazole and an alkaline compound undergo a neutralization reaction to obtain the corresponding energetic ion salts. The above synthesis method has the advantages ofsafe and reasonable process, short reaction time, high yield, low production cost and basically no three wastes.

Description

technical field [0001] The present invention relates to a compound and its energetic ion salt, in particular to a 3,3'-azobis[1,2,4-oxadiazol-5-one-3-yl-]-1,2, The synthesis of 5-oxadiazole and the preparation method of its energetic ion salt belong to the technical field of energetic material synthesis. Background technique [0002] High energy density materials are compounds used as high energy components in explosives, propellants and pyrotechnics. These materials are used in all strategic and tactical weapon systems and are used in equipment for all arms. The performance improvement of high energy density materials (HEDM) will have a great impact on the performance of the weapon system, thereby significantly improving the effectiveness of the weapon system. For example, a 10% increase in the range of submarine-launched strategic missiles will increase the hidden sea area of ​​submarines by millions of square miles, thereby greatly improving the survivability of strateg...

Claims

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Application Information

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IPC IPC(8): C07D271/08C07D249/14C06B25/34
CPCC06B25/34C07D249/14C07D271/08
Inventor 林秋汉孙琦陆明王鹏程
Owner NANJING UNIV OF SCI & TECH
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