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Furazane derivatives, preparation thereof and energetic compositions containing them

A composition and compound technology, applied in the direction of organic chemistry, etc., can solve the problems such as high-performance application of furoxan that have not been reported in the literature

Inactive Publication Date: 2009-11-11
GERAKL +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there is no literature report on the high-performance application of furazan in the field of propulsion and explosives

Method used

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  • Furazane derivatives, preparation thereof and energetic compositions containing them
  • Furazane derivatives, preparation thereof and energetic compositions containing them
  • Furazane derivatives, preparation thereof and energetic compositions containing them

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0125] Place 5 ml of anhydrous acetonitrile in a dry three-necked flask under argon, then add 32.6 mg (1.358 mmol) of NaH, followed by 154 mg (1.35 mmol) of 3-nitro-1,2,4-triazole , the mixture was stirred at room temperature for 15 minutes to complete the formation of the nitrotriazolium anion. Dinitrofurazanyl ether (300 mg, 1.23 mmol) was added in one portion and the medium was stirred at room temperature for 20 hours. 20 ml of water are then added. The product was extracted with chloroform, the chloroform extracts were dried over magnesium sulfate, filtered and evaporated. The product was purified on silica gel. 194 mg of pure product were thus isolated (63% yield).

[0126] The expanded formula of the product and the physicochemical evidence for its structure ( 1 H. 13 C and 14 The results of the N NMR) analysis are shown in the first column of Table 1 below.

Embodiment 2

[0128] Put 5 ml of anhydrous acetonitrile into a dry three-necked flask under argon, then add 165.4 mg (1.03 mmol) of dinitrofurazan, followed by 117.1 mg (1.008 mmol) of 3-nitro-1,2, 4-triazole. 3 ml of a solution of pyridine (92 mg) diluted in acetonitrile are added dropwise to the reaction medium at 20°C. The medium is stirred at room temperature for 5 hours. 20 ml of water are then added. The product was extracted with chloroform, the chloroform extracts were dried over magnesium sulfate, filtered and evaporated. The product was purified on silica gel. 56 mg of pure product were thus isolated (24% yield relative to dinitrofurazan).

[0129] The product obtained is identical to that obtained in Example 1 (see first column of Table 1 below).

Embodiment 3

[0131] Add 2.05g of aminonitrofurazan (15mmol) to a solution of concentrated sulfuric acid (12ml) and concentrated phosphoric acid (12ml) at 0°C-5°C. Sodium nitrite (1.10 g, 15.8 mmol) was added in small portions. 1.64 g of nitroglycetaldoxime are added in one portion to the reaction medium. The reaction medium is stirred for 1 hour and then poured onto 40 g of ice. Separation by precipitation was allowed to occur for several hours, then the intermediate was filtered off, rinsed with water, and subsequently washed with P 2 o 5 dry. 0.46 g of the previously obtained dry product was put into 15 ml of distilled water. 0.75 ml of acetic anhydride was slowly flowed in at 20°C while maintaining the pH at 7 by adding 5% sodium hydroxide. At the end of the addition, the medium is acidified with 10% HCl solution. The product was extracted with ethyl acetate, the ethyl acetate extracts were dried over magnesium sulfate, filtered and evaporated. The product was purified on silica ...

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PUM

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Abstract

The invention relates to compounds of the formula (I) in which Het is an azolyl, nitroazolyl or tetrazolyl radical, with the exception of 3-nitro-4-(4-nitro-l,2,3-triazol-1-yl)furazane. The invention also relates to the preparation of said compounds, and to energetic compositions containing at least one compound selected from the compounds of the formula (I) and the 3-nitro-4-(4-nitro-l,2,3-triazol-1-yl)furazane.

Description

technical field [0001] The subject of the present invention is: [0002] - Novel heterocyclic molecules: novel compounds derived from furazan, obtained by coupling furazan with azole; [0003] - preparation of said novel molecule; and [0004] - Novel energetic compositions. [0005] These novel compounds (these novel molecules) are particularly advantageous in that they simultaneously have high energy and low fragility; also in that they conform to the following specifications particularly advantageously: [0006] - high energetic performance characteristics, [0007] - low sensitivity, and [0008] - High thermal stability. Background technique [0009] Furazan constitutes a family of nitrogen-containing heterocycles with high enthalpy of formation due to high aromatic ring energy. Their energetic potential as well as their high thermal stability make them favorable and promising molecules in the field of energetic materials. [0010] The first document, US Patent N...

Claims

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Application Information

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IPC IPC(8): C07D413/04C07D413/14
CPCC07D413/04C07D413/14
Inventor 盖伊·雅各布格雷瓜尔·赫维盖伊·卡尼翁弗雷德里克·阿尔瓦雷斯
Owner GERAKL
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