Methylene-bridged nitrogen-rich heterocyclic compound and derivatives thereof, and preparation methods thereof

A technology of heterocyclic compounds and methylene bridges, applied in the field of preparation, methylene bridged nitrogen-rich heterocyclic compounds and their derivatives, can solve the problems of high energy and low, difficult to achieve, and mechanical sensitivity cannot be satisfied at the same time, To achieve the effect of good stability and high energy

Inactive Publication Date: 2020-12-01
NORTHWEST UNIV(CN)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, even after decades of efforts, the method of finding a balance between energy characteristics and stability is still elusive, that is, high energy and low mechanical sensitivity cannot simultaneously satisfy the

Method used

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  • Methylene-bridged nitrogen-rich heterocyclic compound and derivatives thereof, and preparation methods thereof
  • Methylene-bridged nitrogen-rich heterocyclic compound and derivatives thereof, and preparation methods thereof
  • Methylene-bridged nitrogen-rich heterocyclic compound and derivatives thereof, and preparation methods thereof

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preparation example Construction

[0033] A method for preparing a methylene bridged nitrogen-rich heterocyclic compound of the present invention comprises the following steps:

[0034] Step 1: Dissolve 2mmol of 1-acetonitrile 5-aminotetrazole in 10ml of acetonitrile, add 2mmol of hydroxylamine solution dropwise at -5~5°C, transfer to room temperature for reaction for 10~14h after the dropwise addition, and the reaction ends Afterwards, the precipitate was filtered off to obtain compound 1, namely methylene-bridged 5-aminotetrazole and 5-amino-1,2,4-oxadiazole.

[0035] The structural formula of compound 1 is:

[0036]

[0037] Step 2: Dissolve 2 mmol of compound 1 in 10 ml of ethanol, add 2 mmol of sodium bicarbonate and stir for 5 min to form a suspension, and add 2.2 mmol of cyanogen bromide to the suspension. Stir at room temperature for 10-14h. The obtained solid was filtered, rinsed with deionized water, and dried in air to obtain a white solid, which was designated as compound 2.

[0038] The struc...

Embodiment 1

[0052] Step 1: Dissolve 2mmol of 1-acetonitrile 5-aminotetrazole in 10ml of acetonitrile, add 2mmol of hydroxylamine solution dropwise at 0°C, transfer to room temperature to react for 12h after the dropwise addition, and filter out the precipitate after the reaction. Compound 1 was obtained.

[0053] Step 2: Dissolve 2 mmol of compound 1 in 10 ml of ethanol, add 2 mmol of solid sodium bicarbonate and stir for 5 min to form a suspension, and add 2.2 mmol of cyanogen bromide to the suspension. Stir at room temperature for 12h. The resulting solid was filtered, rinsed with deionized water, and dried in air to obtain a white solid compound 2 with a yield of 90%, constant volume heat of combustion Qv=8000J / g, IS=40J, FS=360N, indicating high energy and stability it is good.

[0054] Step 3: Take 1ml of fuming nitric acid and stir at 0°C for 10 minutes, take 0.142g of compound 1 and dissolve in fuming nitric acid at 0°C, slowly return to room temperature, and oxidize for 8 hours ...

Embodiment 2

[0062] Step 1: Dissolve 2mmol of 1-acetonitrile 5-aminotetrazole in 10ml of acetonitrile, add 2mmol of hydroxylamine solution dropwise at -5°C, transfer to room temperature to react for 14h after the dropwise addition, and filter out the precipitate after the reaction , to obtain compound 1.

[0063] Step 2: Dissolve 2 mmol of compound 1 in 10 ml of ethanol, add 2 mmol of solid sodium bicarbonate and stir for 5 min to form a suspension, and add 2.2 mmol of cyanogen bromide to the suspension. Stir at room temperature for 10 h. The resulting solid was filtered, rinsed with deionized water, and dried in air to obtain compound 2 as a white solid.

[0064] Step 3: Take 1ml of fuming nitric acid and stir at -5°C for 10min, take 0.142g of compound 1 and dissolve in fuming nitric acid at -5°C, slowly return to room temperature, and oxidize for 9h while stirring. After the reaction was completed, the reaction solution was dropped drop by drop on ice, and a white product was precipita...

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Abstract

The invention relates to a methylene-bridged nitrogen-rich heterocyclic compound and derivatives thereof, and preparation methods thereof. The preparation method of the compound comprises the following steps: adding a hydroxylamine solution into an acetonitrile solution of 1-acetonitrile-5-aminotetrazole at low temperature, reacting at room temperature, separating the product to obtain a precipitate, dispersing the precipitate, sodium bicarbonate and cyanogen bromide into ethanol, reacting at room temperature for 10-14 hours, and separating and drying the product to obtain the methylene-bridged nitrogen-rich heterocyclic compound. The preparation method of the derivatives comprises the following steps: dissolving the methylene-bridged nitrogen-rich heterocyclic compound in fuming nitric acid at -5-5 DEG C at room temperature, reacting at room temperature to obtain a reaction solution, dripping the reaction solution on ice, and separating out a methylene-bridged nitrogen-rich ammonium nitrate compound on the ice; and dissolving a methylene-bridged nitrogen-rich ammonium nitrate compound, respectively adding organic alkali or metal alkali, reacting the obtained system at -5-5 DEG C for 10-30 minutes, finally reacting at room temperature for 30-60 minutes, filtering the product, and drying to obtain the non-metal salt and metal salt of the methylene-bridged nitrogen-rich ammoniumnitrate compound.

Description

technical field [0001] The invention relates to the technical field of energetic materials, in particular to a methylene bridged nitrogen-rich heterocyclic compound and its derivatives, and a preparation method. Background technique [0002] Nitrogen-rich heterocyclic compounds are a class of organic compounds that are widely used in the fields of medicine, pesticides, dyes and energetic materials. Nitrogen heterocyclic compounds have developed into the mainstream of new pesticide research and development, and a variety of fungicides, herbicides and insecticides have been developed. Nitrocyclic pesticides have high efficacy, which can reduce the cost of use and reduce the impact on the environment. Nitrogen-heterocyclic pesticides have low toxicity to warm-blooded animals and have little effect on birds and animals. [0003] Energetic materials represent an important class of materials chemistry with a growing demand for use. Methylene-bridged nitrogen-rich heterocyclic c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D257/06C07D413/06C06B23/00C06B41/00
CPCC07D257/06C07D413/06C06B23/007C06B41/00C07B2200/13
Inventor 郭兆琦杨娜王煜程彦飞耶金马海霞
Owner NORTHWEST UNIV(CN)
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