Methylene-bridged nitrogen-rich diheterocyclic compound, derivative and preparation method thereof

A methylene bridge and compound technology is applied in the field of methylene bridged nitrogen-rich biheterocyclic compounds and their derivatives, and can solve the problems of difficulty in designing new energetic materials, achieve low density and prevent decomposition. , the effect of high stability

Inactive Publication Date: 2020-11-17
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Traditional energetic materials, such as trinitrotoluene (TNT) and cyclotrimethylenetrinitramine (RDX), are mostly nitro-substituted aromatic ring compounds and alicyclic ammonium nitrate compounds, and it has been difficult to design based on such structures New energetic materials with excellent properties

Method used

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  • Methylene-bridged nitrogen-rich diheterocyclic compound, derivative and preparation method thereof
  • Methylene-bridged nitrogen-rich diheterocyclic compound, derivative and preparation method thereof
  • Methylene-bridged nitrogen-rich diheterocyclic compound, derivative and preparation method thereof

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preparation example Construction

[0034] A method for preparing a methylene bridged nitrogen-rich biheterocyclic compound of the present invention comprises the following steps:

[0035] Step 1: Dissolve 2mmol of 1-acetonitrile 5-aminotetrazole in 20ml of 1M NaOH aqueous solution, reflux at 100-105°C for 1.5-2.5h to carry out the oxidation reaction, after returning to room temperature, add hydrochloric acid dropwise to adjust the pH =7, the acidification reaction was carried out to free the product, the product was precipitated, and the precipitate was filtered out. The precipitate was 1-acetoxy 5-aminotetrazole, accompanied by a small amount of impurities, but did not affect the subsequent reaction.

[0036]Step 2: Dissolve 0.214g of the precipitate obtained in step 1 in 10ml of polyphosphoric acid, stir at 40°C for 5 minutes to fully dissolve the precipitate, then add 2mmol of diaminoguanidine hydrochloride, and heat up to 110-130°C for addition After 12-14 hours of reaction, the desired substance was formed...

Embodiment 1

[0053] Step 1: Dissolve 2mmol of 1-acetonitrile 5-aminotetrazole in 20ml of 1 M NaOH aqueous solution, reflux at 100°C for 2h, after returning to room temperature, add hydrochloric acid dropwise to adjust the pH to 7, and filter out the precipitate after the reaction.

[0054] Step 2: Dissolve 0.214 g of the solid obtained in step 1 in 10 ml of polyphosphoric acid, stir at 40° C. for 5 minutes, add 2 mmol of solid diaminoguanidine hydrochloride, and heat up to 120° C. for 12 hours. After the reaction, return to room temperature, add 20 g of ice water at 2° C., adjust pH=8, and filter compound 1.

[0055] From Figure 4 It can be seen that compound 1 has a downward endothermic peak, indicating that it melts before being nitrated, that is, before being dissolved in fuming nitric acid, and then decomposes to carry out oxidation reaction. The heat of combustion at constant volume of compound 1 is 6000J / g, IS>40J, FS>360N, indicating low energy and high stability.

[0056] Table ...

Embodiment 2

[0064] Step 1: Dissolve 2mmol of 1-acetonitrile 5-aminotetrazole in 20ml of 1 M NaOH aqueous solution, reflux at 105°C for 2.5h, after returning to room temperature, add hydrochloric acid dropwise to adjust PH=7, filter out the precipitate after the reaction .

[0065] Step 2: Dissolve 0.214 g of the solid obtained in step 1 in 10 ml of polyphosphoric acid, stir at 40° C. for 5 minutes, add 2 mmol of solid diaminoguanidine hydrochloride, and heat up to 110° C. for 14 hours. After the reaction, return to room temperature, add 20 g of ice water at 0° C., adjust pH=9, and obtain compound 1 by filtration.

[0066] Step 3: Take 1ml of fuming nitric acid and stir at -5°C for 10min, take 0.1g of compound 1 and dissolve in fuming nitric acid at -5°C, slowly return to room temperature, and stir for 7h. After the reaction was completed, it was dropped on ice, and the precipitated white solid was filtered and dried to obtain dinitrate ammonium compound 2.

[0067] Step 4: 2 mmol of com...

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Abstract

The invention relates to a methylene-bridged nitrogen-rich diheterocyclic compound, a derivative and a preparation method thereof. The preparation method of the methylene-bridged nitrogen-rich diheterocyclic compound comprises the following steps: 1, dissolving 1-acetonitrile-5-amino tetrazole in a NaOH aqueous solution, carrying out a reflux reaction at 100-105 DEG C, and separating out a productto obtain a precipitate; 2, dissolving the precipitate and diaminoguanidine hydrochloride in polyphosphoric acid, and carrying out an addition reaction at 110-130 DEG C; and 3, cooling the reaction solution, adjusting the pH value to 7-9, separating the product, dissloving the methylene-bridged nitrogen-rich diheterocyclic compound in low-temperature fuming nitric acid, reacting at room temperature, dropping the reaction liquid on ice to separate out the compound, respectively adding an organic alkali and a metal alkali after dissloving the compound, reacting the obtained mixed system at -5-5DEG C, reacting at room temperature, filtering the product, and drying to obtain metal salt and non-metal salt of the methylene-bridged nitrogen-rich ammonium nitrate compound.

Description

technical field [0001] The invention relates to the technical field of new materials, in particular to a methylene bridged nitrogen-rich biheterocyclic compound, derivatives thereof, 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-rich 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. Energetic materials are a kind of special energy materials, which are characterized in that they can quickly undergo oxidation-reduction reactions and releas...

Claims

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Application Information

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IPC IPC(8): C07D403/06
CPCC07B2200/13C07D403/06
Inventor 马海霞王煜杨娜耶金程彦飞郭兆琦
Owner NORTHWEST UNIV
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