CN115894453B - Pyrazole compound, energetic ionic salt thereof and preparation method thereof - Google Patents

Pyrazole compound, energetic ionic salt thereof and preparation method thereof Download PDF

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CN115894453B
CN115894453B CN202211357012.0A CN202211357012A CN115894453B CN 115894453 B CN115894453 B CN 115894453B CN 202211357012 A CN202211357012 A CN 202211357012A CN 115894453 B CN115894453 B CN 115894453B
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林秋汉
程本端
张立南
王鹏程
陆明
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Nanjing University of Science and Technology
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Abstract

The invention designs and synthesizes a pyrazole compound, and an energetic ion salt and a preparation method thereof, wherein the 3-amino-4- (4, 5-diamino-1, 2, 4-triazole-3-yl) pyrazole ion salt has higher density, better oxygen balance, lower sensitivity and high decomposition temperature basically higher than 240 ℃ through DSC test; the synthesis method has the advantages of safe and reasonable process, short reaction time, mild reaction condition, higher yield, low production cost, basically no three wastes and environmental friendliness; the 3-amino-4- (4, 5-diamino-1, 2, 4-triazole-3-yl) pyrazole energetic ionic salt has good thermal stability, lower impact sensitivity and excellent detonation performance, and can be applied to energetic materials such as explosives, propellants, pyrotechnic technology and the like.

Description

Pyrazole compound, energetic ionic salt thereof and preparation method thereof
Technical Field
The invention relates to a pyrazole compound, and an energetic ionic salt and a preparation method thereof, belonging to the technical field of energetic materials.
Background
The energy-containing material is an important component of explosive technology, is a power source and a damage power source of a weapon system, and the energy level of the energy-containing material directly determines the damage and striking capacity of weapon equipment. With the rapid development of modern military science and technology, more severe use environments and various extreme conditions place higher demands on heat resistance and energy levels of energetic materials. In particular, in the fields of nuclear weapons, space exploration, deep well blasting and the like, energy-containing compounds are required to face high-temperature use environments, so that the compounds are required to have a high melting point, a low vapor pressure and good heat resistance, and the detonation reaction can still be reliably completed after long-time heating. To meet this requirement, the development of new heat resistant energetic compounds with better energy levels is an important development direction in the field of energetic materials, adapting to the development under new circumstances.
The heat-resistant energetic compound is a kind of energetic material which has higher melting point (thermal decomposition point) and lower vapor pressure, can maintain proper sensitivity and higher energy after being subjected to a high-temperature environment for a long time and can be reliably detonated. Generally, the decomposition temperature of not lower than 220 ℃ can be referred to as a heat resistant energetic material. In recent years, many heat-resistant energetic materials studied and synthesized in various countries use aza condensed rings as energetic skeletons, and the heat stability is further improved by the conjugated system extension and the conjugated stabilization effect. However, there are relatively few studies and reports on heat resistant energetic materials of the non-condensed ring class, or because of the lack of such structural advantage, some of the energetic molecules of the non-condensed ring class generally behave in terms of heat resistance. The invention designs and synthesizes the heat-resistant non-condensed ring compound 3-amino-4- (4, 5-diamino-1, 2, 4-triazole-3-yl) pyrazole and energetic ion salt thereof, and the energetic ion salt has good heat stability and lower impact sensitivity, and can be used in the field of energetic materials.
Disclosure of Invention
The invention aims to provide 3-amino-4- (4, 5-diamino-1, 2, 4-triazole-3-yl) pyrazole and energetic ion salts thereof, and a preparation method thereof, wherein the compounds have good thermal stability (decomposition temperature is above 240 ℃) and excellent detonation performance, and can be used as heat-resistant simple substance explosive.
The aim of the invention is achieved by the following technical scheme.
The invention relates to a preparation method of 3-amino-4- (4, 5-diamino-1, 2, 4-triazole-3-yl) pyrazole and energetic ion salt thereof, which has the following general formula:
in the formula (a), the amino acid sequence of the formula (a),is one of chloride ion, nitrate radical, perchlorate radical, 5-nitrotetrazole anion, 3-amino-4-tetrazole furazan anion, picric acid anion, trinitromethane anion, 3, 5-dinitropyrazole anion and dinitramide anion;
due to the introduced anions X - All the compounds except chloridion have oxygen-containing groups or have higher nitrogen content, so that the oxygen balance or nitrogen content of the compounds is improved to a certain extent compared with 3-amino-4- (4, 5-diamino-1, 2, 4-triazole-3-yl) pyrazole.
The 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazoles and energetic ionic salts thereof of the present invention are achieved by the following routes:
the method comprises the following specific steps:
step 1) preparation of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole: compound 1 was added to an aqueous solution of sodium hydroxide at room temperature, and after stirring and dissolution, the mixture was refluxed for 10 hours at a temperature. After the reaction, cooling to room temperature, adjusting the pH to be=1 by concentrated hydrochloric acid, continuously stirring until a large amount of solid is separated out, cooling the reaction to 0 ℃, and filtering to obtain a pale yellow solid 2.
Step 2) at 45 ℃, mixing and grinding 2 and excessive diaminoguanidine hydrochloride into powder, slowly adding the powder into an acid system of phosphoric acid and phosphorus pentoxide, heating to about 125 ℃ for reaction for 6 hours, cooling to room temperature, pouring oily reaction liquid into an ice-water mixture, neutralizing with sodium hydroxide solution, separating out solid, filtering, and washing with a small amount of water to obtain solid 3.
Step 3) preparation of energetic ion salt of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole: dispersing the compound 3 in a solvent, adding an equal amount or an excessive amount of a corresponding alkaline compound into the solvent, heating and dissolving, stirring for reaction for 0.5-1.0 h, filtering to remove filter residues, and concentrating the reaction solution to obtain the product.
Advantageous effects
The 3-amino-4- (4, 5-diamino-1, 2, 4-triazole-3-yl) pyrazole ion salt prepared by the invention has higher density, better oxygen balance, lower sensitivity and high decomposition temperature which is basically higher than 240 ℃ through DSC test; the synthesis method has the advantages of safe and reasonable process, short reaction time, mild reaction condition, higher yield, low production cost, basically no three wastes and environmental friendliness; the 3-amino-4- (4, 5-diamino-1, 2, 4-triazole-3-yl) pyrazole energetic ionic salt prepared by the invention can be applied to energetic materials such as explosives, propellants, pyrotechnic technology and the like.
Drawings
FIG. 1 is a single crystal resolution of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole hydrochloride;
FIG. 2 is a single crystal resolution of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole nitrate;
FIG. 3 is a single crystal resolution of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole perchlorate;
FIG. 4 is a single crystal resolution of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole bis 5-nitrotetrazolium salt;
FIG. 5 is a nuclear magnetic resonance hydrogen spectrum (500 MHz, D) of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole hydrochloride 2 O);
FIG. 6 is a nuclear magnetic resonance hydrogen spectrum (500 MHz, D) of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole nitrate 2 O);
FIG. 7 is a nuclear magnetic resonance hydrogen spectrum (500 MHz, D) of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole perchlorate 2 O)。
Detailed Description
The present invention will be further illustrated with reference to examples, but the scope of the present invention is not limited thereto.
Example 1
Preparation of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole having the structure:
the method comprises the following specific steps:
step 1) 1 (3.243 g,30 mmol) was added to an aqueous solution (30 ml) of sodium hydroxide (6 g,150 mmol) at room temperature, and after dissolution, the mixture was heated to reflux for 10 hours, cooled, 36% hydrochloric acid was adjusted to ph=1, filtered, and a small amount of ice water was washed to give 2 (3.2 g,25 mmol) in 83% yield.
Step 2) phosphorus pentoxide (8 g,56 mmol) was dissolved in phosphoric acid (28 g,285.7 mmol) at room temperature, the solution was heated to 45 ℃, mixed powder of 2 (2.54 g,20 mmol) and diaminoguanidine hydrochloride (3.26 g,26 mmol) was added to the solution in portions, the temperature was raised to 120 ℃ for reaction for 6 hours, after the reaction was completed, cooled to room temperature, the obtained oily reaction solution was poured into an ice-water mixture (70 g), neutral was made with concentrated sodium hydroxide solution, filtered, and washed with water to obtain 3 (2.1 g,11.7 mmol) in 59% yield.
Example 2
Preparation of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole hydrochloride having the following structure:
the method comprises the following specific steps: 3 (0.18 g,1 mmol) is dispersed in 10mL of water, 5mL of 2mol/L hydrochloric acid is added dropwise to the water, the temperature is raised to 80 ℃ after the addition, the mixture is stirred for 0.5h, insoluble matters are removed by filtration, the target product is obtained by rotary evaporation of the reaction solution, the yield is 85%, and the density is 1.662g/cm 3 The decomposition temperature was 308 ℃.
Example 3
Preparation of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole nitrate salt having the structure:
the method comprises the following specific steps: 3 (0.18 g,1 mmol) was dispersed in 10mL of water, then 5mL of 2mol/L nitric acid was added dropwise to the water, the temperature was raised to 80℃after the completion of the dropwise addition, stirring was carried out for 0.5h, insoluble matters were removed by filtration, and the reaction solution was distilled off to obtain the objective product in 86% yield.
The density of the 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole nitrate prepared by the method was 1.758g/cm as measured by a vacuum densitometer 3 DSC measurement shows that the analysis temperature is 244 ℃; the oxygen balance value is-2.9%, the nitrogen content is 45.7%, the generated heat is-215.33 kJ/mol, and detonation performance test is also carried out by using exploer 5.0 software, and the test result is that: detonation velocity: 7990m/s, burst pressure: 24.7GPa.
Example 4
Preparation of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole perchlorate having the structure
The method comprises the following specific steps: 3 (0.18 g,1 mmol) was dispersed in 10mL of water, then 5mL of 2mol/L perchloric acid was added dropwise to the water, the temperature was raised to 80℃after the completion of the dropwise addition, stirring was carried out for 0.5h, insoluble matters were removed by filtration, and the reaction solution was distilled off to obtain the objective product in 88% yield.
The density of the 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole perchlorate prepared by the above method was 1.89g/cm as measured by a vacuum densitometer 3 DSC measurement shows that the analysis temperature is 280 ℃; the oxygen balance value is-1.8%, the nitrogen content is 29.4%, the generated heat is-20.09 kJ/mol, and detonation performance test is carried out by using exploer 5.0 software, wherein the test result is as follows: detonation velocity: 8319m/s, burst pressure: 30.527GPa.
Example 5
Preparation of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole bis 5-nitrotetrazolium salt, its structure is as follows
Step 1) preparation of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole hydrochloride: 3 (0.9 g,5 mmol) is dispersed in 30mL of water, 8mL of 6mol/L hydrochloric acid is added dropwise into the water, the temperature is raised to 80 ℃ after the dropwise addition, the mixture is stirred for 0.5h, insoluble matters are removed by filtration, and the target product is obtained by rotary evaporation of the reaction liquid, and the yield is 85%.
Step 2) preparation of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole bis 5-nitrotetrazolium salt: will be 0.63g
(2.5 mmol) 3-amino-4- (4, 5-diamino-1, 2, 4-triazole-3-yl) pyrazole hydrochloride was dissolved in 20mL of water, then 3.0g of a suspension of 5-nitrotetrazole silver salt in water was added dropwise to the water, the mixture was stirred at room temperature in the absence of light for 1h after the addition, insoluble matters were filtered off after the reaction was completed, and the filtrate was distilled off soon to obtain the objective product with a yield of 83%.
The density of the 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole bis 5-nitrotetrazolium salt prepared by the method is 1.72g/cm measured by a vacuum densitometer 3 The method comprises the steps of carrying out a first treatment on the surface of the The oxygen balance value is-3.6%, the nitrogen content is 61.4% and the heat of formation is 763.45kJ/mol, and detonation performance test is also carried out by using the exploer 5.0 software, and the test result is that: detonation velocity: 8002m/s, burst pressure: 24.1GPa.
Example 6
Preparation of 3-amino-4- (4, 5-diamino-1, 2, 4-triazole-3-yl) pyrazolo bis 3-amino-4-tetrazolium furazane salt with the following structure
The method comprises the following specific steps: 3 (0.18 g,1 mmol) is dispersed in 10mL of water, then 3-amino-4-tetrazole furazan (0.306 g,2 mmol) is added, 2mL of hydrochloric acid (1M) is added dropwise, the temperature is heated to 80 ℃ to change the system into a clear solution, the solution is stirred for 0.5h, the solution is slowly cooled to room temperature, solid is separated out, filtered and dried, and the target product is obtained with the yield of 81%.
The density of the 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazolo bis 3-amino-4-tetrazolium salt prepared by the method is 1.70g/cm measured by a vacuum densitometer 3 Calculated to obtain itThe detonation performance test was also carried out with an exploer 5.0 software with an oxygen balance of-5.5%, a nitrogen content of 63.3% and a heat of formation of 1219.01kJ/mol, and the test results were: detonation velocity: 7796m/s, detonation pressure: 21.4GPa.
Example 7
Preparation of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole bispicrate having the structure
The method comprises the following specific steps: 3 (0.18 g,1 mmol) was dispersed in 10mL of water, and picric acid (0.458 g,2 mmol) was added thereto, heated to 80℃to make the system a clear solution, stirred for 0.5h, slowly cooled to room temperature, and solid precipitated, filtered and dried to give the objective product in 78% yield.
The density of the 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole bispicrate prepared by the method is 1.8g/cm measured by a vacuum densitometer 3 The oxygen balance value is-4.2%, the nitrogen content is 30.7% and the generated heat is-91.46 kJ/mol, and detonation performance test is also carried out by using exploer 5.0 software, and the test result is that: detonation velocity: 7418m/s, burst pressure: 24.1GPa.
Example 8
Preparation of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole bis trinitromethane salt, the structure is as follows
The method comprises the following specific steps: 3 (0.18 g,1 mmol) was dispersed in 10mL of water, trinitromethane (0.302 g,2 mmol) was added, heated to 80℃to make the system a clear solution, stirred for 0.5h, slowly cooled to room temperature, solid precipitated, filtered and dried to give the desired product in 78% yield.
The density of the 3-amino-4- (4, 5-diamino-1, 2, 4-triazole-3-yl) pyrazole bis trinitromethane prepared by the method is measured by a vacuum densitometer1.82g/cm 3 The oxygen balance value is-1.4%, the nitrogen content is 40.7% and the heat of formation is 126.99kJ/mol, and detonation performance test is also carried out by using exploer 5.0 software, and the test result is that: detonation velocity: 8622m/s and detonation pressure: 32.4GPa.
Example 9
Preparation of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole bis 3, 5-dinitropyrazole salt having the following structure
The method comprises the following specific steps: 3 (0.18 g,1 mmol) was dispersed in 10mL of water, then 3, 5-dinitropyrazole (0.316 g,2 mmol) was added, 2mL of hydrochloric acid (1M) was added dropwise, the system was heated to 80℃to turn the system into a clear solution, stirred for 0.5h, cooled slowly to room temperature, solid precipitated, filtered and dried to give the desired product in 80% yield.
The density of the 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole bis 3, 5-dinitropyrazole salt prepared by the method is 1.75g/cm measured by a vacuum densitometer 3 The oxygen balance value is-4.0%, the nitrogen content is 45.1% and the heat of formation is 398.32kJ/mol, and detonation performance test is also carried out by using exploer 5.0 software, and the test result is that: detonation velocity: 7635m/s, burst pressure: 23.7GPa.
Example 10
Preparation of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole bisdinitrate amide salt having the following structure
The method comprises the following specific steps: 3 (0.18 g,1 mmol) was dispersed in 10mL of water, then ammonium dinitramide (0.248 g,2 mmol) was added, 2mL of hydrochloric acid (1M) was added dropwise, the system was heated to 80℃to make a clear solution, stirred for 0.5h, cooled slowly to room temperature, solid was precipitated, filtered and dried to give the objective product in 78% yield.
The method is used for preparingThe prepared 3-amino-4- (4, 5-diamino-1, 2, 4-triazole-3-yl) pyrazole bisdinitrate amide has a density of 1.75g/cm measured by a vacuum densitometer 3 The oxygen balance value is-1.7%, the nitrogen content is 49.7%, the generated heat is 259.99kJ/mol, and detonation performance test is also carried out by using exploer 5.0 software, wherein the test result is as follows: detonation velocity: 8493m/s, detonation pressure: 29.5GPa.
While the invention has been described in detail in connection with specific preferred embodiments, it is not to be construed as limited to the specific embodiments of the invention, but rather as a matter of course, it will be understood by those skilled in the art that various modifications and substitutions can be made without departing from the spirit and scope of the invention.

Claims (5)

1. A3-amino-4- (4, 5-diamino-1, 2, 4-triazole-3-yl) pyrazole compound and its energetic ion salt, wherein the structural formula of the 3-amino-4- (4, 5-diamino-1, 2, 4-triazole-3-yl) pyrazole compound is shown in formula 3, its energetic ion salt is shown in formula (a),
in the formula (a), the amino acid sequence of the formula (a),is any one of chloride ion, nitrate radical, perchlorate radical, 5-nitrotetrazole anion, 3-amino-4-tetrazole furoxan anion, picric acid anion, trinitromethane anion, 3, 5-dinitropyrazole anion and dinitramide anion.
2. The 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole compound of claim 1 wherein the energetic ionic salt represented by formula (a) is:
3. the process for the preparation of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole compounds and energetic ionic salts according to claim 1, comprising the specific steps of:
step 1) preparation of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole: at room temperature, adding the compound 1 into an aqueous solution of sodium hydroxide, stirring and dissolving, and then heating and refluxing for 10 hours; cooling to room temperature after the reaction is finished, regulating the pH value to be 1 by concentrated hydrochloric acid, continuously stirring until a large amount of solid is separated out, cooling the reaction to 0 ℃, filtering to obtain pale yellow solid 2,
step 2) mixing 2 and excessive diaminoguanidine hydrochloride at 45 ℃ and grinding into powder, slowly adding into an acidic system of phosphoric acid and phosphorus pentoxide, heating to about 125 ℃ and reacting for 6 hours, cooling to room temperature, pouring oily reaction liquid into an ice-water mixture, neutralizing with sodium hydroxide solution, separating out solid, filtering, washing with a small amount of water to obtain solid 3, namely 3-amino-4- (4, 5-diamino-1, 2, 4-triazole-3-yl) pyrazole shown in formula 3,
step 3) preparation of energetic ion salt of 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole: dispersing compound 3 in solvent, adding equivalent or excessive corresponding alkaline compound into solvent, heating for dissolving, stirring for reacting for 0.5-1.0 hr, filtering to remove residue, concentrating the reaction solution to obtain 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole energetic ion salt shown in formula (a), wherein M Θ Representing the position Θ
4. Use of a 3-amino-4- (4, 5-diamino-1, 2, 4-triazol-3-yl) pyrazole compound according to claim 1 and energetic ionic salts thereof for the preparation of energetic materials.
5. The use according to claim 4, in explosives, propellants, pyrotechnics.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106188009A (en) * 2016-07-05 2016-12-07 北京理工大学 3,4 dinitro 1 (1H tetrazolium 5 base) 1H pyrazoles 5 amine are containing energy ion salt preparation method and performance
CN106432192A (en) * 2016-07-11 2017-02-22 北京理工大学 Preparation method and performance of high-energy insensitive N-(3,5-binitro-1H-pyrazol-4-yl)-1H-tetrazole-5-amine ionic salt structure
CN108148007A (en) * 2016-12-02 2018-06-12 南京理工大学 4- amino -3- diazanyl -5- methyl-1s, 2,4- triazoles ion salt containing energy and its synthetic method

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106188009A (en) * 2016-07-05 2016-12-07 北京理工大学 3,4 dinitro 1 (1H tetrazolium 5 base) 1H pyrazoles 5 amine are containing energy ion salt preparation method and performance
CN106432192A (en) * 2016-07-11 2017-02-22 北京理工大学 Preparation method and performance of high-energy insensitive N-(3,5-binitro-1H-pyrazol-4-yl)-1H-tetrazole-5-amine ionic salt structure
CN108148007A (en) * 2016-12-02 2018-06-12 南京理工大学 4- amino -3- diazanyl -5- methyl-1s, 2,4- triazoles ion salt containing energy and its synthetic method

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