CN118324697A - High-energy low-inductance eutectic compound based on 3,4, 5-trinitropyrazole and preparation method thereof - Google Patents
High-energy low-inductance eutectic compound based on 3,4, 5-trinitropyrazole and preparation method thereof Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 30
- 230000005496 eutectics Effects 0.000 title claims abstract description 18
- YLTPBDJQPIRWTQ-UHFFFAOYSA-N 3,4,5-trinitro-1h-pyrazole Chemical compound [O-][N+](=O)C1=NNC([N+]([O-])=O)=C1[N+]([O-])=O YLTPBDJQPIRWTQ-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000001914 filtration Methods 0.000 claims abstract description 24
- 239000000706 filtrate Substances 0.000 claims abstract description 18
- 238000002156 mixing Methods 0.000 claims abstract description 17
- 238000001816 cooling Methods 0.000 claims abstract description 14
- 239000013078 crystal Substances 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 238000003756 stirring Methods 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 239000011259 mixed solution Substances 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical compound ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 claims description 4
- FMCUPJKTGNBGEC-UHFFFAOYSA-N 1,2,4-triazol-4-amine Chemical compound NN1C=NN=C1 FMCUPJKTGNBGEC-UHFFFAOYSA-N 0.000 claims description 3
- BADSZRMNXWLUKO-UHFFFAOYSA-N 4-chloro-1h-pyrazole Chemical compound ClC=1C=NNC=1 BADSZRMNXWLUKO-UHFFFAOYSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000001035 drying Methods 0.000 description 10
- 230000001376 precipitating effect Effects 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000005474 detonation Methods 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 230000005311 nuclear magnetism Effects 0.000 description 2
- 125000001894 2,4,6-trinitrophenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
- MZRUFMBFIKGOAL-UHFFFAOYSA-N 5-nitro-1h-pyrazole Chemical compound [O-][N+](=O)C1=CC=NN1 MZRUFMBFIKGOAL-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention provides a high-energy low-inductance eutectic compound based on 3,4, 5-Trinitropyrazole (TNP) and a preparation method thereof, wherein the preparation method specifically comprises the following steps: dissolving TNP in a solvent until the TNP is completely dissolved to obtain TNP solution; step two, ATRZ is dissolved in a solvent until the solution is completely dissolved to obtain ATRZ solution; step three, mixing and uniformly stirring the solutions obtained in the step one and the step two at a certain temperature; step four, cooling the mixture obtained in the step three to a certain temperature, and filtering to obtain filtrate; and step five, volatilizing the filtrate obtained in the step four for a period of time at a certain temperature to separate out colorless crystals, namely the high-energy low-sensitivity eutectic energetic compound.
Description
Technical Field
The invention relates to the field of organic energetic materials, in particular to a high-energy low-inductance eutectic compound based on 3,4, 5-trinitropyrazole and a preparation method thereof.
Background
The energy-containing material is a material with special performance, determines the fight performance of weaponry, is the key for developing advanced weaponry, and has important application in civil use. Nitrogen-rich energetic compounds are a class of compounds containing carbon and nitrogen-containing heterocycles as the main backbone and having a higher nitrogen content, the energy of which is mainly derived from the higher energetic N-N, C-N, N = N, C =n bonds and greater ring tension in the ring structure. The nitrogen-rich energy-containing compound contains no or a small amount of nitro groups in the structure, and most of molecules have conjugated structures, so that the ring tension is smaller than that of pure C or N-less five-membered heterocyclic compounds, the stability of the molecules is high, and the sensitivity is low. From the aspect of thermochemical properties, the compounds have the characteristics of high thermal decomposition temperature, high formation enthalpy and the like; meanwhile, the high nitrogen and low hydrocarbon in the structure make the oxygen balance easier to achieve in the reaction process, and the combustion products are mostly environment-friendly N2. Wherein, because of compactness, stability and modifiable property of the structure of the pyrazole, the electrophilic substitution reactions such as nitration, sulfonation, halogenation and the like are easy to be carried out, the density and nitrogen content of the nitropyrazole are increased along with the existence of the nitro on the ring, the oxygen balance is closer to an ideal value, and the detonation performance of the target compound can be improved. Although nitrogen-rich energetic compounds have been rapidly developed over the last several decades, high energy insensitive compounds that are truly applicable or have great potential are quite rare, mainly because of the following drawbacks of the high energy insensitive compounds reported so far themselves: (1) Energetic compound energy and safety are a pair of natural contradictions; (2) The high-energy compound is generally high in acidity, and can generate great corrosion on a metal shell in long-term storage and use; (3) The strong acid compound has high solubility in aqueous solution, so that the recovery is difficult, and the compound dissolved in water pollutes water and soil.
Disclosure of Invention
The invention mainly aims to provide a high-energy low-inductance eutectic compound based on 3,4, 5-trinitropyrazole and a preparation method thereof, which are used for solving the technical problems.
In order to achieve the above purpose, the invention adopts the following technical scheme: a high-energy low-inductance eutectic compound based on 3,4, 5-trinitropyrazole has the following structural formula:
Wherein TNP is 3,4, 5-trinitropyrazole, and the chemical formula is as follows:
ATRZ is 4, 4-azo-1, 2, 4-triazole, of the formula:
The invention also provides a preparation method for preparing the high-energy low-inductance eutectic compound, which specifically comprises the following steps:
dissolving TNP in a solvent until the TNP is completely dissolved to obtain TNP solution;
Step two, ATRZ is dissolved in a solvent until the solution is completely dissolved to obtain ATRZ solution;
step three, mixing and uniformly stirring the solutions obtained in the step one and the step two at a certain temperature;
step four, cooling the mixture obtained in the step three to a certain temperature, and filtering to obtain filtrate;
And step five, volatilizing the filtrate obtained in the step four for a period of time at a certain temperature to separate out colorless crystals, namely the high-energy low-sensitivity eutectic energetic compound.
Preferably, the solvent in the first step and the second step is one or more of water, methanol and ethanol.
Preferably, the synthetic route of the TNP is as follows:
Step 11, reacting 4-chloropyrazole with a mixed solution of concentrated sulfuric acid and concentrated nitric acid at a certain temperature for a period of time to prepare 3, 5-binitro-4-chloropyrazole;
step 12, carrying out substitution reaction on 3, 5-binitro-4-chloropyrazole in methanol solution of ammonia to obtain 3, 5-binitro-4-aminopyrazole;
Step 13, preparing TNP by 3, 5-binitro-4-aminopyrazole under the conditions of H 2O2 and concentrated sulfuric acid.
Preferably, the ATRZ is synthesized as follows:
Step 21, mixing water, acetic acid and sodium dichloroisocyanurate at a certain temperature;
step 22, adding an aqueous solution of 4-amino-1, 2, 4-triazole into the solution in step 21, and reacting for a period of time to obtain ATRZ.
Compared with the prior art, the invention has the following beneficial effects:
1) 3,4, 5-Trinitropyrazole (TNP) is the only full-carbon nitropyrazole compound, has good thermal stability and chemical stability, shows high detonation velocity (9.0 km/s) and detonation pressure (37.09 GPa), has oxygen balance close to 0, is strong in acidity, forms ATRZ-TNP into eutectic by combining with ATRZ, combines 2 TNPs with one ATRZ, can improve the density of the whole molecule, and solves the problem of strong acidity of TNP.
2) The high-energy low-inductance eutectic compound disclosed by the invention has the advantages of good stability, high density and excellent detonation performance besides low acidity;
3) The preparation method provided by the invention is simple and has mild reaction conditions; can use water as solvent, has no pollution to the environment and completely meets the environmental protection requirement.
Drawings
FIG. 1 is a molecular structure diagram of ATRZ@TNP.
Detailed Description
The following description is presented to enable one of ordinary skill in the art to make and use the invention. The preferred embodiments in the following description are by way of example only and other obvious variations will occur to those skilled in the art.
A high-energy low-inductance eutectic compound based on 3,4, 5-trinitropyrazole has the following structural formula:
Wherein the structural formula of the 3,4, 5-Trinitropyrazole (TNP) is as follows:
the structural formula of the 4, 4-azo-1, 2, 4-triazole (ATRZ) is as follows:
The preparation method of the eutectic compound comprises the following steps:
dissolving TNP in a solvent until the TNP is completely dissolved to obtain TNP solution;
Step two, ATRZ is dissolved in a solvent until the solution is completely dissolved to obtain ATRZ solution;
step three, mixing and uniformly stirring the solutions obtained in the step one and the step two at a certain temperature;
step four, cooling the mixture obtained in the step three to a certain temperature, and filtering to obtain filtrate;
And step five, volatilizing the filtrate obtained in the step four for a period of time at a certain temperature to separate out colorless crystals, namely the high-energy low-sensitivity eutectic energetic compound.
Wherein the solvent in the first step and the second step is one or more of water, methanol and ethanol, and water is preferable.
The temperature in step three is preferably 40-100 ℃.
The synthetic route of TNP is as follows:
Step 11, reacting 4-chloropyrazole with a mixed solution of concentrated sulfuric acid and concentrated nitric acid at 80 ℃ for 8 hours to prepare 3, 5-binitro-4-chloropyrazole;
step 12, carrying out substitution reaction on 3, 5-binitro-4-chloropyrazole in methanol solution of ammonia to obtain 3, 5-binitro-4-aminopyrazole;
Step 13, preparing TNP by 3, 5-binitro-4-aminopyrazole under the conditions of H 2O2 and concentrated sulfuric acid, wherein the specific chemical reaction formula is as follows:
the synthetic route of ATRZ is as follows:
step 21, mixing water, acetic acid and Sodium Dichloroisocyanurate (SDIC) at 30 ℃;
Step 22, slowly adding an aqueous solution of 4-amino-1, 2, 4-triazole into the solution in step 21 at 7 ℃, and reacting for 1h at 15 ℃ to obtain ATRZ, wherein the reaction formula is as follows:
experimental example 1
1Mmol ATRZ was added to 15mL of 85℃water, and after complete dissolution, 1mmol TNP was added to 15mL of 85℃water, and after complete dissolution; then mixing the two solutions, filtering, cooling to room temperature, preserving the filtrate at room temperature for two days, precipitating colorless crystals from the solution, filtering, and drying. The yield was 70.55%.
Experimental example 2
2Mmol ATRZ was added to 15mL of 65℃water, and after complete dissolution, 1mmol TNP was added to 15mL of 65℃water, and after complete dissolution. Then mixing the two solutions, filtering, cooling to room temperature, preserving the filtrate at room temperature for two days, precipitating colorless crystals from the solution, filtering, and drying. The yield was 69.75%.
Experimental example 3
1Mmol ATRZ was added to 15mL of water at 70℃until it was completely dissolved, and 1mmol TNP was added to 15mL of water at 80℃until it was completely dissolved. Then mixing the two solutions, filtering, cooling to room temperature, preserving the filtrate at room temperature for two days, precipitating colorless crystals from the solution, filtering, and drying. The yield was 68.75%.
Experimental example 4
1Mmol ATRZ of TNP was added to 15mL of 85℃water until it was completely dissolved, and 2mmol of TNP was added to 15mL of 85℃water until it was completely dissolved; then mixing the two solutions, filtering, cooling to room temperature, preserving the filtrate at room temperature for two days, precipitating colorless crystals from the solution, filtering, and drying. The yield was 71.46%.
Experimental example 5
1Mmol ATRZ of TNP was added to 15mL of water at 80℃until it was completely dissolved, and 2mmol of TNP was added to 15mL of water at 80℃until it was completely dissolved; then mixing the two solutions, filtering, cooling to room temperature, preserving the filtrate at room temperature for two days, precipitating colorless crystals from the solution, filtering, and drying. The yield was 70.24%.
Experimental example 6
2Mmol ATRZ was added to 15mL of 75℃water, and after complete dissolution, 1mmol TNP was added to 15mL of 75℃water, and after complete dissolution; then mixing the two solutions, filtering, cooling to room temperature, preserving the filtrate at room temperature for two days, precipitating colorless crystals from the solution, filtering, and drying. The yield was 69.68%.
Experimental example 7
1Mmol ATRZ is added to 15mL of a mixed solution of water at 80 ℃ and ethanol (1:1) until it is completely dissolved, and 1mmol TNP is added to 15mL of water at 80 ℃ until it is completely dissolved; then mixing the two solutions, filtering, cooling to room temperature, preserving the filtrate at room temperature for two days, precipitating colorless crystals from the solution, filtering, and drying. The yield was 67.45%.
Experimental example 8
1Mmol ATRZ is added to 15mL of a mixed solution of water at 85 ℃ and ethanol (1:1) until it is completely dissolved, and 1mmol TNP is added to 15mL of water at 85 ℃ until it is completely dissolved; then mixing the two solutions, filtering, cooling to room temperature, preserving the filtrate at room temperature for two days, precipitating colorless crystals from the solution, filtering, and drying. The yield was 68.88%.
Experimental example 9
1Mmol ATRZ is added to 15mL of a mixed solution of water at 85 ℃ and ethanol (1:1) until it is completely dissolved, and 1mmol TNP is added to 15mL of water at 85 ℃ until it is completely dissolved; then mixing the two solutions, filtering, cooling to room temperature, preserving the filtrate at room temperature for two days, precipitating colorless crystals from the solution, filtering, and drying. The yield was 68.29%.
Experimental example 10
1Mmol ATRZ is added to 15mL of a mixed solution of water at 85 ℃ and ethanol (1:1) until it is completely dissolved, and 2mmol TNP is added to 15mL of water at 85 ℃ until it is completely dissolved; then mixing the two solutions, filtering, cooling to room temperature, preserving the filtrate at room temperature for two days, precipitating colorless crystals from the solution, filtering, and drying. The yield was 69.67%.
And (3) structural identification:
Atrz@tnp in experimental example 1:
IR(KBr/cm-1):3436,3145,2857,2387,1920,1573,1533,1463,1364,1326,1176,1150,1038,955,863,809,695,619,535,493;
1H nuclear magnetism (DMSO, delta, ppm): 9.45,7.48;
13C nuclear magnetism (DMSO, δ, ppm): 146.97,138.46,122.10.
Elemental analysis: c 10H6N18O12
Theoretical value: c (21.06%), H (1.06%), N (44.21%);
Actual measurement value: c (21.21%), H (1.24%), N (44.53%).
The structural identification shows that ATRZ@TNP is a eutectic compound.
TABLE 1 physicochemical Property parameters of energetic Compounds
The foregoing has shown and described the basic principles, principal features and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, and that the above embodiments and descriptions are merely illustrative of the principles of the present invention, and various changes and modifications may be made therein without departing from the spirit and scope of the invention, which is defined by the appended claims. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (5)
1. The high-energy low-inductance eutectic compound based on 3,4, 5-trinitropyrazole is characterized by having the following structural formula:
Wherein TNP is 3,4, 5-trinitropyrazole, and the chemical formula is as follows:
ATRZ is 4, 4-azo-1, 2, 4-triazole, of the formula:
2. a method for preparing the high-energy low-inductance eutectic compound according to claim 1, which is characterized by comprising the following steps:
dissolving TNP in a solvent until the TNP is completely dissolved to obtain TNP solution;
Step two, ATRZ is dissolved in a solvent until the solution is completely dissolved to obtain ATRZ solution;
step three, mixing and uniformly stirring the solutions obtained in the step one and the step two at a certain temperature;
step four, cooling the mixture obtained in the step three to a certain temperature, and filtering to obtain filtrate;
And step five, volatilizing the filtrate obtained in the step four for a period of time at a certain temperature to separate out colorless crystals, namely the high-energy low-sensitivity eutectic energetic compound.
3. The preparation method according to claim 2, wherein the solvent in the first and second steps is one or more of water, methanol and ethanol.
4. A method of preparation according to claim 3, wherein the TNP is synthesized as follows:
Step 11, reacting 4-chloropyrazole with a mixed solution of concentrated sulfuric acid and concentrated nitric acid at a certain temperature for a period of time to prepare 3, 5-binitro-4-chloropyrazole;
step 12, carrying out substitution reaction on 3, 5-binitro-4-chloropyrazole in methanol solution of ammonia to obtain 3, 5-binitro-4-aminopyrazole;
Step 13, preparing TNP by 3, 5-binitro-4-aminopyrazole under the conditions of H 2O2 and concentrated sulfuric acid.
5. The method according to claim 2, wherein the ATRZ is synthesized according to the following route:
Step 21, mixing water, acetic acid and sodium dichloroisocyanurate at a certain temperature;
step 22, adding an aqueous solution of 4-amino-1, 2, 4-triazole into the solution in step 21, and reacting for a period of time to obtain ATRZ.
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