CN115991680B - Bis (1, 2, 4-triazole) triazene cationic nitrogen-rich energetic ion salt, and preparation method and application thereof - Google Patents
Bis (1, 2, 4-triazole) triazene cationic nitrogen-rich energetic ion salt, and preparation method and application thereof Download PDFInfo
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title claims abstract description 62
- -1 Bis (1, 2, 4-triazole) triazene Chemical compound 0.000 title claims abstract description 53
- 229910052757 nitrogen Inorganic materials 0.000 title claims abstract description 32
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims description 7
- 239000000463 material Substances 0.000 claims abstract description 11
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims abstract 10
- 238000006243 chemical reaction Methods 0.000 claims description 16
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 10
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims description 8
- 239000012265 solid product Substances 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 239000012153 distilled water Substances 0.000 claims description 6
- 235000010288 sodium nitrite Nutrition 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000007790 solid phase Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 2
- 239000011707 mineral Substances 0.000 claims 2
- 238000005474 detonation Methods 0.000 abstract description 16
- 230000035945 sensitivity Effects 0.000 abstract description 14
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 229910002651 NO3 Inorganic materials 0.000 abstract description 7
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract description 5
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 abstract description 5
- 238000009776 industrial production Methods 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract description 2
- JDFUJAMTCCQARF-UHFFFAOYSA-N tatb Chemical compound NC1=C([N+]([O-])=O)C(N)=C([N+]([O-])=O)C(N)=C1[N+]([O-])=O JDFUJAMTCCQARF-UHFFFAOYSA-N 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- YPJKMVATUPSWOH-UHFFFAOYSA-N nitrooxidanyl Chemical group [O][N+]([O-])=O YPJKMVATUPSWOH-UHFFFAOYSA-N 0.000 description 1
- 239000013384 organic framework Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000004654 triazenes Chemical class 0.000 description 1
Classifications
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a bis (1, 2, 4-triazole) triazene cationic nitrogen-rich energetic ion salt, the chemical structural formula of which is shown as the formula<Ⅰ>As shown. The bis (1, 2, 4-triazole) triazene cationic nitrogen-enriched energetic nitrate provided by the invention is taken as an energetic compound, the impact sensitivity is 45J, the impact sensitivity of perchlorate is 10J, and excellent detonation performance is shown. The impact sensitivity of the nitrate compound is close to TATB, and the impact sensitivity of the perchlorate compound is better than RDX. The invention also provides a method for preparing the bis (1, 2, 4-triazole) triazene cationic nitrogen-rich energetic ion salt, which has a simple synthesis method and is easy for industrial production. On the other hand, the bis (1, 2, 4-triazole) triazene cationic nitrogen-rich energetic ion salt has wide application prospect in the aspect of preparing energetic materials.
Description
Technical Field
The invention belongs to the technical field of energetic materials, and particularly relates to a bis (1, 2, 4-triazole) triazene cationic nitrogen-enriched energetic ion salt, and a preparation method and application thereof.
Background
The performance of an energetic material, which is one of the core materials of a weapon, directly determines to some extent the energy performance of the weapon. The development of energetic materials has been receiving great attention from countries around the world, and in recent years nitrogen-rich energetic ion salts have become one of the hot spots in the field of research of high energy density materials.
The nitrogen-rich energetic ion salts are nitrogen-rich cations or anions or both energetic group-containing salt compounds, generally having relatively high density and good stability. In addition, ionic salts have the characteristic of low or zero vapor pressure, thereby reducing the inhalation risk associated with exposure of the compound to air. The oxygen balance of the nitrogen-enriched energetic ionic salt formed by introducing ionic groups such as nitrate radical, perchlorate radical and the like into the nitrogen-enriched energetic compound can be effectively improved. In addition, nitrogen-rich compounds decompose mainly to produce nitrogen, which makes them candidates for environmentally friendly energetic materials.
In the parent structure of the nitrogen-rich compound, the triazole parent with a planar structure has aromaticity and smaller ring tension, so that the molecular stability is higher, and the triazole parent is a potential energetic framework or intermediate. On the other hand, the triazole parent nitrogen content is high and reaches 60%, so that the heat of formation of the energetic compound can be effectively improved. In addition, the introduction of nitrogen chains into the nitrogen-rich energetic compound can significantly increase the nitrogen content of the compound and generate heat.
Triazenes (-n=n—nh-) are an effective chain of nitrogen atoms, with the most reported based on triazene bridged energetic nitrogen ion salts being triazene bridged organic frameworks as anionic components and neutral energetic nitrogen ion salts. The nitrogen-rich energetic ion salts of the corresponding cationic groups are reported to be less and the detonation performance is not satisfactory. As TangY et al, a cationic triazene compound Cl6.2ATA (Tang Y, yang H, wu B, et al Synthesis and characterization of a stable, treated N) 11 energetic salt[J]Angewandte Chemie,2013,125 (18): 4975-4977) which has good thermal stability and lower sensitivity but has detonation properties far lower than TATB, which are to be improved.
Therefore, developing a novel bis (1, 2, 4-triazole) triazene cationic nitrogen-rich energetic ion salt with good thermal stability and lower sensitivity and excellent detonation performance becomes a very challenging research work in the field.
Disclosure of Invention
Aiming at the defect that nitrogen-enriched energetic ion salt with high thermal stability, good sensitivity performance and excellent detonation performance cannot be obtained in the prior art, the invention aims to provide the bis (1, 2, 4-triazole) triazene cationic nitrogen-enriched energetic ion salt, and a synthesis method and application thereof.
One of the purposes of the invention is to provide a bis (1, 2, 4-triazole) triazene cationic nitrogen-rich energetic ion salt, which has a chemical structural formula shown as the following formula < I >:
wherein the Anion isAny one of them.
The energetic ionic salt with the structure provided by the invention calculates the detonation velocity not lower than 9471ms -1 Detonation pressure is not lower than 42.5GPa, detonation performance of the ionic salt is superior to RDX, and part of the ionic salt can approach or exceed HMX. The impact sensitivity of the nitrate containing energetic ions is 45J, the impact sensitivity of the perchlorate is 10J, and the nitrate containing energetic ions are more insensitive than RDX and HMX. Accordingly, the present invention provides a novel energetic ionic nitrate compound having excellent thermal stability and lower sensitivity, as well as excellent detonation properties.
It is a second object of the present invention to provide a process for preparing a bis (1, 2, 4-triazole) triazene cationic nitrogen-rich energetic ion salt as described above, comprising the steps of:
(1) Placing 3-amino-1, 2, 4-triazole in water, and adding inorganic acid;
(2) Dropwise adding sodium nitrite solution into the product obtained in the step (1) for reaction;
(3) After the reaction is finished, filtering, washing and drying the solid-phase product to obtain a solid product A; evaporating the filtrate, thermally extracting to obtain a solid product B, and combining the solid product A and the solid product B to obtain the bis (1, 2, 4-triazole) triazene cationic nitrogen-rich energetic ion salt.
Further, in the step (1), the inorganic acid includes any one of nitric acid and perchloric acid.
Further, the molar ratio of the inorganic acid to the 3-amino-1, 2, 4-triazole is 2-3:1.
Further, the reaction in the step (2) is carried out in an ice bath; preferably, the initial reaction temperature is not higher than 5 ℃, the reaction time is 6 hours, the subsequent reaction temperature is 10-25 ℃, and the reaction time is 6-24 hours.
Further, in the step (2), the molar ratio of sodium nitrite to 3-amino-1, 2, 4-triazole is 0.5:1.
Further, in the step (3), the washing is performed by using distilled water.
Further, in the step (3), the organic solvent used for the thermal extraction is any one of methanol, ethanol, acetone or dimethylformamide.
The invention also provides application of the bis (1, 2, 4-triazole) triazene cationic nitrogen-rich energetic ion salt in preparation of energetic materials.
The beneficial effects of the invention are as follows:
(1) The invention provides a new energetic ionic salt compound, the calculated detonation velocity is not lower than 9471ms -1 The detonation pressure is calculated to be not lower than 42.5GPa, which shows that the detonation performance of the ionic salt is superior to RDX and the part of the ionic salt can approach or exceed HMX. The impact sensitivity of the nitrate containing energetic ions is 45J, the impact sensitivity of the perchlorate is 10J, and the nitrate containing energetic ions are more insensitive than RDX and HMX. Has great application prospect in the field of energetic materials.
(2) The preparation method of the energetic ionic salt compound provided by the invention has the characteristics of simple preparation process and suitability for industrial production.
Drawings
FIG. 1 is a single crystal molecular structure diagram of the target product bis (1, 2, 4-triazole) triazene nitrate obtained in example 1.
Detailed Description
The present invention is described in detail below by way of examples, which are necessary to be pointed out herein for further illustration of the invention and are not to be construed as limiting the scope of the invention, since numerous insubstantial modifications and adaptations of the invention will occur to those skilled in the art in light of the foregoing disclosure.
Example 1
50.0g (0.595 mol) of 3-amino-1, 2, 4-triazole was added to 500mL of distilled water, to which 100mL of nitric acid (65%) was added at 0℃and the temperature was maintained at 0-5 ℃. 20.5g (0.298 mol) of sodium nitrite was weighed, dissolved in 30mL of distilled water, added to the ice-bath cooled reaction system in portions, and the temperature was controlled to be not more than 5 ℃. After the completion of the dropwise addition, the reaction was continued under ice bath conditions for 12 hours, and then transferred to room temperature for 24 hours. After the reaction, 62.4g of pale yellow solid, namely bis (1, 2, 4-triazole) triazene nitrate, is obtained through decompression filtration, washing and drying.
The product structure was identified as follows:
infrared spectroscopy: IR (ATR, v/cm) -1 ):υ:3126,3112,3050,2876,2751,2677,2127,1584,1509,1471,1426,1384,1312,1280,1249,1225,1186,1082,1039,1013,948,898,852,817,736,678,628,611,568,453.
Nuclear magneto-optical spectrum: 1 HNMR(DMSO-d 6 ,600MHz),δ:10.24(br,NH),8.78； 13 CNMR(DMSO-d 6 ,150MHz),δ:159.11,144.31
the above structural identification data confirm that the resulting material is bis (1, 2, 4-triazole) triazene nitrate.
The physicochemical properties of the obtained product were determined according to the corresponding current standards, and the properties of the bis (1, 2, 4-triazole) triazene nitrate product were determined as follows:
appearance: pale yellow needle-like crystals;
peak decomposition temperature: 181.3 ℃;
actually measured impact sensitivity: 45J;
calculating the detonation velocity: 9853 m.s -1 ；
Calculating the detonation pressure: 42.5GP.
Example 2
50.0g (0.595 mol) of 3-amino-1, 2, 4-triazole was added to 500mL of distilled water, and 130mL of perchloric acid (70%) was added thereto at 0℃and the temperature was maintained at 0-5 ℃. 20.5g (0.298 mol) of sodium nitrite was weighed, dissolved in 30mL of distilled water, added to the ice-bath cooled reaction system in portions, and the temperature was controlled to be not more than 5 ℃. After the completion of the dropwise addition, the reaction was continued under ice bath conditions for 12 hours, and then transferred to room temperature for 24 hours. After the reaction, 68.4g of pale yellow solid, namely bis (1, 2, 4-triazole) triazene perchlorate, is obtained through decompression filtration, washing and drying.
The product structure was identified as follows:
infrared spectroscopy: IR (ATR, v/cm) -1 ):υ:3479,3287,3139,3043,2979,2668,1697,1633,1610,1580,1545,1513,1498,1461,1408,1380,1340,1315,1265,1246,1226,1178,1086,1064,1042,979,963,924,911,890,801,755,736,712,652,621,603,450.
Nuclear magneto-optical spectrum: 1 HNMR(DMSO-d 6 ,600MHz),δ:9.83(br,NH),8.58； 13 CNMR(DMSO-d 6 ,150MHz),δ:159.45,144.99
the above structural identification data confirm that the resulting material is bis (1, 2, 4-triazole) triazene nitrate.
The physicochemical properties of the obtained product are determined according to the corresponding current standards, and the properties of the bis (1, 2, 4-triazole) triazene perchlorate are determined as follows:
appearance: a milky white powdery solid;
peak decomposition temperature: 166.9oC;
actually measured impact sensitivity: 10J;
calculating the detonation velocity: 9471 m.s -1 ；
Calculating the detonation pressure: 43.1GPa.
Claims (10)
1. The bis (1, 2, 4-triazole) triazene cation nitrogen-rich energetic ion salt is characterized in that the chemical structural formula is shown as the following formula < I >:
wherein the anion isAny one of them.
2. A process for preparing the bis (1, 2, 4-triazole) triazene cationic nitrogen-rich energetic ion salt of claim 1, characterized in that the process comprises the following steps:
(1) Placing 3-amino-1, 2, 4-triazole in water, and adding inorganic acid;
(2) Dropwise adding sodium nitrite solution into the product obtained in the step (1) for reaction;
(3) After the reaction is finished, filtering, washing and drying the solid-phase product to obtain a solid product A; evaporating the filtrate, thermally extracting to obtain a solid product B, and combining the solid product A and the solid product B to obtain the bis (1, 2, 4-triazole) triazene cationic nitrogen-rich energetic ion salt.
3. The method of claim 2, wherein in step (1), the mineral acid comprises any one of nitric acid or perchloric acid.
4. A process according to claim 2 or 3, wherein the molar ratio of the mineral acid to 3-amino-1, 2, 4-triazole is from 2 to 3:1.
5. A process according to claim 2 or 3, wherein the reaction of step (2) is carried out in an ice bath.
6. A process according to claim 2 or 3, wherein the reaction of step (2) is carried out at a temperature of not more than 5 ℃ for a reaction time of 6 hours and at a subsequent reaction temperature of 10 to 25 ℃ for a reaction time of 6 to 24 hours.
7. A process according to claim 2 or 3, wherein in step (2) the molar ratio of sodium nitrite to 3-amino-1, 2, 4-triazole is 0.5:1.
8. A method according to claim 2 or 3, wherein in step (3), the washing is with distilled water.
9. A method according to claim 2 or 3, wherein in step (3), the organic solvent used for the thermal extraction is any one of methanol, ethanol, acetone or dimethylformamide.
10. Use of a bis (1, 2, 4-triazole) triazene cationic nitrogen-rich energetic ion salt prepared by the method of claim 1 or any one of claims 2-9 in the preparation of energetic materials.
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|---|---|---|---|---|
| US3431251A (en) * | 1965-09-02 | 1969-03-04 | Us Navy | Triazole triazines and method of preparation |
| US6509473B1 (en) * | 2000-10-16 | 2003-01-21 | The United States Of America As Represented By The Secretary Of The Air Force | Energetic triazolium salts |
| CN109053614A (en) * | 2018-08-21 | 2018-12-21 | 西南科技大学 | Triazine cation base richness nitrogen ion salt containing energy and its preparation method and application |
| EP3481792A1 (en) * | 2016-07-11 | 2019-05-15 | Dynitec GmbH | Lead-free initiating agents or initiating agent mixtures |
| CN111499586A (en) * | 2020-05-25 | 2020-08-07 | 北京理工大学重庆创新中心 | Synthesis method of 5,5' -triazene bridged bis (2-methyl-4-nitro-1, 2, 3-triazole) compound |
| CN113773326A (en) * | 2021-10-21 | 2021-12-10 | 中北大学 | 3, 6-dinitroamine triazole and ionic salt thereof, and preparation method and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL235415A0 (en) * | 2014-10-30 | 2015-01-29 | Univ Ramot | Energetic compounds and compositions |
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| US6509473B1 (en) * | 2000-10-16 | 2003-01-21 | The United States Of America As Represented By The Secretary Of The Air Force | Energetic triazolium salts |
| EP3481792A1 (en) * | 2016-07-11 | 2019-05-15 | Dynitec GmbH | Lead-free initiating agents or initiating agent mixtures |
| CN109053614A (en) * | 2018-08-21 | 2018-12-21 | 西南科技大学 | Triazine cation base richness nitrogen ion salt containing energy and its preparation method and application |
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