CN112125858A - Gemini energetic ion compound and preparation method thereof - Google Patents
Gemini energetic ion compound and preparation method thereof Download PDFInfo
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- CN112125858A CN112125858A CN202010952622.XA CN202010952622A CN112125858A CN 112125858 A CN112125858 A CN 112125858A CN 202010952622 A CN202010952622 A CN 202010952622A CN 112125858 A CN112125858 A CN 112125858A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- -1 ion compound Chemical class 0.000 title claims description 7
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- SWRGUMCEJHQWEE-UHFFFAOYSA-N ethanedihydrazide Chemical compound NNC(=O)C(=O)NN SWRGUMCEJHQWEE-UHFFFAOYSA-N 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 7
- 238000010992 reflux Methods 0.000 claims abstract description 5
- 125000003431 oxalo group Chemical group 0.000 claims 1
- 150000008040 ionic compounds Chemical class 0.000 abstract description 29
- 239000007787 solid Substances 0.000 abstract description 13
- 239000008367 deionised water Substances 0.000 abstract description 5
- 229910021641 deionized water Inorganic materials 0.000 abstract description 5
- 239000000706 filtrate Substances 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 5
- 238000003756 stirring Methods 0.000 abstract description 5
- 238000001816 cooling Methods 0.000 abstract description 3
- 238000001914 filtration Methods 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 238000009835 boiling Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000010189 synthetic method Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 8
- 238000005474 detonation Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000002360 explosive Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OTXHZHQQWQTQMW-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen carbonate Chemical compound OC([O-])=O.N[NH2+]C(N)=N OTXHZHQQWQTQMW-UHFFFAOYSA-N 0.000 description 1
- FZAZPMLWYUKRAE-UHFFFAOYSA-N 2,4,6-trinitrobenzene-1,3-diamine Chemical compound NC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C(N)=C1[N+]([O-])=O FZAZPMLWYUKRAE-UHFFFAOYSA-N 0.000 description 1
- SHHKWIJFVUHKCA-UHFFFAOYSA-N 5-(3-amino-1h-1,2,4-triazol-5-yl)-1h-1,2,4-triazol-3-amine Chemical compound NC1=NNC(C=2NN=C(N)N=2)=N1 SHHKWIJFVUHKCA-UHFFFAOYSA-N 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a Gemini energetic ionic compound and a preparation method thereof, belonging to the technical field of energetic material preparation. The method comprises the following steps: dispersing 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) (DNBT) in deionized water at room temperature, heating the solution to boiling, and stirring for reaction for 30 minutes to obtain a light yellow clear liquid. Then adding oxalyl hydrazine into the solution in batches, placing the reaction at 100 ℃ for reflux reaction for 2 hours, filtering while the reaction is hot, and placing the filtrate at 4 ℃ for cooling overnight to obtain light yellow solid powder. The ionic compound synthesized by the invention is disclosed and reported for the first time, and the synthetic method is simple, stable in property and easy to amplify and prepare.
Description
Technical Field
The invention relates to a preparation method of a Gemini energetic ion compound 5,5 '-binitro-3, 3' -bis (1,2, 4-triazole) oxalyl hydrazine salt, belonging to the field of energetic material preparation.
Background
In recent years, High Energy Density Materials (HEDM) have become a research focus in the field of energetic materials as novel high energy explosives. Desirable characteristics of the novel energetic material include: the high positive enthalpy of formation, high density, high detonation velocity and detonation pressure, good thermal stability and low sensitivity to external stimuli such as impact or friction, wherein the energetic ionic compound shows excellent application prospects in explosives, propellants and pyrotechnic agents. The application research mainly shows two aspects, namely the application research in the propellant and the research on TNT and HMX substitutes in the casting explosive. The characteristics of easy design and low sensitivity of the energetic ionic compound cause the energetic ionic compound to be widely concerned in the research of low-vulnerability fusion-cast explosives. Compared to conventional energetic molecular compounds, energetic ionic compounds have several advantages: (1) the steam pressure is low, and the risk of inhalation through exposure can be eliminated; (2) the designability is high, the detonation property can be optimized and improved through the combination of cations and anions, and the density, the oxygen balance and the thermal stability are easier to regulate and control; (3) the diversity of compounds, by modifying the functional groups of existing energetic compounds, can significantly increase the number of energetic compounds available. In recent years, many scientific achievements have been made on the research of energetic ionic compounds, and based on the current research on energetic ionic compounds, energetic ionic compounds are mainly researched on azole energetic ionic compounds, but most azole energetic ionic compounds are mainly single energetic ionic compounds. Compared with the single energetic ionic compound, the gemini energetic ionic compound has the advantages of stronger ion interaction force, higher density and the like.
Disclosure of Invention
The invention aims to provide a gemini energetic ionic compound and a preparation method thereof.
The gemini energetic ionic compound of the invention, named 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) oxalyl hydrazine salt, has the following structural formula:
the preparation method of the gemini energetic ion compound comprises the step of reacting 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) (DNBT) with oxalyl hydrazine in water to prepare the target product,
preferably, the reaction temperature is reflux temperature.
Preferably, the molar ratio of 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) to oxalyl hydrazine is 1: 1.
Compared with the prior art for synthesizing ionic compounds, the method has the following advantages:
(1) in contrast to other ionic compounds, both anions and cations in the present invention are gemini ions.
(2) Compared with other ion exchange methods for preparing the energetic ion compound, the method has the advantages of simple synthesis steps, easy operation, stable property and easy amplification preparation.
(3) In the synthesis of the ionic compound, other metal ions are not introduced, so that the purity of the obtained energetic ionic compound can be effectively ensured.
Drawings
FIG. 1 is a crystal structure diagram of 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) oxalyl hydrazine salt, an energetic ionic compound according to the present invention.
FIG. 2 shows nuclear magnetic hydrogen spectrum (5, 5 '-dinitro-3, 3' -bis (1,2, 4-triazole) oxalyl hydrazine salt of energetic ionic compound of the invention1H-NMR)。
FIG. 3 is a nuclear magnetic carbon spectrum of 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) oxalyl hydrazine salt containing an energetic ionic compound of the invention (C:)13C-NMR)。
Detailed Description
The present invention will be described in further detail by combining the above synthetic routes for 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) oxalhydrazide salts.
The starting material, 5 '-dinitro-3, 3' -bis (1,2, 4-triazole) (DNBT), referred to in the following examples was prepared by the following procedure: dissolving oxalic acid in concentrated hydrochloric acid, adding aminoguanidine bicarbonate in batches, heating and refluxing for reaction for 2 hours, cooling to room temperature, dissolving the generated white solid in water, adjusting the pH to 14 by using sodium hydroxide solution, refluxing for reaction for 1 hour, adjusting the pH of the reaction solution to 4 by using acetic acid, and filtering to obtain a white solid: 3,3 '-diamino-5, 5' -bis (1H-1,2, 4-triazole) (DABT).
Slowly dripping 20% concentrated sulfuric acid solution of 3,3 '-diamino-5, 5' -bi (1H-1,2, 4-triazole) (DATB) into the aqueous solution of sodium nitrite, heating to 50 ℃ for reaction for 1H, cooling the solution to room temperature, acidifying with 20% concentrated sulfuric acid until no nitrogen oxide is discharged, filtering to obtain a solid, and recrystallizing to obtain a light yellow solid 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) (DNBT).
Example 1
40mL of deionized water was added to a 100mL flask, then 0.226g (1mmol) of 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) was added to the flask, and after stirring the mixture uniformly, the temperature of the solution was heated to 100 ℃ and the 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) was completely dissolved after 30 minutes of reaction, and the system was a pale yellow clear solution. 0.118g (1mmol) of oxalyl hydrazine (commercially available) was then added to the reaction, the reaction stirred for 30 minutes, the mixture was filtered and the filtrate was cooled overnight at 4 ℃ to precipitate a pale yellow solid. The product was filtered and air dried to give 0.176g of a pale yellow solid with 51% yield.
Example 2
40mL of deionized water was added to a 100mL flask, then 0.226g (1mmol) of 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) was added to the flask, and after stirring the mixture uniformly, the temperature of the solution was heated to 100 ℃ and the 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) was completely dissolved after 30 minutes of reaction, and the system was a pale yellow clear solution. Subsequently, 0.118g (1mmol) of oxalyl hydrazine was added to the reaction, the reaction was stirred for 1 hour, the mixture was filtered, and the filtrate was left to stand at 4 ℃ to cool overnight, whereupon a white solid precipitated. The product was filtered and air dried to give 0.258g of a pale yellow solid with a yield of 75%.
Example 3
40mL of deionized water was added to a 100mL flask, then 0.226g (1mmol) of 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) was added to the flask, and after stirring the mixture uniformly, the temperature of the solution was heated to 100 ℃ and the 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) was completely dissolved after 30 minutes of reaction, and the system was a pale yellow clear solution. Subsequently, 0.118g (1mmol) of oxalyl hydrazine was added to the reaction, the reaction was stirred for 2 hours, the mixture was filtered, and the filtrate was left to stand at 4 ℃ to cool overnight, whereupon a white solid precipitated. The product was filtered and air dried to give 0.279g of a pale yellow solid with 81% yield.
Example 4
40mL of deionized water was added to a 100mL flask, then 0.226g (1mmol) of 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) was added to the flask, and after stirring the mixture uniformly, the temperature of the solution was heated to 100 ℃ and the 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) was completely dissolved after 30 minutes of reaction, and the system was a pale yellow clear solution. Subsequently, 0.118g (1mmol) of oxalyl hydrazine was added to the reaction, the reaction was stirred for 5 hours, the mixture was filtered, and the filtrate was left to stand at 4 ℃ to cool overnight, whereupon a white solid precipitated. The product was filtered and air dried to give 0.275g of a pale yellow solid with 80% yield.
From the above results, it can be seen that the yield of the ionic compound was the highest when the reaction time was 2 hours, and the yield did not change significantly after the reaction time was continued to be prolonged.
FIG. 1 is a crystal structure diagram of 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) oxalyl hydrazine salt, an energetic ionic compound according to the present invention.
FIG. 2 shows nuclear magnetic hydrogen spectrum (5, 5 '-dinitro-3, 3' -bis (1,2, 4-triazole) oxalyl hydrazine salt of energetic ionic compound of the invention1H-NMR)。
FIG. 3 is a nuclear magnetic carbon spectrum of 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) oxalyl hydrazine salt containing an energetic ionic compound of the invention (C:)13C-NMR)。
The crystal of the 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) oxalyl hydrazine salt containing the energetic ionic compound is 0.20 mm multiplied by 0.15mm3Cell parameter of
The crystal density is: 1.653g/cm3。
The actually measured density of the energetic ionic compound is as follows: 1.733g/cm3The enthalpy of formation is: -107.691KJ/mol, calculated for the detonation pressure: 25.2GPa, the calculated detonation velocity is as follows: 7983 m/s.
Claims (4)
1. A gemini energetic ion compound, characterized by the name 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) oxalyl hydrazidate, having the following structural formula:
2. a preparation method of a Gemini energetic ion compound is characterized by comprising the step of reacting 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) with oxalyl hydrazine in water to prepare a target product,
3. the process of claim 2, wherein the reaction temperature is reflux temperature.
4. The process of claim 2, wherein the molar ratio of 5,5 '-dinitro-3, 3' -bis (1,2, 4-triazole) to oxalyl hydrazine is 1: 1.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2218986A (en) * | 1988-05-27 | 1989-11-29 | Olin Corp | Preparation of 3-nitro-1,2,4-triazol-5-one |
| CN103483330A (en) * | 2012-06-12 | 2014-01-01 | 北京理工大学 | Energy containing ionic salts of 4, 4'-bi [3, 3'-(1-H-5-tetrazolium)] furazan and preparation method thereof |
| CN103601680A (en) * | 2013-10-28 | 2014-02-26 | 北京理工大学 | Bispyrazolyl energetic compounds and preparation method thereof |
| CN104649984A (en) * | 2015-02-12 | 2015-05-27 | 西安近代化学研究所 | 1,1'-di(dinitromethyl)-3,3'-dinitro-5,5'-di-1,2,4-triazolyl bis hydroxylamine salt |
| CN105272929A (en) * | 2015-11-02 | 2016-01-27 | 西安近代化学研究所 | 5-nitryl-1,2,4-triazole-5-ketone compound of oxalyl dihydrazide |
| CN106632105A (en) * | 2016-12-15 | 2017-05-10 | 中国工程物理研究院化工材料研究所 | 5,5'-di(trinitromethyl)-3,3'-H,H'-di-1,2,4-triazole and synthetic method |
| CN110467581A (en) * | 2018-05-11 | 2019-11-19 | 南京理工大学 | A kind of anhydrous nonmetallic pentazole ion salt and preparation method thereof |
-
2020
- 2020-09-11 CN CN202010952622.XA patent/CN112125858A/en active Pending
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Application publication date: 20201225 |
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| RJ01 | Rejection of invention patent application after publication |