CN105111156A - 2-amino-5, 5'-dinitro-3, 3'-bis (1, 2, 4-triazole) compound - Google Patents
2-amino-5, 5'-dinitro-3, 3'-bis (1, 2, 4-triazole) compound Download PDFInfo
- Publication number
- CN105111156A CN105111156A CN201510603835.0A CN201510603835A CN105111156A CN 105111156 A CN105111156 A CN 105111156A CN 201510603835 A CN201510603835 A CN 201510603835A CN 105111156 A CN105111156 A CN 105111156A
- Authority
- CN
- China
- Prior art keywords
- triazole
- bis
- amino
- compound
- dinitrobenzene
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 20
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 title abstract 3
- 239000000463 material Substances 0.000 abstract description 7
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000005474 detonation Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004880 explosion Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
Classifications
-
- 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
- C07D249/14—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a 2-amino-5, 5'-dinitro-3, 3'-bis (1, 2, 4-triazole) compound. The structural formula is described as (I) referring to the description. The 2-amino-5, 5'-dinitro-3, 3'-bis (1, 2, 4-triazole) compound is mainly applied to the field of energetic materials.
Description
Technical field
The present invention relates to a kind of energetic material, be specifically related to amino-5,5 '-dinitrobenzene-3,3 '-bis-(1,2, the 4-triazole) compound of a kind of 2-.
Background technology
In recent years, rich nitrogen energy-containing compound, as the energetic material of a class unique properties, because of end product mainly friendly, the free of contamination nitrogen of build environment of its burning or blast, and is usually applied to the research field such as explosive, propelling agent.Containing a large amount of N-N and N=N keys in this type of molecular structure of compounds, during decomposition, a large amount of nitrogen can be discharged, produce higher-energy; Stimulate insensitive to heat, friction, electrical spark etc., and have the features such as higher density, just Heat of Formation are large, better heat stability, therefore, countries in the world energetic material investigator creates larger concern to this compounds.Filter out part energy-containing compound simultaneously and carry out the research of its explorative research in fields such as the low sense explosive of high energy, gas-evolution agents.The people such as such as AlexanderA.Dippold are at " InsensitiveNitrogen-RichEnergeticCompoundsBasedonthe5,5 '-Dinitro-3,3 '-bi-1,2,4-triazol-2-ideAnion ", Eur.J.Inorg.Chem.2012,3474-3484 mono-discloses 5,5 '-dinitrobenzene-3 in literary composition, 3 '-bis-(1,2,4-triazole) structure of compound and the calculated performance of this compound, its structure is as shown in (II):
The calculated performance of this compound: nitrogen content is 49.6%, explosion velocity is 8413m/s, and detonation pressure is 32.0GPa, and Heat of Formation is 285.0kJ/mol.But this compound Heat of Formation is less, energy is lower.
Summary of the invention
Technical problem to be solved by this invention is the deficiency and the defect that overcome background technology, provides amino-5,5 '-dinitrobenzene-3,3 '-bis-(1,2, the 4-triazole) compound of the 2-that a kind of Heat of Formation is higher, energy is larger.
The synthetic route of amino-5,5 '-dinitrobenzene-3,3 '-bis-(1,2, the 4-triazole) compound of 2-of the present invention is as follows:
With the single sodium salt of 5,5 '-dinitrobenzene-3,3 '-bis-(1,2,4-triazole) for raw material, generate amino-5,5 '-dinitrobenzene-3,3 '-bis-(1,2, the 4-triazole) of 2-with hydroxylamine acid generation amination reaction.
Amino-5,5 '-dinitrobenzene-3,3 '-bis-(1,2, the 4-triazole) compound of 2-of the present invention, its structural formula is as shown in (I):
The synthetic method of amino-5,5 '-dinitrobenzene-3,3 '-bis-(1,2, the 4-triazole) of 2-of the present invention, comprises the following steps:
Under stirring at 20 ~ 25 DEG C, successively by 0.5g (2.02mmol) 5, 5 '-dinitrobenzene-3, 3 '-bis-(1, 2, 4-triazole) single sodium salt, 0.4g (3.77mol) sodium carbonate joins in 10.0mL water, be heated to 70 DEG C, drip the hydroxylamine acid aqueous solution of 2.0mL containing 0.46g (4.03mmol) hydroxylamine acid, after dropwising, add 0.7g (8.33mol) sodium bicarbonate in batches, at temperature 70 ~ 75 DEG C reaction 2.5h, reaction solution is cooled to 20 ~ 25 DEG C, with 36% ~ 38% (quality) concentrated hydrochloric acid adjust ph to 4 ~ 5, reacting liquid filtering, filter cake is through washing, dry 2-amino-5, 5 '-dinitrobenzene-3, 3 '-bis-(1, 2, 4-triazole).
Advantage of the present invention
Amino-5, the 5 '-dinitrobenzene-3,3 '-bis-(1,2 of 2-of the present invention, 4-triazole) compound Heat of Formation is higher, and its Heat of Formation is 490.7kJ/mol, 5 of documents, 5 '-dinitrobenzene-3, the Heat of Formation of 3 '-bis-(1,2,4-triazole) is 285.0kJ/mol; Amino-5, the 5 '-dinitrobenzene-3,3 '-bis-(1 of 2-of the present invention, 2,4-triazole) compound energy is higher, and calculating its explosion velocity is 8900.4m/s, detonation pressure is 35.9GPa, and quick-fried heat is 5666.9kJ/kg, 5 of documents, 5 '-dinitrobenzene-3, the calculating explosion velocity of 3 '-bis-(1,2,4-triazole) is 8413.0m/s, detonation pressure is 32.0GPa, and quick-fried heat is 4888.0kJ/kg.
Embodiment
Below in conjunction with embodiment, the present invention is described in further detail.
Embodiment 1
The synthesis of amino-5,5 '-dinitrobenzene-3,3 '-bis-(1,2, the 4-triazole) of 2-
Under stirring at 20 ~ 25 DEG C, successively by 0.5g (2.02mmol) 5, 5 '-dinitrobenzene-3, 3 '-bis-(1, 2, 4-triazole) single sodium salt, 0.4g (3.77mol) sodium carbonate joins in 10.0mL water, be heated to 70 DEG C, drip the hydroxylamine acid aqueous solution of 2.0mL containing 0.46g (4.03mmol) hydroxylamine acid, after dropwising, add 0.7g (8.33mol) sodium bicarbonate in batches, at temperature 70 ~ 75 DEG C reaction 2.5h, reaction solution is cooled to 20 ~ 25 DEG C, with 36% ~ 38% (quality) concentrated hydrochloric acid adjust ph to 4 ~ 5, reacting liquid filtering, filter cake is through washing, dry 2-amino-5, 5 '-dinitrobenzene-3, 3 '-bis-(1, 2, 4-triazole) 0.146g, yield is 30.1%.
Structural Identification:
Infrared spectra: IR (KBr, cm
-1), υ: 3567 (-NH), 3446,3384 (-NH
2), 1553,1529,1388,1312 (-NO
2), 1647,1042,839 (triazole ring)
Nuclear magnetic spectrum:
1hNMR (DMSO-d
6, 500MHz), δ: 3.393 (s, 1H, NH), 7.926 (s, 2H, NH
2);
13cNMR (DMSO-d
6, 125MHz), δ: 144.15,151.76,157.74,166.21
Ultimate analysis: molecular formula C
4h
3n
9o
4
Theoretical value: C19.92, H1.25, N52.28
Measured value: C19.87, H1.29, N52.32
Mass spectrum: (APCI) m/z:240 [M-H]
-.
Said structure appraising datum confirms that obtaining material is amino-5,5 '-dinitrobenzene-3,3 '-bis-(1,2, the 4-triazole) of 2-really.
The performance of amino-5,5 '-dinitrobenzene-3,3 '-bis-(1,2, the 4-triazole) of 2-
(1) physical and chemical performance
Outward appearance: pale pink solid
Solubleness: be soluble in DMF, acetone, acetonitrile, methyl alcohol, ethanol etc.; Be slightly soluble in methylene dichloride, ether, sherwood oil, hexanaphthene etc.
Density: 1.88g/cm
3gaussian09 program B3LYP method nitrogen content: 52.3%
(2) detonation property
The purposes of amino-5,5 '-dinitrobenzene-3,3 '-bis-(1,2, the 4-triazole) of 2-
Amino-5,5 '-dinitrobenzene-3,3 '-bis-(1,2, the 4-triazole) compound of 2-of the present invention has that nitrogen content is high, Heat of Formation large, energy high, can be applied to energetic material field as high energy material component.
Claims (1)
1. 2-amino-5,5 '-dinitrobenzene-3,3 '-bis-(1,2,4-triazole) compound, its structural formula is as shown in (I):
Priority Applications (1)
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CN201510603835.0A CN105111156B (en) | 2015-09-21 | 2015-09-21 | 2 amino, 5,5 ' dinitro, 3,3 ' double (1,2,4 triazole) compounds |
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CN201510603835.0A CN105111156B (en) | 2015-09-21 | 2015-09-21 | 2 amino, 5,5 ' dinitro, 3,3 ' double (1,2,4 triazole) compounds |
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Publication Number | Publication Date |
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CN105111156A true CN105111156A (en) | 2015-12-02 |
CN105111156B CN105111156B (en) | 2018-01-23 |
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CN201510603835.0A Expired - Fee Related CN105111156B (en) | 2015-09-21 | 2015-09-21 | 2 amino, 5,5 ' dinitro, 3,3 ' double (1,2,4 triazole) compounds |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109020906A (en) * | 2018-06-14 | 2018-12-18 | 西南科技大学 | A kind of energy-containing compound and its synthetic method and application |
-
2015
- 2015-09-21 CN CN201510603835.0A patent/CN105111156B/en not_active Expired - Fee Related
Non-Patent Citations (2)
Title |
---|
ALEXANDER A.DIPPOLD,ET AL.: "Insensitive Nitrogen-Rich Energetic Compounds Based on the 5,5’-Dinitro-3,3’-bi-1,2,4-triazol-2-ide Anion", 《EUR.J.INORG.CHEM.》 * |
LULU HUANG,ET AL.: "APPLICATIONS OF ENERGETIC MATERIALS BY A THEORETICAL METHOD(DISCOVER ENERGETIC MATERIALS BY A THEORETICAL METHOD)", 《INTERNATIONAL JOURNAL OF ENERGETIC MATERIALS AND CHEMICAL PROPULSION》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109020906A (en) * | 2018-06-14 | 2018-12-18 | 西南科技大学 | A kind of energy-containing compound and its synthetic method and application |
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