CN105601581B - A kind of double furazanyl ether compounds of 3 azido of energetic plasticiser, 3 ' nitro - Google Patents
A kind of double furazanyl ether compounds of 3 azido of energetic plasticiser, 3 ' nitro Download PDFInfo
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- CN105601581B CN105601581B CN201610133949.8A CN201610133949A CN105601581B CN 105601581 B CN105601581 B CN 105601581B CN 201610133949 A CN201610133949 A CN 201610133949A CN 105601581 B CN105601581 B CN 105601581B
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- nitro
- furazanyl
- double
- azido
- azidos
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- -1 furazanyl ether compounds Chemical class 0.000 title claims abstract description 24
- 239000004014 plasticizer Substances 0.000 title claims abstract description 9
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 title abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 title abstract 2
- 239000002131 composite material Substances 0.000 abstract description 2
- 239000002360 explosive Substances 0.000 abstract description 2
- 239000004449 solid propellant Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000004880 explosion Methods 0.000 description 4
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical group C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VPQBALMSVBPDNW-UHFFFAOYSA-N [Na].N(=[N+]=[N-])C1=NON=C1O Chemical class [Na].N(=[N+]=[N-])C1=NON=C1O VPQBALMSVBPDNW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005474 detonation Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 0 *c1n[o]nc1COc1n[o]nc1[N+]([O-])=O Chemical compound *c1n[o]nc1COc1n[o]nc1[N+]([O-])=O 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KIJCKNUNZABDBC-UHFFFAOYSA-N 3,4-dinitro-1,2,5-oxadiazole Chemical compound [O-][N+](=O)C1=NON=C1[N+]([O-])=O KIJCKNUNZABDBC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical compound NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B25/00—Compositions containing a nitrated organic compound
- C06B25/34—Compositions containing a nitrated organic compound the compound being a nitrated acyclic, alicyclic or heterocyclic amine
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06D—MEANS FOR GENERATING SMOKE OR MIST; GAS-ATTACK COMPOSITIONS; GENERATION OF GAS FOR BLASTING OR PROPULSION (CHEMICAL PART)
- C06D5/00—Generation of pressure gas, e.g. for blasting cartridges, starting cartridges, rockets
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Combustion & Propulsion (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a kind of double furazanyl ether compounds of 3 azido of energetic plasticiser, 3 ' nitro, its structural formula is such as shown in (I)：
Description
Technical field
The present invention relates to a kind of double furazanyl ether compounds of energetic plasticiser 3- azidos -3 '-nitro, belong to energetic material
Technical field.
Technical background
Furazan ether compound is one kind important in furazano energetic compound, due to the ehter bond introduced in molecule, is increased
The pliability of molecule is added, plasticising performance improves therewith；Ehter bond oxygen atom is in same plane with furazan ring, forms one big
Conjugated system, compound stability significantly improves.Furazan ether compound have fusing point is low, standard enthalpy of formation is big, quick-fried heat is high,
The characteristics of hydrogen content few (or hydrogen-free), thermostability are good, the gas flow of generation is big and acting ability is strong, plasticity waits by force spy
Point, can be used as castexplosive or energetic plasticiser use, become at present domestic and international energetic material research field hot spot it
One.Such as:Wang Baizhou, Li Hui, Li Yanan, Lian Peng, Zhou Yanshui, king's tin outstanding person's furazan ether energy-containing compound progress materials containing energy
Material, 2012,20 (4)：385-390. discloses the structure and performance data of a kind of two furazanyl ether (FOF-2) of 3,3 '-dicyano.
Its structure is as follows：
The density of the compound is 1.64g/cm3, explosion velocity 6820m/s, but the compound energy is relatively low, and density is relatively low.
The content of the invention
The technical problems to be solved by the invention are to overcome the shortcomings of background technology and defect, there is provided a kind of energy is higher,
The double furazanyl ether compounds of higher 3- azidos-the 3 '-nitro of density.
The synthetic route of the double furazanyl ether compounds of 3- azidos -3 '-nitro of the present invention is as follows：
The compound is using 3- azido -4- nitro furazans as raw material, and under the action of sodium hydroxide hydrolyzing to form 3- folds
Nitrogen base -4- hydroxyl furazans, then 3- azidos -4- hydroxyls furazan and sodium methoxide with dinitro furazan into being etherified synthesis 3- after salt again
The double furazanyl ether compounds of azido -3 '-nitro.
The compound of the double furazanyl ethers of energetic plasticiser 3- azidos -3 '-nitro of the present invention, has such as lower structure：
The compounds process for production thereof of the double furazanyl ethers of energetic plasticiser 3- azidos -3 '-nitro of the present invention, including it is following
Step：
(1) under stirring, in 15 DEG C~25 DEG C of temperature, the sodium hydrate aqueous solution that mass percent concentration is 20% is added
Into the tetrahydrofuran solution of 3- azido -4- nitro furazans, 40 DEG C~60 DEG C reaction 2h~5h, reaction are then heated to
Liquid is poured into frozen water, and it is 1~3 that the hydrochloric acid for being 36% with mass percent concentration, which is acidified to pH, then is extracted with ether, organic phase warp
Anhydrous magnesium sulfate is dried, and filtering, is concentrated to give 3- azido -4- hydroxyl furazans, wherein 3- azidos -4- nitro furazans, quality hundred
Specific concentration is divided to be 20% sodium hydrate aqueous solution, tetrahydrofuran mass ratio is 1:5~20:7~11；
(2) under stirring, in 15 DEG C~25 DEG C of temperature, the 3- azido -4- hydroxyl furazans that step (1) obtains are added to nothing
In water ether, add the methanol solution of sodium methylate that mass percent concentration is 30%, 15 DEG C~25 DEG C of temperature reaction 1h~
Acetonitrile, ether washing, dry 3- azido -4- hydroxyl furazan sodium salts, wherein 3- is respectively adopted in 3h, reacting liquid filtering, filter cake
Azido -4- hydroxyls furazan, mass percent concentration are 30% methanol solution of sodium methylate, anhydrous ether mass ratio is 1:1.2~
1.4:40~50；
(3) under stirring, in 15 DEG C~25 DEG C of temperature, the 3- azido -4- hydroxyl furazans sodium salt that step (2) is obtained adds
Into the anhydrous acetonitrile of 3,4- dinitro furazans, 30 DEG C~40 DEG C reaction 5h~10h are heated to, reaction solution pours into water
In, extracted with dichloromethane, organic phase is dried through anhydrous magnesium sulfate, and filtering, the yellow liquid thing being concentrated to give is through column chromatography point
From the double furazanyl ethers of 3- azidos -3 '-nitro are obtained, wherein 3,4- dinitro furazans, 3- azido -4- hydroxyl furazans sodium salt, nothing
Water-acetonitrile mass ratio is 1:0.95~1.05:7~9.
Advantages of the present invention
The compound energy of the double furazanyl ethers of 3- azidos -3 '-nitro of the present invention is higher, its explosion velocity is 8538.3m/s,
It is 6820m/s and the energy of 3,3 '-dicyano of documents, two furazanyl ether is relatively low；3- azidos -3 '-nitro of the present invention
The compound density of double furazanyl ethers is higher, its density is 1.81g/cm3, and 3,3 '-dicyano of documents, two furazanyl ether
Density it is relatively low, be 1.64g/cm3。
Embodiment
The present invention is described in further detail with reference to embodiments.
It is the embodiment that inventor provides below, it is necessary to explanation, these embodiments are preferably examples, are mainly used for
Understand the present invention, but the present invention is not limited to these Examples.
Embodiment 1
Under stirring, it is 20 DEG C in temperature, the sodium hydrate aqueous solution that 10g mass percent concentrations are 20% is added drop-wise to and is contained
In the 9g tetrahydrofuran solutions for there are 1g 3- azido -4- nitro furazans, 50 DEG C of insulation reaction 3h are warming up to after being added dropwise, instead
After answering, cooling, is poured into water, and it is 3 that the concentrated hydrochloric acid for being 36% with mass percent concentration, which is acidified to pH, and ether extracts 3 times,
Combining extraction liquid, anhydrous magnesium sulfate drying, filtering, concentration remove solvent and obtain 0.753g 3- azido -4- hydroxyl furazans, yield
For 92.5%.
Infrared spectrum：IR(KBr,cm-1),υ:3424,2150,1605,1561,1371,1268,1166,1006,864.
Nuclear magnetic spectrum：13C NMR(DMSO-d6,125MHz):145.920,158.441.1H NMR(DMSO-d6),
500MHz):13.5203
Elemental analysis:Molecular formula C2HN5O2
Theoretical value (%):C,18.91；H,0.79；N,55.12；Measured value (%):C,18.74；H,0.73；N,54.98
Embodiment 2
Under stirring, in 20 DEG C of temperature, 1g 3- azido -4- hydroxyl furazans are dissolved in 45g anhydrous ethers, are slowly added to
1.3g mass percent concentrations are 30% methanol solution of sodium methylate, in 20 DEG C of temperature reaction 2h, filtering, be respectively adopted acetonitrile,
Ether washs, dry 1.09g 3- azido -4- hydroxyl furazan sodium salts, yield 92.8%.
Infrared spectrum：IR(KBr,cm-1),υ:2160,1693,1581,1543,1449,1385,1014,863.
Elemental analysis:Molecular formula C2N5NaO2
Theoretical value (%):C,16.11；H,0；N,46.98；Measured value (%):C,16.44；H,0；N,46.63
Embodiment 3
Under stirring, in 15 DEG C of temperature, 0.95g 3- azido -4- hydroxyl furazan sodium salts are added to containing 1g 3,4- bis-
In the 7g anhydrous acetonitriles of nitro furazan, 30 DEG C of reaction 5h are warming up to, are poured into water, dichloromethane extraction, combining extraction liquid,
Anhydrous magnesium sulfate is dried, and the yellow liquid thing that concentration organic phase obtains obtains 0.78g 3- azidos -3 '-nitre through pillar layer separation
The double furazanyl ethers of base, yield 52.1%.
Infrared spectrum：IR(KBr,cm-1),υ:2146,1594,1532,1487,1357,1292,1197,1034,840.
Nuclear magnetic spectrum：13C NMR(DMSO-d6,125MHz):146.729,152.936,154.980,155.099.
Mass spectrum：MS (ESI-), m/z (%):239[M-H]-
Elemental analysis:Molecular formula C4N8O5
Theoretical value (%):C,20.00；H,0；N,46.67；Measured value (%):C,20.42；H,0；N,46.19；
Said structure appraising datum confirms that the material that this step obtains is strictly the double furazanyl ethers of 3- azidos -3 '-nitro.
The performance of the double furazanyl ethers of 3- azidos -3 '-nitro
The double furazanyl ethers of 3- azidos -3 '-nitro
(1) physical and chemical performance
Density：1.81g/cm309 program B3LYP/6-31G** methods of Gaussian
Standard enthalpy of formation：09 program B3LYP/6-31G** methods of 637.0kJ/mol Gaussian
(2) detonation property
Explosion velocity：Density is 1.81g/cm3, calculating explosion velocity is 8538.3m/s K-J equations
Detonation pressure：Density is 1.81g/cm3, calculating detonation pressure is 33.1Gpa K-J equations
The purposes of the double furazanyl ethers of 3- azidos -3 '-nitro
The double furazanyl ether compounds of 3- azidos -3 '-nitro of the present invention can be used as energetic plasticiser, castexplosive application
In propellant, composite explosives field.
Claims (1)
1. a kind of double furazanyl ether compounds of energetic plasticiser 3- azidos -3 '-nitro, its structural formula is such as shown in (I)：
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101578282A (en) * | 2007-01-16 | 2009-11-11 | Snpe巨能材料公司 | Furazane derivatives, preparation thereof and energetic compositions containing them |
| RU2536041C1 (en) * | 2013-10-11 | 2014-12-20 | ФЕДЕРАЛЬНОЕ ГОСУДАРСТВЕННОЕ БЮДЖЕТНОЕ УЧРЕЖДЕНИЕ НАУКИ ИНСТИТУТ ОРГАНИЧЕСКОЙ ХИМИИ им. Н.Д. ЗЕЛИНСКОГО РОССИЙСКОЙ АКАДЕМИИ НАУК (ИОХ РАН) | 3,3'-bis(fluorodinitromethyl-onn-azoxy)-4,4'-difurazanyl ether and method for production thereof |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101578282A (en) * | 2007-01-16 | 2009-11-11 | Snpe巨能材料公司 | Furazane derivatives, preparation thereof and energetic compositions containing them |
| RU2536041C1 (en) * | 2013-10-11 | 2014-12-20 | ФЕДЕРАЛЬНОЕ ГОСУДАРСТВЕННОЕ БЮДЖЕТНОЕ УЧРЕЖДЕНИЕ НАУКИ ИНСТИТУТ ОРГАНИЧЕСКОЙ ХИМИИ им. Н.Д. ЗЕЛИНСКОГО РОССИЙСКОЙ АКАДЕМИИ НАУК (ИОХ РАН) | 3,3'-bis(fluorodinitromethyl-onn-azoxy)-4,4'-difurazanyl ether and method for production thereof |
Non-Patent Citations (1)
| Title |
|---|
| 用分子子图法计算硝基呋咱化合物的生成热;刘剑洪，等;《化学物理学报》;20021031;第15卷(第5期);第351页左栏、第353页表2 * |
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