CN106432113A - 1,1'-azo bis(5-chloro-3-nitro-1,2,4-triazole) compound - Google Patents
1,1'-azo bis(5-chloro-3-nitro-1,2,4-triazole) compound Download PDFInfo
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- CN106432113A CN106432113A CN201610807719.5A CN201610807719A CN106432113A CN 106432113 A CN106432113 A CN 106432113A CN 201610807719 A CN201610807719 A CN 201610807719A CN 106432113 A CN106432113 A CN 106432113A
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- Prior art keywords
- nitro
- compound
- chloro
- azo
- triazole
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- -1 1,1'-azo bis(5-chloro-3-nitro-1,2,4-triazole) compound Chemical class 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000002360 explosive Substances 0.000 abstract 1
- CCQBFHMMQFUKKZ-UHFFFAOYSA-N 5-chloro-3-nitro-1h-1,2,4-triazole Chemical compound [O-][N+](=O)C1=NNC(Cl)=N1 CCQBFHMMQFUKKZ-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000005474 detonation Methods 0.000 description 8
- HRDWPQPUIGIEFU-UHFFFAOYSA-N 3,5-dinitro-1,2,4-triazol-1-amine Chemical class NN1N=C([N+]([O-])=O)N=C1[N+]([O-])=O HRDWPQPUIGIEFU-UHFFFAOYSA-N 0.000 description 5
- 238000004880 explosion Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- FTBBGQKRYUTLMP-UHFFFAOYSA-N 2-nitro-1h-pyrrole Chemical class [O-][N+](=O)C1=CC=CN1 FTBBGQKRYUTLMP-UHFFFAOYSA-N 0.000 description 3
- KUEFXPHXHHANKS-UHFFFAOYSA-N 5-nitro-1h-1,2,4-triazole Chemical class [O-][N+](=O)C1=NC=NN1 KUEFXPHXHHANKS-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 208000035126 Facies Diseases 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- SXMBECNFEHPCNP-UHFFFAOYSA-N 3,5-dinitro-1h-1,2,4-triazole Chemical compound [O-][N+](=O)C1=NNC([N+]([O-])=O)=N1 SXMBECNFEHPCNP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- PWBVDDKZTBDTJH-UHFFFAOYSA-N di(pyrrol-1-yl)diazene Chemical class N(=NN1C=CC=C1)N1C=CC=C1 PWBVDDKZTBDTJH-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- ZHZOIVSXSKARMO-UHFFFAOYSA-N tert-butyl chlorate Chemical compound CC(C)(C)OCl(=O)=O ZHZOIVSXSKARMO-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a 1,1'-azo bis(5-chloro-3-nitro-1,2,4-triazole) compound with a structural formula (I) shown in the specification. The 1,1'-azo bis(5-chloro-3-nitro-1,2,4-triazole) compound is mainly used for the field of explosives.
Description
Technical field
The invention belongs to energetic material field is and in particular to a kind of 1,1 '-azo double (5- chloro- 3- nitro -1,2,4- tri-
Azoles) compound.
Background technology
High Nitrogen Heterocyclic Energetic Compounds, because containing substantial amounts of N-N and N=N key in its molecule, can discharge a large amount of during decomposition
Nitrogen, therefore the features such as there is high density, high positive generation heat and detonation product clean.In recent years, multiple nitro azoles contain energy
Compound is synthesized in succession, such as：3,5- dinitro -1,2,4- triazole, 1- amino 3,5- dinitro -1,2,4- three
Azoles, 4- amino -3, the nitro azole energy-containing compound that 5- binitropyrazole etc., wherein 1- amino replace, the introducing of amino is permissible
Forming more intramoleculars and intermolecular hydrogen bonding, thus improving the heat stability of compound, reducing sensitivity；More due to defining
N-N key, can increase compound generation heat.Simultaneously because the reactivity of amino is so as to can conduct on 1 N atom
Containing derivative reaction intermediate further occurring, formed and contain N, N '-azo group, nitramino, trinitro- ethylamino etc. contain energy
The high energy energetic material of group.In the design of new energetic material and building-up process, substantial amounts of experience and test result indicate that：
The N-N containing in compound molecule be joined directly together number of nitrogen atoms more although successfully synthesizing more difficult, but obtain compound
There is higher just generation heat, therefore there is excellent comprehensive detonation property.
Ping Yin et al. exists《N-Diazo-Bridged Nitroazoles:Catenated Nitrogen-Atom
Chains Compatible with Nitro Functionalities》, Chem.Eur.J., 2014,20,6707-6712 mono-
Disclosed herein 1, the structure of double (3- nitro -1,2, the 4- triazoles) compound of 1 '-azo and performance, its structure is as shown in (II)：
The density of this compound is 1.80g/cm3, calculate and generate hot 718.8kJ/mol, explosion velocity 8825m/s, detonation pressure
33.5GPa.But this compound density is less, it is less to generate heat, energy is relatively low.
Content of the invention
The technical problem to be solved is to overcome not enough present in background technology and defect, provides a kind of density
Double (the 5- chloro- 3- nitro -1,2,4- triazole) compound of 1,1 ' larger, generation heat is larger, energy is higher-azo.
The synthetic route of the 1,1 ' of the present invention-azo double (5- chloro- 3- nitro -1,2,4- triazole) is as follows：
With 1- amino -3,5- dinitro -1,2,4- triazoles are raw material, with t-butyl hypochlorate, oxidative coupling, chloro occur
Reaction generation 1,1 '-azo is double (5- chloro- 3- nitro -1,2,4- triazole).
The 1 of the present invention, double (5- chloro- 3- nitro -1,2, the 4- triazoles) compound of 1 '-azo, its structural formula is as shown in (I)：
The 1 of the present invention, the synthetic method of 1 '-azo double (5- chloro- 3- nitro -1,2,4- triazoles), comprise the following steps：Stir
Mix down, 20 DEG C～25 DEG C, by 1- amino -3,5- dinitro -1,2,4- triazoles are added in anhydrous acetonitrile, 0 DEG C～5 DEG C additions time
The chloric acid tert-butyl ester, is heated to 15 DEG C～45 DEG C reaction 15h～25h, adds ethyl acetate, cold water washs organic faciess, anhydrous
Magnesium sulfate is dried, and removes organic solvent under reduced pressure and obtains 1, and 1 '-azo is double (5- chloro- 3- nitro -1,2,4- triazoles)；Wherein 1- amino-
3,5- dinitro -1,2,4- triazole is 1 with the mol ratio of t-butyl hypochlorate:1.5～2.5, the consumption of anhydrous acetonitrile is every gram
1- amino -3,5- dinitro -1,2,4- triazole 30.0～100.0mL.
Advantages of the present invention：
The 1 of the present invention, double (5- chloro- 3- nitro -1,2,4- triazoles) the compound density of 1 '-azo is larger, and its density is
1.922g/cm3, the 1 of documents, the density of 1 '-azo double (3- nitro -1,2,4- triazoles) is 1.80g/cm3；The present invention's
1,1 '-azo double (5- chloro- 3- nitro -1,2,4- triazoles) compound calculating generation heat is larger, and it generates heat for 774.8kJ/
Mol, the 1 of documents, the generation heat of 1 '-azo double (3- nitro -1,2,4- triazoles) is 718.8kJ/mol；The 1 of the present invention,
Double (5- chloro- 3- nitro -1,2,4- triazoles) the compound energy of 1 '-azo is higher, and calculating its explosion velocity is 8827m/s, and detonation pressure is
35.8GPa, the 1 of documents, the calculating explosion velocity of 1 '-azo double (3- nitro -1,2,4- triazoles) is 8825m/s, and detonation pressure is
33.5GPa.
Specific embodiment
With reference to embodiment, the present invention is described in further details.
Embodiment 1
Under stirring, in 20 DEG C～25 DEG C of temperature, by 0.174g (1mmol) 1- amino -3,5- dinitro -1,2,4- triazoles add
Enter in 7.0mL anhydrous acetonitrile, ice-water bath is cooled to 0 DEG C～5 DEG C, add 0.185g (1.7mmol) t-butyl hypochlorate, heating
It is warming up to 25 DEG C～30 DEG C reaction 20h, add 30.0mL ethyl acetate, cold water (8.0mL × 5) washs organic faciess, anhydrous slufuric acid
Magnesium is dried, and removes organic solvent under reduced pressure and obtains 1, double (5- chloro- 3- nitro -1,2, the 4- triazoles) 0.113g of 1 '-azo, and yield is
65.7%.
Structural Identification：
Infrared spectrum：IR(KBr,cm-1),υ：1650,1574,1507,1446,1388,1347,1303,1242,1218,
1097,1000,844,743,678,664,630,579
Nuclear magnetic spectrum：13CNMR(DMSO-d6,125MHz),δ：141.73,158.73
Elementary analysiss：Molecular formula C4N10O4Cl2
Theoretical value：C 14.87,N 43.36
Measured value：C 14.92,N 43.29
Mono-crystalline structures：This compound crystal is monoclinic system, and space group is P2 (1)/c, and crystallographic parameter is： α=90 °, β=105.495 (11) °, γ=90 °,Z=
4, μ=0.619mm-1, F (000)=640.
Said structure appraising datum confirms that obtaining material is strictly double (the 5- chloro- 3- nitro -1,2,4- three of 1,1 '-azo
Azoles).
The performance of 1,1 '-azo double (5- chloro- 3- nitro -1,2,4- triazole)
(1) physical and chemical performance
Outward appearance：Yellowish-brown mealy crystal
Dissolubility：It is soluble in dimethyl sulfoxide, N,N-dimethylformamide, acetone, acetonitrile, methanol, ethanol, ethyl acetate
Deng；
It is slightly soluble in water, ether, petroleum ether, hexamethylene etc.
Density：1.922g/cm3X- monocrystalline x ray diffractometer x
(2) detonation property
Explosion velocity：Density is 1.922g/cm3, calculating explosion velocity is 8827m/s K-J equation
Detonation pressure：Density is 1.922g/cm3, calculating detonation pressure is 35.8GPa K-J equation
Generate heat：Density is 1.922g/cm3, calculating and generating heat is 774.8kJ/mol K-J equation
Quick-fried heat：Density is 1.922g/cm3, calculating quick-fried heat is 6283.4kJ/kg K-J equation
The purposes of 1,1 '-azo double (5- chloro- 3- nitro -1,2,4- triazole)
Double (the 5- chloro- 3- nitro -1,2,4- triazole) compound of the 1,1 ' of the present invention-azo has that density is big, it is big to generate heat,
The features such as energy is high, can apply to energetic material field.
Claims (1)
1. one kind 1, double (5- chloro- 3- nitro -1,2, the 4- triazoles) compound of 1 '-azo, its structural formula is as shown in (I)：
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610807719.5A CN106432113B (en) | 2016-09-07 | 2016-09-07 | Bis- (the chloro- 3- nitros -1,2,4- triazoles of the 5-) compounds of 1,1 '-azos |
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|---|---|---|---|
| CN201610807719.5A CN106432113B (en) | 2016-09-07 | 2016-09-07 | Bis- (the chloro- 3- nitros -1,2,4- triazoles of the 5-) compounds of 1,1 '-azos |
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| Publication Number | Publication Date |
|---|---|
| CN106432113A true CN106432113A (en) | 2017-02-22 |
| CN106432113B CN106432113B (en) | 2018-10-12 |
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| CN201610807719.5A Expired - Fee Related CN106432113B (en) | 2016-09-07 | 2016-09-07 | Bis- (the chloro- 3- nitros -1,2,4- triazoles of the 5-) compounds of 1,1 '-azos |
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Cited By (2)
| 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 |
| CN114573518A (en) * | 2022-03-14 | 2022-06-03 | 中国科学院上海有机化学研究所 | 4-cyano-5-nitro-1, 2, 3-triazole metal salt, and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5889161A (en) * | 1998-05-13 | 1999-03-30 | Sri International | N,N'-azobis-nitroazoles and analogs thereof as igniter compounds for use in energetic compositions |
| CN104725328A (en) * | 2015-03-20 | 2015-06-24 | 西安近代化学研究所 | Synthesis method of 1,1'-azo-bis(3,5-dinitro-1,2,4-triazole) |
-
2016
- 2016-09-07 CN CN201610807719.5A patent/CN106432113B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5889161A (en) * | 1998-05-13 | 1999-03-30 | Sri International | N,N'-azobis-nitroazoles and analogs thereof as igniter compounds for use in energetic compositions |
| CN104725328A (en) * | 2015-03-20 | 2015-06-24 | 西安近代化学研究所 | Synthesis method of 1,1'-azo-bis(3,5-dinitro-1,2,4-triazole) |
Non-Patent Citations (1)
| Title |
|---|
| 《J MOL MODEL》 * |
Cited By (3)
| 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 |
| CN114573518A (en) * | 2022-03-14 | 2022-06-03 | 中国科学院上海有机化学研究所 | 4-cyano-5-nitro-1, 2, 3-triazole metal salt, and preparation method and application thereof |
| CN114573518B (en) * | 2022-03-14 | 2024-02-06 | 中国科学院上海有机化学研究所 | 4-cyano-5-nitro-1, 2, 3-triazole metal salt, preparation method and application thereof |
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| Publication number | Publication date |
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| CN106432113B (en) | 2018-10-12 |
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