CN105669582B - Double (1- nitre aminotetrazole) the double potassium salt compounds of 5,5 '-azo - Google Patents
Double (1- nitre aminotetrazole) the double potassium salt compounds of 5,5 '-azo Download PDFInfo
- Publication number
- CN105669582B CN105669582B CN201610133948.3A CN201610133948A CN105669582B CN 105669582 B CN105669582 B CN 105669582B CN 201610133948 A CN201610133948 A CN 201610133948A CN 105669582 B CN105669582 B CN 105669582B
- Authority
- CN
- China
- Prior art keywords
- double
- azo
- sylvite
- tetrazoliums
- methoxymethylamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 159000000001 potassium salts Chemical class 0.000 title abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 17
- 239000001103 potassium chloride Substances 0.000 claims description 17
- 235000011164 potassium chloride Nutrition 0.000 claims description 17
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical compound [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 claims description 14
- KZRAAPTWXAMZHQ-UHFFFAOYSA-N methoxymethanamine Chemical compound COCN KZRAAPTWXAMZHQ-UHFFFAOYSA-N 0.000 claims description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- -1 1- methoxy methyl Chemical group 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000012065 filter cake Substances 0.000 claims description 6
- 239000005457 ice water Substances 0.000 claims description 6
- 239000012286 potassium permanganate Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000010792 warming Methods 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 238000010189 synthetic method Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 5
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000005474 detonation Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- POCJOGNVFHPZNS-ZJUUUORDSA-N (6S,7R)-2-azaspiro[5.5]undecan-7-ol Chemical compound O[C@@H]1CCCC[C@]11CNCCC1 POCJOGNVFHPZNS-ZJUUUORDSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BSPUVYFGURDFHE-UHFFFAOYSA-N Nitramine Natural products CC1C(O)CCC2CCCNC12 BSPUVYFGURDFHE-UHFFFAOYSA-N 0.000 description 3
- 238000004880 explosion Methods 0.000 description 3
- 239000002360 explosive Substances 0.000 description 3
- 235000011167 hydrochloric acid Nutrition 0.000 description 3
- POCJOGNVFHPZNS-UHFFFAOYSA-N isonitramine Natural products OC1CCCCC11CNCCC1 POCJOGNVFHPZNS-UHFFFAOYSA-N 0.000 description 3
- 230000037452 priming Effects 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- IGRCWJPBLWGNPX-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-(4-chlorophenyl)-n,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl IGRCWJPBLWGNPX-UHFFFAOYSA-N 0.000 description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000010953 base metal Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- OMBRFUXPXNIUCZ-UHFFFAOYSA-N dioxidonitrogen(1+) Chemical compound O=[N+]=O OMBRFUXPXNIUCZ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004449 solid propellant Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B41/00—Compositions containing a nitrated metallo-organic compound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/06—Potassium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
Abstract
The invention discloses a kind of double (1 nitre aminotetrazole) the double potassium salt compounds of 5,5 ' azos, its structural formula is such as shown in (I)：
Description
Technical field
The present invention relates to a kind of energetic material, and in particular to one kind 5, double (1- nitre aminotetrazole) the double sylvite of 5 '-azo
Compound.
Background technology
At present, design, synthesis and the explorative research research of Nitrogen Heterocyclic Energetic Compounds are subject to the generally pass of various countries researcher
Note, contain substantial amounts of N-N, N=N key in such compound, there is the higher positive enthalpy of formation, high nitrogen, low-carbon hydrogen content make it more
Easily reach oxygen balance, and higher nitrogen content makes its catabolite be mainly nitrogen, and gas production is larger, cleanliness without any pollution,
Future has broad application prospects in fields such as composite explosives, solid propellant and gas-forming agents.1,5- diaminourea tetrazoliums
And its correlative is a kind of important tetrazolium energy-containing compound precursor, the amino in its structure can be modified further, derive and contain
Nitramine base, azo group etc. containing can group high energy material, so as to design, synthesize a variety of detonation properties preferably containing can derive
Thing, particularly its nitramine Base Metal potassium salt compound, can replace traditional Azide as a kind of novel green high energy priming
Lead priming, avoid because the latter use and caused by lead heavy metal pollution, there is potential application prospect.
Lianjie Zhai et al.《A green high-initiation-power primary explosive:
synthesis,3D structure and energetic properties of dipotassium 3,4-bis(3-
dinitromethylfurazan-4-oxy)furazan》, RSC Adv., 2015,5,57833-57841 disclose 1,1 '-two
Nitramine base -5, the molecular structure and performance data of the double sylvite of 5 '-bis- tetrazoliums, the compound structure are as follows：
The compound crystal density is 2.11g/cm3, nitrogen content 50.28%, calculating explosion velocity is 8055m/s, and detonation pressure is
28.9GPa, generation heat is 326.4kJ/mol, and quick-fried heat is 4959kJ/kg.But compound generation heat is smaller, energy 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 one kind generation heat compared with
Greatly, double (1- nitre aminotetrazole) double potassium salt compounds of 5,5 ' higher-azo of energy.
The synthetic route of double (1- nitre aminotetrazole) the double potassium salt compounds of 5,5 '-azo of the present invention is as follows：
With 1- methoxy methyl acyl group -1,5- diaminourea tetrazoliums for raw material, react give birth to the hydrochloric acid solution of potassium permanganate first
It is double (1- methoxymethylamide bases tetrazolium) into 5,5 '-azo, then reacted through Nitrolysis with Nitrogen Peroxide, potassium hydroxide alkaline hydrolysis etc., most
After generate double (1- nitre aminotetrazole) the double sylvite of 5,5 '-azo.
The 5 of the present invention, double (1- nitre aminotetrazole) the double potassium salt compounds of 5 '-azo, its structural formula is such as shown in (I)：
The 5 of the present invention, the synthetic method of double (1- nitre aminotetrazole) the double sylvite of 5 '-azo, comprise the following steps：
The synthesis of (1) 5,5 '-azo double (1- methoxymethylamide bases tetrazoliums)
Under ice-water bath stirring, successively by 36~38% (quality) concentrated hydrochloric acids, 1- methoxy methyl acyl group -1,5- diaminourea tetrazoliums
It is added in flask, potassium permanganate solution is added dropwise, 50~55 DEG C of reaction 5h is warming up to after adding, are cooled to 20~25 DEG C, mistake
Filter, wash, be dry that 5,5 '-azo is double (1- methoxymethylamide bases tetrazolium)；Wherein 1- methoxy methyls acyl group -1,5- diaminourea
The molar ratio of tetrazolium and potassium permanganate is 1:1~3.
The synthesis of double (1- nitre aminotetrazole) the double sylvite of (2) 5,5 '-azos
Under ice-water bath stirring, 5,5 '-azo double (1- methoxymethylamide bases tetrazoliums) is distributed in anhydrous acetonitrile, 0
DEG C add dinitrogen pentoxide acetonitrile solution, after adding 0 DEG C~5 DEG C react 2h~5h, then add potassium hydroxide aqueous solution
The h of 0.5h~2 is reacted, solvent is evaporated off, adds methanol, 3h~5h are stirred at 20~25 DEG C, filtering, is added to the water stirring by filter cake
10min~60min, filtering, filter cake are washed through methanol, dry 5, double (1- nitre aminotetrazole) the double sylvite of 5 '-azo；Wherein 5,
The molar ratio of 5 '-azo double (1- methoxymethylamide bases tetrazoliums) and dinitrogen pentoxide is 1:2~5, dinitrogen pentoxide and hydrogen-oxygen
The molar ratio for changing potassium is 1:1~3.
Advantages of the present invention：
The 5 of the present invention, the double potassium salt compounds calculating generation heat of 5 '-azo double (1- nitre aminotetrazoles) are larger, it generates heat
For 617.0 kJ/mol, the 1 of documents, 1 '-dinitro amido -5, the calculating generation heat of 5 '-bis- double sylvite of tetrazolium is
326.4kJ/mol；The 5 of the present invention, double (1- nitre aminotetrazole) the double potassium salt compound energy of 5 '-azo are higher, it calculates explosion velocity
For 8367m/s, detonation pressure 31.5GPa, quick-fried heat is 5358kJ/kg, the 1 of documents, 1 '-dinitro amido -5,5 '-bis- tetrazoliums are double
The calculating explosion velocity of sylvite is 8055m/s, and detonation pressure 28.9GPa, quick-fried heat is 4959kJ/kg.
Embodiment
The present invention is described in further detail with reference to embodiments.
Embodiment 1
The synthesis of (1) 5,5 '-azo double (1- methoxymethylamide bases tetrazoliums)
Under ice-water bath stirring, successively by concentrated hydrochloric acid of the 12.9mL mass percents for 36%~38%, 0.79g (5mmol)
1- methoxy methyl acyl group -1,5- diaminourea tetrazoliums are added in flask, and 14.0mL is added dropwise and contains 0.79g (5mmol) potassium permanganate
Aqueous solution, is warming up to 50~55 DEG C of reaction 5h after adding, reaction solution is cooled to 20~25 DEG C, filtering, washing, it is dry 5,5 '-
Double (the 1- methoxymethylamide bases tetrazolium) 0.7g of azo, yield 89.7%.
Structural Identification：
Infrared spectrum：IR(KBr,cm-1),υ：3242,3024,2968,1767,1638,1536,1504,1467,1437,
1309, 1248,1147,1074,1049,964,848,767,751,594
Nuclear magnetic spectrum：1HNMR(DMSO-d6,500MHz),δ:3.808(s,6H,2CH3),12.843(s,2H,2NH)；13CNMR(DMSO-d6,125MHz),δ:54.473,155.24,158.00
Elemental analysis：Molecular formula C6H8N12O4
Theoretical value：C 23.08,H 2.58,N 53.84
Measured value：C 23.13,H 2.52,N 53.90
No. CCDC：1442365.
It is strictly that 5,5 '-azo is double (1- methoxymethylamide bases tetrazolium) that said structure appraising datum, which confirms to obtain material,.
The synthesis of double (1- nitre aminotetrazole) the double sylvite of (2) 5,5 '-azos
Under ice-water bath stirring, by 1.87g (6mmol) 5,5 '-azo double (1- methoxymethylamide bases tetrazoliums) is distributed to
In 58.0mL anhydrous acetonitriles, acetonitrile solutions of the 32.0mL containing 2.59g (24mmol) dinitrogen pentoxide is added at 0 DEG C, 0 after adding
DEG C~5 DEG C of reaction 3h, the reactant aqueous solution 1h that 24.0mL contains 2.69g (48mmol) potassium hydroxide is then added, solvent is evaporated off, adds
Enter 35.0mL methanol and 4h is stirred at 20~25 DEG C, filtering, filter cake is added in 20.0mL water and stirs 30min, mistake at 20~25 DEG C
Filter, filter cake are washed through methanol, dry 5, double (1- nitre aminotetrazole) the double sylvite 0.46g of 5 '-azo, yield 21.2%.
Structural Identification：
Infrared spectrum：IR(KBr,cm-1),υ：3442,1635,1479,1456,1431,1298,1242,1226,1154,
1079, 1015,927,879,775,753,739,613
Nuclear magnetic spectrum：13CNMR(DMSO-d6,125MHz),δ:157.96
Elemental analysis：Molecular formula K2C2N14O4
Theoretical value：C 6.63,N 54.12
Measured value：C 6.71,N 54.06
No. CCDC：1439593.
It is strictly double (1- nitre aminotetrazole) the double sylvite of 5,5 '-azo that said structure appraising datum, which confirms to obtain material,.
The performance of double (1- nitre aminotetrazole) double sylvite of 5,5 '-azo of the invention
(1) physical and chemical performance
Appearance：Tan solid
Solubility：It is soluble easily in water；It is slightly soluble in dimethyl sulfoxide (DMSO), N,N-dimethylformamide, methanol etc.
Crystalline density：2.11g/cm3X-ray diffraction method
(2) detonation property
The purposes of double (1- nitre aminotetrazole) the double sylvite of 5,5 '-azo of the present invention
Double (1- nitre aminotetrazole) the double potassium salt compounds of 5,5 '-azo of the present invention are with generation heat is larger, energy is higher
The features such as, it can be applied to the fields such as composite explosives, high energy priming.
Claims (1)
1. one kind 5, the synthetic method of double (1- nitre aminotetrazole) the double sylvite of 5 '-azo, 5,5 '-azo is double (1- nitre aminotetrazole)
Double sylvite structural formulas are such as shown in (I)：
With 1- methoxy methyl acyl group -1,5- diaminourea tetrazoliums for raw material, its structural formula such as shown in (II), comprises the following steps：
The synthesis of (1) 5,5 '-azo double (1- methoxymethylamide bases tetrazoliums)
Under ice-water bath stirring, successively by concentrated hydrochloric acid of the mass percent for 36%~38%, 1- methoxy methyl acyl group -1,5- diaminos
Base tetrazolium is added in flask, and potassium permanganate solution is added dropwise, and 50 DEG C~55 DEG C reaction 5h are warming up to after adding, are cooled to 20 DEG C
~25 DEG C, filtering, washing, dry 5,5 '-azo is double (1- methoxymethylamide bases tetrazolium)；Wherein 1- methoxy methyls acyl group-
The molar ratio of 1,5- diaminourea tetrazolium and potassium permanganate is 1:1~3；
The synthesis of double (1- nitre aminotetrazole) the double sylvite of (2) 5,5 '-azos
Under ice-water bath stirring, 5,5 '-azo double (1- methoxymethylamide bases tetrazoliums) is distributed in anhydrous acetonitrile, is added at 0 DEG C
Enter the acetonitrile solution of dinitrogen pentoxide, react 2h~5h at 0 DEG C~5 DEG C after adding, then add potassium hydroxide aqueous solution reaction
0.5h~2h, is evaporated off solvent, adds methanol, 3h~5h is stirred at 20 DEG C~25 DEG C, filtering, is added to the water stirring by filter cake
10min~60min, filtering, filter cake are washed through methanol, dry 5, double (1- nitre aminotetrazole) the double sylvite of 5 '-azo；Wherein 5,
The molar ratio of 5 '-azo double (1- methoxymethylamide bases tetrazoliums) and dinitrogen pentoxide is 1:2~5, dinitrogen pentoxide and hydrogen-oxygen
The molar ratio for changing potassium is 1:1~3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610133948.3A CN105669582B (en) | 2016-03-09 | 2016-03-09 | Double (1- nitre aminotetrazole) the double potassium salt compounds of 5,5 '-azo |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610133948.3A CN105669582B (en) | 2016-03-09 | 2016-03-09 | Double (1- nitre aminotetrazole) the double potassium salt compounds of 5,5 '-azo |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105669582A CN105669582A (en) | 2016-06-15 |
| CN105669582B true CN105669582B (en) | 2018-04-27 |
Family
ID=56307332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610133948.3A Expired - Fee Related CN105669582B (en) | 2016-03-09 | 2016-03-09 | Double (1- nitre aminotetrazole) the double potassium salt compounds of 5,5 '-azo |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105669582B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106892933B (en) * | 2017-03-21 | 2018-11-09 | 中国工程物理研究院化工材料研究所 | A kind of high Energy Density Materials and its synthetic method |
| CN107382891A (en) * | 2017-09-11 | 2017-11-24 | 西安近代化学研究所 | A kind of synthetic method of 5,5 ' azos double (1 nitre aminotetrazoles) |
| CN107698532B (en) * | 2017-10-09 | 2019-08-27 | 西安近代化学研究所 | Two diazanyl tetrazine salt compound of 1,5- dinitro aminotetrazole |
| CN108424397B (en) * | 2018-03-15 | 2019-08-27 | 西安近代化学研究所 | 1,5- dinitro aminotetrazole diamino tetrazolium salt compound |
| CN108424398B (en) * | 2018-03-15 | 2019-08-23 | 西安近代化学研究所 | 1,5- dinitro aminotetrazole 4- amino -1,2,4- triazole salt compound |
| CN108285435B (en) * | 2018-03-15 | 2019-08-27 | 西安近代化学研究所 | 1,5- dinitro aminotetrazole dicyandiamidines salt compound |
-
2016
- 2016-03-09 CN CN201610133948.3A patent/CN105669582B/en not_active Expired - Fee Related
Non-Patent Citations (2)
| Title |
|---|
| 1,1’-Diamino-5,5’-azotetrazole: a nitrogen rich compound;Fang Li,等;《New J. Chem.》;20120727;第36卷;1953-1956 * |
| 1,1’-Diisopropylideneamino-5,5"-azotetrozole;Zhiyue Han，等;《J Therm Anal Calorim》;20141011;第119卷(第1期);461-469 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105669582A (en) | 2016-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105669582B (en) | Double (1- nitre aminotetrazole) the double potassium salt compounds of 5,5 '-azo | |
| CN105669574B (en) | 3 fluorine are together with the triazole compounds of dinitro methyl 1,2,4 | |
| CN107488181B (en) | 1,4- dinitro amido -3,6- binitropyrazole [4,3-c] and two diazanyl tetrazine salt compound of pyrazoles | |
| CN104672158B (en) | 1, 1'-bi(germinal dinitro methyl)-3, 3'-dinitro-5, 5'-co-1, 2, 4-triazole guazatine | |
| CN107698532B (en) | Two diazanyl tetrazine salt compound of 1,5- dinitro aminotetrazole | |
| Yin et al. | Nitrogen-rich salts of 1-aminotetrazol-5-one: oxygen-containing insensitive energetic materials with high thermal stability | |
| CN108840833B (en) | Two (1,5- nitre aminotetrazoles)-four are hydrated copper potassium compound | |
| CN108299442B (en) | 1, 4-dinitroamino-3, 6-dinitropyrazolo [4,3-c ] pyrazolecarboxylamido urea salt compound | |
| CN106432113B (en) | Bis- (the chloro- 3- nitros -1,2,4- triazoles of the 5-) compounds of 1,1 '-azos | |
| CN105111157A (en) | 2, 2'-diamino-5, 5'-dinitro-3, 3'-bis (1, 2, 4-triazole) compound | |
| CN108424399B (en) | 1,5- dinitro aminotetrazole -1- hydroxyl -5- Aminotetrazole salt compound | |
| CN114891006A (en) | Fused ring energetic compound containing pyridazinoimidazole or energetic salt thereof and preparation method | |
| CN108840835B (en) | Two (1,5- nitre aminotetrazoles)-four are hydrated cobalt potassium compound | |
| CN108840834B (en) | Two (1,5- dinitro aminotetrazoles)-four are hydrated zinc impregnation potassium compound | |
| CN108218877B (en) | 1, 4-dinitroamino-3, 6-dinitropyrazolo [4,3-c ] pyrazolemicarbazide salt compound | |
| CN108727289B (en) | 1,5- nitre aminotetrazole barium salt dihydrate | |
| CN108863968B (en) | Two (1,5- nitre aminotetrazoles)-four are hydrated ferrous ironization potassium compound | |
| CN108299326B (en) | 1,5- dinitro aminotetrazole -3,4- diamino furazan salt compound | |
| CN108840836B (en) | Two (1,5- nitre aminotetrazoles)-four are hydrated nickel potassium compound | |
| CN105111156B (en) | 2 amino, 5,5 ' dinitro, 3,3 ' double (1,2,4 triazole) compounds | |
| CN108424397B (en) | 1,5- dinitro aminotetrazole diamino tetrazolium salt compound | |
| CN105153053B (en) | A kind of 3 together with 1,2,4 triazole of dinitro methyl synthetic method | |
| CN105646390A (en) | 3,4-bis(dinitromethyl) benzofuroxan dihydrazinium salt | |
| CN105111213B (en) | 1,4-dyhydroxy-3,6-dinitropyrazole[4,3-c]benzothiazolyl compound | |
| CN110218192A (en) | A kind of preparation method of 2- amino -4,6- dimethoxypyridin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20180427 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |