CN104557761A - 3,3'-dinitramino-4,4'-azoxyfurazan energetic ion salt compound - Google Patents

3,3'-dinitramino-4,4'-azoxyfurazan energetic ion salt compound Download PDF

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Publication number
CN104557761A
CN104557761A CN201510011625.2A CN201510011625A CN104557761A CN 104557761 A CN104557761 A CN 104557761A CN 201510011625 A CN201510011625 A CN 201510011625A CN 104557761 A CN104557761 A CN 104557761A
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nitramino
bis
azoxy
furazan
salt compound
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刘敏
郭涛
黄晓川
王子俊
邱少君
唐望
姜俊
秦明娜
石强
李洪丽
吕英迪
郑晓东
陈志强
姚冰洁
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Xian Modern Chemistry Research Institute
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Xian Modern Chemistry Research Institute
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    • 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

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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 3,3'-dinitramino-4,4'-azoxyfurazan energetic ion salt compound. The structural formula is as shown in the specification. The compound disclosed by the invention is mainly used for energetic materials.

Description

A kind of 3,3 '-two nitramino-4,4 '-azoxy furazan is containing energy ionic salt compound
Technical field
The present invention relates to a kind of azoxy furazan class containing energy ionic salt compound, be specifically related to a kind of 3,3'-bis-nitramino-4,4'-azoxy furazan containing energy ionic salt compound.
Background technology
Furazan compounds, with advantages such as its high-density, high nitrogen-containing and high oxygen balances, is subject to extensive research as novel high-performance energetic material.Recent decades, by furazan structural unit and other are containing being combined and being never interrupted with the research of the energy-containing compound obtaining more excellent physical and chemical performance by group, and achieve significant achievement.As " 3,3'-Dinitroamino-4,4'-azoxyfurazan andIts Derivatives:An Assembly of Diverse NO Building Blocks for High-performance EnergeticMaterials " (Journal of the American Chemical Society, 2014,136 (11): 4437-4445), a kind of 3,3'-bis-nitramino-4 is disclosed, 4'-azoxy furazan compound, its structural formula is as follows:
3,3'-bis-nitramino-4,4'-azoxy furazan is a kind of azoxy furazano energetic compound with high energy, and density is 1.96gcm -3, explosion velocity is 9746ms -1, detonation pressure is 44.1GPa, specific impulse 283s, and density is suitable with CL-20 with detonation property, but decomposition point is 90 DEG C, there is the problem that thermostability is lower.
Summary of the invention
In order to overcome shortcomings and deficiencies of the prior art, the invention provides 3,3'-bis-higher nitramino-4,4'-azoxy furazans of a class thermostability containing energy ionic salt compound.
3,3'-bis-nitramino-4,4'-azoxy furazans provided by the invention are containing energy ionic salt compound, and its structural formula is as follows:
The present invention 3,3'-bis-nitramino-4,4'-azoxy furazan is as follows containing the synthetic route of energy ionic salt compound:
When positively charged ion is carbohydrazide ion, 3,3'-bis-nitramino-4,4'-azoxy furazan is containing can ionic salt compound be 3,3'-bis-nitramino-4,4'-azoxy furazan phosphinylidyne hydrazonium salt, and its structural formula is:
When positively charged ion is aminoguanidine ion, 3,3'-bis-nitramino-4,4'-azoxy furazan is containing can ionic salt compound be 3,3'-bis-nitramino-4,4'-azoxy furazan aminoguanidine salt, and its structural formula is:
This route is for raw material with 3,3'-bis-amido-4,4'-azoxy furazan, 3 are obtained through pure nitric acid nitrating, 3'-bis-nitramino-4,4'-azoxy furazan, 3,3'-bis-nitramino-4,4'-azoxy furazan obtains 3,3'-bis-nitramino-4,4'-azoxy furazan phosphinylidyne hydrazonium salt and 3 respectively at carbohydrazide hydrochloride and aminoguanidine monohydrochloride through replacement(metathesis)reaction, 3'-bis-nitramino-4,4'-azoxy furazan aminoguanidine salt.
The present invention 3,3'-bis-nitramino-4,4'-azoxy furazan, containing the synthetic method of energy ionic salt compound, comprises the following steps:
Under (1)-5 DEG C of condition, 3,3'-bis-nitramino-4,4'-azoxy furazan 9.5mmol joins in the pure nitric acid of 10ml in batches, stirs 20min; React 3h under 0 DEG C of condition, filtration, washing, drying obtain white solid 3,3'-bis-nitramino-4,4'-azoxy furazan;
By 3 under (2) 25 DEG C of conditions, 3'-bis-nitramino-4,4'-azoxy furazan 2mmol is dissolved in 10ml ethanol, add carbohydrazide hydrochloride 3mmol or aminoguanidine monohydrochloride 4.5mmol, after reacting 1h under 25 DEG C of conditions, after filtration, washing, drying can obtain faint yellow solid 3 respectively, 3'-bis-nitramino-4,4'-azoxy furazan phosphinylidyne hydrazonium salt and orange/yellow solid 3,3'-bis-nitramino-4,4'-azoxy furazan aminoguanidine salt.
The invention has the advantages that:
Advantage of the present invention: 3,3'-bis-nitramino-4,4'-azoxy furazans of the present invention are higher containing the temperature of initial decomposition of energy ionic salt compound, wherein 3, the temperature of initial decomposition of 3'-bis-nitramino-4,4'-azoxy furazan phosphinylidyne hydrazonium salt is 144.9 DEG C, 3,3'-bis-nitramino-4,4'-azoxy furazan aminoguanidine salt temperature of initial decomposition is 151.6 DEG C, with 3,3'-bis-nitramino-4,4'-azoxy furazan (90 DEG C) is compared, and has had raising by a relatively large margin.
Embodiment
The invention will be further described by the following examples, but the present invention is not by the restriction of the following example.
The synthesis of embodiment 13,3'-bis-nitramino-4,4'-azoxy furazan carbohydrazide salt compound
Under (1)-5 DEG C of condition, 3,3'-bis-nitramino-4,4'-azoxy furazan 2.0g (9.5mmol) joins in the pure nitric acid of 10ml in batches, stirs 20min; React 3h under 0 DEG C of condition, filtration, washing, drying obtain white solid 3,3'-bis-nitramino-4,4'-azoxy furazan.
By 3 under (2) 25 DEG C of conditions, 3'-bis-nitramino-4,4'-azoxy furazan 0.6g (2mmol) is dissolved in 10ml ethanol, add carbohydrazide hydrochloride 0.383g (3mmol), after reacting 1h under 25 DEG C of conditions, after filtration, washing, drying can obtain faint yellow solid 3,3'-bis-nitramino-4,4'-azoxy furazan phosphinylidyne hydrazonium salt 0.7g (yield 89%) respectively.
Structural Identification:
Ultimate analysis:
Molecular formula: C 5h 8n 14o 8
Theoretical value: C 15.31, H 2.06, N 50.00;
Measured value: C 15.56, H 2.14, N 49.58.
Infrared (KBr, cm -1): 3525 (w), 3493 (w), 3315 (m), 2966 (vw), 2713 (w), 1708 (s), 1663 (w), 1639 (vw), 1614 (vw), 1580 (w), 1561 (w), 1531 (w), 1517 (w), 1489 (m), 1473 (m), 1421 (s), 1399 (s), 1324 (vs), 1300 (s), 1203 (m), 1053 (m), 1015 (m), 966 (w), 937 (m), 896 (w), 863 (vs), 836 (m), 799 (vw), 772 (vw), 740 (vw), 723 (m), 68 (w), 641 (vw), 591 (vw), 567 (v), 468 (vw), 405 (vw).
1h nuclear-magnetism (DMSO-d 6, ppm): 9.73 (s, 2H), δ 3.60 (s, br, 6H);
13c nuclear-magnetism (DMSO-d 6, ppm): 156.9,155.1,154.5,153.9,151.2.
Thermal performance test:
Carry out thermal characteristics mensuration with TGA-DTG, the temperature of initial decomposition of 3,3'-bis-nitramino-4,4'-azoxy furazan phosphinylidyne hydrazonium salt is 144.9 DEG C.
The synthesis of embodiment 23,3'-bis-nitramino-4,4'-azoxy furazan aminoguanidine salt compound
Under (1)-5 DEG C of condition, 3,3'-bis-nitramino-4,4'-azoxy furazan 2.0g (9.5mmol) joins in the pure nitric acid of 10ml in batches, stirs 20min; React 3h under 0 DEG C of condition, filtration, washing, drying obtain white solid 3,3'-bis-nitramino-4,4'-azoxy furazan.
By 3 under (2) 25 DEG C of conditions, 3'-bis-nitramino-4,4'-azoxy furazan 0.6g (2mmol) is dissolved in 10ml ethanol, add aminoguanidine monohydrochloride 0.995g (4.5mmol), after reacting 1h under 25 DEG C of conditions, after filtration, washing, drying can obtain orange/yellow solid 3,3'-bis-nitramino-4,4'-azoxy furazan aminoguanidine salt 0.81g (yield 90%) respectively.
Structural Identification:
Ultimate analysis:
Molecular formula: C 6h 14n 18o 7
Theoretical value: C 16.00, H 3.13, N 55.99;
Measured value: C 16.23, H 3.27, N 54.11.
Infrared (KBr, cm -1): 3381 (m), 3245 (w), 3172 (m), 1687 (vs), 1665 (vs), 1560 (m), 1524 (m), 1468 (s), 1441 (vw), 1410 (m), 1387 (s), 1294 (vs), 1177 (w), 1073 (vw), 1044 (m), 1015 (vw), 982 (vw), 950 (m), 908 (vw), 883 (vw), 872 (vw), 827 (m), 773 (w), 745 (vw), 716 (w), 675 (vw), 585 (m), 565 (m), 511 (vw), 468 (w), 404 (vw)
1h nuclear-magnetism (DMSO-d 6, ppm): 8.58 (s, 1H), 7.11 (s, 2H), 4.99 (s, 4H);
13c nuclear-magnetism (DMSO-d 6, ppm): 158.7,155.1,153.8,153.1,151.1.
Above-mentioned analytical data confirms that the material obtained by this synthetic method is 3,3 '-two nitramino-4,4 '-azoxy furazan phosphinylidyne hydrazonium salt and 3,3 '-two nitramino-4,4 '-azoxy furazan aminoguanidine salt really.
Thermal performance test:
Carry out thermal characteristics mensuration with TGA-DTG, 3,3'-bis-nitramino-4,4'-azoxy furazan aminoguanidine salt temperature of initial decomposition is 151.6 DEG C.

Claims (3)

1. bis-nitramino-4,4'-azoxy furazans are containing energy ionic salt compound, and its structural formula is as follows:
2. 3,3'-bis-nitramino-4,4'-azoxy furazans are containing energy ionic salt compound according to claim 1, and its structural formula is:
3. 3,3'-bis-nitramino-4,4'-azoxy furazans are containing energy ionic salt compound according to claim 1, and its structural formula is:
CN201510011625.2A 2015-01-09 2015-01-09 3,3'-dinitramino-4,4'-azoxyfurazan energetic ion salt compound Pending CN104557761A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105777587A (en) * 2016-03-22 2016-07-20 中国科学院上海有机化学研究所 N-nitrotrinitroethyl carbamate energetic ionic salt and preparation method and application thereof
CN106892933A (en) * 2017-03-21 2017-06-27 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
CN108689959A (en) * 2017-04-11 2018-10-23 南京理工大学 Compound and its ion salt containing energy
CN109232460A (en) * 2018-10-18 2019-01-18 西南科技大学 The feather weight preparation method of 3,3 '--4,4 '-azoxy furazans of diamino

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US20090306355A1 (en) * 2008-06-04 2009-12-10 The Regents Of The University Of California Preparation of 3,3'-diamino-4,4'-azoxyfurazan, 3,3'-4,4'-azofurazan, and pressed articles
CN101891698A (en) * 2010-07-21 2010-11-24 西安近代化学研究所 3,4-di(3',5'-dinitryl-4'-methyl phenyl) furoxan compound
CN103086997A (en) * 2013-01-30 2013-05-08 西安近代化学研究所 Synthetic method of 3,3'-diamino-4,4'-azofuroxan
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

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US20090306355A1 (en) * 2008-06-04 2009-12-10 The Regents Of The University Of California Preparation of 3,3'-diamino-4,4'-azoxyfurazan, 3,3'-4,4'-azofurazan, and pressed articles
CN101891698A (en) * 2010-07-21 2010-11-24 西安近代化学研究所 3,4-di(3',5'-dinitryl-4'-methyl phenyl) furoxan compound
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105777587A (en) * 2016-03-22 2016-07-20 中国科学院上海有机化学研究所 N-nitrotrinitroethyl carbamate energetic ionic salt and preparation method and application thereof
CN105777587B (en) * 2016-03-22 2018-06-26 中国科学院上海有机化学研究所 N- nitro Trinitroethyls carbamate ion salt containing energy, preparation method and application
CN106892933A (en) * 2017-03-21 2017-06-27 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
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
CN108689959A (en) * 2017-04-11 2018-10-23 南京理工大学 Compound and its ion salt containing energy
CN108689959B (en) * 2017-04-11 2021-04-06 南京理工大学 Compounds and energetic ionic salts thereof
CN109232460A (en) * 2018-10-18 2019-01-18 西南科技大学 The feather weight preparation method of 3,3 '--4,4 '-azoxy furazans of diamino

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Application publication date: 20150429