DE19501377B4 - Verfahren zur Herstellung von trans-1,4,5,8-Tetranitro-1,4,5,8-tetraazadecalin (TNAD) - Google Patents
Verfahren zur Herstellung von trans-1,4,5,8-Tetranitro-1,4,5,8-tetraazadecalin (TNAD) Download PDFInfo
- Publication number
- DE19501377B4 DE19501377B4 DE1995101377 DE19501377A DE19501377B4 DE 19501377 B4 DE19501377 B4 DE 19501377B4 DE 1995101377 DE1995101377 DE 1995101377 DE 19501377 A DE19501377 A DE 19501377A DE 19501377 B4 DE19501377 B4 DE 19501377B4
- Authority
- DE
- Germany
- Prior art keywords
- tnad
- tetraazadecalin
- tad
- tetranitro
- trans
- 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
- 238000000034 method Methods 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- HNIYFQYULIZVBV-UHFFFAOYSA-N 1,4,5,8-tetranitro-2,3,4a,6,7,8a-hexahydropyrazino[2,3-b]pyrazine Chemical compound [O-][N+](=O)N1CCN([N+]([O-])=O)C2C1N([N+](=O)[O-])CCN2[N+]([O-])=O HNIYFQYULIZVBV-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 239000007858 starting material Substances 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims 2
- 239000001272 nitrous oxide Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical compound [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HQJLFRMMLKYIJX-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydropyrazino[2,3-b]pyrazine Chemical compound N1CCNC2NCCNC21 HQJLFRMMLKYIJX-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
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 230000000802 nitrating effect Effects 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- HNIYFQYULIZVBV-IZLXSQMJSA-N [N+](=O)([O-])N1CCN([C@@H]2N(CCN([C@@H]12)[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-] Chemical compound [N+](=O)([O-])N1CCN([C@@H]2N(CCN([C@@H]12)[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-] HNIYFQYULIZVBV-IZLXSQMJSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1995101377 DE19501377B4 (de) | 1995-01-18 | 1995-01-18 | Verfahren zur Herstellung von trans-1,4,5,8-Tetranitro-1,4,5,8-tetraazadecalin (TNAD) |
FR9600298A FR2729391A1 (fr) | 1995-01-18 | 1996-01-12 | Procede de synthese de la trans-1,4,5,8-tetranitro-1,4,5,8- tetraazadecaline (tnda) |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1995101377 DE19501377B4 (de) | 1995-01-18 | 1995-01-18 | Verfahren zur Herstellung von trans-1,4,5,8-Tetranitro-1,4,5,8-tetraazadecalin (TNAD) |
Publications (2)
Publication Number | Publication Date |
---|---|
DE19501377A1 DE19501377A1 (de) | 1996-07-25 |
DE19501377B4 true DE19501377B4 (de) | 2004-01-08 |
Family
ID=7751763
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1995101377 Expired - Fee Related DE19501377B4 (de) | 1995-01-18 | 1995-01-18 | Verfahren zur Herstellung von trans-1,4,5,8-Tetranitro-1,4,5,8-tetraazadecalin (TNAD) |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE19501377B4 (enrdf_load_stackoverflow) |
FR (1) | FR2729391A1 (enrdf_load_stackoverflow) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105440037A (zh) * | 2014-09-09 | 2016-03-30 | 南京理工大学 | 1,4,5,8-四硝基-1,4,5,8-四氮杂双环[4,4,0]癸烷的制备方法 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9539012B2 (en) | 2002-10-30 | 2017-01-10 | Zimmer Spine, Inc. | Spinal stabilization systems with quick-connect sleeve assemblies for use in surgical procedures |
EP3222231A1 (en) | 2002-10-30 | 2017-09-27 | Zimmer Spine, Inc. | Spinal stabilization system insertion |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4614800A (en) * | 1985-02-15 | 1986-09-30 | The United States Of America As Represented By The Secretary Of The Navy | Synthesis of cyclic dinitramines useful as explosive and propellant ingredients, gas generants and in other ordnance applications |
-
1995
- 1995-01-18 DE DE1995101377 patent/DE19501377B4/de not_active Expired - Fee Related
-
1996
- 1996-01-12 FR FR9600298A patent/FR2729391A1/fr active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4614800A (en) * | 1985-02-15 | 1986-09-30 | The United States Of America As Represented By The Secretary Of The Navy | Synthesis of cyclic dinitramines useful as explosive and propellant ingredients, gas generants and in other ordnance applications |
Non-Patent Citations (2)
Title |
---|
M.S.Lui et al. "Study on the preparation of highly energetic material trans-1,4,5,8-tetranitro-1,4,5, 8-tetraazadecalin", Huoyao Jishu, 1992, 8(3), 1-8, zitiert als Chemical Abstract, 1994, Vol.120, Nr. 80856. |
M.S.Lui et al. "Study on the preparation of highlyenergetic material trans-1,4,5,8-tetranitro-1,4,5,8-tetraazadecalin", Huoyao Jishu, 1992, 8(3), 1-8,zitiert als Chemical Abstract, 1994, Vol.120, Nr. 80856. * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105440037A (zh) * | 2014-09-09 | 2016-03-30 | 南京理工大学 | 1,4,5,8-四硝基-1,4,5,8-四氮杂双环[4,4,0]癸烷的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
FR2729391B1 (enrdf_load_stackoverflow) | 1997-03-07 |
DE19501377A1 (de) | 1996-07-25 |
FR2729391A1 (fr) | 1996-07-19 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
8110 | Request for examination paragraph 44 | ||
8364 | No opposition during term of opposition | ||
8339 | Ceased/non-payment of the annual fee |