FR2729391A1 - Procede de synthese de la trans-1,4,5,8-tetranitro-1,4,5,8- tetraazadecaline (tnda) - Google Patents
Procede de synthese de la trans-1,4,5,8-tetranitro-1,4,5,8- tetraazadecaline (tnda) Download PDFInfo
- Publication number
- FR2729391A1 FR2729391A1 FR9600298A FR9600298A FR2729391A1 FR 2729391 A1 FR2729391 A1 FR 2729391A1 FR 9600298 A FR9600298 A FR 9600298A FR 9600298 A FR9600298 A FR 9600298A FR 2729391 A1 FR2729391 A1 FR 2729391A1
- Authority
- FR
- France
- Prior art keywords
- tad
- tnad
- tetraazadecalin
- trans
- synthesis
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 14
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 6
- 238000003786 synthesis reaction 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 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentoxide Inorganic materials [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 claims description 20
- 239000007858 starting material Substances 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims 2
- 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 claims 1
- 239000002360 explosive Substances 0.000 abstract description 2
- 239000003380 propellant Substances 0.000 abstract description 2
- 239000000843 powder Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 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 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000006396 nitration reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000011833 salt mixture 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
- 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
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 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
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000126 substance Substances 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)
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 |
|---|---|
| FR2729391A1 true FR2729391A1 (fr) | 1996-07-19 |
| FR2729391B1 FR2729391B1 (enrdf_load_stackoverflow) | 1997-03-07 |
Family
ID=7751763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR9600298A Granted 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) |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE19501377B4 (enrdf_load_stackoverflow) |
| FR (1) | FR2729391A1 (enrdf_load_stackoverflow) |
Cited By (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 |
| US9603631B2 (en) | 2002-10-30 | 2017-03-28 | Zimmer Spine, Inc. | Spinal stabilization systems and methods |
Families Citing this family (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 |
Family Cites Families (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
Non-Patent Citations (2)
| Title |
|---|
| CHEMICAL ABSTRACTS, vol. 120, no. 8, Columbus, Ohio, US; abstract no. 80856t, M.S. LIU ET AL.: "Study on the preparation of highly energetic material trans-1,4,5,8-tetranitro-1,4,5,8-tetraazadecalin" page 243; * |
| HUOYAO JISHU, vol. 8, no. 3, pages 1 - 8 * |
Cited By (6)
| 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 |
| US9603631B2 (en) | 2002-10-30 | 2017-03-28 | Zimmer Spine, Inc. | Spinal stabilization systems and methods |
| US10052137B2 (en) | 2002-10-30 | 2018-08-21 | Zimmer Spine, Inc. | Spinal stabilization systems and methods |
| US10130394B2 (en) | 2002-10-30 | 2018-11-20 | Zimmer Spine, Inc. | Spinal stabilization systems and methods |
| US10945772B2 (en) | 2007-07-18 | 2021-03-16 | Zimmer Spine, Inc. | Spinal stabilization systems with quick-connect sleeve assemblies for use in surgical procedures |
| US11737794B2 (en) | 2007-07-18 | 2023-08-29 | Zimmer Spine, Inc. | Spinal stabilization systems with quick-connect sleeve assemblies for use in surgical procedures |
Also Published As
| Publication number | Publication date |
|---|---|
| DE19501377A1 (de) | 1996-07-25 |
| DE19501377B4 (de) | 2004-01-08 |
| FR2729391B1 (enrdf_load_stackoverflow) | 1997-03-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |