DE3917228A1 - Verfahren zur herstellung von 3-nitro-1,2,4-triazol-5-on - Google Patents
Verfahren zur herstellung von 3-nitro-1,2,4-triazol-5-onInfo
- Publication number
- DE3917228A1 DE3917228A1 DE3917228A DE3917228A DE3917228A1 DE 3917228 A1 DE3917228 A1 DE 3917228A1 DE 3917228 A DE3917228 A DE 3917228A DE 3917228 A DE3917228 A DE 3917228A DE 3917228 A1 DE3917228 A1 DE 3917228A1
- Authority
- DE
- Germany
- Prior art keywords
- triazol
- reaction
- nitric acid
- solution
- aqueous
- 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
- 238000004519 manufacturing process Methods 0.000 title description 6
- NVKJOXRVEKMMHS-UHFFFAOYSA-N 5-nitro-1,2,4-triazol-3-one Chemical compound [O-][N+](=O)C1=NC(=O)N=N1 NVKJOXRVEKMMHS-UHFFFAOYSA-N 0.000 title 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 38
- QJTIRVUEVSKJTK-UHFFFAOYSA-N 5-nitro-1,2-dihydro-1,2,4-triazol-3-one Chemical compound [O-][N+](=O)C1=NC(=O)NN1 QJTIRVUEVSKJTK-UHFFFAOYSA-N 0.000 claims abstract description 31
- MDTUWBLTRPRXBX-UHFFFAOYSA-N 1,2,4-triazol-3-one Chemical compound O=C1N=CN=N1 MDTUWBLTRPRXBX-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 239000011541 reaction mixture Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- 239000007787 solid Substances 0.000 claims description 13
- 230000035484 reaction time Effects 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 238000005474 detonation Methods 0.000 abstract description 3
- 230000035945 sensitivity Effects 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- 239000002360 explosive Substances 0.000 description 5
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000006396 nitration reaction Methods 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000005121 nitriding Methods 0.000 description 2
- 235000010333 potassium nitrate Nutrition 0.000 description 2
- 239000004323 potassium nitrate Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QGOUKZPSCTVYLX-UHFFFAOYSA-N 5-chloro-1h-1,2,4-triazole Chemical compound ClC1=NC=NN1 QGOUKZPSCTVYLX-UHFFFAOYSA-N 0.000 description 1
- KNSPHEMRHVERJM-UHFFFAOYSA-N 5-oxo-1,2-dihydro-1,2,4-triazole-3-carboxylic acid Chemical compound OC(=O)C1=NC(=O)NN1 KNSPHEMRHVERJM-UHFFFAOYSA-N 0.000 description 1
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- -1 ethylethoxymethylene carbamate Chemical compound 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000010327 methods by industry Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 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
- C07D249/12—Oxygen or sulfur atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19973988A | 1988-05-27 | 1988-05-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3917228A1 true DE3917228A1 (de) | 1989-12-07 |
| DE3917228C2 DE3917228C2 (enrdf_load_stackoverflow) | 1993-09-09 |
Family
ID=22738813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3917228A Granted DE3917228A1 (de) | 1988-05-27 | 1989-05-26 | Verfahren zur herstellung von 3-nitro-1,2,4-triazol-5-on |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE3917228A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2631962B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2218986B (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2067367B1 (es) * | 1992-07-22 | 1995-11-01 | Espanola Explosivos | Procedimiento para la obtencion de una composicion explosiva de alta energia y estabilidad. |
| FR3004178B1 (fr) | 2013-04-08 | 2015-04-24 | Herakles | Obtention de solutions d'ota en milieu acide sulfurique concentre; lesdites solutions, preparation d'onta |
| CN112125858A (zh) * | 2020-09-11 | 2020-12-25 | 南京理工大学 | 一种双子型含能离子化合物及其制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0210881A1 (fr) * | 1985-06-28 | 1987-02-04 | Societe Nationale Des Poudres Et Explosifs | Utilisation du 5-oxo 3-nitro 1,2,4-triazole comme explosif secondaire et compositions pyrotechniques contenant du 5-oxo 3-nitro 1,2,4-triazole |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4733610A (en) * | 1987-01-30 | 1988-03-29 | The United States Of America As Represented By The United States Department Of Energy | 3-nitro-1,2,4-triazol-5-one, a less sensitive explosive |
-
1989
- 1989-05-15 GB GB8911095A patent/GB2218986B/en not_active Expired - Fee Related
- 1989-05-26 FR FR898906962A patent/FR2631962B1/fr not_active Expired - Lifetime
- 1989-05-26 DE DE3917228A patent/DE3917228A1/de active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0210881A1 (fr) * | 1985-06-28 | 1987-02-04 | Societe Nationale Des Poudres Et Explosifs | Utilisation du 5-oxo 3-nitro 1,2,4-triazole comme explosif secondaire et compositions pyrotechniques contenant du 5-oxo 3-nitro 1,2,4-triazole |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3917228C2 (enrdf_load_stackoverflow) | 1993-09-09 |
| GB8911095D0 (en) | 1989-06-28 |
| FR2631962B1 (fr) | 1994-10-14 |
| GB2218986A (en) | 1989-11-29 |
| FR2631962A1 (fr) | 1989-12-01 |
| GB2218986B (en) | 1992-01-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |