DE2105156C3 - Verfahren zur Herstellung schwefelsaurer Lösungen des 2-Amino-5-nitrothiazols - Google Patents
Verfahren zur Herstellung schwefelsaurer Lösungen des 2-Amino-5-nitrothiazolsInfo
- Publication number
- DE2105156C3 DE2105156C3 DE2105156A DE2105156A DE2105156C3 DE 2105156 C3 DE2105156 C3 DE 2105156C3 DE 2105156 A DE2105156 A DE 2105156A DE 2105156 A DE2105156 A DE 2105156A DE 2105156 C3 DE2105156 C3 DE 2105156C3
- Authority
- DE
- Germany
- Prior art keywords
- amino
- sulfuric acid
- thiazole
- bisulfite
- nitro
- 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
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title claims description 53
- MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical compound NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 title claims description 19
- 229940018167 2-amino-5-nitrothiazole Drugs 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 20
- FRTDJTCZPSPLJY-UHFFFAOYSA-N sulfurous acid;1,3-thiazol-2-amine Chemical compound OS([O-])=O.[NH3+]C1=NC=CS1 FRTDJTCZPSPLJY-UHFFFAOYSA-N 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 238000006396 nitration reaction Methods 0.000 description 13
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 229910017604 nitric acid Inorganic materials 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLQODIZGYLUQIR-UHFFFAOYSA-N nitric acid;1,3-thiazol-2-amine Chemical compound O[N+]([O-])=O.NC1=NC=CS1 VLQODIZGYLUQIR-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 235000010333 potassium nitrate Nutrition 0.000 description 2
- 239000004323 potassium nitrate Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- -1 amine salt Chemical class 0.000 description 1
- 229950003476 aminothiazole Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- WDJXDOCQCALXMV-UHFFFAOYSA-N hydron;1,3-thiazol-2-amine;chloride Chemical compound Cl.NC1=NC=CS1 WDJXDOCQCALXMV-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910001959 inorganic nitrate Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- LZDVHJSVPSREIA-UHFFFAOYSA-N n-(1,3-thiazol-2-yl)nitramide Chemical compound [O-][N+](=O)NC1=NC=CS1 LZDVHJSVPSREIA-UHFFFAOYSA-N 0.000 description 1
- ASGINYMSPZYKAZ-UHFFFAOYSA-N n-(5-nitro-1,3-thiazol-2-yl)nitramide Chemical compound [O-][N+](=O)NC1=NC=C([N+]([O-])=O)S1 ASGINYMSPZYKAZ-UHFFFAOYSA-N 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/58—Nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2105156A DE2105156C3 (de) | 1971-02-04 | 1971-02-04 | Verfahren zur Herstellung schwefelsaurer Lösungen des 2-Amino-5-nitrothiazols |
| US00221412A US3799941A (en) | 1971-02-04 | 1972-01-27 | Process for the production of sulfuric acid solutions of 2-amino-5-nitrothiazole |
| IT20049/72A IT986013B (it) | 1971-02-04 | 1972-01-31 | Procedimento per la preparazione di soluzioni in acido solforico del 2 ammino 5 nitro tiazolo |
| JP1189472A JPS5623988B1 (OSRAM) | 1971-02-04 | 1972-02-03 | |
| FR7203615A FR2125055A5 (OSRAM) | 1971-02-04 | 1972-02-03 | |
| CH156272A CH570991A5 (OSRAM) | 1971-02-04 | 1972-02-03 | |
| BE778940A BE778940A (fr) | 1971-02-04 | 1972-02-03 | Procede de preparation de solutions de 2-amino-5-nitro-thiazole |
| GB511472A GB1334984A (en) | 1971-02-04 | 1972-02-03 | Process for the production of sulphuric acid solutions of 2-amino-5-nitro-thiazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2105156A DE2105156C3 (de) | 1971-02-04 | 1971-02-04 | Verfahren zur Herstellung schwefelsaurer Lösungen des 2-Amino-5-nitrothiazols |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2105156A1 DE2105156A1 (de) | 1972-08-24 |
| DE2105156B2 DE2105156B2 (de) | 1979-01-18 |
| DE2105156C3 true DE2105156C3 (de) | 1979-09-06 |
Family
ID=5797770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2105156A Expired DE2105156C3 (de) | 1971-02-04 | 1971-02-04 | Verfahren zur Herstellung schwefelsaurer Lösungen des 2-Amino-5-nitrothiazols |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3799941A (OSRAM) |
| JP (1) | JPS5623988B1 (OSRAM) |
| BE (1) | BE778940A (OSRAM) |
| CH (1) | CH570991A5 (OSRAM) |
| DE (1) | DE2105156C3 (OSRAM) |
| FR (1) | FR2125055A5 (OSRAM) |
| GB (1) | GB1334984A (OSRAM) |
| IT (1) | IT986013B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3225472A1 (de) * | 1982-07-08 | 1984-01-26 | Cassella Ag, 6000 Frankfurt | Verfahren zur herstellung von 2-amino-5-nitro-thiazol |
-
1971
- 1971-02-04 DE DE2105156A patent/DE2105156C3/de not_active Expired
-
1972
- 1972-01-27 US US00221412A patent/US3799941A/en not_active Expired - Lifetime
- 1972-01-31 IT IT20049/72A patent/IT986013B/it active
- 1972-02-03 GB GB511472A patent/GB1334984A/en not_active Expired
- 1972-02-03 JP JP1189472A patent/JPS5623988B1/ja active Pending
- 1972-02-03 BE BE778940A patent/BE778940A/xx not_active IP Right Cessation
- 1972-02-03 CH CH156272A patent/CH570991A5/xx not_active IP Right Cessation
- 1972-02-03 FR FR7203615A patent/FR2125055A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH570991A5 (OSRAM) | 1975-12-31 |
| FR2125055A5 (OSRAM) | 1972-09-22 |
| JPS5623988B1 (OSRAM) | 1981-06-03 |
| GB1334984A (en) | 1973-10-24 |
| US3799941A (en) | 1974-03-26 |
| IT986013B (it) | 1975-01-10 |
| DE2105156A1 (de) | 1972-08-24 |
| BE778940A (fr) | 1972-08-03 |
| DE2105156B2 (de) | 1979-01-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |