DE2436459A1 - Verfahren zur herstellung von 1,4diamino-5-nitroanthrachinon - Google Patents
Verfahren zur herstellung von 1,4diamino-5-nitroanthrachinonInfo
- Publication number
- DE2436459A1 DE2436459A1 DE19742436459 DE2436459A DE2436459A1 DE 2436459 A1 DE2436459 A1 DE 2436459A1 DE 19742436459 DE19742436459 DE 19742436459 DE 2436459 A DE2436459 A DE 2436459A DE 2436459 A1 DE2436459 A1 DE 2436459A1
- Authority
- DE
- Germany
- Prior art keywords
- nitration
- liquid
- disulfonimide
- sulfone
- anthraquinone
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 25
- SDICTISQCKLMEB-UHFFFAOYSA-N 1,4-diamino-5-nitroanthracene-9,10-dione Chemical compound O=C1C=2C(N)=CC=C(N)C=2C(=O)C2=C1C=CC=C2[N+]([O-])=O SDICTISQCKLMEB-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 238000006396 nitration reaction Methods 0.000 claims description 16
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 12
- 230000000873 masking effect Effects 0.000 claims description 9
- 239000012429 reaction media Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 6
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 claims description 2
- YBJCDTIWNDBNTM-UHFFFAOYSA-N 1-methylsulfonylethane Chemical compound CCS(C)(=O)=O YBJCDTIWNDBNTM-UHFFFAOYSA-N 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims 1
- 150000004056 anthraquinones Chemical class 0.000 claims 1
- CFRVORMUGQWQNZ-UHFFFAOYSA-N thiepane 1,1-dioxide Chemical compound O=S1(=O)CCCCCC1 CFRVORMUGQWQNZ-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000003756 stirring Methods 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- PHZPGLMKVOOUGI-UHFFFAOYSA-N 1-amino-5-nitroanthracene-9,10-dione Chemical compound O=C1C=2C(N)=CC=CC=2C(=O)C2=C1C=CC=C2[N+]([O-])=O PHZPGLMKVOOUGI-UHFFFAOYSA-N 0.000 description 1
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000001047 purple dye Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/24—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings
- C07C225/26—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings
- C07C225/32—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings of condensed quinone ring systems formed by at least three rings
- C07C225/34—Amino anthraquinones
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 |
|---|---|---|---|
| CH1114573A CH580661A5 (enrdf_load_stackoverflow) | 1973-07-31 | 1973-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2436459A1 true DE2436459A1 (de) | 1975-02-20 |
Family
ID=4370521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742436459 Withdrawn DE2436459A1 (de) | 1973-07-31 | 1974-07-29 | Verfahren zur herstellung von 1,4diamino-5-nitroanthrachinon |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5045017A (enrdf_load_stackoverflow) |
| BE (1) | BE818239A (enrdf_load_stackoverflow) |
| CH (1) | CH580661A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2436459A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2239448B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1468413A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3524833A1 (de) * | 1984-07-19 | 1986-01-30 | Sumitomo Chemical Co., Ltd., Osaka | Verfahren zur herstellung eines 1-amino-2-(unsubstituierten oder substituierten)-phenoxy-4-hydroxyanthrachinons |
-
1973
- 1973-07-31 CH CH1114573A patent/CH580661A5/xx not_active IP Right Cessation
-
1974
- 1974-07-08 GB GB3023374A patent/GB1468413A/en not_active Expired
- 1974-07-25 FR FR7425927A patent/FR2239448B1/fr not_active Expired
- 1974-07-29 DE DE19742436459 patent/DE2436459A1/de not_active Withdrawn
- 1974-07-30 BE BE147070A patent/BE818239A/xx unknown
- 1974-07-31 JP JP8710974A patent/JPS5045017A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3524833A1 (de) * | 1984-07-19 | 1986-01-30 | Sumitomo Chemical Co., Ltd., Osaka | Verfahren zur herstellung eines 1-amino-2-(unsubstituierten oder substituierten)-phenoxy-4-hydroxyanthrachinons |
Also Published As
| Publication number | Publication date |
|---|---|
| CH580661A5 (enrdf_load_stackoverflow) | 1976-10-15 |
| BE818239A (fr) | 1975-01-30 |
| FR2239448B1 (enrdf_load_stackoverflow) | 1977-01-07 |
| GB1468413A (en) | 1977-03-23 |
| FR2239448A1 (enrdf_load_stackoverflow) | 1975-02-28 |
| JPS5045017A (enrdf_load_stackoverflow) | 1975-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |