GB1477038A - Production of aminoanthraquinones from nitroanthraquinones - Google Patents
Production of aminoanthraquinones from nitroanthraquinonesInfo
- Publication number
- GB1477038A GB1477038A GB3793174A GB3793174A GB1477038A GB 1477038 A GB1477038 A GB 1477038A GB 3793174 A GB3793174 A GB 3793174A GB 3793174 A GB3793174 A GB 3793174A GB 1477038 A GB1477038 A GB 1477038A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitro
- aminoanthraquinone
- amino
- dinitroanthraquinone
- diamino
- 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
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 title abstract 4
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- JTYJHBWDNMUPSP-UHFFFAOYSA-N 1,4,5-trichloro-8-nitroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C(Cl)=CC=C2[N+](=O)[O-] JTYJHBWDNMUPSP-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- DNIHCFWMWZCKCQ-UHFFFAOYSA-N 1,4-diamino-9,10-dioxoanthracene-2-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(C(O)=O)C=C2N DNIHCFWMWZCKCQ-UHFFFAOYSA-N 0.000 abstract 1
- HSYLKWSCFRLSKB-UHFFFAOYSA-N 1,5-diamino-4,8-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=CC(O)=C2C(=O)C2=C1C(O)=CC=C2N HSYLKWSCFRLSKB-UHFFFAOYSA-N 0.000 abstract 1
- PCRDLMIEOJEVOE-UHFFFAOYSA-N 1,5-dichloro-4,8-dinitroanthracene-9,10-dione Chemical compound O=C1C2=C([N+]([O-])=O)C=CC(Cl)=C2C(=O)C2=C1C(Cl)=CC=C2[N+](=O)[O-] PCRDLMIEOJEVOE-UHFFFAOYSA-N 0.000 abstract 1
- UKYHPHKDJDQTAH-UHFFFAOYSA-N 1,5-dimethoxy-4,8-dinitroanthracene-9,10-dione Chemical compound O=C1C2=C(OC)C=CC([N+]([O-])=O)=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2OC UKYHPHKDJDQTAH-UHFFFAOYSA-N 0.000 abstract 1
- XVMVHWDCRFNPQR-UHFFFAOYSA-N 1,5-dinitroanthracene-9,10-dione Chemical compound O=C1C=2C([N+](=O)[O-])=CC=CC=2C(=O)C2=C1C=CC=C2[N+]([O-])=O XVMVHWDCRFNPQR-UHFFFAOYSA-N 0.000 abstract 1
- UQKJUEALIQRECQ-UHFFFAOYSA-N 1,6-dinitroanthracene-9,10-dione Chemical compound O=C1C2=CC([N+](=O)[O-])=CC=C2C(=O)C2=C1C=CC=C2[N+]([O-])=O UQKJUEALIQRECQ-UHFFFAOYSA-N 0.000 abstract 1
- SJHHHHHQWQOCDQ-UHFFFAOYSA-N 1,8-diamino-4,5-dihydroxyanthracene-9,10-dione Chemical class O=C1C2=C(O)C=CC(N)=C2C(=O)C2=C1C(O)=CC=C2N SJHHHHHQWQOCDQ-UHFFFAOYSA-N 0.000 abstract 1
- QWXDVWSEUJXVIK-UHFFFAOYSA-N 1,8-diaminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC(N)=C2C(=O)C2=C1C=CC=C2N QWXDVWSEUJXVIK-UHFFFAOYSA-N 0.000 abstract 1
- RTMQUPOSAXABDD-UHFFFAOYSA-N 1,8-dimethoxy-4,5-dinitroanthracene-9,10-dione Chemical compound O=C1C(C(=CC=C2OC)[N+]([O-])=O)=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2OC RTMQUPOSAXABDD-UHFFFAOYSA-N 0.000 abstract 1
- MBIJFIUDKPXMAV-UHFFFAOYSA-N 1,8-dinitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC([N+]([O-])=O)=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] MBIJFIUDKPXMAV-UHFFFAOYSA-N 0.000 abstract 1
- ZLCUIOWQYBYEBG-UHFFFAOYSA-N 1-Amino-2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=C(N)C(C)=CC=C3C(=O)C2=C1 ZLCUIOWQYBYEBG-UHFFFAOYSA-N 0.000 abstract 1
- FXXOWMASCSSPPJ-UHFFFAOYSA-N 1-amino-2-ethylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(CC)=CC=C3C(=O)C2=C1 FXXOWMASCSSPPJ-UHFFFAOYSA-N 0.000 abstract 1
- PZHGBWKPRMYCEF-UHFFFAOYSA-N 1-amino-2-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(O)=C2N PZHGBWKPRMYCEF-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- GHUZWOWTEPWYHT-UHFFFAOYSA-N 1-aminobenzo[b]phenalen-7-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C3=C2C1=CC=C3N GHUZWOWTEPWYHT-UHFFFAOYSA-N 0.000 abstract 1
- PHLHEYMNKXWDMC-UHFFFAOYSA-N 1-anilino-4,8-dihydroxy-5-nitroanthracene-9,10-dione Chemical compound C1=2C(=O)C3=C(O)C=CC([N+]([O-])=O)=C3C(=O)C=2C(O)=CC=C1NC1=CC=CC=C1 PHLHEYMNKXWDMC-UHFFFAOYSA-N 0.000 abstract 1
- BJBLQNJVZAMPMT-UHFFFAOYSA-N 1-anilino-5-nitroanthracene-9,10-dione Chemical compound [N+](=O)([O-])C1=CC=CC=2C(C3=C(C=CC=C3C(C12)=O)NC1=CC=CC=C1)=O BJBLQNJVZAMPMT-UHFFFAOYSA-N 0.000 abstract 1
- XXUOKOYLVBHBCG-UHFFFAOYSA-N 1-hydroxy-4-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C([N+]([O-])=O)=CC=C2O XXUOKOYLVBHBCG-UHFFFAOYSA-N 0.000 abstract 1
- XFLONXIGNOXKCG-UHFFFAOYSA-N 2,7-dinitroanthracene-9,10-dione Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C(=O)C2=C1 XFLONXIGNOXKCG-UHFFFAOYSA-N 0.000 abstract 1
- QCVMOSGPTRRUQZ-UHFFFAOYSA-N 2-nitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C(=O)C2=C1 QCVMOSGPTRRUQZ-UHFFFAOYSA-N 0.000 abstract 1
- YLFWHISGXDKCIT-UHFFFAOYSA-N 3-amino-1,2-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(N)C(O)=C2O YLFWHISGXDKCIT-UHFFFAOYSA-N 0.000 abstract 1
- CNSNLRXGBRBCAU-UHFFFAOYSA-N 5-amino-1,4-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C=CC=C2N CNSNLRXGBRBCAU-UHFFFAOYSA-N 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 abstract 1
- 229940067157 phenylhydrazine Drugs 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1477038 Aminoanthraquinones from nitroanthraquinones BASF AG 30 Aug 1974 [1 Sept 1973] 37931/74 Heading C4P A process for the production of an aminoanthraquinone (or aminobenzanthrone) is claimed, wherein the corresponding nitro compound is reduced in an aqueous solution containing from 0À5 to 50% by weight of an alkaline-reacting agent with at least the stoichiometrically necessary amount of a hydrazine at a temperature of from 25‹ C. to the boiling temperatures of the reaction mixture. Hydrazine, methylhydrazine, N,N-dimethylhydrazine or phenylhydrazine may be used, and as alkaline reagent NaOH, KOH, Na 2 CO 3 or K 2 CO 3 or mixtures may be employed. Examples describe the preparation of: a mixture of 1,5-diamino-4,8-dihydroxy- and 1,8- diamino - 4,5 - dihydroxyanthraquinones; 1- aminoanthraquinone; 2 - carboxy -, 5 - chloro-, 2 - and 2 - ethyl - 1 - aminoanthraquinone; 1,4 - dichloro - 5 - amino - anthraquinone; 1,2- dihydroxy - 3 - aminoanthraquinone; a mixture of 1,5- and 1,8-diaminoanthraquinones; 1,5 - diamino - 4,8 - dihydroxyanthraquinone; 1,4 - diaminoanthraquinone - 2 - carboxylic acid; 1 - amino - 2 - methylanthraquinone; 1- amino - 5 - [4<SP>1 </SP>- chlorophenylamino] - 4,8 - dihydroxyanthraquinone; Bz - 1 - aminobenzanthrone; Bz - 1,6 - diaminobenzanthrone; and 1-amino-2-hydroxyanthraquinone. In addition the use of: 1,5-dinitroanthraquinone; 1,8 - dinitroanthraquinone; 1 - nitro- 4 - hydroxyanthraquinone; 1 - nitro - 4,5,8- trichloroanthraquinone; 5 - nitro - 1 - aminoanthraquinone; 1,5 - dinitro - 4,8 - dichloroanthraquinone; 1,5 - dinitro - 4,8 - dimethoxyanthraquinone; 1,8 - dinitro - 4,5 - dimethoxyanthraquinone; 1 - nitro - 5 - phenylamino- 4,8 - dihydroxyanthraquinone; 1 - nitro - 5- phenylaminoanthraquinone; 1,4 - diamino - 5- nitroanthraquinone; 2 - nitroanthraquinone; 1,6 - dinitroanthraquinone; 2,7 - dinitroanthraquinone and Bz - 1 - bromo - 6 - nitrobenzanthrone in the preparation of the corresponding amino compounds is also claimed.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732344195 DE2344195C3 (en) | 1973-09-01 | 1973-09-01 | Process for the preparation of aminoanthraquinones from nitroanthraquinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1477038A true GB1477038A (en) | 1977-06-22 |
Family
ID=5891388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3793174A Expired GB1477038A (en) | 1973-09-01 | 1974-08-30 | Production of aminoanthraquinones from nitroanthraquinones |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5051126A (en) |
| BE (1) | BE819381A (en) |
| CH (1) | CH601178A5 (en) |
| DE (1) | DE2344195C3 (en) |
| FR (1) | FR2242370B3 (en) |
| GB (1) | GB1477038A (en) |
| IT (1) | IT1019164B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109810008A (en) * | 2019-02-26 | 2019-05-28 | 海门市五洋化工有限公司 | A kind of synthetic method of dyestuff intermediate |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005206B1 (en) * | 1978-04-28 | 1981-04-01 | Ciba-Geigy Ag | Method of preparing 1,4-diaminoanthraquinone-2-carboxylic acid |
| DE2916958A1 (en) * | 1978-04-28 | 1979-11-08 | Ciba Geigy Ag | METHOD FOR PRODUCING 1,2-DIAMINOANTHRACHINONE |
| WO1998018764A1 (en) * | 1996-10-28 | 1998-05-07 | Merck Patent Gmbh | Dihydrobenzoanthracenone, -pyrimidinone or dihydronaphtoquinolinone |
-
1973
- 1973-09-01 DE DE19732344195 patent/DE2344195C3/en not_active Expired
-
1974
- 1974-08-28 CH CH1174974A patent/CH601178A5/xx not_active IP Right Cessation
- 1974-08-30 GB GB3793174A patent/GB1477038A/en not_active Expired
- 1974-08-30 FR FR7429637A patent/FR2242370B3/fr not_active Expired
- 1974-08-30 IT IT5281174A patent/IT1019164B/en active
- 1974-08-30 BE BE148068A patent/BE819381A/en unknown
- 1974-09-02 JP JP9998774A patent/JPS5051126A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109810008A (en) * | 2019-02-26 | 2019-05-28 | 海门市五洋化工有限公司 | A kind of synthetic method of dyestuff intermediate |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2242370B3 (en) | 1977-06-17 |
| DE2344195C3 (en) | 1980-12-11 |
| CH601178A5 (en) | 1978-06-30 |
| DE2344195A1 (en) | 1975-04-03 |
| IT1019164B (en) | 1977-11-10 |
| BE819381A (en) | 1975-02-28 |
| JPS5051126A (en) | 1975-05-07 |
| DE2344195B2 (en) | 1980-04-17 |
| FR2242370A1 (en) | 1975-03-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1416612A (en) | Catalyst and the use of this catalyst for reducing nitrocompounds | |
| GB1477038A (en) | Production of aminoanthraquinones from nitroanthraquinones | |
| US2874168A (en) | Process for the preparation of 1-nitroanthraquinone | |
| GB1237780A (en) | Processing offgas from the synthesis of melamine | |
| US4154747A (en) | Production of virtually pure 1-amino-8-nitro-4,5-dihydroxyanthraquinone | |
| GB1454849A (en) | Process for the preparation of pure 1-aminoanthraquinone | |
| ES424749A1 (en) | Vat dyestuffs prepared from crude aminoanthraquinone mixtures | |
| GB1274048A (en) | Process for the production of pure basic dyestuffs | |
| GB1433517A (en) | Preparation of fluoroanilines | |
| US2228885A (en) | Manufacture of amino-hydroxy-anthraquinones | |
| GB1429282A (en) | Explosive compositions | |
| US5424461A (en) | Preparation of 1-amino-4-hydroxyanthraquinone | |
| GB1312329A (en) | Process for the preparation of sodium dithionite | |
| US2487110A (en) | Preparation of 1-amino-4-hydroxy-5-chloroanthraquinone | |
| GB1465739A (en) | Process for the preparation of pure 1-nitroanthraquinone | |
| US2228884A (en) | Production of 1,4-di-(mono-substituted-amino)-anthraquinone compounds | |
| GB1212846A (en) | Derivatives of 1-aminoanthraquinone and processes for their manufacture | |
| GB1311915A (en) | Anthraquinones and processes for their manufacture | |
| GB1428620A (en) | Process for the preparation of 1-aminoanthraquinone 1,5- diaminoanthraquinone and 1,8-diaminoanthraquinone | |
| GB1433091A (en) | Process for the preparation of 1,5- and 1,8-dinitroanthraquinone | |
| US4351774A (en) | Process for the production of methoxyanthraquinones | |
| JPS587615B2 (en) | Dimethoxyanthraquinone luino | |
| GB1485900A (en) | Process for preparing amino-anthraquinones | |
| JPS5615252A (en) | Preparation of anthrimide or anthraouinonylaminobenzanthrone | |
| GB1283015A (en) | Process for the recovery of 2,4,7-trinitrofluorenone |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |