DE2526651C3 - Verfahren zur Herstellung von Aminoanthrachinonen aus Nitroanthrachinonen - Google Patents
Verfahren zur Herstellung von Aminoanthrachinonen aus NitroanthrachinonenInfo
- Publication number
- DE2526651C3 DE2526651C3 DE2526651A DE2526651A DE2526651C3 DE 2526651 C3 DE2526651 C3 DE 2526651C3 DE 2526651 A DE2526651 A DE 2526651A DE 2526651 A DE2526651 A DE 2526651A DE 2526651 C3 DE2526651 C3 DE 2526651C3
- Authority
- DE
- Germany
- Prior art keywords
- nitroanthraquinones
- nitro
- ammonia
- amino
- water
- 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
- 238000000034 method Methods 0.000 title claims description 32
- 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 claims description 19
- 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 claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 229910021529 ammonia Inorganic materials 0.000 claims description 19
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 150000002334 glycols Chemical class 0.000 claims description 7
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 6
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 claims description 5
- 235000019270 ammonium chloride Nutrition 0.000 claims description 5
- 239000000975 dye Substances 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 claims description 3
- 239000011877 solvent mixture Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 13
- 238000001816 cooling Methods 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- -1 amino compound Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- 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 description 3
- MTXKQBHZBNCFSC-UHFFFAOYSA-N 2-amino-1-nitroanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C([N+]([O-])=O)C(N)=CC=C3C(=O)C2=C1 MTXKQBHZBNCFSC-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000002828 nitro derivatives Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LRMDXTVKVHKWEK-UHFFFAOYSA-N 1,2-diaminoanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C(N)C(N)=CC=C3C(=O)C2=C1 LRMDXTVKVHKWEK-UHFFFAOYSA-N 0.000 description 2
- UIVAZSZXLKMDHT-UHFFFAOYSA-N 1,2-dihydroxy-3,4-dinitroanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C([N+]([O-])=O)=C([N+]([O-])=O)C(O)=C2O UIVAZSZXLKMDHT-UHFFFAOYSA-N 0.000 description 2
- 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 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 238000011403 purification operation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- VWBVCOPVKXNMMZ-UHFFFAOYSA-N 1,5-diaminoanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=CC=C2C(=O)C2=C1C=CC=C2N VWBVCOPVKXNMMZ-UHFFFAOYSA-N 0.000 description 1
- QWXDVWSEUJXVIK-UHFFFAOYSA-N 1,8-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC(N)=C2C(=O)C2=C1C=CC=C2N QWXDVWSEUJXVIK-UHFFFAOYSA-N 0.000 description 1
- ZJDUDTHYWUAWMW-UHFFFAOYSA-N 1-amino-6-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC([N+]([O-])=O)=CC=C2C(=O)C2=C1C=CC=C2N ZJDUDTHYWUAWMW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229960001156 mitoxantrone Drugs 0.000 description 1
- 150000005181 nitrobenzenes Chemical class 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000008096 xylene 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)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2526651A DE2526651C3 (de) | 1975-06-14 | 1975-06-14 | Verfahren zur Herstellung von Aminoanthrachinonen aus Nitroanthrachinonen |
| US05/693,038 US4076736A (en) | 1975-06-14 | 1976-06-04 | Preparation of aminoanthraquinones from nitroanthraquinones |
| CH737776A CH611266A5 (https=) | 1975-06-14 | 1976-06-10 | |
| JP51067844A JPS51151726A (en) | 1975-06-14 | 1976-06-11 | Process for producing aminoanthraquinone |
| GB24329/76A GB1497959A (en) | 1975-06-14 | 1976-06-11 | Process for the preparation of aminoanthraquinones for nitroanthraquinones |
| BE2055116A BE842907A (fr) | 1975-06-14 | 1976-06-14 | Procede pour la preparation d'aminoanthraquinones a partir de nitroanthraquinones |
| FR7618003A FR2314172A1 (fr) | 1975-06-14 | 1976-06-14 | Procede pour la preparation d'aminoanthraquinones a partir de nitroanthraquinones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2526651A DE2526651C3 (de) | 1975-06-14 | 1975-06-14 | Verfahren zur Herstellung von Aminoanthrachinonen aus Nitroanthrachinonen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2526651A1 DE2526651A1 (de) | 1976-12-16 |
| DE2526651B2 DE2526651B2 (de) | 1981-07-30 |
| DE2526651C3 true DE2526651C3 (de) | 1982-05-13 |
Family
ID=5949115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2526651A Expired DE2526651C3 (de) | 1975-06-14 | 1975-06-14 | Verfahren zur Herstellung von Aminoanthrachinonen aus Nitroanthrachinonen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4076736A (https=) |
| JP (1) | JPS51151726A (https=) |
| BE (1) | BE842907A (https=) |
| CH (1) | CH611266A5 (https=) |
| DE (1) | DE2526651C3 (https=) |
| FR (1) | FR2314172A1 (https=) |
| GB (1) | GB1497959A (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2827197A1 (de) * | 1978-06-21 | 1980-01-10 | Bayer Ag | Verfahren zur herstellung von aminoanthrachinonen |
| JP2007070300A (ja) * | 2005-09-08 | 2007-03-22 | Teijin Ltd | ２，５−ジアミノ−１，４−ベンゾキノン及び２，５−ジアミノ−１，４−ベンゼンジオール、およびその塩の製造方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH86306A (de) * | 1919-01-09 | 1920-08-16 | Geigy Ag J R | Verfahren zur Darstellung von 2-Aminoanthrachinon. |
| DE2211411A1 (de) * | 1971-03-11 | 1972-09-21 | Sandoz Ag, Basel (Schweiz) | Verfahren zur Herstellung von Aminoanthrachinonen |
| CH573464A5 (https=) * | 1972-10-05 | 1976-03-15 | Ciba Geigy Ag | |
| BE812616A (fr) * | 1973-03-22 | 1974-09-23 | Procede de production de la 1-amino-anthraquinone | |
| IT1005693B (it) * | 1973-03-22 | 1976-09-30 | Bayer Ag | Processo per la produzione di i aminoantrachinone 1, 5 e 1, 8 diamino antrachinone |
| DE2334991C3 (de) * | 1973-07-10 | 1981-08-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von α -Amino- β'-nitro-anthrachinonen |
| DE2343977B2 (de) * | 1973-08-31 | 1978-10-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von reinem 1-Aminoanthrachinon |
| DE2409542A1 (de) * | 1974-02-28 | 1975-09-11 | Bayer Ag | Verfahren zur herstellung von aminoanthrachinonen |
-
1975
- 1975-06-14 DE DE2526651A patent/DE2526651C3/de not_active Expired
-
1976
- 1976-06-04 US US05/693,038 patent/US4076736A/en not_active Expired - Lifetime
- 1976-06-10 CH CH737776A patent/CH611266A5/xx not_active IP Right Cessation
- 1976-06-11 GB GB24329/76A patent/GB1497959A/en not_active Expired
- 1976-06-11 JP JP51067844A patent/JPS51151726A/ja active Pending
- 1976-06-14 FR FR7618003A patent/FR2314172A1/fr active Granted
- 1976-06-14 BE BE2055116A patent/BE842907A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1497959A (en) | 1978-01-12 |
| FR2314172B1 (https=) | 1980-04-04 |
| FR2314172A1 (fr) | 1977-01-07 |
| BE842907A (fr) | 1976-12-14 |
| DE2526651A1 (de) | 1976-12-16 |
| DE2526651B2 (de) | 1981-07-30 |
| CH611266A5 (https=) | 1979-05-31 |
| JPS51151726A (en) | 1976-12-27 |
| US4076736A (en) | 1978-02-28 |
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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 |