CH683004A5 - Prodn. of 1-amino:anthraquinone derivs., useful as dye intermediates - Google Patents
Prodn. of 1-amino:anthraquinone derivs., useful as dye intermediates Download PDFInfo
- Publication number
- CH683004A5 CH683004A5 CH1714/92A CH171492A CH683004A5 CH 683004 A5 CH683004 A5 CH 683004A5 CH 1714/92 A CH1714/92 A CH 1714/92A CH 171492 A CH171492 A CH 171492A CH 683004 A5 CH683004 A5 CH 683004A5
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- anthraquinone
- prodn
- amino
- derivs
- Prior art date
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- 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 title description 2
- 150000004056 anthraquinones Chemical class 0.000 title description 2
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 8
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims abstract description 4
- TUZZWPYZPHNFJY-UHFFFAOYSA-N 1-chloro-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2O TUZZWPYZPHNFJY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RYYXDZDBXNUPOG-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine;dihydrochloride Chemical compound Cl.Cl.C1C(N)CCC2=C1SC(N)=N2 RYYXDZDBXNUPOG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
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CH 683 004 A5 CH 683 004 A5
Beschreibung description
Die Erfindung betrifft ein Verfahren zur Herstellung von 1-Aminoanthrachinon, das dadurch gekennzeichnet ist, dass man Verbindungen der Formel I The invention relates to a process for the preparation of 1-aminoanthraquinone, which is characterized in that compounds of the formula I
O OH O OH
0 X 0 X
in der in the
X Chlor, Brom oder Hydroxy bedeutet, mit Ammoniak in Gegenwart von Reduktionsmitteln bei erhöhter Temperatur umsetzt. X means chlorine, bromine or hydroxy, reacted with ammonia in the presence of reducing agents at elevated temperature.
Vorzugsweise ist X Chlor, das entsprechende Anthrachinonderivat ist durch Umsetzung von Phthal-säureanhydrid mit p-Chlorphenol z.B. in Gegenwart von Aluminiumchlorid zugänglich. X is preferably chlorine, the corresponding anthraquinone derivative can be obtained by reacting phthalic anhydride with p-chlorophenol e.g. accessible in the presence of aluminum chloride.
Als Reduktionsmittel eignen sich z.B. Thioharnstoffdioxid und insbesondere Alkalidithionit sowie Wasserstoff in Gegenwart von Katalysatoren. Das Reduktionsmittel wird in mindestens molaren Mengen angewendet. Suitable reducing agents are e.g. Thiourea dioxide and especially alkalidithionite and hydrogen in the presence of catalysts. The reducing agent is used in at least molar amounts.
Das erfindungsgemässe Verfahren wird zweckmässigerweise so durchgeführt, dass man die Verbindung der Formel I, Ammoniak (in Wasser, Lösungsmitteln oder gasförmig) und das Reduktionsmittel auf Temperaturen von 30 bis 200°C, vorzugsweise 40 bis 130°C, erhitzt. Bei der Reduktion mit Wasserstoff wird gasförmiger Wasserstoff bei der Reaktionstemperatur eingepresst. The process according to the invention is expediently carried out in such a way that the compound of the formula I, ammonia (in water, solvents or gaseous) and the reducing agent are heated to temperatures of 30 to 200 ° C., preferably 40 to 130 ° C. When reducing with hydrogen, gaseous hydrogen is injected at the reaction temperature.
Die Reaktion kann auch in Gegenwart von Phasentransferkatalysatoren vorgenommen werden. The reaction can also be carried out in the presence of phase transfer catalysts.
Üblicherweise benötigt man Reaktionszeiten von Vz bis 15 Stunden abhängig von der Temperatur, dem Reduktions- und gegebenenfalls Lösungsmittel. Reaction times of Vz to 15 hours are usually required, depending on the temperature, the reduction solvent and, if appropriate, solvent.
Das 1-Aminoanthrachinon kann wie üblich, z.B. durch Ausfällen mit Wasser, isoliert werden. The 1-aminoanthraquinone can be used as usual, e.g. by precipitation with water.
Im folgenden Beispiel beziehen sich Angaben über Teile und Prozente auf das Gewicht. In the following example, parts and percentages are by weight.
Beispiele 1 bis 3 Beispiel 1 Examples 1 to 3 Example 1
In einem 1 1-Autoklaven werden in 316 Teilen 19%igem Ammoniak 45 Teile 1-Hydroxi-4-chlor-an-thrachinon vorgelegt. Nach Zugabe von 44,3 Teilen Natriumdithionit wirli das Gefäss druckdicht verschlossen und in 2 Stunden auf 90°C erwärmt. Man hält 10 Stunden bei dieser Temperatur. Nach dem Abkühlen auf Raumtemperatur wird das ausgefallene Reaktionsprodukt abgesaugt, mit Wasser neutral und salzfrei gewaschen und getrocknet. Man erhält 39,3 Teile Produkt mit einem 1-Aminoanthrachinon-anteil von 45,6%. 45 parts of 1-hydroxy-4-chloro-an-thrachinone are placed in 316 parts of 19% ammonia in a 1 liter autoclave. After adding 44.3 parts of sodium dithionite, the vessel is sealed pressure-tight and heated to 90 ° C. in 2 hours. It is kept at this temperature for 10 hours. After cooling to room temperature, the precipitated reaction product is filtered off, washed neutral with water and salt-free and dried. 39.3 parts of product with a 1-aminoanthraquinone content of 45.6% are obtained.
Beispiel 2 Example 2
In einem 1 1-Autoklaven werden in 700 Teilen 18%igem Ammoniak 40 Teile 1-Hydroxi-4-chlor-an-thrachinon vorgelegt. Nach Zugabe von 25 Teilen Thioharnstoffdioxid wird das Gefäss druckdicht verschlossen und in 5 Stunden auf 90°C erwärmt. Nach dem Abkühlen auf Raumtemperatur wird das ausgefallene Reaktionsprodukt abgesaugt, mit Wasser neutral und salzfrei gewaschen und getrocknet. Man erhält 23,8 Teile Produkt mit einem 1-Amino-anthrachinonanteil von 23,3%. 40 parts of 1-hydroxy-4-chloro-an-thrachinone are placed in 700 parts of 18% ammonia in a 1 liter autoclave. After adding 25 parts of thiourea dioxide, the vessel is closed pressure-tight and heated to 90 ° C in 5 hours. After cooling to room temperature, the precipitated reaction product is filtered off, washed neutral with water and salt-free and dried. 23.8 parts of product with a 1-amino-anthraquinone content of 23.3% are obtained.
Beispiel 3 Example 3
58,2 Teile 1-Hydroxi-4-chlor-anthrachinon werden in 500 Teilen Wasser mit 16,5 Teilen 50%iger Natronlauge versetzt und 30 Minuten unter Überleiten von Stickstoff bei Raumtemperatur gerührt. Nach Zugabe von 86,2 Teilen Natiumdithionit wird in 1 Stunde auf 90 bis 92°C erwärmt. Dabei wird der pH-Wert der Suspension durch Zugabe von 50%iger Natronlauge bei 7,8 bis 8,0 gehalten. Nach 1 stündigem Rühren wird die Suspension in einen 1 1-Autoklaven überführt und mit 300 Teilen 25%igem Ammoniak versetzt. Das Gefäss wird druckdicht verschlossen und in 1 Stunde auf 90 bis 92°C erwärmt. Man hält 4 Stunden bei dieser Temperatur. Nach dem Abkühlen auf Raumtemperatur wird das ausgefallene Produkt abgesaugt, mit Wasser neutral und salzfrei gewaschen und getrocknet. Man erhält 47,8 Teile Produkt mit einem 1-Amino-anthrachinonanteil von 23,9%. 58.2 parts of 1-hydroxy-4-chloro-anthraquinone are added to 500 parts of water with 16.5 parts of 50% sodium hydroxide solution and stirred at room temperature for 30 minutes while passing nitrogen over them. After addition of 86.2 parts of sodium dithionite, the mixture is heated to 90 to 92 ° C. in 1 hour. The pH of the suspension is kept at 7.8 to 8.0 by adding 50% sodium hydroxide solution. After stirring for 1 hour, the suspension is transferred to a 1 liter autoclave and 300 parts of 25% ammonia are added. The vessel is closed pressure-tight and heated to 90 to 92 ° C in 1 hour. It is kept at this temperature for 4 hours. After cooling to room temperature, the precipitated product is filtered off, washed neutral with water and free of salt and dried. 47.8 parts of product with a 1-amino-anthraquinone content of 23.9% are obtained.
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CH 683 004 A5 CH 683 004 A5
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4117978 | 1991-05-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH683004A5 true CH683004A5 (en) | 1993-12-31 |
Family
ID=6432963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1714/92A CH683004A5 (en) | 1991-05-31 | 1992-05-27 | Prodn. of 1-amino:anthraquinone derivs., useful as dye intermediates |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPH05163214A (en) |
| CH (1) | CH683004A5 (en) |
| IT (1) | IT1260470B (en) |
-
1992
- 1992-05-27 CH CH1714/92A patent/CH683004A5/en not_active IP Right Cessation
- 1992-05-27 IT ITMI921303A patent/IT1260470B/en active IP Right Grant
- 1992-05-28 JP JP4136501A patent/JPH05163214A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IT1260470B (en) | 1996-04-09 |
| ITMI921303A1 (en) | 1992-12-01 |
| JPH05163214A (en) | 1993-06-29 |
| ITMI921303A0 (en) | 1992-05-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |