Pyridine → 1,4-Diamino-9,10-dihydro-9,10-dioxoanthracene-2-sulphonic acid

HRID 255846

Reaktionsgleichung

Reaktionsgleichung von HRID 255846
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([NH2:18])=[CH:4][CH:3]=1.[OH:19][S:20](O)(=[O:22])=[O:21].O=S(=O)=O.N1C=CC=CC=1>O>[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([NH2:18])=[CH:4][C:3]=1[S:20]([OH:22])(=[O:21])=[O:19]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 24681Fuming sulfuric acidHCID 31420Disperse Violet 1

Produkt 1

HCID 777251,4-Diamino-9,10-dihydro-9,10-dioxoanthracene-2-sulphonic acidAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

60 parts of 1,4-diaminoanthraquinone are added to 228 parts of 25% oleum over one hour and then 20 parts of pyridine are added. The temperature of the reaction mixture is 70°-80° C. and is further raised to 120° C. The reaction mixture is stirred at this temperature for 3 hours, then cooled to 70°-80° C., and 220 parts of water are slowly added dropwise. The resultant thick suspension is filtered at room temperature and the filter cake is washed with 100 parts of 50% sulfuric acid and subsequently dispersed in water. The pH of the aqueous suspension is then adjusted to 7.5 with 35% sodium hydroxide solution, whereupon the 1,4-diaminoanthraquinone-2sulfonic acid goes into solution. The solution is then heated to 85°-90° C. and 40 parts of magnesium sulfate are added. Upon cooling the reaction solution, the 1,4-diaminoanthraquinone-2-sulfonic acid crystallises in the form of the magnesium salt, which is isolated by filtration, washed with a 5% solution of magnesium sulfate and dried, affording 72.4 parts of the magnesium salt of 1,4-diaminoanthraquinone-2-sulfonic acid, corresponding to a yield of 85%. According to chromatographic analysis, the product is homogeneous with a trace of starting material. The Rf value is 0.57, which confirms that this product is identical with that obtained in Example 1.

Aufarbeitung

  1. customis 70°-80° C.
  2. temperaturecooled to 70°-80° C.
  3. filtrationThe resultant thick suspension is filtered at room temperature
  4. washthe filter cake is washed with 100 parts of 50% sulfuric acid
  5. additionsubsequently dispersed in water
  6. temperatureThe solution is then heated to 85°-90° C.
  7. addition40 parts of magnesium sulfate are added
  8. temperatureUpon cooling the reaction solution
  9. customthe 1,4-diaminoanthraquinone-2-sulfonic acid crystallises in the form of the magnesium salt
  10. customwhich is isolated by filtration
  11. washwashed with a 5% solution of magnesium sulfate
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1d98f2ab2e504a8d9ae12b84ca777f41
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04699735

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