Dimethyl Sulfate → Solvent Red 111

HRID 2051375

Reaktionsgleichung

Reaktionsgleichung von HRID 2051375
[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[CH:5]=[CH:4][CH:3]=1.[N+]([C:21]1C=CC=CC=1)([O-])=O.[OH-].[K+].COS(=O)(=O)OC>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C.O>[CH3:21][NH: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[CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 6497Dimethyl SulfateHCID 67101-AminoanthraquinoneHCID 7416Nitrobenzene2×HCID 14797Potassium Hydroxide

Produkt 1

HCID 6706Solvent Red 111Ausbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

A mixture of 1-aminoanthraquinone (purity 99.6%, 22.4 g), nitrobenzene (224 g), 96% potassium hydroxide (11.7 g), tetra-n-butyl ammonium bromide (1.7 g) and dimethylsulfuric acid (25 g) was stirred, while being maintained at 30° C. for 24 hours. Then, after water (150 g) was added, the solution was stirred for one hour while being maintained at 50° C. The aqueous phase had pH of 10 or higher. After acetic acid (0.5 g) was added for neutralization until pH of the aqueous phase was 7, nitrobenzene was recovered. The solution was cooled down to 50° C., and filtered. The solid material was washed and dried, to obtain 1-methylaminoanthraquinone (23.7 g, purity: 99.5%, yield 99.5%).

Aufarbeitung

  1. stirringthe solution was stirred for one hour
  2. temperaturewhile being maintained at 50° C
  3. customwas recovered
  4. temperatureThe solution was cooled down to 50° C.
  5. filtrationfiltered
  6. washThe solid material was washed
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d9e53a716ba04b998f9de63b4b3c8d8b
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05017713

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