Toluene → 1-Aminoanthraquinone

HRID 622322

Reaktionsgleichung

[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:5]=1[C:6](=[O:19])[CH:7]1[CH:12]([C:13]2=[O:18])[CH2:11][CH:10]=[CH:9][CH2:8]1)([O-])=O.C1(C)C=CC=CC=1.[SH-].[Na+]>O>[NH2:1][C:4]1[C:5]2[C:6](=[O:19])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13](=[O:18])[C:14]=2[CH:15]=[CH:16][CH:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

A 2 liter autoclave equipped with anchor stirrer is charged with 64.3 parts of 5-nitro-1,4,4a,9a-tetrahydroanthraquinone, 750 parts of toluene, 250 parts of water and 8.8 parts of sodium bisulfide. With stirring, the phase mixture is heated to 160° C. under an excess pressure of 10 to 11 bar. Stirring is then discontinued and the lower layer is separated under this pressure. The upper phase is cooled to room temperature, whereupon the pure 1-aminoanthraquinone crystallises and is then isolated by filtration, washed with 75 parts of toluene and vaccum dried at 80° C. In the further batches, the bulk (e.g. 3/4) of the toluene-containing mother liquor is used instead of fresh toluene. In this manner 55 parts of 1-aminoanthraquinone in 99% purity are obtained, corresponding to a yield of about 99% of theory.

Aufarbeitung

customA 2 liter autoclave equipped with anchor stirrer
stirringStirring
customthe lower layer is separated under this pressure
temperatureThe upper phase is cooled to room temperature, whereupon the pure 1-aminoanthraquinone
customcrystallises
customis then isolated by filtration
washwashed with 75 parts of toluene and vaccum
customdried at 80° C
additionIn the further batches, the bulk (e.g. 3/4) of the toluene-containing mother liquor

Quellen und Nachweise

ORD-Eintrag: ord-18c6fe837ea745d48877d1d50ffb1899
Quelldatensatz: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04770818

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