Hydroquinone → 1-Aminoanthraquinone

HRID 973000

Reaktionsgleichung

Reaktionsgleichung von HRID 973000
[N+:1]([C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[N+](C1C2C(=O)C3C(=C([N+]([O-])=O)C=CC=3)C(=O)C=2C=CC=1)([O-])=O.[N+](C1C2C(=O)C3C(=CC=CC=3[N+]([O-])=O)C(=O)C=2C=CC=1)([O-])=O.C1C2C(=O)C3C(=CC=CC=3)C(=O)C=2C=CC=1.[N+](C1C=CC2C(=O)C3C(=CC=CC=3)C(=O)C=2C=1)([O-])=O.[H][H].C1(C=CC(O)=CC=1)O>>[NH2:1][C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Komponenten

8

Edukt 7

HCID 785HydroquinoneHCID 67041-Nitroanthraquinone2×HCID 67059,10-Anthracenedione, 1,5-dinitro-HCID 6780AnthraquinoneHCID 672101,8-Dinitro-9,10-anthraquinoneHCID 39285932-NitroanthraquinoneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 67101-AminoanthraquinoneAusbeute 72,6 %

Versuchsvorschrift

5.0 g of crude 1-nitroanthraquinone containing dinitroanthraquinones having a purity of 81% and containing 8% of 1,5-dinitroanthraquinone, 4% of 1,8-dinitroanthraquinone and 7% of other dinitroanthraquinones and being free from anthraquinone and 2-nitroanthraquinone (0.016 mole of 1-nitroanthraquinone and 0.0032 mold of all the dinitroanthraquinones) was hydrogenated in the same way as in Example 5. The reaction was stopped when the amount of hydrogen absorbed reached 0.0816 mole, and the inside of the flask was purged with nitrogen. The amount of hydrogen absorbed corresponded to the sum of the amount of hydrogen required to convert the nitro group to an amino group (0.0672 mole) and 90% of the amount of hydrogen required to convert 1-aminoanthraquinone to its hydroquinone derivative (0.0144 mole). The reaction mixture was filtered in a stream of nitrogen to separate the catalyst and insoluble materials from it. The filtrate was oxidized with air at 20° to 30° C. for 2 hours with stirring to afford 3.2 g of 1-aminoanthraquinone having a purity of 98%. The yield of the product was 88% on a purity basis. The resulting 1-aminoanthraquinone contained about 1% of 1,8-diaminoanthraquinone and only traces of other diamino isomers.

Aufarbeitung

  1. customabsorbed
  2. customthe inside of the flask was purged with nitrogen
  3. customThe amount of hydrogen absorbed
  4. filtrationThe reaction mixture was filtered in a stream of nitrogen
  5. customto separate the catalyst and insoluble materials from it

Quellen und Nachweise

ORD-Eintrag
ord-967d535ca9b3419b8022045db011473e
Quelldatensatz
uspto-grants-1977_10
Patentnummer
US04054586

Verknüpfte Notizen

Wird geladen…