Process for the preparation of 1-aminoanthraquinone

Details Process for the preparation of 1-aminoanthraquinone Process for the preparation of 1-aminoanthraquinone

1975-03-19

1976-11-30

Demers, Arthur P.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260369, C07C 9724

Patent

active

039949320

ABSTRACT:
1-Aminoanthraquinone of high purity is obtained either by catalytically hydrogenating 5-nitro-1,4,4a,9a-tetrahydroanthraquinone dissolved in a polar organic solvent such as methyl cellosolve (i.e., .beta.-hydroxyethyl methyl ether) in the presence of a hydrogenation catalyst such as palladium on carbon or Raney nickel and then treating the resultant hydrogenated product with a base such as sodium hydroxide or pyridine, or by catalytically hydrogenating the 5-nitro-1,4,4a,9a-tetrahydroanthraquinone in the presence of both the hydrogenation catalyst and the base. By the action of the base, the 5-nitro-1,4,4a,9a-tetrahydroanthraquinone nucleus releases hydrogen atoms and is converted to the anthraquinone nucleus, and the released hydrogen serves to reduce the nitro group. Where an excess of hydrogen is introduced into the reaction system for hydrogenation, 1-aminoanthraquinone is further reduced into a leuco type compound thereof which can easily be returned to 1-aminoanthraquinone by oxidation.

REFERENCES:
patent: 2860036 (1958-11-01), Lait
patent: 2948739 (1960-08-01), Harris et al.
patent: 3433811 (1969-03-01), Jentzsch
Fliege et al.; Chemical Abstracts, vol. 79 (1973) No. 136904.
Vorozhtsov et al.; Chemical Abstracts, vol. 55 (1961) column 1547 e-i.

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