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ChemicalBook CAS DataBase List 1-Aminoanthraquinone
82-45-1

1-Aminoanthraquinone synthesis

9synthesis methods
1-Aminoanthraquinone (1-AAQ) is synthesized by the condensation of 2-substituted benzoic acid and xylene to yield 2-substituted-dimethylbenzophenone, subsequent oxidation of the methyl groups, ring closure to form a 1-substituted anthraquinone carboxylic acid, replacement of the 1-substituent with ammonia, and decarboxylation.
-

Yield:82-45-1 99.3%

Reaction Conditions:

with sodium hydrogensulfide

Steps:

4 EXAMPLE 4
EXAMPLE 4 A 1-nitroanthraquinone (98.0% purity) and water mixture with slurry concentration of 17.2% and a 12.0% aqueous solution of sodium hydrosulfide were added dropwise into a 2,000-volume-part glass-made vessel under agitation while maintaining the internal temperature of the vessel at 94°-96° C. The feeding rates of the 1-nitroanthraquinone-water mixture and the 12.0% sodium hydrosulfide solution were maintained constant at 1,055 part/hr and 945 part/hr, respectively. One hour after start of pouring, withdrawal of the reaction mixture from the bottom of the flask was started, with the efflux rate being maintained constant at 2,000 part/hr. The flow rate of 1-aminoanthraquinone (98.5% purity) in the effluent obtained from the 6th hour and afterward was 158 part/hr. 1-aminoanthraquinone was obtained in the yield of 99.3% based on the starting material 1-nitroanthraquinone, and the crystals of 1-aminoanthraquinone had very excellent filterability.

References:

Sumitomo Chemical Company, Limited US4407756, 1983, A

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