1-Nitroanthraquinone → 1-Aminoanthraquinone

HRID 647026Notes

Reaction equation

HRID 647026 reaction equation
[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.[SH-].[Na+].[N+](C1C2C(=O)C3C(=CC=CC=3)C(=O)C=2C=CC=1)([O-])=O.O>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

Participants

5

Reactant 3

HCID 67041-NitroanthraquinoneHCID 28015Sodium hydrosulfide2×HCID 70523385HCID 70523385, compound

Product 1

HCID 67101-AminoanthraquinoneYield 98.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  1. temperaturewhile maintaining the internal temperature of the vessel at 94°-96° C
  2. additionOne hour after start of pouring
  3. temperaturebeing maintained constant at 2,000 part/hr

Sources & evidence

ORD record
ord-1ffe95e10ea1458faa46b2d077befd11
Source dataset
uspto-grants-1983_10
Patent number
US04407756

Reaction notes

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