1-Nitroanthraquinone → 1-Aminoanthraquinone

HRID 647029Notes

Reaction equation

HRID 647029 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.[S-2].[Na+].[Na+]>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

4

Reactant 2

HCID 67041-NitroanthraquinoneHCID 14804Sodium Sulfide

Product 1

HCID 67101-Aminoanthraquinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5,500 Parts of water was added to a mixture of 200 parts of the nitroanthraquinone (98.0% 1-nitro content) used in Example 4 and 400 parts of 32% sodium sulfide and the mixed solution was heated from room temperature till boiling by spending 70 minutes. A part of the reaction mixture was sampled out and the heating was continued until substantially no unreacted nitro component became detectable by gas-chromatography. Approximately 3 hours was required for this treatment. Thereafter the reaction mixture was cooled to 70° C., filtered, sufficiently washed and dried to obtain 171 parts of 1-aminoanthraquinone. The purity of 1-aminoanthraquinone as determined by gas-chromatography was 98.1%, and the yield of 1-aminoanthraquinone from 1-nitroanthraquinoen was 97.1%. The thus obtained 1-aminoanthraquinone crystals were the substantially same size as those obtained in Referential Example 1, and because of poor filterability, a great deal of time and labor were required for separating them from waste water of reduction.

Workup

  1. aliquotA part of the reaction mixture was sampled out
  2. customApproximately 3 hours
  3. temperatureThereafter the reaction mixture was cooled to 70° C.
  4. filtrationfiltered
  5. washsufficiently washed
  6. customdried

Sources & evidence

ORD record
ord-54a9abb240714471895ae8ab8270fd5d
Source dataset
uspto-grants-1983_10
Patent number
US04407756

Reaction notes

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