Ammonia → 1,5-Diaminoanthraquinone

HRID 616857

Reaction equation

HRID 616857 reaction equation
[N+:1]([C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[C:11]([N+:19]([O-])=O)[CH:12]=[CH:13][CH:14]=3)[C:9](=[O:22])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.N.[NH4+].[Cl-]>O>[NH2:1][C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[C:11]([NH2:19])[CH:12]=[CH:13][CH:14]=3)[C:9](=[O:22])[C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 67059,10-Anthracenedione, 1,5-dinitro-HCID 25517Ammonium Chloride

Product 1

HCID 85131,5-DiaminoanthraquinoneYield 96.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

45 g of 1,5-dinitroanthraquinone (97 %) are heated to 200° C in 100 ml of water in a 0.7 liter steel autoclave. 300 ml of a cold, 25% strength aqueous ammonia solution, which contains 10% of NH4Cl, are pumped into this mixture over a period of 30 minutes. Thereafter, the temperature is kept constant for another 5 1/2 hours, the pressure thereby rising to 60 bar. The product is left to cool without outside help, the pressure released and the product filtered off with suction. The entire filtrate, 350 ml, is faintly yellow in color, E47010 cm = 6.0. After washing and drying there are obtained 34.8 g of 93.0 % pure 1,5-diaminoanthraquinone (92.7 % of theory). The product still contains 4.5 % (4.0 % of theory) of 1-amino-5-nitroanthraquinone.

Workup

  1. customis kept constant for another 5 1/2 hours
  2. waitThe product is left
  3. temperatureto cool without outside help
  4. filtrationthe product filtered off with suction
  5. washAfter washing
  6. customdrying there

Sources & evidence

ORD record
ord-bc8c11b00f7d408d95b768ba1bd99755
Source dataset
uspto-grants-1978_02
Patent number
US04076736

Linked notes

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