Hydrogen Peroxide → 1-Aminoanthraquinone

HRID 435755Notes

Reaction equation

HRID 435755 reaction equation
[NH2:1][C:2]1[C:15]2[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:16])[C:6]=2[CH:5]=[CH:4][CH:3]=1.OO.C(C(C)=[O:22])C>O>[NH2:1][C:2]1[C:15]2[C:14](=[O:22])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:16])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 6569Methyl Ethyl KetoneHCID 10954793HCID 10954793, compound

Product 1

HCID 67101-Aminoanthraquinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

The moist paste of 4-aminoanthrone is introduced into 300 ml of water and warmed to 60° C under nitrogen. The pH is checked every 1/4 of an hour and should lie in the range between 7.5 and 8.5. 75 ml of potassium waterglass (d = 1.25) are then added, whereupon a pH of 11 results. 375 ml of H2O2 solution are then added dropwise in the course of 2.5 hours, the solution being prepared by diluting 200 ml of 35% strength hydrogen peroxide (d = 1.135) to 1.0 liter. The mixture is warmed to 70° C and kept at this temperature for one hour. 500 ml of the azeotrope of methyl ethyl ketone (88%) and water (12%) which boils at 73.4° C, are then added and the mixture is heated to the boil for 10 hours (temperature 74° C). It is then cooled to 20° C, stirred for 1 hour at room temperature and then filtered. The residue is covered twice with 150 ml of water at a time, to remove the adhering methyl ethyl ketone. The azeotrope (boiling point 73° C) is recovered almost quantitatively from the combined filtrates by distillation. 4 g of a solid substance which contains about 50% of 1-aminoanthraquinone are isolated from the distillation residue. To remove adhering silica the moist paste of the 1-aminoanthraquinone, in 500 ml of water and 60 ml of concentrated sodium hydroxide solution (d = 1.48) must be subjected to incipient distillation for ~15 minutes. To avoid objectionable foaming during this operation, 5 drops of anti-foam agent are added. The product is filtered off hot, and the adhering sodium hydroxide solution is eluted with a little hot water. The paste weighs 140 g. It is dried at 70° C. 91 g are obtained.

Workup

  1. customevery 1/4 of an hour
  2. customresults
  3. customthe solution being prepared
  4. temperatureThe mixture is warmed to 70° C
  5. temperaturethe mixture is heated to the boil for 10 hours (temperature 74° C)
  6. temperatureIt is then cooled to 20° C
  7. filtrationfiltered
  8. customto remove the adhering methyl ethyl ketone
  9. distillationThe azeotrope (boiling point 73° C) is recovered almost quantitatively from the combined filtrates by distillation
  10. customare isolated from the distillation residue
  11. customTo remove
  12. distillationin 500 ml of water and 60 ml of concentrated sodium hydroxide solution (d = 1.48) must be subjected to incipient distillation for ~15 minutes
  13. additionare added
  14. filtrationThe product is filtered off hot
  15. washthe adhering sodium hydroxide solution is eluted with a little hot water
  16. customIt is dried at 70° C
  17. custom91 g are obtained

Sources & evidence

ORD record
ord-ed2902e186c442bfa4a812e5b08c40d1
Source dataset
uspto-grants-1977_02
Patent number
US04006170

Reaction notes

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