Hydrogen Peroxide → Quinacridone

HRID 357502

Reaction equation

HRID 357502 reaction equation
[CH2:1]1[C:6]2[NH:7][C:8]3[C:13]([C:14](=[O:15])[C:5]=2[CH2:4][C:3]2[NH:16][C:17]4[C:22]([C:23](=[O:24])[C:2]1=2)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:12][CH:11]=[CH:10][CH:9]=3.[OH-].[Na+].OO>[Na+].C1C2C(=O)C3C(=CC=CC=3)C(=O)C=2C=CC=1S([O-])(=O)=O.CO>[CH:20]1[CH:21]=[C:22]2[C:23]([C:2]3[C:3]([NH:16][C:17]2=[CH:18][CH:19]=1)=[CH:4][C:5]1[C:14]([C:13]2[C:8]([NH:7][C:6]=1[CH:1]=3)=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:15])=[O:24]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 79973Quino(2,3-b)acridine-7,14-dione, 5,6,12,13-tetrahydro-

Product 1

HCID 13976QuinacridoneYield 97.9%

Reagents, catalysts & solvents 2

HCID 23661981Sodium 2-anthraquinonesulfonateCatalystHCID 887MethanolSolvent

Procedure

A one liter flask equipped with a thermometer, stirrer and condenser is charged with 40 grams 6,13-dihydroquinacridone, 250 ml methanol and 52.8 grams 50% aqueous sodium hydroxide. The mixture is stirred under a slow flow of nitrogen at 50°-55° C. for one hour generating 6,13-dihydroquinacridone di-sodium salt. 0.8 grams anthraquinone-2-sulfonic acid sodium salt are added and the mixture is heated to reflux temperature. 73.5 grams of an aqueous 16.9% hydrogen peroxide solution are added into the reaction mixture with a peristaltic pump at a rate of 0.4 ml/minute maintaining reflux under a slow nitrogen flow over 2 hours and 35 minutes. The resulting reddish suspension is further stirred for 4 hours at reflux then filtered. The presscake is washed with methanol followed by hot water then dried, yielding 38.9 grams red quinacridone.

Workup

  1. customA one liter flask equipped with a thermometer, stirrer and condenser
  2. temperaturethe mixture is heated
  3. temperatureto reflux temperature
  4. temperaturemaintaining
  5. temperaturereflux under a slow nitrogen flow over 2 hours
  6. custom35 minutes
  7. stirringThe resulting reddish suspension is further stirred for 4 hours
  8. temperatureat reflux
  9. filtrationthen filtered
  10. washThe presscake is washed with methanol
  11. customthen dried

Sources & evidence

ORD record
ord-cc32c46c851540efb6524fb1e7478e43
Source dataset
uspto-grants-1998_11
Patent number
US05840901

Linked notes

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