Hydrogen Peroxide → Quinacridone

HRID 1385799Notes

Reaction equation

HRID 1385799 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+].[Na].OO>C1C2C(=O)C3C(=CC=CC=3)C(=O)C=2C=CC=1.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

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 79973Quino(2,3-b)acridine-7,14-dione, 5,6,12,13-tetrahydro-2×HCID 5360545Sodium

Product 1

HCID 13976QuinacridoneYield 97.9%

Reagents, catalysts & solvents 3

HCID 6780AnthraquinoneCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
37.5 °C

Procedure

A one liter flask equipped with a thermometer, stirrer and condenser was charged with 40 grams 6,13-dihydroquinacridone, 180 ml methanol and 40.9 grams 50% aqueous sodium hydroxide. The mixture was stirred under a slow flow of nitrogen at 30-45° C. for five minutes. 2.4 grams of the pigment additive prepared according to Example 4, followed by 0.5 grams anthraquinone mono sulfonic acid sodium salt as catalyst, were added and the reaction mixture was heated to reflux for one hour generating the sodium salt of 6,13-dihydroquinacridone. 73.5 grams of an aqueous 16.9% hydrogen peroxide solution were added into the reaction mixture with a peristaltic pump at a rate of 0.3 ml/minute while maintaining reflux under a slow nitrogen flow. The resulting reddish suspension was further stirred for 10 minutes at reflux then diluted with 100 ml cold water and filtered. The presscake was washed with hot water then dried, yielding 38.9 grams red quinacridone.

Workup

  1. customA one liter flask equipped with a thermometer, stirrer and condenser
  2. custom2.4 grams of the pigment additive prepared
  3. additionwere added
  4. temperaturethe reaction mixture was heated
  5. temperatureto reflux for one hour
  6. temperaturewhile maintaining
  7. temperaturereflux under a slow nitrogen flow
  8. stirringThe resulting reddish suspension was further stirred for 10 minutes
  9. temperatureat reflux
  10. filtrationfiltered
  11. washThe presscake was washed with hot water
  12. customthen dried

Sources & evidence

ORD record
ord-c7e5aef1a5d84fb59957983bff6ad755
Source dataset
uspto-grants-2001_07
Patent number
US06264733B1

Reaction notes

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