Hydrogen Peroxide → Quinacridone

HRID 430817Notes

Reaction equation

HRID 430817 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.CO.[OH-].[Na+].OO>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.C1C2C(=O)C3C(=CC=CC=3)C(=O)C=2C=CC=1.O>[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 887MethanolHCID 14798Sodium HydroxideHCID 79973Quino(2,3-b)acridine-7,14-dione, 5,6,12,13-tetrahydro-

Product 1

HCID 13976QuinacridoneYield 97.9%

Reagents, catalysts & solvents 3

HCID 6780AnthraquinoneCatalystHCID 159952Benzyltributylammonium chlorideCatalystHCID 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, 250 ml methanol, 52.8 grams 50% aqueous sodium hydroxide and 3.0 grams 50% aqueous benzyl tributyl ammonium chloride. The mixture was stirred under a slow flow of nitrogen at 30 to 45° C. for five minutes, heated to 50 to 55° C. and stirred at 50 to 55° C. for one hour. 0.8 grams of the pigment additive toluene sulfonic acid methyl quinacridone in accordance with the teachings in pending application Ser. No. 60/118,405, was added, followed by the addition of 0.5 grams anthraquinone mono sulfonic acid sodium salt as catalyst, and the reaction mixture was heated to reflux. 73 grams of an aqueous 17% hydrogen peroxide solution were added into the reaction mixture with a peristaltic pump at a setting of 0.3 ml/minute 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. temperatureheated to 50 to 55° C.
  3. stirringstirred at 50 to 55° C. for one hour
  4. addition60/118,405, was added
  5. temperaturethe reaction mixture was heated to reflux
  6. temperaturemaintaining
  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-be2009a296524f769bb775ee1ea084ee
Source dataset
uspto-grants-2001_11
Patent number
US06323342B1

Reaction notes

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