Hydrogen Peroxide → Quinacridone

HRID 1976278Notes

Reaction equation

HRID 1976278 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 6,13dihydroquinacridone, 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. 0.6 grams of pigment additive melamine methyl dihydroquinacridone prepared according to Example 4 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. additionwas 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-fa5711984c8a45568a498541761cb270
Source dataset
uspto-grants-2001_05
Patent number
US06225472B1

Reaction notes

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