Hydrogen Peroxide → Quinacridone

HRID 1385801Notes

Reaction equation

HRID 1385801 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 98.4%

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 50 grams 6,13-dihydroquinacridone, 310 ml methanol and 66 grams 50% aqueous sodium hydroxide and 3.8 grams 50% aqueous benzyl tributyl ammonium chloride solution and stirred for 5 minutes at 35-40° C. 0.9 grams anthraquinone sulfonic acid methyl quinacridone pigment additive prepared according to Example 4 was added followed by the addition of 0.5 grams anthraquinone mono sulfonic acid sodium salt as catalyst. The mixture was stirred under a slow flow of nitrogen and heated to reflux. 91.4 grams of an aqueous 17% hydrogen peroxide solution were added into the reaction mixture with a peristaltic pump at a pumping rate of 0.3 minute. The resulting red 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 48.9 grams red quinacridone.

Workup

  1. customA one liter flask equipped with a thermometer, stirrer and condenser
  2. additionwas added
  3. stirringThe mixture was stirred under a slow flow of nitrogen
  4. temperatureheated to reflux
  5. stirringThe resulting red suspension was further stirred for 10 minutes
  6. temperatureat reflux
  7. filtrationfiltered
  8. washThe presscake was washed with hot water
  9. customthen dried

Sources & evidence

ORD record
ord-b6678f5d4cc047ba870c32ea01bb38e3
Source dataset
uspto-grants-2001_07
Patent number
US06264733B1

Reaction notes

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