Hydrogen Peroxide → Quinacridone

HRID 983656Notes

Reaction equation

HRID 983656 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+].C1C(S(O)(=O)=O)=CC2C(C3C=C(S(O)(=O)=O)C=CC=3C(=O)C=2C=1)=O.OO>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

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 665332,7-Anthracenedisulfonic acid, 9,10-dihydro-9,10-dioxo-HCID 79973Quino(2,3-b)acridine-7,14-dione, 5,6,12,13-tetrahydro-

Product 1

HCID 13976Quinacridone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
23.5 °C

Procedure

A one-liter flask equipped with a thermometer, stirrer and condenser is charged with 50 g 6,13-dihydroquinacridone, 180 ml methanol, 1 g polyvinyl pyrrolidone powder (Luviskol® K-30/BASF) are stirred at 20 to 27° C. for 10 minutes. 73 g 50% aqueous sodium hydroxide are added. The mixture is stirred under a slow flow of nitrogen at 50-53° C. for 50 minutes then heated to reflux. 1.2 g 2,7-anthraquinone disulfonic acid is added as catalyst. 76 g of an aqueous 18.9% hydrogen peroxide solution is added into the reaction mixture with a peristaltic pump at a pumping rate of 0.4 ml/minute. The resulting pigment suspension is further stirred for 10 minutes at reflux then diluted with 100 ml cold water and filtered. The presscake is washed with hot water then dried, yielding a bronze colored large particle size beta quinacridone.

Workup

  1. customA one-liter flask equipped with a thermometer, stirrer and condenser
  2. stirringThe mixture is stirred under a slow flow of nitrogen at 50-53° C. for 50 minutes
  3. temperaturethen heated to reflux
  4. stirringThe resulting pigment suspension is further stirred for 10 minutes
  5. temperatureat reflux
  6. filtrationfiltered
  7. washThe presscake is washed with hot water
  8. customthen dried

Sources & evidence

ORD record
ord-903ace8a0d934ab6beb25a8b31185d7a
Source dataset
uspto-grants-2005_03
Patent number
US06864371B2

Reaction notes

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