Hydrogen Peroxide → Quinacridone

HRID 1070356Notes

Reaction equation

HRID 1070356 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.C1C=C2C(C3C(NC2=CC=1)=CC1C(C2C(NC=1C=3)=CC=CC=2)=O)=O.C=O.C1(S(O)(=O)=O)C2C(=CC=CC=2)C=CC=1.[OH-].[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 Peroxide2×HCID 14798Sodium HydroxideHCID 79973Quino(2,3-b)acridine-7,14-dione, 5,6,12,13-tetrahydro-HCID 131724965HCID 131724965, compound

Product 1

HCID 13976Quinacridone

Reagents, catalysts & solvents 3

HCID 6780AnthraquinoneCatalystHCID 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, 200 ml methanol, 1 g polyvinylpyrrolidone powder (Luviskol® K-30, BASF) and 7 g of the aqueous presscake of the nanosize quinacridone/naphthalene sulfonic acid formaldehyde polymer mixture according to Example 1 are stirred at 20-27° C. for 10 minutes. 50 g 50% aqueous sodium hydroxide are added. The mixture is stirred under a slow flow of nitrogen at 50-53° C. for one hour. 0.8 g anthraquinone mono sulfonic acid sodium salt as catalyst is added and the reaction mixture is heated to reflux for 10 minutes. 76 g of an aqueous 18.9% by weight hydrogen peroxide solution are added into the reaction mixture with a peristaltic pump at a pumping rate of 0.4 ml/minute, whereby after 25 minutes addition time 1.6 g phthalimidomethyl-quinacridone are introduced into the reaction mixture followed by continuing the hydrogen peroxide addition while maintaining reflux and a slow nitrogen flow. The resulting violet 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 violet 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 one hour
  3. temperaturethe reaction mixture is heated
  4. temperatureto reflux for 10 minutes
  5. additionare introduced into the reaction mixture
  6. temperaturewhile maintaining
  7. temperaturereflux
  8. stirringThe resulting violet suspension is further stirred for 10 minutes
  9. temperatureat reflux
  10. filtrationfiltered
  11. washThe presscake is washed with hot water
  12. customthen dried

Sources & evidence

ORD record
ord-a250d0997c924a3f9d1e40cc1631d062
Source dataset
uspto-grants-2005_06
Patent number
US06902613B2

Reaction notes

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