Hydrogen Peroxide → Quinacridone

HRID 1070357Notes

Reaction equation

HRID 1070357 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>[Na+].[Na+].C1C2C(=O)C3C(=CC=C(S([O-])(=O)=O)C=3)C(=O)C=2C=CC=1S([O-])(=O)=O.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 70069Disodium anthraquinone-2,7-disulfonateCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

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. 73 g 50% aqueous sodium hydroxide are added. The mixture is stirred under a slow flow of nitrogen at 50-53° C. for 30 minutes. 4.6 g of a 37% aqueous solution of anthraquinone-2,7-disulfonic acid disodium salt as catalyst is added followed by 10 ml water and the reaction mixture is heated to reflux for 40 minutes. 79 g of an aqueous 18.2% 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 20 minutes addition time 2.3 g phthalimido methyl-quinacridone and after another 70 minutes 0.3 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 30 minutes
  3. temperaturethe reaction mixture is heated
  4. temperatureto reflux for 40 minutes
  5. temperaturewhile maintaining
  6. temperaturereflux
  7. stirringThe resulting violet suspension is further stirred for 10 minutes
  8. temperatureat reflux
  9. filtrationfiltered
  10. washThe presscake is washed with hot water
  11. customthen dried

Sources & evidence

ORD record
ord-bc65e8bf48ee45ca961259aa5b73646a
Source dataset
uspto-grants-2005_06
Patent number
US06902613B2

Reaction notes

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