Hydrogen Peroxide → Quinacridone

HRID 1070361Notes

Reaction equation

HRID 1070361 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 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 and 5 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. 0.9 g anthraquinone-2,7-disulfonic acid disodium salt as catalyst is added and the reaction mixture is heated to reflux for 5 minutes. 77 g of an aqueous 19.1% 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 15 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 red 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 red quinacridone. The X-ray shows the diffraction pattern of a gamma quinacridone. The pigment shows outstanding pigment properties and can be applied for the red coloration of paints, inks and plastics.

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 5 minutes
  5. additionare introduced into the reaction mixture
  6. temperaturewhile maintaining
  7. temperaturereflux
  8. stirringThe resulting red 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-968a251e43134cb8938938c515776c4b
Source dataset
uspto-grants-2005_06
Patent number
US06902613B2

Reaction notes

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