Hydrogen Peroxide → Quinacridone

HRID 1373376Notes

Reaction equation

HRID 1373376 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>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

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 14798Sodium HydroxideHCID 79973Quino(2,3-b)acridine-7,14-dione, 5,6,12,13-tetrahydro-

Product 1

HCID 13976Quinacridone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A one-liter flask equipped with a thermometer, stirrer and condenser is charged with 50 g 6,13-dihydroquinacridone, 250 ml methanol, 36 ml water, 0.6 g phthalimidomethyl quinacridone as crystal phase director and particle size reducing agent and 75 g 50% aqueous sodium hydroxide. The mixture is stirred under a slow flow of nitrogen at reflux temperature for one hour generating the corresponding 6,13-dihydroquinacridone-di-sodium salt. 1.2 g 2,7-anthraquinone-disulfonic acid sodium salt is added and the resulting mixture is further stirred at reflux for 10 minutes. Subsequently, 91.4 g of an aqueous 17% hydrogen peroxide solution are added at a rate of 0.3 ml/minute maintaining reflux temperature under a slow nitrogen flow. The resulting bright red suspension is diluted with 100 ml cold water, stirred for 5 minutes and then filtered at 50–60° C. The presscake is washed with hot water then dried yielding a high chroma red gamma quinacridone pigment, which shows less than 100 ppm catalyst residues when analyzed by HPLC.

Workup

  1. customA one-liter flask equipped with a thermometer, stirrer and condenser
  2. temperatureat reflux temperature for one hour
  3. stirringthe resulting mixture is further stirred
  4. temperatureat reflux for 10 minutes
  5. temperaturemaintaining
  6. temperaturereflux temperature under a slow nitrogen flow
  7. stirringstirred for 5 minutes
  8. filtrationfiltered at 50–60° C
  9. washThe presscake is washed with hot water
  10. customthen dried

Sources & evidence

ORD record
ord-a36df582c4484bdba2407351a20ab8d1
Source dataset
uspto-grants-2007_01
Patent number
US07161007B2

Reaction notes

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