Hydrogen Peroxide → Quinacridone

HRID 2288552

Reaction equation

HRID 2288552 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+].OO>[Na+].C1C2C(=O)C3C(=CC=CC=3)C(=O)C=2C=CC=1S([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

6

Reactant 3

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

Product 1

HCID 13976QuinacridoneYield 97.9%

Reagents, catalysts & solvents 2

HCID 23661981Sodium 2-anthraquinonesulfonateCatalystHCID 887MethanolSolvent

Conditions

Temperature
52.5 °C

Procedure

A one liter flask equipped with a thermometer, stirrer and condenser is charged with 40 grams 6,13-dihydroquinacridone, 0.3 grams pyrazolylmethylquinacridone, 250 ml methanol and 52.8 grams 50% aqueous sodium hydroxide. The mixture is stirred under a slow flow of nitrogen at 50-55° C. for one hour, generating 6,13-dihydroquinacridone disodium salt. 0.6 grams anthraquinone-2-sulfonic acid sodium salt are added and the mixture is heated to reflux temperature. 73.5 grams of an aqueous 16.9% hydrogen peroxide solution are added into the reaction mixture with a peristaltic pump at a rate of 0.4 ml/minute maintaining reflux under a slow nitrogen flow over 2 hours and 35 minutes. The resulting pigment suspension is further stirred for 1 hour at reflux; then filtered. The presscake is washed with hot water and then dried, yielding 38.9 grams beta quinacridone pigment. This product shows similar good pigment properties and similar color characteristics to the beta quinacridone obtained following the procedure of Example 1.

Workup

  1. customA one liter flask equipped with a thermometer, stirrer and condenser
  2. temperaturethe mixture is heated
  3. temperatureto reflux temperature
  4. temperaturemaintaining
  5. temperaturereflux under a slow nitrogen flow over 2 hours
  6. custom35 minutes
  7. stirringThe resulting pigment suspension is further stirred for 1 hour
  8. temperatureat reflux
  9. filtrationthen filtered
  10. washThe presscake is washed with hot water
  11. customdried

Sources & evidence

ORD record
ord-8f2cbffacdc6410f8889880010fdde25
Source dataset
uspto-grants-2000_07
Patent number
US06090196

Linked notes

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