Hydrogen Peroxide → Quinacridone

HRID 1385800Notes

Reaction equation

HRID 1385800 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+].[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-2×HCID 5360545Sodium

Product 1

HCID 13976QuinacridoneYield 97.9%

Reagents, catalysts & solvents 3

HCID 6780AnthraquinoneCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
52.5 °C

Procedure

A one liter flask equipped with a thermometer, stirrer and condenser was charged with 40 grams 6,13-dihydroquinacridone, 180 ml methanol and 42 grams 50% aqueous sodium hydroxide and 14.6 grams of the aqueous presscake of the naphthalin-1-sulfonic acid methyl quinacridone pigment additive prepared according to Example 2. The mixture was stirred under a slow flow of nitrogen at 50-55° C. for one hour. 0.5 gram anthraquinone mono sulfonic acid sodium salt as catalyst were added and the reaction mixture was heated to reflux for one hour generating the sodium salt of 6,13-dihydro-quinacridone. 67 grams of an aqueous 19.3% hydrogen peroxide solution were added into the reaction mixture with a peristaltic pump at a pumping rate of 0.3 ml/minute, whereby after ½ hour addition time 1.2 grams phthalimidomethyl-quinacridone were introduced into the reaction mixture followed by continuing the hydrogen peroxide addition while maintaining reflux and a slow nitrogen flow. The resulting violet suspension was further stirred for 10 minutes at reflux then diluted with 100 ml cold water and filtered. The presscake was washed with hot water then dried, yielding 38.9 grams violet quinacridone.

Workup

  1. customA one liter flask equipped with a thermometer, stirrer and condenser
  2. customprepared
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux for one hour
  5. additionwere introduced into the reaction mixture
  6. temperaturewhile maintaining
  7. temperaturereflux
  8. stirringThe resulting violet suspension was further stirred for 10 minutes
  9. temperatureat reflux
  10. filtrationfiltered
  11. washThe presscake was washed with hot water
  12. customthen dried

Sources & evidence

ORD record
ord-5a405509635f418dbf866d984cb24c04
Source dataset
uspto-grants-2001_07
Patent number
US06264733B1

Reaction notes

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