Hydrogen Peroxide → Quinacridone

HRID 1976279Notes

Reaction equation

HRID 1976279 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>C1C2C(=O)C3C(=CC=CC=3)C(=O)C=2C=CC=1.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

7

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 887MethanolHCID 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 6780AnthraquinoneCatalystHCID 962WaterSolvent

Conditions

Temperature
52.5 °C

Procedure

A one liter flask equipped with a thermometer, stirrer and condenser was charged with 40 grams 6,13dihydroquinacridone, 180 ml methanol, 42.5 grams 50% aqueous sodium hydroxide and 14.6 grams of an aqueous presscake containing 1.6 grams naphthalin-1-sulfonic acid methyl quinacridone pigment additive prepared according to Example 2 of Copending U.S. Provisional Patent Application entitled “PIGMENT PARTICLE GROWTH AND/OR CRYSTAL PHASE DIRECTORS”. The mixture was stirred under a slow flow of nitrogen at 50 to 55° C. for one hour. 0.5 grams anthraquinone mono sulfonic acid sodium salt, as catalyst, were added and the reaction mixture was heated to reflux. 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 15 minutes addition time, 1.2 grams phthalimidomethyl dihydroquinacridone obtained according to Example 2 were added into the reaction mixture followed by another addition of 0.8 grams phthalimidomethyl dihydroquinacridone after 45 minutes while continuously adding the hydrogen peroxide by 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 to reflux
  4. additionaddition time, 1.2 grams phthalimidomethyl
  5. customdihydroquinacridone obtained
  6. additionwere added into the reaction mixture
  7. additionfollowed by another addition of 0.8 grams phthalimidomethyl dihydroquinacridone after 45 minutes
  8. temperatureby maintaining
  9. temperaturereflux
  10. stirringThe resulting violet suspension was further stirred for 10 minutes
  11. temperatureat reflux
  12. filtrationfiltered
  13. washThe presscake was washed with hot water
  14. customdried

Sources & evidence

ORD record
ord-519afeb5c1074abab0fadff1397f525f
Source dataset
uspto-grants-2001_05
Patent number
US06225472B1

Reaction notes

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