Methanol → Quinacridone

HRID 861203Notes

Reaction equation

HRID 861203 reaction equation
[NH:1]([C:8]1[CH:16]=[C:15]([C:17](O)=[O:18])[C:14]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:13][C:9]=1[C:10](O)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(=O)(O)(O)O.CO>O.CCN1C2C(=CC3N=C4C(=C(Cl)C5C(=C4Cl)OC4C=C6N(CC)C7C(=CC=CC=7)C6=CC=4N=5)OC=3C=2)C2C1=CC=CC=2>[CH:24]1[CH:25]=[C:26]2[C:17]([C:15]3[C:14]([NH:20][C:21]2=[CH:22][CH:23]=1)=[CH:13][C:9]1[C:10]([C:7]2[C:2]([NH:1][C:8]=1[CH:16]=3)=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:11])=[O:18]

Participants

6

Reactant 3

HCID 887MethanolHCID 1004Phosphoric AcidHCID 823512,5-Dianilinoterephthalic acid

Product 1

HCID 13976QuinacridoneYield 92.9%

Reagents, catalysts & solvents 2

HCID 61387Carbazole VioletCatalystHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To 240 g of polyphosphoric acid (116% phosphoric acid) heated at 85° C. was added 0.15 g of Carbazole Violet followed by 60 g of 2,5-dianilinoterephthalic acid. The mixture was heated at 120°-125° C. for two hours. After the melt was cooled to 95° C., the acid strength was adjusted to 110% by the dropwise addition of phosphoric acid. The resultant melt was stirred for 15 minutes and then slowly poured into 400 g of methanol at 24° C. During the drown, the temperature was allowed to increase to 60° C., with the temperature being controlled by external cooling and adjustment of melt addition rate. The slurry was heated at reflux (68°-72° C.) for one hour, diluted with water, and stirred at 60° C. for 30 minutes. The solid component was collected by filtration and washed with water until acid free. The resultant presscake was reslurried in water. After adjustment of the pH to greater than 7, 5 g of 50% sodium hydroxide was added and the resultant slurry was heated at 90° C. for two hours. The slurry was cooled, filtered, and washed with water until alkali free, then reslurried in water. After adjustment of the pH to greater than 9.0-9.5, 3.2 g of a cycloaliphatic carboxylic acid was added. The resultant slurry was heated at about 140°-145° C. for four hours in a closed system, cooled to less than 45° C., acidified with phosphoric acid, and stirred. The solid component was collected by filtration and washed with water. The wet cake can be dried or used as is for specific applications. Here, the wet cake was dried in an oven at 60° C. to give approximately 50 g of quinacridone as a violet pigment.

Workup

  1. temperatureThe mixture was heated at 120°-125° C. for two hours
  2. temperatureto increase to 60° C., with the temperature
  3. temperatureby external cooling
  4. additionadjustment of melt addition rate
  5. temperatureThe slurry was heated
  6. temperatureat reflux (68°-72° C.) for one hour
  7. stirringstirred at 60° C. for 30 minutes
  8. filtrationThe solid component was collected by filtration
  9. washwashed with water until acid free
  10. additionAfter adjustment of the pH to greater than 7, 5 g of 50% sodium hydroxide was added
  11. temperaturethe resultant slurry was heated at 90° C. for two hours
  12. temperatureThe slurry was cooled
  13. filtrationfiltered
  14. washwashed with water until alkali free,
  15. additionAfter adjustment of the pH to greater than 9.0-9.5, 3.2 g of a cycloaliphatic carboxylic acid was added
  16. temperatureThe resultant slurry was heated at about 140°-145° C. for four hours in a closed system
  17. temperaturecooled to less than 45° C.
  18. stirringstirred
  19. filtrationThe solid component was collected by filtration
  20. washwashed with water
  21. customThe wet cake can be dried
  22. customHere, the wet cake was dried in an oven at 60° C.

Sources & evidence

ORD record
ord-4e0af361063b4fbf9065ad184ac7eae6
Source dataset
uspto-grants-1998_02
Patent number
US05713999

Reaction notes

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