Methanol → Quinacridone

HRID 861191Notes

Reaction equation

HRID 861191 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>[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

5

Reactant 3

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

Product 1

HCID 13976QuinacridoneYield 81.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To 250 g of polyphosphoric acid (117% phosphoric acid) heated to 80°-85° C. was added 1.6 g N-[3-(N,N-dimethylaminopropyl)] copper phthalocyanine sulfonamide. The mixture was stirred for about ten minutes, after which was added 83.3 g of 2,5-dianilinoterephthalic acid at 85°-120° C. The reaction mixture was then heated at 120°-125° C. for three hours. After the melt was cooled to 95° C., the acid strength was adjusted to 112% by the dropwise addition of phosphoric acid. The resultant melt was stirred for 30 minutes and then slowly poured into 400 g of methanol at 24° C. During the drown, the temperature was allowed to increase to 55° C., with the temperature being controlled by external cooling and adjustment of melt addition rate. The slurry was heated at reflux 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, 7.5 g of 50% sodium hydroxide was added and the resultant slurry was heated at 90° C. for one hour. The slurry was cooled, filtered, and washed with water until alkali free, then reslurried in water. After adjustment of the pH to 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 two hours in a closed system, cooled, acidified with phosphoric acid, and stirred at 70° C. for one hour. 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 61 g of quinacridone as a violet pigment.

Workup

  1. temperatureThe reaction mixture was then heated at 120°-125° C. for three hours
  2. stirringThe resultant melt was stirred for 30 minutes
  3. temperatureto increase to 55° C., with the temperature
  4. temperatureby external cooling
  5. additionadjustment of melt addition rate
  6. temperatureThe slurry was heated
  7. temperatureat reflux for one hour
  8. stirringstirred at 60° C. for 30 minutes
  9. filtrationThe solid component was collected by filtration
  10. washwashed with water until acid free
  11. additionAfter adjustment of the pH to greater than 7, 7.5 g of 50% sodium hydroxide was added
  12. temperaturethe resultant slurry was heated at 90° C. for one hour
  13. temperatureThe slurry was cooled
  14. filtrationfiltered
  15. washwashed with water until alkali free,
  16. additionAfter adjustment of the pH to 9.0-9.5, 3.2 g of a cycloaliphatic carboxylic acid was added
  17. temperatureThe resultant slurry was heated at about 140°-145° C. for two hours in a closed system
  18. temperaturecooled
  19. stirringstirred at 70° C. for one hour
  20. filtrationThe solid component was collected by filtration
  21. washwashed with water
  22. customThe wet cake can be dried
  23. customHere, the wet cake was dried in an oven at 60° C.

Sources & evidence

ORD record
ord-19ba0e12c263401ea46d22356b28ddf3
Source dataset
uspto-grants-1998_02
Patent number
US05713999

Reaction notes

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