Methanol → Quinacridone

HRID 861195Notes

Reaction equation

HRID 861195 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 86.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

To 300 g of polyphosphoric acid (117% phosphoric acid) heated at 90° C. was added 0.68 g of N-[3-(N,N-dimethylaminopropyl)] copper phthalocyanine sulfonamide followed by 68.2 g of 2,5-dianilinoterephthalic acid. The mixture was heated at 120°-125° C. for two hours. After the melt was cooled to 90°-95° C., the acid strength was adjusted to 112% by the dropwise addition of phosphoric acid. The resultant melt was stirred for 15 minutes and then slowly poured into 453 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 (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, 7.5 g of 50% sodium hydroxide was added and the resultant slurry was heated at 88° 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 dissolved in alkaline water 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. The solid component was collected by filtration and washed with water. The wet cake was dried in an oven at 60° C. to give approximately 53.0 g of quinacridone as a violet pigment. The quinacridone thus obtained was blended with 5.3 g of phthalimidomethylquinacridone (prepared according to U.S. Pat. No. 3,275,637) to give a violet pigment.

Workup

  1. temperatureThe mixture was heated at 120°-125° C. for two hours
  2. temperatureAfter the melt was cooled to 90°-95° C.
  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, 7.5 g of 50% sodium hydroxide was added
  11. temperaturethe resultant slurry was heated at 88° C. for one hour
  12. temperatureThe slurry was cooled
  13. filtrationfiltered
  14. washwashed with water until alkali free,
  15. dissolutionAfter adjustment of the pH to 9.0-9.5, 3.2 g of a cycloaliphatic carboxylic acid dissolved in alkaline water
  16. additionwas added
  17. temperatureThe resultant slurry was heated at about 140°-145° C. for two hours in a closed system
  18. temperaturecooled
  19. stirringstirred
  20. filtrationThe solid component was collected by filtration
  21. washwashed with water
  22. customThe wet cake was dried in an oven at 60° C.

Sources & evidence

ORD record
ord-acd9e552722b4028b992ed8a409a1e52
Source dataset
uspto-grants-1998_02
Patent number
US05713999

Reaction notes

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