Methanol → Quinacridone

HRID 861197

반응식

HRID 861197 반응식
[CH:1]1[C:6](Cl)=[CH:5][C:4]2[C:8]([C:10]3[C:15]([NH:16][C:3]=2[CH:2]=1)=[CH:14][C:13]1[C:17]([C:19]2[CH:25]=[C:24](Cl)[CH:23]=[CH:22][C:20]=2[NH:21][C:12]=1[CH:11]=3)=[O:18])=[O:9].COC1C=CC(NC2C=C(C(O)=O)C(NC3C=CC(OC)=CC=3)=CC=2C(O)=O)=CC=1.P(=O)(O)(O)O.CO>O>[CH:24]1[CH:25]=[C:19]2[C:17]([C:13]3[C:12]([NH:21][C:20]2=[CH:22][CH:23]=1)=[CH:11][C:10]1[C:8]([C:4]2[C:3]([NH:16][C:15]=1[CH:14]=3)=[CH:2][CH:1]=[CH:6][CH:5]=2)=[O:9])=[O:18]

참가 물질

6

반응물 4

HCID 887MethanolHCID 1004Phosphoric AcidHCID 76530Quino[2,3-b]acridine-7,14-dione, 2,9-dichloro-5,12-dihydro-HCID 30848371,4-Benzenedicarboxylic acid, 2,5-bis[(4-methoxyphenyl)amino]-

생성물 1

HCID 13976Quinacridone수율 434%

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
113 °C

실험 절차

To 270 g of polyphosphoric acid (117% phosphoric acid) heated at 85° C. was added 0.54 g of N-[3-(N,N-dimethylaminopropyl)] copper phthalocyanine followed by 13.5 g of 2,9-dichloroquinacridone. The mixture was stirred at 113° C. for 30 minutes, after which 40.5 g of 2,5-di(4-methoxyanilino)terephthalic acid was added. The resultant mixture was heated at 113° C. for five hours. After the melt was cooled to 95° C., the acid strength was adjusted to 113% by the dropwise addition of phosphoric acid. The mixture was slowly poured into 470 g methanol. The slurry was heated at reflux for two hours, diluted with water, and stirred at 60° C. for thirty minutes. The slurry was further diluted with water, after which the solid component was collected by filtration and washed with water until acid free. The presscake was reslurried in water (320 g total water), the pH adjusted to 8.5 with dilute aqueous sodium hydroxide, and 320 g of methanol was added. The resultant slurry was heated at 120° C. for six hours in a closed system (e.g., a pressure reactor). After the slurry was cooled to 45°-50° C., 4.8 g of wood rosin (as the sodium salt) was added. After the mixture was stirred for 30 minutes, 10.0 g of CaCl2.2H2O (dissolved in water) was added, the slurry stirred for one hour, and the pH acidified (if necessary) with phosphoric acid. 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 oven dried at 60° C. to give approximately 48 g of quinacridone as a deep violet pigment.

후처리

  1. temperatureAfter the melt was cooled to 95° C.
  2. temperatureThe slurry was heated
  3. temperatureat reflux for two hours
  4. stirringstirred at 60° C. for thirty minutes
  5. filtrationafter which the solid component was collected by filtration
  6. washwashed with water until acid free
  7. additionwas added
  8. temperatureThe resultant slurry was heated at 120° C. for six hours in a closed system (e.g., a pressure reactor)
  9. temperatureAfter the slurry was cooled to 45°-50° C.
  10. addition4.8 g of wood rosin (as the sodium salt) was added
  11. stirringAfter the mixture was stirred for 30 minutes
  12. addition10.0 g of CaCl2.2H2O (dissolved in water) was added
  13. stirringthe slurry stirred for one hour
  14. filtrationThe solid component was collected by filtration
  15. washwashed with water
  16. customThe wet cake can be dried
  17. customdried at 60° C.

출처 및 근거

ORD 기록
ord-ce72f452d14e4692b4dedfcc597a461d
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05713999

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