Methanol → Quinacridone

HRID 861196

反応式

HRID 861196 の反応式
[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]

参加物

6

反応物 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]-

生成物 1

HCID 13976Quinacridone収率 434%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
113 °C

実験手順

To 270 g of polyphosphoric acid (117% phosphoric acid) heated at 85° C. was added 2.5 g of N-[3-(N,N-dimethylaminopropyl)] copper phthalocyanine sulfonamide 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 of methanol. The slurry was heated at reflux for two hours, diluted with water and stirred at 60° C. for 30 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 resultant presscake was reslurried in water (320 g total water), the pH was adjusted to 8.5 with dilute aqueous sodium hydroxide, and 320 g of methanol was added. The resultant slurry was then heated at 120° C. for six hours in a closed system. 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 was stirred for one hour, and the pH was 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 dried in an oven at 60° C. to give approximately 48 g of quinacridone as a deep violet pigment.

後処理

  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 30 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 then heated at 120° C. for six hours in a closed system
  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 was stirred for one hour
  14. filtrationThe solid component was collected by filtration
  15. washwashed with water
  16. customThe wet cake can be dried
  17. customHere, the wet cake was dried in an oven at 60° C.

出典と根拠

ORDレコード
ord-b6b4bd5e5dc0430887fad2d080818f11
出典データセット
uspto-grants-1998_02
特許番号
US05713999

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