HCID 11221833, compound → Quinacridone

Temperature

85 °C

To 320 g of polyphosphoric acid (116.5% phosphoric acid) was sequentially added 6.8 g of 2,5-bis[4-(3-methoxypropylsulfamoyl)anilino]-1,4-cyclohexadiene-1,4-dicarboxylic acid, dimethyl ester and 64 g of 2,5-dianilino-3,6-dihydroterephthalic acid over a period of 45 minutes, the temperature being maintained below 110° C. The reaction mixture was stirred at 100° to 110° C. for one hour and then allowed to cool to 85° C., after which the phosphoric acid concentration was reduced to 85% by the slow addition of chilled water. The mixture was stirred at 85° to 90° C. for 30 minutes, then slowly poured into 1200 ml of ice/water and stirred at less than 30° C. for an additional hour. The solid component was collected by filtration and washed with water. The resultant wet presscake was reslurried in 181.3 g of methanol and 73.9 g of water and stirred until uniform. After 37.3 g of 50% aqueous sodium hydroxide was added, the slurry was stirred at less than 35° C. for one hour. The slurry was then heated to 60° C., diluted with 12.6 g of water, and heated at reflux for 30 minutes. After the slurry was allowed to cool to 60° C., 37.3 g of 92% sodium 3-nitrobenzenesulfonate and 31.6 g of water were added sequentially. After ten minutes, the slurry was heated at 88° C. for 15 hours. Upon being cooled to room temperature, the solid component was isolated by filtration and washed with water. The wet presscake cake was reslurried in 357.1 g of methanol and 357.1 g of water (which includes the amount of water in the presscake). When the slurry became uniform, 95.2 g of 50% aqueous sodium hydroxide and an additional 60.0 g of 92% sodium 3-nitrobenzenesulfonate were added. The resultant slurry was heated in a sealed system at 115° to 120° C. for six hours. Upon being cooled to room temperature, the solid component was isolated by filtration and washed with water. The wet presscake cake was dried to give 41.0 g of gamma quinacridone.

1. customof 45 minutes
2. temperaturethe temperature being maintained below 110° C
3. concentrationafter which the phosphoric acid concentration
4. additionwas reduced to 85% by the slow addition of chilled water
5. stirringThe mixture was stirred at 85° to 90° C. for 30 minutes
6. additionslowly poured into 1200 ml of ice/water
7. stirringstirred at less than 30° C. for an additional hour
8. filtrationThe solid component was collected by filtration
9. washwashed with water
10. stirring73.9 g of water and stirred until uniform
11. additionAfter 37.3 g of 50% aqueous sodium hydroxide was added
12. stirringthe slurry was stirred at less than 35° C. for one hour
13. temperatureThe slurry was then heated to 60° C.
14. additiondiluted with 12.6 g of water
15. temperatureheated
16. temperatureat reflux for 30 minutes
17. temperatureto cool to 60° C.
18. addition37.3 g of 92% sodium 3-nitrobenzenesulfonate and 31.6 g of water were added sequentially
19. waitAfter ten minutes
20. temperaturethe slurry was heated at 88° C. for 15 hours
21. temperatureUpon being cooled to room temperature
22. customthe solid component was isolated by filtration
23. washwashed with water
24. addition95.2 g of 50% aqueous sodium hydroxide and an additional 60.0 g of 92% sodium 3-nitrobenzenesulfonate were added
25. temperatureThe resultant slurry was heated in a sealed system at 115° to 120° C. for six hours
26. temperatureUpon being cooled to room temperature
27. customthe solid component was isolated by filtration
28. washwashed with water
29. customThe wet presscake cake was dried

ORD record

ord-dde51a7195c742138024b5fdc5c397fc

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05755873