Methanol → 5,12-Dihydro-2,9-dimethylquino(2,3-b)acridine-7,14-dione

HRID 2298709Notes

Reaction equation

HRID 2298709 reaction equation
[CH3:1][C:2]1[CH:28]=[CH:27][C:5]([NH:6][C:7]2[CH:15]=[C:14]([C:16]([OH:18])=O)[C:13]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)=[CH:12][C:8]=2[C:9](O)=[O:10])=[CH:4][CH:3]=1.CO>O>[CH3:1][C:2]1[CH:28]=[CH:27][C:5]2[NH:6][C:7]3[C:8]([C:9](=[O:10])[C:4]=2[CH:3]=1)=[CH:12][C:13]1[NH:19][C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][C:21]=2[C:16](=[O:18])[C:14]=1[CH:15]=3

Participants

4

Reactant 2

HCID 887MethanolHCID 825242,5-Di-p-toluidinoterephthalic acid

Product 1

HCID 704235,12-Dihydro-2,9-dimethylquino(2,3-b)acridine-7,14-dioneYield 93.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
93 °C

Procedure

To 720 g of polyphosphoric acid (112%) heated at 89° C. were added 160 g of 2,5-di(4-methylanilino)terephthalic acid over a period of approximately 40 minutes, the temperature being maintained below 100° C. by adjustment of the addition rate. The reaction mixture was held at 123° C. for two hours, cooled to 93° C., and poured slowly into 1120 g of methanol, the temperature being maintained below reflux using a water bath. The pigment slurry was heated at reflux for one hour, cooled below 65° C., diluted with water, collected by filtration, and washed with water until free of acid. The resultant presscake was reslurried in water. After adjustment of the pH to 7.1, 74.2 g of 50% sodium hydroxide were added and the resultant slurry was heated at 90° C. for one hour. The slurry was cooled to 65° C., filtered, and washed with water until alkaline free, then reslurried in water. After adjustment of the pH to 9, the slurry was heated at 143° C. for two hours and allowed cooled to 45° C. After the slurry was acidified to pH 3.5, an emulsion of 4.7 g of an anionic surfactant, 69.6 g of a petroleum distillate, and 160 g of water was added, and the slurry was stirred for three hours. The resultant slurry 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 135 g of 2,9-dimethylquinacridone as a magenta pigment.

Workup

  1. temperaturethe temperature being maintained below 100° C. by adjustment of the addition rate
  2. temperaturethe temperature being maintained
  3. temperaturebelow reflux
  4. temperatureThe pigment slurry was heated
  5. temperatureat reflux for one hour
  6. temperaturecooled below 65° C.
  7. filtrationcollected by filtration
  8. washwashed with water until free of acid
  9. additionAfter adjustment of the pH to 7.1, 74.2 g of 50% sodium hydroxide were added
  10. temperaturethe resultant slurry was heated at 90° C. for one hour
  11. temperatureThe slurry was cooled to 65° C.
  12. filtrationfiltered
  13. washwashed with water until alkaline free,
  14. temperatureAfter adjustment of the pH to 9, the slurry was heated at 143° C. for two hours
  15. temperatureallowed cooled to 45° C
  16. additionan emulsion of 4.7 g of an anionic surfactant, 69.6 g of a petroleum distillate, and 160 g of water was added
  17. filtrationThe resultant slurry was collected by filtration
  18. washwashed with water
  19. customThe wet cake can be dried
  20. customHere, the wet cake was dried in an oven at 60° C.

Sources & evidence

ORD record
ord-9d75d0f854dc4b899c0b90ada782d652
Source dataset
uspto-grants-2002_12
Patent number
US06494948B2

Reaction notes

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