Phosphoric Acid → Quino[2,3-b]acridine-7,14-dione, 2,9-dichloro-5,12-dihydro-

HRID 2371717Notes

Reaction equation

HRID 2371717 reaction equation
[Cl: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]([Cl:26])=[CH:22][CH:21]=3)=[CH:12][C:8]=2[C:9]([OH:11])=O)=[CH:4][CH:3]=1.OP(O)(O)=O>O>[CH:3]1[C:2]([Cl:1])=[CH:28][C:27]2[C:9]([C:8]3[C:7]([NH:6][C:5]=2[CH:4]=1)=[CH:15][C:14]1[C:16]([C:21]2[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=2[NH:19][C:13]=1[CH:12]=3)=[O:18])=[O:11]

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 1705571,4-Benzenedicarboxylic acid, 2,5-bis[(4-chlorophenyl)amino]-

Product 1

HCID 76530Quino[2,3-b]acridine-7,14-dione, 2,9-dichloro-5,12-dihydro-Yield 97.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

A 2 liter flask equipped with a thermometer, stirrer and condenser is charged with 200 g polyphosphoric acid which is heated to 70° C. Thereafter, 40 g of 2,5-di-(p-chloranilino)terephthalic acid is added, the mixture is heated to 145°-150° C. and held at this temperature for 2 hours. 34.9 g water are slowly dropped into the mixture at 130° C. (to 90% H3PO4) and held for two additional hours at 145°-150° C. With the mixture at 140° C., 350 ml water is added over a 30 minute period with the mixture being maintained at 90°-95° C. for an additional 30 minutes. The reaction slurry is filtered, the presscake reslurried in 400 ml water and the pH adjusted to 12.0 by the addition of 50% aqueous sodium hydroxide solution. The pigment suspension is stirred for 30 minutes at 90° C. and filtered. The presscake is washed base free with water and dried yielding 35.62 g of 2,9-dichloroquinacridone pigment manifesting a specific surface area of 28.5 m2 /g.

Workup

  1. customA 2 liter flask equipped with a thermometer, stirrer and condenser
  2. temperaturethe mixture is heated to 145°-150° C.
  3. customheld for two additional hours at 145°-150° C
  4. temperaturebeing maintained at 90°-95° C. for an additional 30 minutes
  5. filtrationThe reaction slurry is filtered
  6. additionthe pH adjusted to 12.0 by the addition of 50% aqueous sodium hydroxide solution
  7. filtrationfiltered
  8. washThe presscake is washed base free with water
  9. customdried

Sources & evidence

ORD record
ord-d5260afd989d46fb842b9c4da67d614b
Source dataset
uspto-grants-1992_03
Patent number
US05095056

Reaction notes

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