2,5-Di-p-toluidinoterephthalic acid → Quinacridone

HRID 1065970Notes

Reaction equation

HRID 1065970 reaction equation
C1(C)C=CC(NC2C=C(C(O)=O)C(NC3C=CC(C)=CC=3)=CC=2C(O)=O)=CC=1.Cl[C:30]1[CH:31]=[C:32]([CH:54]=[CH:55][CH:56]=1)[NH:33][C:34]1[CH:42]=[C:41]([C:43]([OH:45])=O)[C:40]([NH:46][C:47]2[CH:52]=[CH:51][CH:50]=[C:49](Cl)[CH:48]=2)=[CH:39][C:35]=1[C:36](O)=[O:37]>>[CH:50]1[CH:51]=[C:52]2[C:43]([C:41]3[C:40]([NH:46][C:47]2=[CH:48][CH:49]=1)=[CH:39][C:35]1[C:36]([C:31]2[C:32]([NH:33][C:34]=1[CH:42]=3)=[CH:54][CH:55]=[CH:56][CH:30]=2)=[O:37])=[O:45]

Participants

3

Reactant 2

HCID 825242,5-Di-p-toluidinoterephthalic acidHCID 1199161,4-Benzenedicarboxylic acid, 2,5-bis[(3-chlorophenyl)amino]-

Product 1

HCID 13976Quinacridone

Conditions

Temperature
125 °C

Procedure

A stirred vessel is charged with 1000 parts of polyphosphoric acid containing 85.0% P2O5. Then 150 parts of 2,5-di(4-toluidino)terephthalic acid and 50 parts of 2,5-di(3-chloroanilino)terephthalic acid are introduced at 90° C. with stirring over 40 minutes. During this addition the temperature rises to 103° C. The mixture is heated at 125° C. and stirred at 125° C. for 1.5 hours during which ring closure takes place to form the quinacridone. The reaction mixture is then metered into a toothed-disk disperser IKA SD 41 (supplier: Janke u. Kunkel, Staufen) at 13,000 rpm with a stator slot width of 3 mm, with a volume flow of 3.3 parts by volume per hour in a volume flow of 23.5 parts by volume per hour of 70% strength phosphoric acid at 95° C. and is hydrolyzed in 4.3 seconds (a precipitate is formed). During this procedure, the temperature rises to 102° C. Following the hydrolysis the phosphoric acid strength is 74.6%. This gives 6815 parts of mixed-crystal crude pigment suspension. 1315 parts thereof are heated to 130° C. and are stirred at 130° C. for 5 hours. Thereafter, the mixture is cooled to 70° C. and 1116 parts of water at 25° C. are run in with stirring. Following the addition of the water, the phosphoric acid strength is 40%. The mixed-crystal pigment is subsequently filtered off with suction, washed to neutrality with water and dried at 80° C.

Workup

  1. additionDuring this addition the temperature
  2. customrises to 103° C
  3. stirringstirred at 125° C. for 1.5 hours during which ring closure

Sources & evidence

ORD record
ord-5d7ff4e7fb7540ce97cf0a9d8e403bb3
Source dataset
uspto-grants-2001_06
Patent number
US06241814B1

Reaction notes

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