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2,5-Dianilinoterephthalic acid → Quinacridone

HRID 378533
Notes
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Reaction equation

HRID 378533 reaction equation
[C:1]1([NH:7][C:8]2[CH:16]=[C:15]([C:17](O)=[O:18])[C:14]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:13][C:9]=2[C:10](O)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O>[CH:24]1[CH:25]=[C:26]2[C:17]([C:15]3[C:14]([NH:20][C:21]2=[CH:22][CH:23]=1)=[CH:13][C:9]1[C:10]([C:6]2[C:1]([NH:7][C:8]=1[CH:16]=3)=[CH:2][CH:3]=[CH:4][CH:5]=2)=[O:11])=[O:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 823512,5-Dianilinoterephthalic acid

Product 1

HCID 13976QuinacridoneYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To 120.0 g of polyphosphoric acid (116%) was added with stirring 20.0 g (57.4 mmol) of 2,5-bis(phenylamino)terephthalic acid. The stirred mixture was irradiated in the microwave oven for 1.5 minutes. The reaction mixture was cooled to 80° C. and added with stirring to 1.0 liter of water. The resultant slurry was stirred for 30 minutes, after which the solid component was collected by filtration and washed with 6.0 liters of water. The presscake was dried overnight in an oven at 60° C. to give 17.9 g of crude quinacridone (C. I. Pigment Violet 19) (100% yield).

Workup

  1. customThe stirred mixture was irradiated in the microwave oven for 1.5 minutes
  2. additionadded
  3. filtrationafter which the solid component was collected by filtration
  4. washwashed with 6.0 liters of water
  5. customThe presscake was dried overnight in an oven at 60° C.

Sources & evidence

ORD record
ord-b2333242bbf04797a8350addf14491bd
Source dataset
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06031100

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes