Phosphoric Acid → Quinacridone

HRID 377009

Reaction equation

HRID 377009 reaction equation
[NH:1]([C:8]1[CH:16]=[C:15]([C:17]([OH:19])=[O:18])[C:14]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:13][C:9]=1[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(=O)(O)(O)O>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:7]2[C:2]([NH:1][C:8]=1[CH:16]=3)=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:11])=[O:18].[NH:1]([C:8]1[CH:16]=[C:15]([C:17]([OH:19])=[O:18])[C:14]([NH:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:13][C:9]=1[C:10]([OH:12])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 1004Phosphoric AcidHCID 823512,5-Dianilinoterephthalic acid

Product 2

HCID 13976QuinacridoneHCID 823512,5-Dianilinoterephthalic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

It is important to drive the reaction far enough to react all of the 2,5-dianilinoterephthalic acid. Generally this takes about 1 hour at about 85° C., at which point the reaction is stopped by cooling and combining the mixture with water. The resulting solid, suspended in the dilute aqueous phosphoric acid, is filtered and washed with water until neutral. However, even under optimized conditions for cyclization, a minor amount of quinacridone, the by-product formed by double cyclization of the 2,5-dianilinoterephthalic acid, is obtained, i.e. ##STR6##

Workup

  1. customthe reaction far enough
  2. temperatureby cooling
  3. filtrationis filtered
  4. washwashed with water until neutral

Sources & evidence

ORD record
ord-2d4196352a644880ba02688a19d5fd5b
Source dataset
uspto-grants-2000_02
Patent number
US06022970

Linked notes

Loading…