2,5-Dianilinoterephthalic acid → Quinacridone

HRID 1108537Notes

Reaction equation

HRID 1108537 reaction equation
[NH:1]([C:8]1[CH:16]=[C:15]([C:17](O)=[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](O)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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: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]

Participants

3

Reactant 1

HCID 823512,5-Dianilinoterephthalic acid

Product 1

HCID 13976QuinacridoneYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Into a 3/4 inch (about 20 mm) single screw extruder having a ratio of length to diameter of about 30:1 and three zones heated at 90° C., 120° C., and 180° C. were introduced 11.7 g per minute of 2,5-dianilinoterephthalic acid and 27.2 g per minute of polyphosphoric acid (117.7% phosphoric acid). The resultant mass was introduced into water. The resultant solid was collected by filtration and reslurried in water containing sodium hydroxide (pH greater than 10). The slurry was heated at 90 to 95° C. for one hour, then collected by filtration, washed until free of alkali, and dried to give an 85% yield of quinacridone (91.3% purity).

Workup

  1. filtrationThe resultant solid was collected by filtration
  2. additioncontaining sodium hydroxide (pH greater than 10)
  3. temperatureThe slurry was heated at 90 to 95° C. for one hour
  4. filtrationcollected by filtration
  5. washwashed until free of alkali, and
  6. customdried

Sources & evidence

ORD record
ord-e2e20096910b44afa08045c4d97b8854
Source dataset
uspto-grants-2000_05
Patent number
US06068695

Reaction notes

Loading…