Methanol → Quinacridone

HRID 866529Notes

Reaction equation

HRID 866529 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.CO>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

4

Reactant 2

HCID 887Methanol3×HCID 823512,5-Dianilinoterephthalic acid

Product 1

HCID 13976Quinacridone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To 130 parts of 118 percent polyphosphoric acid (118 percent H3PO4) are added 18 parts of 2,5-dianilinoterephthalic acid and the mixture is heated at 102° to 106° C. for 16 hours. The resulting thick solution is cooled to 90° C. and poured into 250 parts of methanol over a period of 5 minutes at a rate such that the temperature of the methanol is not allowed to exceed 15° C. The methanol is maintained at between 0° and 15° C. by means of an ice bath. After addition is complete, the mixture is stirred for 15 minutes at 15° C. or below and then heated to reflux for 11/2 hours. After allowing the mixture to cool to about 90° C it is drowned into 400 parts of water at 20° C., heated at 60° C. and boiled for 1/2 hour. The solid is filtered, washed acid free, reslurried with 1000 parts of water and boiled with 50 parts of 50 percent NaOH for 1 hour. The solid is again filtered, washed acid free and dried at 180° F. to yield 15 parts of pure pigmentary gamma quinacridone.

Workup

  1. temperaturethe mixture is heated at 102° to 106° C. for 16 hours
  2. customto exceed 15° C
  3. additionAfter addition
  4. temperatureheated
  5. temperatureto reflux for 11/2 hours
  6. temperatureto cool to about 90° C it
  7. temperatureheated at 60° C.
  8. waitboiled for 1/2 hour
  9. filtrationThe solid is filtered
  10. washwashed acid free
  11. waitreslurried with 1000 parts of water and boiled with 50 parts of 50 percent NaOH for 1 hour
  12. filtrationThe solid is again filtered
  13. washwashed acid free
  14. customdried at 180° F.

Sources & evidence

ORD record
ord-973d7999c485444694d8ade42a76171f
Source dataset
uspto-grants-1978_07
Patent number
US04100162

Reaction notes

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