Phthalonitrile → Phthalocyanine

HRID 964859Notes

Reaction equation

HRID 964859 reaction equation
[C:1](#[N:10])[C:2]1[C:3](=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:4]#[N:5]>ClC1C2C(=CC=CC=2)C=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[CH:7]1[CH:8]=[CH:9][C:2]2[C:3](=[C:4]3[N:5]=[C:4]4[N:10]=[C:1]([C:2]5[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=54)[N:10]=[C:1]4[NH:5][C:4]([C:3]5[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=54)=[N:10][C:1]4=[N:5][C:4]([C:3]5[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=54)=[N:10][C:1]=2[NH:5]3)[CH:6]=1

Participants

4

Reactant 1

HCID 7042Phthalonitrile

Product 1

HCID 86280045Phthalocyanine

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 70031-ChloronaphthaleneSolvent

Conditions

Temperature
140 °C

Procedure

Phthalonitrile (1100 grams) and titanium tetrachloride (813 grams) were suspended in 6800 ml of 1-chloronaphthalene and heated to 215°-220° C. and maintained for 2.5 hours at this temperature. The reaction mixture was cooled to 140° C., and the dark solid was collected, and washed with acetone, and methanol. After drying, the dark blue solid (1090 grams) was refluxed twice in 10 liters of distilled water for two hours, filtered hot each time, and washed with acetone to yield crude titanyl phthalocyanine.

Workup

  1. temperatureheated to 215°-220° C.
  2. temperaturemaintained for 2.5 hours at this temperature
  3. customthe dark solid was collected
  4. washwashed with acetone, and methanol
  5. customAfter drying
  6. temperaturethe dark blue solid (1090 grams) was refluxed twice in 10 liters of distilled water for two hours
  7. filtrationfiltered hot each time
  8. washwashed with acetone

Sources & evidence

ORD record
ord-5fa66b8f15e9449f83857fc3ec7d99a7
Source dataset
uspto-grants-1998_06
Patent number
US05773181

Reaction notes

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