Phthalonitrile → Phthalocyanine

HRID 618958Notes

Reaction equation

HRID 618958 reaction equation
[C:1](#[N:10])[C:2]1[C:3](=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:4]#[N:5]>N1C2C(=CC=CC=2)C=CC=1>[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

3

Reactant 1

HCID 7042Phthalonitrile

Product 1

HCID 86280045Phthalocyanine

Reagents, catalysts & solvents 1

HCID 7047QuinolineSolvent

Procedure

78.2 mmoles of phthalonitrile and 15.8 mmoles of a trihalogenometal are added to 100 ml of quinoline purified by distillation twice. The mixture is heated under reflux for 0.5 to 3 hours and cooled to room temperature, and the reaction product is filtered. The solid product is washed with successive, toluene, acetone and methanol, and then with methanol by using a Soxhlet's extractor. The washed product is dried in vacuo at 60° C., to obtain a monohalogenometal phthalocyanine.

Workup

  1. distillationpurified by distillation twice
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for 0.5 to 3 hours
  4. filtrationthe reaction product is filtered
  5. washThe solid product is washed with successive, toluene, acetone and methanol
  6. customThe washed product is dried in vacuo at 60° C.

Sources & evidence

ORD record
ord-f3cdc323a0504cf8bb7b3f1e15cc7fc9
Source dataset
uspto-grants-1999_09
Patent number
US05958637

Reaction notes

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