Phthalonitrile → Phthalocyanine

HRID 1196448Notes

Reaction equation

HRID 1196448 reaction equation
[CH:1]1[CH:6]=[C:5]([C:7]#[N:8])[C:4]([C:9]#[N:10])=[CH:3][CH:2]=1>[Ti](Cl)(Cl)(Cl)Cl.ClC1C2C(=CC=CC=2)C=CC=1>[CH:1]1[CH:2]=[CH:3][C:4]2[C:5](=[C:7]3[N:8]=[C:7]4[N:10]=[C:9]([C:4]5[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=54)[N:10]=[C:9]4[NH:8][C:7]([C:5]5[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=54)=[N:10][C:9]4=[N:8][C:7]([C:5]5[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=54)=[N:10][C:9]=2[NH:8]3)[CH:6]=1

Participants

4

Reactant 1

HCID 7042Phthalonitrile

Product 1

HCID 86280045Phthalocyanine

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 70031-ChloronaphthaleneSolvent

Procedure

Titanium tetrachloride (6.5 ml) is added dropwise to a mixture of phthalodinitrile (25.6 g) and α-chloronaphthalene (150 ml) in a nitrogen stream, and the mixture is subjected to reaction at 200°-220° C. for 5 h. The resulting precipitate is recovered by filtration and successively washed with α-chloronaphthalene, chloroform and methanol in the order written. Subsequently, the washed precipitate is refluxed in aqueous ammonia to complete its hydrolysis, followed by successive washing with water and methanol and drying to obtain titanyl phthalocyanine in an amount of 21.8 g (75.6%).

Workup

  1. customthe mixture is subjected to reaction at 200°-220° C. for 5 h
  2. filtrationThe resulting precipitate is recovered by filtration
  3. washsuccessively washed with α-chloronaphthalene, chloroform and methanol in the order
  4. temperatureSubsequently, the washed precipitate is refluxed in aqueous ammonia
  5. customits hydrolysis
  6. washby successive washing with water and methanol
  7. customdrying

Sources & evidence

ORD record
ord-1140e980578e4fd08e35faa6c7a739fe
Source dataset
uspto-grants-1992_05
Patent number
US05114815

Reaction notes

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