Phthalonitrile → Phthalocyanine

HRID 1196447Notes

Reaction equation

HRID 1196447 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 washed successively with α-chloronaphthalene, chloroform and methanol in the order written. Thereafter, the 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. washwashed successively with α-chloronaphthalene, chloroform and methanol in the order
  4. temperatureThereafter, the precipitate is refluxed in aqueous ammonia
  5. customits hydrolysis
  6. washby successive washing with water and methanol
  7. customdrying

Sources & evidence

ORD record
ord-1ecb8284307a4a37ac8c7971c331a299
Source dataset
uspto-grants-1992_05
Patent number
US05114815

Reaction notes

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