Phthalonitrile → Dichlorotitanium phthalocyanine

HRID 2248263Notes

Reaction equation

HRID 2248263 reaction equation
[Ti:1](Cl)(Cl)([Cl:3])[Cl:2].[CH:6]1[CH:11]=[C:10]([C:12]#[N:13])[C:9]([C:14]#[N:15])=[CH:8][CH:7]=1>ClC1C2C(=CC=CC=2)C=CC=1>[Cl:2][Ti:1][Cl:3].[CH:6]1[CH:7]=[CH:8][C:9]2[C:10](=[C:12]3[N:13]=[C:12]4[N:15]=[C:14]([C:9]5[CH:8]=[CH:7][CH:6]=[CH:11][C:10]=54)[N:15]=[C:14]4[NH:13][C:12]([C:10]5[CH:11]=[CH:6][CH:7]=[CH:8][C:9]=54)=[N:15][C:14]4=[N:13][C:12]([C:10]5[CH:11]=[CH:6][CH:7]=[CH:8][C:9]=54)=[N:15][C:14]=2[NH:13]3)[CH:11]=1

Participants

4

Reactant 2

HCID 7042PhthalonitrileHCID 24193Titanium Tetrachloride

Product 1

HCID 136368297Dichlorotitanium phthalocyanine

Reagents, catalysts & solvents 1

HCID 70031-ChloronaphthaleneSolvent

Conditions

Temperature
250 °C

Procedure

Titanium tetrachloride (18 g) was added dropwise to a mixture of phthalodinitrile (40 g) and α-chloronaphthalene (500 ml) in a nitrogen stream. Thereafter, the reaction mixture was slowly heated to 250° C., at which it was stirred for 3 h to complete the reaction. Subsequently, the reaction mixture was left to cool to room temperature and filtered to obtain dichlorotitanium phthalocyanine as the reaction product. The dichlorotitanium phthalocyanine thus obtained was hydrolyzed with 300 ml of concentrated aqueous ammonia and thereafter washed with acetone to obtain TiOPc.

Workup

  1. customthe reaction
  2. waitSubsequently, the reaction mixture was left
  3. temperatureto cool to room temperature
  4. filtrationfiltered

Sources & evidence

ORD record
ord-c069a6c407524c5ca14dc97259c1791a
Source dataset
uspto-grants-1991_08
Patent number
US05039586

Reaction notes

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