Phthalonitrile → Dichlorotitanium phthalocyanine

HRID 1279159Notes

Reaction equation

HRID 1279159 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:11](Cl)(Cl)([Cl:13])[Cl:12]>ClC1C2C(=CC=CC=2)C=CC=1>[Cl:12][Ti:11][Cl:13].[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 2

HCID 7042PhthalonitrileHCID 24193Titanium Tetrachloride

Product 1

HCID 136368297Dichlorotitanium phthalocyanine

Reagents, catalysts & solvents 1

HCID 70031-ChloronaphthaleneSolvent

Conditions

Temperature
225 °C

Procedure

40 g of o-phthalodinitrile, 18 g of titanium tetrachloride and 500 ml of α-chloronaphthalene were reacted by heating and agitating in a nitrogen atmosphere at 200 to 250° C. for 3 hours, and after standing to cool to 100 to 130° C., filtered under hot, and the reaction product was washed with 200 ml of α-chloronaphthalene heated to 100° C. to obtain a crude product of dichlorotitanium phthalocyanine. The crude product was washed at room temperature with 200 ml of α-chloronaphthalene and then with 200 ml of methanol, and was further washed by suspending under hot in 500 ml of methanol for 1 hour. The crude product obtained by filtering was repeatedly washed by suspending under hot in 500 ml of water until the pH became 6 to 7, and it was dried to obtain TiOPc crystals. When the crystals were subjected to X-ray diffractiometry, the spectrum shown in FIG. 3 was obtained. It is understood from FIG. 3 that the crystals are crystalline TiOPc called Y type disclosed in JP-A 64-17066 having a maximum diffraction peak at a Bragg angle (2θ±0.2°) of 27.3° and diffraction peaks at Bragg angles (2θ±0.2°) of 9.5°, 9.7°, 11.7°, 15°, 23.5° and 24.1°.

Workup

  1. temperatureby heating
  2. temperatureto cool to 100 to 130° C.
  3. filtrationfiltered under hot, and the reaction product
  4. washwas washed with 200 ml of α-chloronaphthalene
  5. temperatureheated to 100° C.

Sources & evidence

ORD record
ord-d881f1daf10542a49e9b62b4c230123e
Source dataset
uspto-grants-2002_09
Patent number
US06447965B1

Reaction notes

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