Phthalonitrile → Dichlorotitanium phthalocyanine

HRID 487842

Reaction equation

HRID 487842 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
200 °C

Procedure

In 100 g of α-chloronaphthalene, 5.0 g of o-phthalodinitrile and 2.0 g of titanium tetrachloride were stirred for 3 hours under heating at 200° C. Thereafter the reaction mixture was cooled to 50° C. and the crystals precipitated were filtered to give a paste of dichlorotitanium phthalocyanine. Next, this product was washed with 100 ml of N,N'-dimethylformamide heated to 100° C., with stirring, and subsequently the washing was repeated twice using 100 ml of methanol kept at 60° C., followed by filtration. The resulting paste was stirred at 80° C. for 1 hour in 100 ml of deionized water, followed by filtration to give blue oxytitanium phthalocyanine crystals. Yield: 4.3 g.

Workup

  1. temperatureThereafter the reaction mixture was cooled to 50° C.
  2. customthe crystals precipitated
  3. filtrationwere filtered

Sources & evidence

ORD record
ord-35acc3026414474f8d9e10e9ffd26bb9
Source dataset
uspto-grants-1994_03
Patent number
US05298353

Linked notes

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