Phthalonitrile → Phthalocyanine

HRID 1018873Notes

Reaction equation

HRID 1018873 reaction equation
[CH:1]1[CH:6]=[C:5]([C:7]#[N:8])[C:4]([C:9]#[N:10])=[CH:3][CH:2]=1>ClC1C2C(=CC=CC=2)C=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[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

20.0 g of phthalodinitrile was dissolved in 200 ml of α-chloronaphthalene, and to the resultant solution was added dropwise 9.0 g of titanium tetrachloride in an atmosphere of nitrogen gas. After completion of the addition, the resultant mixture was heated at 240° C. for 3 hours while stirring, and then, the reaction was terminated. The resultant precipitated crystal was collected by filtration and washed well with α-chloronaphthalene and methanol, to thereby obtain dichlorotitanyl phthalocyanine. The obtained dichlorotitanyl phthalocyanine was heated under reflux while stirring, together with 150 ml of concentrated aqueous ammonia. After 1 hour, the reaction was terminated, and the resultant crystal was collected by filtration, to thereby obtain 17.4 g of a TiOPc. A crystal structure of the obtained TiOPc was confirmed by measuring an X-ray diffraction spectrum with an X-ray of Cu Kα, using an X-ray diffractometer, Model RAD-C System (trade name, manufactured by Rigaku Denki K. K.). The measurement result is shown in FIG. 1.

Workup

  1. additionAfter completion of the addition
  2. customthe reaction was terminated
  3. customThe resultant precipitated crystal
  4. filtrationwas collected by filtration
  5. washwashed well with α-chloronaphthalene and methanol

Sources & evidence

ORD record
ord-7a48a6cd8ea74ba6b3a3fde8abc95dd2
Source dataset
uspto-grants-2002_11
Patent number
US06485658B1

Reaction notes

Loading…