Phthalonitrile → HCID 178514814, Verbindung

HRID 550329

Reaktionsgleichung

Reaktionsgleichung von HRID 550329
[CH:1]1[CH:2]=[CH:3][C:4]2[C:5](=[C:7]3[N:39]=[C:38]4[N:40]=[C:31]([C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][C:37]=54)[N:30]=[C:28]4[NH:29][C:21]([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=54)=[N:20][C:18]4=[N:19][C:11]([C:12]5[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=54)=[N:10][C:9]=2[NH:8]3)[CH:6]=1.N=C1C2C(=CC=CC=2)C(=N)N1.C1C=C(C#N)C(C#N)=CC=1.[O-:62]CCC.[O-]CCC.[O-]CCC.[O-]CCC.[Ti+4:78]>CN1CCCC1=O>[CH:2]1[CH:3]=[C:4]2[C:9]3[N-:8][C:7]([C:5]2=[CH:6][CH:1]=1)=[N:39][C:38]1=[N:40][C:31]([C:32]2[C:37]1=[CH:36][CH:35]=[CH:34][CH:33]=2)=[N:30][C:28]1=[N:29][C:21]([C:22]2[C:27]1=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:20][C:18]1[N-:19][C:11](=[C:12]2[C:17]=1[CH:16]=[CH:15][CH:14]=[CH:13]2)[N:10]=3.[O-2:62].[Ti+4:78]

Komponenten

6

Edukt 4

HCID 7042PhthalonitrileHCID 9903917Titanium tetrapropoxideHCID 86280045PhthalocyanineHCID 178508669HCID 178508669, Verbindung

Produkt 1

HCID 178514814HCID 178514814, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
198 °C

Versuchsvorschrift

A Type I titanyl phthalocyanine was prepared as follows: To a 300 milliliter three-necked flask fitted with mechanical stirrer, condenser and thermometer maintained under an argon atmosphere was added 3.6 grams (0.025 mole) of 1,3-diiminoisoindoline, 9.6 grams (0.075 mole) of o-phthalonitrile, 75 milliliters (80 weight percent) of N-methylpyrrolidone and 7.11 grams (0.025 mole) of titanium tetrapropoxide (all obtained from Aldrich Chemical Company except phthalonitrile which was obtained from BASF). The resulting mixture (20 weight percent of solids) was stirred and warmed to reflux (about 198° C.) for 2 hours. The resultant black suspension was cooled to about 150° C. and then was filtered by suction through a 350 milliliter, M-porosity sintered glass funnel, which had been preheated with boiling dimethyl foramide (DMF). The solid Type I TiOPc product resulting was washed with two 150-milliliter portions of boiling DMF and the filtrate, initially black, became a light blue-green color. The solid was slurried in the funnel with 150 milliliters of boiling DMF and the suspension was filtered. The resulting solid was washed in the funnel with 150 milliliters of DMF at 25° C. and then with 50 milliliters of methanol. The resultant shiny purple solid was dried at 70° C. overnight to yield 10.9 grams (76 percent) of pigment, which was identified as Type I TiOPc on the basis of its X-ray powder diffraction trace. Elemental analysis of the product indicated C, 66.54; H, 2.60; N, 20.31; and Ash (TiO2), 13.76. TiOPc requires (theory): C, 66.67; H, 2.80; N, 19.44; and Ash, 13.86.

Aufarbeitung

  1. customwas prepared
  2. customTo a 300 milliliter three-necked flask fitted with mechanical stirrer, condenser
  3. temperaturethermometer maintained under an argon atmosphere
  4. temperaturewarmed
  5. temperatureThe resultant black suspension was cooled to about 150° C.
  6. filtrationwas filtered by suction through a 350 milliliter, M-porosity

Quellen und Nachweise

ORD-Eintrag
ord-ebe8b26163a84c6cb10340231a7f0602
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947417B2

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