4,4'-Difluorobenzophenone → Phthalonitrile

Participants

Reaction Conditions

Reaction Steps

To a 100 ml, 3-necked flask equipped with a thermometer and a Dean-Stark trap was added 5.0 gm (22.9 mmol) of 4,4'-difluorobenzophenone, 8.03 gm (23.9 mmol) of bisphenol A6F, and 50 ml of dimethylacetamide (DMAC). After flushing the mixture for 30 minutes with dry nitrogen, 3.9 gm (28.7 mmol) of pulverized anhydrous potassium carbonate was added with stirring. The reaction mixture was stirred at 70° C. for 1 hour. Toluene was added to the Dean-Stark trap and to the reaction vessel (4 ml). The reaction mixture was refluxed at 145°-150° C. for 24 hours. Water which formed as a by-product was removed by azeotropic distillation. The toluene was removed by distillation while heating to 160° C. Upon cooling to 50° C., 3.10 gm (17.9 mmol) of 4-nitrophthalonitrile was added. Since the reaction mixture was somewhat viscous, the temperature of the mixture was increased to 110° C. and held at this temperature for 18 hours (overnight). FTIR spectroscopy showed the absence of hydroxy and nitro bands. The room temperature mixture was then poured into 300 ml of water with stirring to break the precipitate into a powdery form. The solid precipitate was collected by suction filtration, washed exhaustively with water, and dried to afford 11.5 gm of oligomeric phthalonitrile monomer.

Provenance & Evidence