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, 11.56 gm (36.7 mmol) of bisphenol A6F, and 40 ml of dimethylacetamide (DMAC). After flushing the mixture for 30 minutes with dry nitrogen, 7.6 gm (55.1 mmol) of pulverized anhydrous potassium carbonate was added with stirring. The light pink reaction mixture was stirred at 90° 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 10 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 room temperature, 6.37 gm (36.8 mmol) of 4-nitrophthalonitrile was added. The temperature of reaction mixture was increased to 70° C. and held at this temperature for 16 hours (overnight). The temperature was further increased to 110° C. and held for 1 hour. The room temperature mixture was poured into 400 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 16.9 gm of oligomeric phthalonitrile monomer.

Provenance & Evidence