Acetone → HCID 178439265, compound

Participants

Reaction Conditions

Reaction Steps

A 456.60 gram (2.00 mole) portion of 4,4'-isopropylidenediphenol, 444.91 grams (4.20 moles) of cyanogen bromide and 1000 milliliters of acetone were added to a reactor and maintained under a nitrogen atmosphere with stirring. The stirred solution was cooled to -5° C. then 406.82 grams (4.02 moles) of triethylamine was added to the reactor over a thirty minute (1800 s) period and so as to maintain the reaction temperature at -5° to -2° C. After completion of the triethylamine addition, the reactor was maintained at -5° to -3° C. for an additional forty-five minutes (2700 s), followed by addition of the reactor contents of 1.5 gallons (5.69 l) of deionized water. After 5 minutes (300 s) the water and product mixture was extracted with three 500 milliliter volumes of methylene chloride. The combined methylene chloride extract was washed with 500 milliliters of one percent aqueous hydrochloric acid followed by washing with 1000 milliliters of deionized water then drying over anhydrous sodium sulfate. The dry methylene chloride extract was filtered and solvent removed by rotary evaporation under vacuum. Bisphenol A dicyanate (521.2 grams) was recovered in 93.6 percent yield as a white crystalline solid. Infrared spectrophotometric analysis of a film sample of the product confirmed the product structure (disappearance of phenolic hydroxyl group, appearance of --O--C≡N group).

Provenance & Evidence