Bisphenol A → HCID 178439265, compound

Participants

Reaction Conditions

Reaction Steps

A quantity of 222.45 grams of cyanogen bromide (2.10 moles) was added to a reactor containing 350 milliliters of stirred acetone under a nitrogen atmosphere. The cyanogen bromide-acetone solution was colled to -15° C., then 228.30 grams of Bisphenol A (1.00 mole) dissolved in 700 milliliters of chilled acetone was added to the reactor. The stirred solution was allowed to equilibrate at -5° C., then 203.39 grams of triethylamine (2.01 moles) was added to the reactor over a 125 minute (7500 s) period and so as to maintain the reaction temperature at -5° C. After completion of the triethylamine addition, the reactor was maintained at -5° C. for 30 minutes (1800 s), followed by addition of the reaction product to 650 milliliters of chilled water with agitation. After 15 minutes (900 s), the water and product mixture was multiply extracted with methylene chloride. The combined methylene chloride extracts were sequentially washed with dilute 5 percent hydrochloric acid, water, dilute hydrochloric acid, water and then dried over anhydrous magnesium sulfate. The dry methylene chloride extract was filtered and solvent removed by rotary evaporation under vacuum. Bisphenol A dicyanate, 255.0 grams, was recovered in 91.6 percent yield as a white crystalline solid. Infrared spectrophotometric analysis confirmed the product structure.

Provenance & Evidence