Styrene → Styrene

Participants

Reaction Steps

An 88.0 gram portion of the hydrolyzed p-isopropenylphenyl acetate and styrene copolymer and 600 grams of chloroform were added to a reactor and maintained under a nitrogen atmosphere with stirring. The transparent viscous solution was coold to 0° C., then 34.96 grams of cyanogen bromide (0.30 mole) was added. Thirteen minutes (780 s) later, 34.96 grams of triethylamine (0.33 mole) was added to the reactor over a 31 minute (1860 s) period and so as to maintain the reaction temperature at -1° to 2° C. After completion of triethylamine addition, the reactor was maintained at 2° to 5° C. for an additional 30 minutes (1800 s), followed by addition of 1000 milliliters of chilled water to the reactor. After 15 minutes (900 s), the water and chloroform plus product layers were separated. The chloroform plus product layer was washed with 500 milliliters 5 percent aqueous hydrochloric acid and then dried over anhydrous sodium sulfate. Filtration provided a dry chloroform solution of cyanate of hydrolyzed p-isopropenylphenyl acetate and styrene copolymer. Infrared spectrophotometric analysis confirmed the product structure as indicated by the disappearance of phenolic hydroxyl group absorbance of the appearance of cyanate group absorbance.

Provenance & Evidence