Phenol → Bisphenol S

Participants

Reaction Steps

A mixture of 290 g (3.09 moles) of phenol, 146 g (1.46 moles) of 98% sulfuric acid and 90 g of tetrachloroethane is heated with stirring. When the temperature of the reaction system reaches about 140° C., the mixture begins to boil, giving off an azeotropic mixture of water and tetrachloroethane, which is condensed and separated into two phases, i.e., water and tetrachloroethane. The tetrachloroethane is continuously returned to the reaction mixture. With continuous heating, when the amount of the aqueous phase reaches 45 ml, the temperature of reaction mixture is about 160° C. Subsequently tetrachloroethane containing small amounts of water and phenol is completely distilled off over a period of 4 hours by reducing a pressure of the reaction system to produce the dried reaction mixture in a solid state, while adjusting the temperature to 160° to 170° C. A solution of 62 g of sodium hydroxide in 3.5 l of water is added to the residue, 5 g of active carbon is added to the solution, the mixture is filtered and the filtrate is neutralized with sulfuric acid. The resulting cyrstals are filtered off, then washed with water and dried, giving 332 g of 4,4'-dihydroxydiphenylsulfone, melting at 248° C., in a yield of 91.2% based on the sulfuric acid starting material. When analyzed by gas chromatography, the isomer content is found to be 1.2% in the dried reaction mixture and 0.8% in the product.

Provenance & Evidence