Acetone → Phenol Acetone

Participants

Reaction Steps

A mixture of 400 grams (4.26 moles) of phenol, 20 grams (0.345 mole) of acetone, and 70 ml of phenolazeotrope-dried sulfonic acid cation exchange resin in acid form (DOWEX 50WX4 resin, H+ form, 4.08 meq/g dry resin) promoted as in Example 1 was brought to equilibrium in a stirred glass pot at 60° C. A 200-gram sample of liquid was removed from the pot. By distilling off excess phenol and water to final conditions of 200° C., 10 mm Hg vac, 7.25 grams of crystalline, light yellow solid was recovered from the distillation pot. This crystalline substance was identified as bisphenol A by elution time on the gel permeation chromatograph (GPC). To the remaining reaction mixture in the pot was added dropwise 17.3 grams (0.177 mole) of bisisopropenyl ether. The temperature rose from 60° to 65° C. The absence of water and rise of acetone was detected by gas chromatograph. After stopping the BIPE addition the temperature fell and water was detected by GC. From 180 grams of reaction mixture was recovered 36 grams of product by distilling off excess phenol and water under vacuum. The crystalline product was identified as bisphenol A by elution time on the GPC. The addition of BIPE raised acetone conversion from 19.4 to 58.2% of theoretical in this example of an ion exchange catalyzed stirred pot.

Provenance & Evidence