Phenol → Diglycidyl ether

Participants

Reaction Conditions

Reaction Steps

A reaction vessel was charged with 94.1 g (1 mol) of phenol, 1.5 g of boron trifluoride-etherate and 100 ml. of toluene, and with good stirring, the temperature was maintainined at 55° to 65°C., and 277.5 g (3 mols) of epichlorohydrin was added dropwise over the course of 3 hours and 20 minutes. The mixture was further stirred for 1 hour at this temperature to complete an addition polymerization reaction of these monomers. At this point, a part of the addition polymer was withdrawn, and analysis of it showed no presence of epichlorohydrin. 400 ml. of toluene was added to the reaction mixture, and the mixture stirred thoroughly. While maintaining the inside temperature of the reactor at 40° to 45°C., 67.3 g (1.2 mols) of solid sodium hydroxide was added over the course of 1 hour. The mixture was further stirred at this temperature for 1 hour, and then cooled to about 30°C. 440 ml. of water was added to remove the resulting potassium chloride. The organic layer was further washed with 150 ml. of water, and the toluene was evaporated off at reduced pressure. The residue was filtered to afford phenylpolyepichlorohydrin monoglycidyl ether as a transparent light yellow liquid.

Provenance & Evidence