Bisphenol A → Benzene, 1,1'-(1-methylethylidene)bis(4-(2-propen-1-yloxy)-

Participants

Reaction Conditions

Reaction Steps

Bisphenol A diallyl ether was synthesized as described in U.S. Pat. No. 4,740,330. In a four-necked reactor, equipped with a condenser, stirrer, thermometer with temperature controller, and an addition funnel, were added 800 mL of bis-(2-methoxy ethyl) ether (diglyme), 400 mL of dimethyl sulfoxide (DMSO), 228 g (1 mole) bisphenol-A, and 284 g (4 moles) of 85% KOH at ambient temperature (˜25° C.). The mixture was stirred and heated to 35-40° C., and the addition of 304 g (4 moles) of allyl chloride was begun. This reaction was exothermic and was controlled at less than 45° C. by controlling the allyl chloride addition rate. The allyl chloride was added over a 4-hour period, and the reaction was continued at 45° C. for an additional 12 hours to convert the bisphenol-A into diallyl ether. The reaction mixture was cooled to ambient temperature and filtered to remove salts formed in the reaction. The filtrate was mixed with 1000 mL of 50:50 (volume:volume) methyl ethyl ketone-toluene mixture and washed four times with 200 mL portions of water. The solvents were removed from the diallyl product by rotary evaporation first at 50-60° C. and 120 mmHg and then at 120-130° C. at 10 mmHg until gas chromatography (GC) showed all the diglyme and DMSO had disappeared. The yield was 235 g (76% yield) of a light yellow product, bis A diallyl ether, with greater than 95% purity as determined by GC.

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