Toluene → 2,2'-((1-Methylethylidene)bis(cyclohexane-4,1-diyloxymethylene))bisoxirane

Participants

Reaction Conditions

Reaction Steps

A reactor of the kind described in Example 8 is charged with 240.4 g (1.0 mol) of perhydrobisphenol A, 3.14 g (0.02 mol) of powdered tin difluoride and 5.28 g (0.02 mol) of 18-crown-6, and the charge is heated to 145° C., whereupon the educt melts. Then, with efficient stirring 152.12 ml (1.94 mol) of epichlorohydrin are added over 30 minutes. The reaction is allowed to continue for 12 hours, then cooled to 55° C., 250 ml of toluene are added and, then, at this temperature, 155.2 g (1.94 mol) of a 50% aqueous solution of sodium hydroxide are added dropwise with efficient stirring over 30 minutes. After stirring for 4.5 hours at 55°-60° C. and cooling to room temperature, the suspension is filtered and the filtrate is washed with toluene. The phases are separated, and the aqueous phase is extracted with 2×100 ml of ethyl acetate. The combined organic phases are washed with a small an amount of 10% KH2PO4 solution as possible and then with water until neutral, dried over magnesium sulfate and filtered. The filtrate is freed from solvent on a rotary evaporator under vacuum (bath temperature 70° C.). Yield: 330.8 g (94% of theory) of yellowish perhydrobisphenol A diglycidyl ether for which the following analytical values are obtained: epoxy value: 4.31 eq/kg (76% of theory); total chlorine content: 2.1%; hydrolysable chlorine content: 171 ppm.

Provenance & Evidence