Water → Butanediol glycidyl ether

Participants

Reaction Steps

5.0 g of paratoluenesulfonic acid and 140 g of pure water were charged in a 1 L four-necked separable flask, and a vacuum pump equipped with a stirrer, a thermometer, an air introduction tube and a cooling trap was installed. Under stirring, 500 g of the vinyloxybutyl glycidyl ether synthesized above was slowly added to the flask while the liquid temperature was adjusted so as to be kept at 40° C. After the addition was completed, the pressure was reduced to 20 kPa, and stirring was continued for 1 hour while dry air was introduced at 100 ml/min. The reaction solution was then analyzed by gas chromatography, and no peak of the vinyloxybutyl glycidyl ether was observed. However, since 5.2% of an acetal dimer was generated according to an analysis by liquid chromatography, 26 g of a 0.04% aqueous solution of paratoluenesulfonic acid was added, and an acetal decomposition reaction was conducted at a pressure of 5 kPa while the temperature was kept at 40° C. When the reactant was analyzed 1 hour after the reaction, the peak of the acetal dimer had almost disappeared, and thus the reaction was quenched. 2.1 g of sodium hydrogen carbonate was put into the solution in which the reaction had been completed to thereby neutralize the solution, and the water in the system was distilled off by concentration with a rotary evaporator, the water content in the system was confirmed to be 800 ppm or less, and the concentrated liquid was filtered to give the objective butanediol monoglycidyl ether with a purity of 92% and a yield of 99%. At this time, the butanediol contained in the obtained substance was 0.2%, and no acetal dimer was detected.

Provenance & Evidence