Diethyl Ether → Butyl Methacrylate

Participants

Reaction Steps

A 74.1 g (1.0 mole) amount of n-butyl alcohol, 250.2 g (2.5 mols) of methyl methacrylate, 187 g (2.18 mols) of n-hexane and 0.17 g of hydroquinonemonomethyl ether were added to the apparatus described in Example 1 and were heated and agitated under full reflux to remove water from the reaction system. The amount of water obtained in the reaction solution was 0.001 mol. To the reaction solution was added 0.0035 mol of sodium methylate as a catalyst and the solution was heated and agitated. An azeotropic mixture of n-hexane and methanol from the upper part (top) of the fractionating tower was obtained and was kept stationary in a decanter. The n-hexane layer which separated was returned to the tower and the methanol layer was removed continuously to advance the reaction. Meanwhile, the temperature at the top of the tower was 56° to 59.8° C. and the flask temperature was 83° to 90° C. The results of the experiment were a 99.4% conversion of n-butyl alcohol and a 87.3% yield of n-butyl methacrylate. However, it was found by gas chromatography that an additive of methyl methacrylate was produced as a by-product as well as a polymer. As soon as this reaction solution was distilled, it polymerized.

Provenance & Evidence