Ethanolamine → N-(2-Hydroxyethyl)methacrylamide

Participants

Reaction Steps

A round-bottom flask with a magnetic stirrer is charged with 61.1 g of ethanolamine, 5.4 g of sodium methoxide and 0.4 g of phenothiazine. The contents are stirred. A mixture of 100.1 g of methyl methacrylate and 0.6 g of Irganox 1010* are added with stirring from a dropping funnel over a period of 90 minutes. The temperature is maintained below 40° C. during the addition. The mixture is left to stand at room temperature for about 23 hours. One gram of Irganox 1010* is added and the mixture is stripped on a rotary evaporator at about 60° C. and 8 mm Hg pressure. Product (125 g) is recovered and analyzed by gas chromatography to be 90 percent HEMA. Proton nuclear magnetic resonance spectra show that about 17 mole percent of the product has addition across the double bond and 83 percent is HEMA.

Provenance & Evidence