Dimethylaminoethyl acrylate
chemical compound
Dimethylaminoethyl acrylate (2-dimethylaminoethyl acrylate) or DMAEA is an unsaturated carboxylic acid ester having a tertiary amino group. It is a colorless to yellowish, water-miscible liquid with a pungent, amine-like odor. DMAEA is an important acrylic monomer that gives basic properties to copolymers.
Preparation
2-Dimethylaminoethyl acrylate is prepared via transesterification of acrylic acid esters such as methyl acrylate (R = -CH3) or ethyl acrylate (R = -CH2-CH3) with 2-dimethylaminoethanol under acid catalysis with tin compounds (for example stannoxanes) or titanium compounds (for example tetraisopropyl orthotitanate). More than 95% yield can be achieved.
During the reaction, inhibitors must be present (such as phenothiazine), because of the high tendency of starting material and product to polymerize. When ethyl acrylate is used as a reactant, ethanol is formed; this forms with the ethyl acrylate an azeotrope of the composition ethanol/ethyl acrylate 72.7:26.3%, which boils at 77.5 °C under atmospheric pressure. To achieve a high reaction yield, the ethanol is distilled off from the reaction mixture. The product is purified by vacuum distillation and stabilized with about 1,000 ppm 4-methoxyphenol (MEHQ).
Properties
Dimethylaminoethyl acrylate is a clear, colorless to slightly yellowish liquid with a pungent amine-like odor.
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