Methyl Methacrylate → Di(butylamino)ethyl methacrylate

Participants

Reaction Conditions

Reaction Steps

A 500 mL round bottomed flask fitted with a magnetic stirrer, heating mantle, and distillation head was charged with a mixture of methyl methacrylate (100 g, 1.0 mol, available from TCI), 2-dibutylaminoethanol (43.3 g, 0.25 mol, available from Matheson, Coleman and Bell, Norwood, Ohio), aluminum isopropoxide (5.0 g, 24 mmol, available form Alfa Aesar), and N-phenyl-1-naphthylamine (2.5 g, 11 mmol, available from Aldrich). The mixture was stirred and heated at 80° C. for one hour. The temperature of the reaction mixture was increased 10° C. per hour until a temperature of 110° C. was reached. By this time about 20 mL of material (methanol and methyl methacrylate) had distilled over from the reaction flask. The reaction mixture was left at room temperature overnight. The next day, the reaction mixture was heated at 115° C. for 2 hours and then heated at 135° C. as material distilled from the reaction flask. After 1 hour at 135° C., the desired product, di(butylamino)ethyl methacrylate, was distilled from the reaction flask at reduced pressure and collected at a temperature of 113-118° C. at 2.5 mm pressure. NMR spectral analyses confirmed the structure of the product. The boiling point reported previously for this methacrylate (U.S. Pat. No. 2,138,763 (DuPont)) is 108-109° C. at 2 mm pressure.

Provenance & Evidence