Methyl Methacrylate → HCID 67172764, compound

Participants

Reaction Steps

A 750 ml reactor with Oldershaw column and liquid distributor was initially charged with 280 mg of hydroquinone monomethyl ether (350 ppm), 600 g (6.0 mol) of methyl methacrylate (MMA) and 194 g (1.5 mol) of N-hydroxyethylpyrrolidone, which were stirred at a stirrer speed (anchor stirrer) of 400 rpm and an air supply of 1.5 l/h. Subsequently, 6.37 g (30 mmol; 2.0 mol % based on N-hydroxyethylpyrrolidone) of anhydrous potassium phosphate were added, the vacuum was established (300 mbar) and the suspension was heated (the jacket temperature was adjusted to 120° C. by means of thermostat control). After approx. 20 minutes, the suspension began to boil (t=0 min). During the reaction, distillate was removed continuously (reflux:efflux ratio was 25:1) and the temperature in the bottom rose from approx. 63° C. to 79° C. After 300 min, the reaction was ended and the vacuum was removed. The suspension was cooled and then filtered through a pressure suction filter (30 ml of methyl methacrylate were added to flush the residue). 492 g of crude product were obtained, which were admixed with 200 ppm of N,N-di-sec-butyl-p-phenylenediamine (98 mg) and were distilled with a supply of air. This first removed the excess methyl methacrylate and then afforded the product of value (130° C., 1.3 mbar). 273 g (92%) of N-hydroxyethylpyrrolidone methacrylate (N-(2-(methacryloyl)ethyl)pyrrolidone) were obtained in high purity (GC analysis: 99.6%). The color number was 50 (APHA color number).

Provenance & Evidence