Ethylene Glycol → 2-Morpholinoethanol

Participants

Reaction Conditions

Reaction Steps

A 22 ml stainless steel Parr bomb reactor was charged with 5.5 g ethylene glycol (88.6 mol), 1.01 g morpholine (11.5 mol), 130 mg RuCl3 (PPh3)3 (1.3×10-4 mol) 250 mg PPh3 (9.5×10-4 mol) 0.52 g N-methylpyrrolidinone (as internal standard) and a magnetic stirring bar in a nitrogen-filled glove box. The bomb was sealed and placed in a previously-heated oil bath with stirring. After heating for 2.5 h at 180° C., the reactor pressure was 44 psig. At this point, the bomb was cooled to room temperature at which point the pressure stood at 17 psig. The reactor was vented, opened and the contents analyzed by GLC. The analysis showed that all of the morpholine had reacted to give 1.42 g hydroxyethylmorpholine (93% yield) and 0.04 g bismorpholinoethane (3% yield).

Provenance & Evidence