Azobisisobutyronitrile → N-vinyl-2-pyrrolidinone dibutyl maleate

Participants

Reaction Conditions

Reaction Steps

N-vinyl-2-pyrrolidinone (32 g, 0.29 mole) and dibutyl maleate (68 g, 0.29 mole) were dissolved in 400 ml of xylene in a reaction vessel and the temperature was increased to 90° C. t-Butyl perbenzoate (1 g, 0.005 mole) and azobisisobutyronitrile (2 g, 0.012 mole) were added slowly to the xylene solution over two hours. The reaction was carried out in a nitrogen atmosphere. The temperature was increased to 140° C. for one hour and then the reaction was allowed to cool to room temperature. The xylene was evaporated in a vacuum, leaving a reddish orange oil residue. This oil was purified by dissolving it in boiling heptane, from which it separated upon cooling as a viscous, orange liquid: IR cm-1 1700 ##STR13## 1730 ##STR14## Anal. calcd. for C18H29O5N: C, 63.69; H, 8.61; N, 4.12. Found: C, 63.69; H, 8.59; N, 4.25. Residual N-vinyl-2-pyrolidinone, as measured by gas/liquid chromatography (GLC), was 1.0±0.1%.

Provenance & Evidence