Cyanoethylation of alcohols over solid base catalysts

Cyanoethylation of alcohols with acrylonitrile to form 3-alkoxypropanenitriles proceeds effectively over solid base catalysts such as alkaline metal oxides and hydroxides, lanthanum oxide, and alumina supported potassium fluoride and hydroxide at a reaction temperature below 323 K. The order of the reactivity of alcohols varied with the types of catalyst. With magnesium hydroxide and calcium hydroxide, the reactivity of alcohol decreased: methanol>ethanol>2-propanol, while with the alkaline earth oxides, lanthanum oxide, and alumina supported KOH and KF, the reactivity order was opposite. The reactivity orders are interpreted by the acidity of alcohol combined with the basic strength of the catalysts. The catalytic activity of solid base catalysts were scarcely affected by exposure of the catalyst to air before use for the reaction. (C) 1998 Elsevier Science B.V. All rights reserved.