Studies of the Organic Reactions of Metal Carbonyl. III. The Hydroformylation of Olefin Oxides

Abstract

Abstract The hydroformylation reactions of ethylene oxide and propylene oxide have been carried out; the character of this type of reaction may be summarized as follows: 1) Propylene oxide reacts with water gas, in the presence of dicobalt octacarbonyl serving as a catalyst, to give β-hydroxy-n-butyraldehyde as the major product, but it is important to keep the reaction temperature between 80 to 100°C in order to hold the high selectivity of this reaction. 2) At temperatures below 80°C, the reaction does not take place; on the other hand, at temperatures above 100°C, the isomerization of propylene oxide to acetone predominates, and the other side-reactions, such as the dehydration of the hydroformylation products, hydrogenation, condensation and polymerization, take place simultaneously. 3) Ethylene oxide seems to undergo hydroformylation under the same conditions as those used for the propylene oxide, but only a small amount of acrolein is obtained as the hydroformylation product. The expected product, i.e., β-hydroxypropionaldehyde, is formed, but this compound is easily converted into acrolein and the latter seems to polymerize to give a large amount of a resinous or oily material.