OXIRANE RING-OPENING BY FORMIC-ACID

The kinetics of oxirane ring opening in epoxidized soybean oil by formic acid have been studied at 10, 20, 30 and 40-degrees-C. The reaction, conducted in presence of isobutanol, was found to be second order in the oxirane. The activation energy of this reaction, E(a), and the frequency factor, A, are equal to 21.15 kcal mol-1 and 3.265 x 10(12) min-1, respectively. The results have shown also that the cleavage reaction by formic acid is thousands times as fast as that by acetic acid. Acetic acid is thus preferred to formic acid in the preparation of epoxy compounds and the reverse is true whenever it is desired to prepare the hydroxylated derivatives of these compounds.