Abstract
The transformation ofcis- andtrans-2,3-dimethyloxiranes on a Pd/SiO2catalyst, leading to the formation of 2-butanone and 2-butanol, was studied in hydrogen and deuterium atmosphere. The effect of hydrogen pressure (1.3–100 kPa) and temperature (323–423 K) on the reaction rate was also measured. The transformation of the two stereoisomers involves different mechanisms. In the case of thecis-isomer, hydrogen participates in the cleavage of the C–O bond and different surface species belong to the two products. In the case of thetrans-isomer, ring opening by hydrogen (the formation of 2-butanol) is less significant and the main reaction is intramolecular hydrogen migration leading to the formation of 2-butanone. Considering the geometry of the adsorbed species,cis-2,3-dimethyloxirane is most probably adsorbed on the surface of the Pd catalyst in a planar manner, while the adsorption of thetrans-isomer is intermediate between edgewise and planar adsorption mode.
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