Oxidation of propene‐1‐¹⁴C to acrolein on copper catalysts

Abstract

Propene‐1‐14C was partially oxidised with air to acrolein on a copper catalyst. The acrolein formed was degraded: equal amounts of radioactivity were found on carbon atoms 1 and 3, while essentially no radioactivity was found on the middle carbon atom (2). The “unreacted” propene was also degraded: a major part of the radioactivity was still on carbon atom 1, while a small part (10‐20%) was on carbon atom 3; no radioactivity was found on the middle carbon atom (2). These facts indicate that the oxidation of propene to acrolein on a copper catalyst takes place via a symmetrical intermediate. Partial isomerisation of unreacted propene also occurred when copper shavings were used as a catalyst. When D2O was present during the reaction, the unreacted propene was monodeuterated to only a very small extent (∼2%).

Heterogeneous Catalytic Oxidation of Hydrocarbons

“…If 1or 3-labeled propylenes are oxidized then, according to (B), 50% of the labeled isotope should appear in the CH2 and CHO groups. This has been shown to be the case over both Gu and Bi/Mo catalysts using 13C-, 14C-, and D-labeled propylenes (3,38,44,49,55). In the case of (A), it is unlikely that the amounts of attack at the two and carbon atoms would be exactly equal.…”