Telomerization (dimerization)

The reaction was independently discovered by E. J. Smutny at Shell and Takahashi at the Osaka University in the late sixties.

The commercial route to produce 1-octene based on butadiene as developed by Dow Chemical came on stream in Tarragona in 2008.

The telomerization of butadiene with methanol in the presence of a palladium catalyst yields 1-methoxy-2,7-octadiene, which is fully hydrogenated to 1-methoxyoctane in the next step.

Once the Pd(0) catalyst is formed it can coordinate two butadienes which by oxidative coupling give the intermediate B.

Even though the oxidative coupling is facile it is nonetheless reversible; the latter is illustrated by the fact that B is only stable at high butadiene concentration.