Triphenylphosphine → Tetradec-7-ene

Participants

Reaction Steps

7-Tetradecene and 9-octadecene were cross-metathesized employing a homogeneous modified catalyst. For the reaction, 1 mole 7-tetradecene and 1 mole 9-octadecene were combined in the reactor with 13 millimoles tungsten hexachloride. Triphenylphosphine (6.5 millimoles) was then charged to the reactor followed by the addition of 13 millimoles tetrabutyl tin. The reaction was conducted at 115° C and after 330 minutes reaction, near equilibrium conversion of the olefins was obtained with high selectivity to the equilibrium mixture of 1-part 7-tetradecene, 1 part 9-octadecene and 2 parts 7-hexadecene. When the experiment was repeated in an identical manner but using an unmodified catalyst (13 millimoles tungsten hexachloride with 13 millimoles tetrabutyl tin) conversion of the olefins was significantly greater than the theoretical equilibrium conversion due to the lower selectivity of the reaction to the desired cross-metathesized products.

Provenance & Evidence