Decanoic Acid → 1-Nonene

Participants

Reaction Conditions

Reaction Steps

A mixture of decanoic acid (100 g, 0.581 mol), acetic anhydride, dichlorobis(triphenylphosphine)palladium (0.0407 g, 5.81×10-5 mol), and triphenylphosphine (0.761 g, 0.00290 mol) was heated under a slow stream of nitrogen using an oil bath maintained at 255° C. As product distilled from the reactor, it was continuously replaced with a mixture of decanoic acid and acetic anhydride, identical in ratio to that of the initial charge, in a rate that maintained the initial level of the reactor contents throughout the course of the entire reaction. The distillate products from several runs which contained varied decanoic acid: acetic anhydride ratios were examined by GC analysis (using n-decane as internal standard) and the catalyst efficiency and product α-olefin selectivity calculated. For example, using of a 1:1.5 ratio of decanoic acid:acetic anhydride throughout the course of an entire reaction produced 1-nonene with a catalyst TON of 14,800 and an α-olefin selectivity of 97.4%. The data for this series of reactions appears in Table 4.

Provenance & Evidence