Decanoic Acid → 1-Nonene

Participants

Reaction Conditions

Reaction Steps

A mixture of decanoic acid (10.0 g, 0.0581 mol), acetic anhydride (5.93 g, 0.0581 mol), chlorodicarbonylrhodium (I) dimer (0.113 g, 2.9×10-4 mol), and dimethylphenylphosphine (0.16 g, 0.0012 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 an equimolar mixture of decanoic acid and acetic anhydride, which also contained 0.6 mol % of dimethylphenylphosphine (relative to the decanoic acid content of the feed), in a rate that maintained the initial level of the reactor contents throughout the course of the entire reaction. The olefin product was removed as rapidly as possible from the reactor. The formation of product ceased after ca. 90 hours of reaction time. Examination of the combined distillate product by GC (using n-decane as an internal standard) showed the presence of 433 g of 1-nonene (isolated yield of 94% based on decanoic acid employed), which was found to be 99.2% of the α-olefin. TON=5915.

Provenance & Evidence