Stearic Acid → 1-Heptadecene

Participants

Reaction Conditions

Reaction Steps

In a procedure similar to example 3, a mixture of stearic acid (70.0 g, 0.246 mol), propionic anhydride (16.0 g, 0.123 mol), chlorodicarbonylrhodium (I) dimer (0.48 g, 0.0012 mol), and dimethylphenylphosphine (0.68 g, 0.0049 mol) was heated under reduced pressure (35-45 torr) using an oil bath maintained at 255° C. and the product collected as it distilled from the reactor. The material removed from the reactor was continuously replaced with a mixture of stearic acid and propionic anhydride (4:3 molar mixture, respectively) in a rate that maintained the initial level of the reactor contents throughout the course of the entire reaction. The formation of product ceased after ca. 8 hours of reaction time. The combined distillate product was washed with water and distilled to provide 375 g of 1-heptadecene (bp 140° C./0.6 torr) which was found by GC analysis to be 93.4% of the α-olefin. TON=657.

Provenance & Evidence