(625at) Synthesis of Nylon Precursors Via Cross-Metathesis of Methyl Oleate and Unsaturated Alcohols

A new strategy for the synthesis of nylon precursors by olefin cross-metathesis from renewable feedstock is presented. High-order nylons are high-strength polymers that have wide usage in a number of industries. We have previously developed methods for the synthesis of precursors of these nylons from methyl oleate, a renewable feedstock, using olefin metathesis as the key step. However, the existing methods use non-renewable material as coupling partners to adjust the length of the carbon chain. They also require high temperatures, halogenated solvents, and in one case high-pressure hydrogenation.  Our new method couples methyl oleate with readily available unsaturated alcohols from renewable feedstock. The new strategy further enables the reaction to be performed at low temperatures using nearly solvent-free conditions in high yield.  The stability of the catalyst under the above conditions indicates the possibility of catalyst recycling. Full details of our study and conversion of the metathesis intermediate to the final product will be reported.