A new "cross metathesis" synthesis route for producing nylon 12 and nylon 13 precursors from methyl oleate

Due to the concerns related to limited fossil resources and increasing CO₂ emissions, there is a strong interest in use of renewable resources in production of valuable synthetic materials. Nylons 11, 12 and 13 are high-strength polymers that find use in various industrial sectors (e.g. automotive brake and fuel lines, solar panels and sporting boots) and are traditionally produced from petroleum-derived material or exotic fatty acids using reaction sequences that involve 4-6 steps. We have developed a new and simpler two-step synthetic process for producing nylon 12 and 13 precursors using a cross-metathesis reaction approach that allows for high carbon efficiency and mild reaction conditions.1'2 In contrast to other reported methods, our method uses methyl oleate, a fatty acid derivative that can be obtained from most plant oils or oleaginous microalgae, as the feed material.