Simple Ring-Closing Metathesis Approach for Synthesis of PA11, 12, and 13 Precursors from Oleic Acid

Abstract

Due to the concerns over limited fossil resources and increasing CO2 emissions, there is a strong interest in use of renewable resources in production of valuable synthetic materials. PA11, 12, and 13, more commonly known as Nylon, are high-strength polymers that find use in various industrial sectors. They are traditionally produced from petroleum-derived material or exotic fatty acids using reaction sequences that involve 4–6 steps. Herein we report a simple three-step synthesis of these polyamide precursors from oleic acid, an abundant natural fatty acid available from common plant sources as well as oleaginous micro-organisms such as microalgae. This approach represents the first example where ring-closing metathesis was used for the key C–C bond forming step, featuring introduction of amine functionality required in the final product. Our versatile approach allows preparation of nylon precursors of various chain-lengths from a single starting material for economical and sustainable production of these polymers.