Due to the concerns over limited fossil resources and increasing CO 2 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.
Fatty acid alkanolamides (FAAA) are lipid derivatives with industrial applications as biosurfactants and biolubricants. Although conventionally produced from vegetable oils, use of alternative renewable sources that do not compete with the food supply chain, such as microalgae, is desirable. We studied the production of FAAA through direct in situ amidation of algal biomass or by amidation of fatty acid methyl esters (FAME) recovered from in situ transesterification of algae. In situ transesterification resulted in spontaneous formation of a distinct FAME phase, which could be easily recovered and converted to FAAA. With this two-step transesterification-followed-by-amidation method, >95% of algal lipids were recovered as FAAA products. In situ amidation did not result in a separate product phase, likely because of the amphiphilic nature of the product. However, extraction with ethyl acetate allowed recovery of nearly 90% of the biomass lipids as FAAA after in situ amidation.
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