Organic Chemistry

Olefins from seed oils at industrial scales

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Science  30 Jan 2015:
Vol. 347, Issue 6221, pp. 516
DOI: 10.1126/science.347.6221.516-f
PHOTO: © MARTIN SHIELDS/ALAMY

Linear-chain olefins with terminal double bonds (linear α-olefins, or LAOs) are essential building blocks for both commodity products, such as lubricants and thermoplastics, and fine chemicals and drugs. Many fatty acids derived from seed oils have a linear tail containing a central double bond, and exchanging this tail with ethylene (ethenolysis) would provide a renewable source of LAOs. However, most catalysts for this reaction deactivate after thousands of reaction cycles (turnovers) and require unacceptable amounts of catalyst. Marx et al. now report a ruthenium ethenolysis catalyst bearing a cyclic alkyl amino carbene ligand that achieves more than 100,000 turnovers at a catalyst loading of only three parts per million.

Angew. Chem. Int. Ed. 10.1002/anie.201410797 (2014).

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