Olefin Metathesis: Commercial Applications and Future Opportunities

Of the numerous commercial opportunities for olefin metathesis, this chapter focuses on renewable feedstock processes, hydrogenated nitrile butadiene rubber (HNBR) products, candidates for pharmaceuticals, and ROMP-derived functionalized oligomers. Among the renewable feedstock processes was the startup of a 180 k MT per year bio-refinery plant in Gresik, Indonesia. Lanxess' Therban™ products, consisting of reduced molecular weight HNBR enabled by metathesis, are more easily processed than the parent nitrile rubber. Pharmaceutical candidates, featuring ring-closing metathesis as a key synthetic step, include two constrained peptides: Aileron's ALRN-5281 is a stapled peptide prescribed for endocrine disorders and Olysio™ (Simeprevir) is a macrocyclic NS3/4A protease inhibitor used to treat the hepatic C virus. Lastly, solid-supported ROMP-derived functionalized reagents and scavengers have found extensive use in organic synthesis and combinatorial chemistry due to their wide functional group tolerance, well controlled nature, and tunable properties.