Olefin metathesis is a chemical reaction in which a molecule with a pair of carbon-carbon double bonds, known also as olefins or hydrocarbons, come together and exchange carbon atoms with one another, forming new value-added molecules in the process.
Represented in this example, two groups of symmetrical olefins (shown in pairs of two blue and two green carbon groups) are transformed into two pairs of new non-symmetrical olefins (shown with one blue and one green carbon group per olefin). The transformation occurs via a cross metathesis reaction, where ruthenium metathesis catalyst (shown as a red ‘Ru’) breaks the double bonds between the two blue and two green carbon groups and swaps the carbon groups, regenerating new double bonds between a blue and green carbon group, forming two new olefinic molecules.
Benefits of Olefin Metathesis Reactions
- Cost-Effective. Low catalyst loadings, solvent-free conditions, and high yielding processes make olefin metathesis both economical and manufacturing-ready.
- Green Process. What makes olefin metathesis cost-effective also makes it green. With fewer reaction steps, solvents, and byproducts, olefin metathesis is environmentally friendly and efficient.
- Scalable. Grubbs Catalyst-based olefin metathesis reactions have achieved commercial success on scales ranging from milligram to multi-ton.
Broad Commercial Applications Enable Broad Industry Adoption
Metathesis is broadly used by chemists in a wide range of fields, including petrochemicals, pharmaceuticals, and materials. The robust nature of Grubbs Catalyst technology, coupled with Materia’s industry leading know-how has led to groundbreaking applications of the technology.
At Materia, we use our expertise in olefin metathesis chemistry to develop innovative and cost-effective solutions to great industrial challenges. We use this catalyst technology in the discovery and development of a new generation of advanced materials.
Common Metathesis Reactions
The olefin metathesis reaction process involves the scission and reassembly of carbon-carbon double bonds to generate a completely new olefins. While there are many variations of this reaction, the most common are:
Ring Opening Metathesis Polymerization
Ring Closing Metathesis
Acyclic Diene Metathesis (ADMET)
Nobel Prize in Chemistry
In 2005, the Royal Swedish Academy of Sciences awarded the Nobel Prize in Chemistry to Dr. Robert H. Grubbs, Yves Chauvin, and Dr. Richard R. Schrock for the development of the metathesis method in organic synthesis. This achievement further highlights the practical and scientific importance of catalysis and the significance of olefin metathesis in modern organic chemistry.
Nobel Prize Press Release
“This year’s Nobel Prize Laureates in chemistry have made metathesis into one of organic chemistry’s most important reactions.”
“In 1971 Yves Chauvin was able to explain in detail how metathesis reactions function and what types of metal compound act as catalysts in the reactions. Now the “recipe” was known. Richard Schrock was the first to produce an efficient metal-compound catalyst for metathesis. This was in 1990. Two years later Robert Grubbs developed an even better catalyst, stable in air, that has found many applications.”
“Metathesis is used daily in the chemical industry, mainly in the development of pharmaceuticals and of advanced plastic materials. Thanks to the Laureates’ contributions, synthesis methods have been developed that are more efficient (fewer reaction steps, fewer resources required, less wastage), simpler to use (stable in air, at normal temperatures and pressures) and environmentally friendlier (non-injurious solvents, less hazardous waste products).”
Grubbs Catalyst® technology is owned by Umicore.