Olefin Metathesis as a Practical Solution for Modern Industrial Chemistry

Olefin metathesis is one of the most versatile carbon–carbon bond transformations used across the chemical industry. Its impact was recognized with the 2005 Nobel Prize in Chemistry, which highlighted the reaction’s significance in enabling new molecular architectures with high atom economy. Today, metathesis provides a scalable, selective, and resource-efficient alternative to traditional C=C bond constructions, particularly when supported by application-tailored ruthenium catalysts such as those developed by Apeiron Synthesis (https://apeiron-synthesis.com/).

What Makes Olefin Metathesis Valuable for Industry?

Olefin metathesis enables the controlled formation of new C=C double bonds via redistribution of alkene fragments. In practice, industrial chemistry relies on four main types of metathesis reaction:

• Cross Metathesis (CM) – enables access to functional intermediates, pharmaceutical fragments, and renewable feedstock-derived building blocks, including those generated through FAME ethenolysis.
• Ring-Closing Metathesis (RCM) – enables efficient formation of cyclic and macrocyclic structures for fragrances, APIs synthesis, and fine chemicals.
  Ring-Opening Metathesis (ROM) / ROM Polymerization (ROMP) – enables the synthesis of advanced materials, composites, and high-performance resins.
• Acyclic Diene Metathesis (ADMET) – enables the preparation of tailored polymer chains and specialty materials.

Key industrial advantages:

• High atom economy and reduced by-products
• Functional group tolerance, including free COOH and OH groups
• Compatibility with green and renewable feedstocks
• Scalability from small-scale R&D to robust multitonne manufacturing
  

A representative case is ethenolysis of fatty acid esters, which converts methyl oleate into 9-DAME and 1-decene, allowing greener production routes.

 As noted in a recent review ( Poater, Challenges in olefin metathesis: past, present and future, Coordination Chemistry Reviews,2025,(10.1016/j.ccr.2025.216827) the reaction plays an essential role in sustainable valorization of bio-derived raw materials.

Fundamental context and mechanistic background are covered in the Nobel Foundation’s official explanation of the discovery ( Handbook of Metathesis, Robert H. Grubbs, Anna G. Wenzel, Daniel J. O’Leary, Ezat Khosravi, First published: 27 March 2015 Print ISBN:9783527334247 |Online ISBN:9783527674107 |DOI:10.1002/9783527674107), which remains a widely cited summary of the reaction’s scientific basis.

Catalyst Engineering: Addressing Real-World Process Challenges

While conceptually simple, olefin metathesis requires catalysts that perform reliably under realistic process conditions. Industrial chemists routinely face challenges such as:

• Unwanted self-metathesis competing with CM
• E/Z selectivity control
• Isomerization side reactions, for example, with substrates containing –COOH or –OH
• Sensitivity to impurities, air, or moisture
• Need for low catalyst loadings and simplified purification
  

Traditional catalysts often promote Ru–H mediated isomerization or degrade under process conditions. To overcome these barriers, Apeiron Synthesis designs ruthenium catalysts with tailored ligand environments (NHC, CAAC), engineered to deliver:

• Suppression of Ru-H species formation responsible for izomerization pathways
• High selectivity and clean product profiles
• Stability in green solvents and tolerance to variable feedstock quality
• Extremely high turnover numbers (TON) under mild conditions
• Low ppm-level catalyst loadings

These solutions are detailed on Apeiron’s dedicated CM technology page:
https://apeiron-synthesis.com/cross-metathesis

Independent Evidence of Industrial Relevance

A notable example of catalyst performance comes from the Renata Lab (Rice University), which published a demanding CM transformation in the total synthesis of fostriecin (J. Am. Chem. Soc., 2025). The study provides quantitative evidence demonstrating clear differences in reactivity between commercial systems and application-engineered catalysts.
Key findings:

• 16 catalysts screened; most commercial systems produced <20% yield
• Apeiron’s Nitro-Grela-I₂ SIPr catalyst delivered:
  • 48% yield on small scale
  • 41% isolated yield on a gram scale
  • Successful reaction under constant nitrogen sparging
• Demonstrated suitability for densely functionalized, alcohol-containing substrates

This study illustrates how purpose-designed metathesis catalysts directly enable transformations considered impractical with standard systems.

A Platform for Scalable and Sustainable Synthesis

Apeiron’s broader technological framework integrates catalyst innovation with application support: catalyst screening, reaction optimization, consulting, and services focused exclusively on olefin metathesis. Details are available at:
https://apeiron-synthesis.com/the-science/technology

Thanks to this integrated approach, modern metathesis supports:

• Pharmaceutical intermediates requiring clean RCM or CM
• Renewable chemicals, especially FAME ethenolysis
• Fine chemicals, including macrocyclic musks
• Polymers via ROMP and ADMET 

As modern chemical manufacturing increasingly prioritizes efficiency, reduced waste, and regulatory expectations, application-optimized ruthenium catalysts offer a tangible, scalable pathway to align process performance with sustainability goals.

In this context, olefin metathesis continues to evolve not as an academic curiosity, but as a proven industrial tool grounded in mechanistic understanding, catalyst design, and reproducible performance.

Sources

1. Abera et al., 2021 – Abera Tsedalu, A.; Abebe, A.; Tessema, Y.“A Review on Olefin Metathesis Reactions as a Green Method of Chemical Synthesis.”Chemistry Africa, 2021. DOI: https://onlinelibrary.wiley.com/doi/10.1155/2021/3590613

2. Handbook of Metathesis, Robert H. Grubbs, Anna G. Wenzel, Daniel J. O’Leary, Ezat Khosravi First published:27 March 2015 Print ISBN:9783527334247 |Online ISBN:9783527674107 |DOI:10.1002/9783527674107