Improved, more efficient ethenolysis reactions with Grubbs type catalysts

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University: University of St Andrews

Sector(s): Chemical

About Opportunity: The metathesis of alkenes with ethene, ethenolysis, is one of the most important and difficult of all metathesis reactions. It is used for making terminal alkenes from any source of internal alkenes. One interesting application is in the formation of linear alpha olefins from natural oils. Ethenolysis is also one of the most difficult metathesis reactions, because ethene often hastens the decomposition of the most desirable catalysts.

The development of processes that allow the ethenolysis reaction to occur using cheap, readily available, offpatent catalysts is therefore highly desirable.

Although they are cheap and not restricted by patents, Grubbs first generation catalysts are not usually effective for ethenolysis reactions of alkenes. For example, in Ruthenium Complexes as Remarkably Active Catalysts for Ethenolysis” Angew. Chem. Int. Ed. 2015, 54, 1919-23 the authors state: “First generation Grubbs catalyst shows very high selectivity for ethenolysis but decomposes very quickly in the presence of ethylene. Second generation catalysts are significantly less selective for ethenolysis due to their propensity for self-metathesis reactions.”

Our technology relates to the use of an additive such as 1,4-cyclohexadiene in ethenolysis reactions. 1,4-cyclohexadiene allows ethenolysis of a variety of alkenes to be carried out cleanly using cheap off-patent metathesis catalysts of the Grubbs first generation type. This will greatly reduce the cost of ethenolysis reactions and make more of them commercially viable.

Key Benefits:

  • Efficient ethenolysis of alkenes using cheap off-patent caytalysts
  • Uses Grubbs first generation type catalysts
  • Additives such as 1,4-cyclohexadiene enable the chemistry
  • Potentially allows cheap formation of terminsl alkenes from bioderived oils
  • Ethenolysis of the bio-derived oils also gives precursors to polyesters and plyamides
  • Applicable to petroleum derived feedstocks


  • Our technology can potentially be applied to any ethenolysis reaction
  • The reactions allow for the production of valuable terminal alkenes from cheap internal ones.
  • One major application could be in the ethenolysis of natural oils to give linear alpha olefins and terminally unsaturated carboxylic acid esters, which in turn can be converted into bio-derived precursors to polyesters and polyamides (nylons)

IP Status:

This novel process for ethanolysis of cardanol is patented and was published as WO 2015/114323 on 6th August 2015 and is now proceeding in National Phase states in US, Europe, China and India.

The University research group continues to perform research & development in this area of chemistry. The University would welcome enquiries from commercial parties interested in developing this novel chemistry on n industrial scale.

Additional Information will be made available under a Confidentiality Agreement.


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