Metathesis of Cardanol

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Chemical
Chemical

University: University of St Andrews

Sector(s): Chemical

About Opportunity:

Metathesis of cardanol with ethane (ethenolysis) converts cardanol into 1-octene a major plasticiser for polyethylene, and into 3-nonenylylphenol which can be further treated to produce 3-nonylphenol to replace 4-nonylphenol in detergent production.

1-octene is the major plasticiser for polyethylene and has a $1bn p.a.market value.

Our technology :

• Converts cardanol into 1-octene, the major plasticiser for polyethylene.

• Converts cardanol into 3-nonenylphenol which can then be hydrogenated to produce 3-nonylphenol, potentially a much less endocrine disrupting replacement for the banned 4-nonylphenol which was previously used widely in detergent production.

• Both products are formed by reaction of cardanol with ethene in the presence of a metathesis catalyst.

• Uses the cheapest ruthenium (Grubbs first generation type) catalysts which are off-patent and are the best metathesis catalysts in terms of stability and catalytic lifetime.

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 selfmetathesis reactions.” Our novel technology relates to carrying out this ethenolysis reaction using these cheap off-patent catalysts of the “Grubbs first generation” type. Using our method, these give a much cleaner product than any other metathesis catalysts that have been tested.

Key Benefits:

  • Converts cardanol into 1-octene, the major plasticiser in polyethylene
  • Converts cardanol into 3-nonenylphenol which can then be hydrogenated to produce 3-nonylphenol, potentially a much less endocrine disrupting replacement for the banned 4-nonylphenol which was previously used widely in detergent production
  • Both products are formed by reaction of cardanol with ethene in the presence of a metathesis catalyst
  • The reaction uses the cheapest ruthenium (Grubbs first generation type) catalysts which are off-patent and are the best metathesis catalysts in terms of stability and catalytic lifetime

Applications:

  • Metathesis of Cardanol
  • Production of 1-octene from waste
  • Production of 3-nonylphenol from waste

IP Status:

This novel process for ethanolysis of cardanol is patented and was published as WO 2014/041344 on 20 March 2014 and is now proceeding in National Phase states in US, Canada, Europe, Brazil 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 an industrial scale.

Additional Information will be made under a Confidentiality Agreement.

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