Selective ethenolysis and oestrogenicity of compounds from cashew nut shell liquid

Jennifer Julis*, Stuart A. Bartlett, Sabrina Baader, Nicola Beresford, Edwin J. Routledge, Catherine S. J. Cazin, David J. Cole-Hamilton

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)

Abstract

The ethenolysis of cardanol (2), a waste product from cashew kernel production, was carried out using a variety of metathesis catalysts. Surprisingly, the best activities and selectivities could be observed with ruthenium based 1st generation type catalysts converting cardanol (2) almost completely to the corresponding 1-octene (6) and 3-non-8-enylphenol (4), a potential detergent precursor. Detailed investigation of the reaction system showed that the high activity and selectivity were due to a combination of ethenolysis and internal self-metathesis of the unsaturated cardanol mixture, 2. Self-metathesis of cardanol (2) containing three double bonds led to the formation of 3-non-8-enylphenol (4) and 1,4-cyclohexadiene (7). The latter was crucial for a high selectivity and activity in the ethenolysis, not only of cardanol (2), but also of other substrates like methyl oleate (10) when using ruthenium based 1st generation catalysts. The endocrine disrupting properties of 3-nonylphenol and related compounds are compared.

Original languageEnglish
Pages (from-to)2846-2856
Number of pages11
JournalGreen Chemistry
Volume16
Issue number5
Early online date14 Mar 2014
DOIs
Publication statusPublished - 1 May 2014

Keywords

  • Olefin metathesis catalysts
  • Imidazolin-2-ylidene ligands
  • Cardanol
  • Chemicals
  • Complexes
  • Hydrogenation
  • Degradation
  • Derivatives
  • Generation
  • Strategy

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