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

doi:10.1039/C4GC00111G

Selective ethenolysis and oestrogenicity of compounds from cashew nut shell liquid

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

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* Corresponding authors

^a EaStCHEM, School of Chemistry, University of St. Andrews, St. Andrews, UK
E-mail: djc@st-and.ac.uk
Fax: +44 (0)-1334-463808
Tel: +44 (0)-1334-463805

^b Fachbereich Chemie, Organische Chemie, TU Kaiserslautern, Erwin-Schrödinger-Straße 54, 67663 Kaiserslautern, Germany

^c Institute for the Environment, Brunel University, Cleveland Road, Uxbridge, UK

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.

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The article was received on 21 Jan 2014, accepted on 14 Mar 2014 and first published on 14 Mar 2014

Article type: Paper

DOI: 10.1039/C4GC00111G

Author version available: Download Author version (PDF)

Citation: Green Chem., 2014,16, 2846-2856

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Selective ethenolysis and oestrogenicity of compounds from cashew nut shell liquid

J. Julis, S. A. Bartlett, S. Baader, N. Beresford, E. J. Routledge, C. S. J. Cazin and D. J. Cole-Hamilton, Green Chem., 2014, 16, 2846
DOI: 10.1039/C4GC00111G
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Green Chemistry

Selective ethenolysis and oestrogenicity of compounds from cashew nut shell liquid

Abstract

Supplementary files

Publication details

Selective ethenolysis and oestrogenicity of compounds from cashew nut shell liquid

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