Selective ethenolysis and oestrogenicity of compounds from cashew nut shell liquid

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...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2014-01, Vol.16 (5), p.2846-2856
Main Authors: Julis, Jennifer, Bartlett, Stuart A, Baader, Sabrina, Beresford, Nicola, Routledge, Edwin J, Cazin, Catherine SJ, Cole-Hamilton, David J
Format: Article
Language:English
Subjects:
Anacardium
Catalysis
Catalysts
Kernels
Liquids
Precursors
Ruthenium
Selectivity
Wastes
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Summary: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.
ISSN:1463-9262
1463-9270
DOI:10.1039/c4gc00111g