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Synthesis of a kairomone and other chemicals from cardanol, a renewable resource
Author(s) -
Mmongoyo Juma A.,
Mgani Quintino A.,
Mdachi Stephen J. M.,
Pogorzelec Peter J.,
ColeHamilton David J.
Publication year - 2012
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.201200097
Subject(s) - cardanol , chemistry , phenol , metathesis , organic chemistry , isomerization , yield (engineering) , polymerization , polymer , catalysis , epoxy , materials science , metallurgy
Synthesis of a tsetse fly kairomone component (3‐propylphenol), a detergent [sodium 2‐(dec‐8‐enyl)‐6‐hydroxybenzenesulfonate], a polymer additive (1‐octene), and a detergent precursor [3‐(non‐8‐enyl)phenol] using cardanol [3‐(pentadec‐8‐enyl)phenol], has been accomplished. Both carbon–carbon double bond isomerization and metathesis methodologies were employed in the syntheses of these target molecules. The kairomone component was obtained, albeit in low yield, in three steps starting with cardanol. Synthesis of a new detergent, sodium 2‐(dec‐8‐enyl)‐6‐hydroxybenzenesulfonate, was achieved by direct metathesis of cardanol with cis ‐2‐butene followed by sulfonation and basification. Finally, synthesis of 1‐octene and 3‐(non‐8‐enyl)phenol was accomplished in one pot by direct metathesis of cardanol with ethylene. These products have been characterized spectroscopically, especially using 1 H and 13 C NMR.