Browsing by Author "Pogorzelec, Peter J."

Now showing 1 - 4 of 4
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    Synthesis of A Kairomone and Other Chemicals From Cardanol, A Renewable Resource
    (Wiley, 2012-09) Mmongoyo, Juma A.; Mgani, Quintino A.; Mdachi, Stephen J. M.; Pogorzelec, Peter J.; Cole‐Hamilton, David J.
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    Synthesis of a kairomone and other chemicals from cardanol, a renewable resource
    (2012-06-05) Mmongoyo, Juma A.; Mgani, Quintino A.; Mdachi, Stephen J. M.; Pogorzelec, Peter J.; Cole‐Hamilton, David J.
    Synthesis of a tsetse fly kairomone component (3-propylphenol), a detergent [sodium 2-(dec-8-enyl)-6hydroxybenzenesulfonate], a polymer additive (1-octene), and a detergent precursor [3-(non-8enyl)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 1H and 13C NMR.
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    Synthesis of Bifunctional Monomers by The Palladium-Catalyzed Carbonylation Of Cardanol And Its Derivatives
    (2016-02) Mgaya, James E.; Bartlett, Stuart A.; Mubofu, Egid B.; Mgani, Quintino A.; Slawin, Alexandra M. Z.; Pogorzelec, Peter J.; Cole‐Hamilton, David J.
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    Synthesis of Bifunctional Monomers by the Palladium-Catalyzed Carbonylation of Cardanol and its Derivatives
    (Wiley, 2016) Mgaya, James E.; Bartlett, Stuart A.; Mubofu, Egid B.; Mgani, Q. A.; Slawin, Alexandra M. Z.; Pogorzelec, Peter J.; Cole‐Hamilton, David J.
    A 1,2-bis(di-tert-butylphosphinomethyl)benzene-modified palladium catalyst has been used to synthesize bifunctional monomers of different chain lengths from cardanol. Short-chain derivatives of cardanol, such as (E)-3-(dodec-8-enyl)phenol; HOPhC12-ene, (E)-3-(undec-8-enyl)phenol; HOPhC11-ene, (E)-3-(dec-8-enyl)phenol; HOPhC10-ene, and 3-(non-8-enyl)phenol; HOPhC9-ene, were synthesized by the metathesis of cardanol with symmetrical internal alkenes. These derivatives were methoxycarbonylated to produce monomers with different chain lengths such as methyl-16-(3-hydroxyphenyl)hexadecanoate; HOPhC15COOMe, methyl-13-(3-hydroxyphenyl)tridecanoate; HOPhC12COOMe, methyl-12-(3-hydroxyphenyl)dodecanoate; HOPhC11COOMe, methyl-11-(3-hydroxyphenyl)undecanoate; HOPhC10COOMe, and methyl-10-(3-hydroxyphenyl)decanoate; HOPhC9COOMe, respectively. Polymerization of the synthesized monomers produced oligomers that consist of up to seven monomer units as confirmed by MALDI-TOF-MS. Lactone formation was also observed in some cases under polymerization conditions.