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Synthesis of Bifunctional Monomers by the Palladium-Catalyzed Carbonylation of Cardanol and its Derivatives

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dc.creator Mgaya, James E.
dc.creator Bartlett, Stuart A.
dc.creator Mubofu, Egid B.
dc.creator Mgani, Q. A.
dc.creator Slawin, Alexandra M. Z.
dc.creator Pogorzelec, Peter J.
dc.creator Cole‐Hamilton, David J.
dc.date 2016-06-15T20:55:25Z
dc.date 2016-06-15T20:55:25Z
dc.date 2016
dc.identifier Mgaya, J.E., Bartlett, S.A., Mubofu, E.B., Mgani, Q.A., Slawin, A.M., Pogorzelec, P.J. and Cole‐Hamilton, D.J., 2016. Synthesis of Bifunctional Monomers by the Palladium‐Catalyzed Carbonylation of Cardanol and its Derivatives. ChemCatChem, 8(4), pp.751-757.
dc.identifier http://hdl.handle.net/20.500.11810/2499
dc.identifier 10.1002/cctc.201501110
dc.description Full text can be accessed at http://onlinelibrary.wiley.com/doi/10.1002/cctc.201501110/full
dc.description 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.
dc.language en
dc.publisher Wiley
dc.title Synthesis of Bifunctional Monomers by the Palladium-Catalyzed Carbonylation of Cardanol and its Derivatives
dc.type Journal Article


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