Synthesis of Bifunctional Monomers by the Palladium-Catalyzed Carbonylation of Cardanol and its Derivatives
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Wiley
Abstract
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.
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http://onlinelibrary.wiley.com/doi/10.1002/cctc.201501110/full
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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.