Synthesis of bifunctional monomers by the palladium-catalyzed carbonylation of cardanol and its derivatives

James E. Mgaya, Stuart A. Bartlett, Egid B. Mubofu, Quintino A. Mgani, Alexandra M. Z. Slawin, Peter Pogorzelec, David J. Cole-Hamilton

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)
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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.
Original languageEnglish
Pages (from-to)751-757
Number of pages7
JournalChemCatChem
Volume8
Issue number4
Early online date26 Jan 2016
DOIs
Publication statusPublished - 18 Feb 2016

Keywords

  • Lactones
  • Oligomerization
  • Palladium
  • Polymerization
  • Renewable resources

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