Synthesis of bifunctional monomers by the palladium-catalyzed carbonylation of cardanol and its derivatives
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Date
18/02/2016Author
Grant ID
EP/J018139/1
EP/J018139/1
EP/K031252/1
EP/K039210/1
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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.
Citation
Mgaya , J E , Bartlett , S A , Mubofu , E B , Mgani , Q A , Slawin , A M Z , Pogorzelec , P & Cole-Hamilton , D J 2016 , ' Synthesis of bifunctional monomers by the palladium-catalyzed carbonylation of cardanol and its derivatives ' , ChemCatChem , vol. 8 , no. 4 , pp. 751-757 . https://doi.org/10.1002/cctc.201501110
Publication
ChemCatChem
Status
Peer reviewed
ISSN
1867-3880Type
Journal article
Description
The authors thank the Royal Society Leverhulme Africa Program for funding this project.Collections
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