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

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

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Date

18/02/2016

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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.

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

DOI

https://doi.org/10.1002/cctc.201501110

ISSN

1867-3880

Type

Journal article

Rights

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1002/cctc.201501110

Description

The authors thank the Royal Society Leverhulme Africa Program for funding this project.

Collections

University of St Andrews Research

URI

http://hdl.handle.net/10023/10184