Premium
Synthesis of Bifunctional Monomers by the Palladium‐Catalyzed Carbonylation of Cardanol and its Derivatives
Author(s) -
Mgaya James E.,
Bartlett Stuart A.,
Mubofu Egid B.,
Mgani Quintino A.,
Slawin Alexandra M. Z.,
Pogorzelec Peter J.,
ColeHamilton David J.
Publication year - 2016
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201501110
Subject(s) - cardanol , bifunctional , chemistry , phenol , monomer , polymerization , metathesis , catalysis , polymer chemistry , organic chemistry , palladium , polymer , epoxy
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; HOPhC 12 ‐ene, ( E )‐3‐(undec‐8‐enyl)phenol; HOPhC 11 ‐ene, ( E )‐3‐(dec‐8‐enyl)phenol; HOPhC 10 ‐ene, and 3‐(non‐8‐enyl)phenol; HOPhC 9 ‐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; HOPhC 15 COOMe, methyl‐13‐(3‐hydroxyphenyl)tridecanoate; HOPhC 12 COOMe, methyl‐12‐(3‐hydroxyphenyl)dodecanoate; HOPhC 11 COOMe, methyl‐11‐(3‐hydroxyphenyl)undecanoate; HOPhC 10 COOMe, and methyl‐10‐(3‐hydroxyphenyl)decanoate; HOPhC 9 COOMe, 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.