Catalytic hydrogenation of cardanol derived bifunctional monomers for polymerization with diesters

Abstract

ABSTRACT. Cardanol extracted from cashew nut shell liquid (agro-waste) was used to synthesize a bifunctional monomer; methyl 16-(3-hydroxyphenyl)hexadecanoate using DTBPMB modified palladium catalyst. Hydrogenation of this monomer using a Ru(acac)3/triphos/MSA catalytic system in aqueous dioxane and ammonia solution gave 3-(16-hydroxyhexadecyl)phenol (75% yield) and 3-(16-aminohexadecyl)phenol (37% yield) respectively. Polymerization of 3-(16-aminohexadecyl)phenol and 3-(16-hydroxyhexadecyl)phenol with dimethyl nonadecanedioate (a di-ester obtained from methoxycarbonylation of methyl oleate) resulted into oligomers consisting of up to nine condensed monomer units (in the volatile fraction) as was revealed by MALDI-TOF MS.                 KEY WORDS: Cardanol, Bifunctional monomers, Catalytic hydrogenation, Polymerization   Bull. Chem. Soc. Ethiop. 2022, 36(1), 173-186.                                                             DOI: https://dx.doi.org/10.4314/bcse.v36i1.14