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The Aqueous Barbier Polycondensation of Biomass‐Derived 5‐Chloromethylfurfural: A Proof of Concept Study to Access Functional Polymers
Author(s) -
Arslan Mehmet
Publication year - 2018
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201800087
Subject(s) - monomer , condensation polymer , bifunctional , polymer , furan , polymerization , aqueous solution , functional polymers , polymer chemistry , chemistry , materials science , organic chemistry , catalysis
The versatility of the zinc‐mediated aqueous Barbier reaction in functional polymer synthesis is demonstrated in instance of a biomass‐derived bifunctional monomer, 5‐chloromethylfurfural (CMF). CMF is a renewable furan derivative that can be directly obtained from various sugars and cellulose in high yields and is a versatile precursor that can be converted into several valuable building blocks. In this study, CMF is utilized as a monomer in metal‐catalyzed conditions to access both furan and hydroxyl functional polymers. The effect of different reaction conditions on polymerization is explored. Polymers through Barbier polycondensation of bifunctional monomer are obtained with moderately good polymer conversions (54–89%) and molecular weights (8.7–15.1 kDa). The crosslinking of obtained functional polymers is studied by employing bismaleimide and dianhydride crosslinkers for possible application of synthesized polymers as hydrophilically modified membrane materials. The crosslinked materials are obtained by reaction of furan and alcohol groups through Diels–Alder and ester formation reactions, respectively. Synthesis and characterization procedures of linear and crosslinked polymers are described. The reported proof of concept study demonstrates the efficiency of aqueous Barbier reaction in functional polymer synthesis.