Work

5‐Hydroxymethylfurfural Derived Epoxy Monomers Reactions With COS: Synthesis of Polymeric Thiocarbonates with Pendant Aldehyde or Vinyl Groups

Year: 2025

Type: article

Abstract: ABSTRACT The shift toward eco‐friendly polymers is undeniably exciting and necessary, especially as industries strive to reduce their reliance on petroleum‐based materials. In this communication, we have showcased the synthesis of epoxy monomers derived from biobased platform chemicals, specifically 5‐hydroxymethyl‐2‐furfural (5‐HMF) and epichlorohydrin (ECH), used as starting materials. The study of its coupling reactions with CO2 and its sulfur congener COS has been evaluated utilizing a well‐defined binary (salen)MX/PPNX catalyst system. It was found that the reactions with CO2 predominantly produced cyclic products, while the more reactive COS led to the formation of aldehyde functional poly(monothiocarbonate)s (PMTC) in a regioselective manner at ambient temperature. Furthermore, the post‐polymerization reactions of aldehydes with primary amines bearing alkene, alkyne, and radical functional groups led to the production of corresponding imine derivatives, thereby providing a pathway to well‐defined, highly modifiable polymers. This process has the potential to promote a more sustainable approach for transforming a wide array of polymeric materials while introducing desirable features such as (bio)degradability for various applications.

Source: Macromolecular Rapid Communications

DOI: 10.1002/marc.202500451

Authors: Mani Sengoden, Donald J. Darensbourg

Institution: Texas A&M University

Language: English

Topic: Carbon dioxide utilization in catalysis

Subfield: Process Chemistry and Technology

Field: Chemical Engineering

Domain: Physical Sciences

SDGs: Responsible consumption and production, Climate action

Open Access status: hybrid

Estimated APC paid: $4,550