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One‐Step Solvent‐Free Synthesis of Polyglycolic Acid from Sustainable C1 Feedstocks
Author(s) -
Reyhanoglu Yusuf,
Kalayci Berkant,
Gokturk Ersen
Publication year - 2021
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.202000284
Subject(s) - cationic polymerization , polymerization , polymer chemistry , copolymer , chemistry , solvent , trioxane , catalysis , polyester , formaldehyde , organic chemistry , polymer
Abstract Polyglycolic acid (PGA) is an aliphatic biodegradable polyester commonly synthesized through the ring opening polymerization of glycolide using mostly tin (II) octoate catalyst. Previously, a very convenient method for the synthesis of PGA from the cationic alternating copolymerization of formaldehyde (from trioxane) and carbon monoxide (CO) with triflic acid (TfOH) catalyst in dichloromethane (DCM) at 170 °C is described with 92% of yield. The need of using harmful DCM solvent for this polymerization directs to discover solvent‐free polymerization of formaldehyde and CO. Here, one‐step solvent‐free synthesis of PGA from the cationic alternating copolymerization of formaldehyde and CO is presented. Unlike the polymerization carried out in DCM solvent, optimum polymerization in solvent‐free conditions with TfOH catalyst is achieved in 80% of yield at 130 °C. It is considered that utilization of solvent‐free conditions and lower reaction temperatures compared to the previous report provides a more green and economic way of the synthesis of PGA. The method is also extended to copolymerization strategy by adding a minor amount of an epoxide compound to the reaction mixture, and PGA‐based copolymer with improved physical properties (such as solubility and appearance) is obtained in solvent‐free conditions.