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Closed-loop chemically recyclable aromatic polyesters using asymmetric dicarboxylates obtainable from lignocellulose

Valsange, Nitin G. LU ; Warlin, Niklas LU ; Mankar, Smita V. LU ; Rehnberg, Nicola LU orcid ; Zhang, Baozhong LU and Jannasch, Patric LU orcid (2025) In Green Chemistry 27(20). p.5770-5781
Abstract
Utilizing building blocks derived from lignocellulose is an attractive strategy towards biobased aromatic polyesters. Here, we present the straightforward synthesis of three new asymmetric di-aromatic diester monomers by one-step reactions of lignin-derived hydroxybenzoates (methyl paraben, methyl vanillate and methyl syringate, respectively) with potentially sugar-based methyl 5-chloromethyl-2-furoate. The two diester monomers based on methyl paraben and methyl vanillate were polymerized with 1,6-hexanediol, 1,4-butanediol, and neopentyl glycol, respectively, to produce two series of polyesters with reasonably high molecular weights (12-37 kg mol−1). The fully amorphous polyesters showed high thermal stability... (More)
Utilizing building blocks derived from lignocellulose is an attractive strategy towards biobased aromatic polyesters. Here, we present the straightforward synthesis of three new asymmetric di-aromatic diester monomers by one-step reactions of lignin-derived hydroxybenzoates (methyl paraben, methyl vanillate and methyl syringate, respectively) with potentially sugar-based methyl 5-chloromethyl-2-furoate. The two diester monomers based on methyl paraben and methyl vanillate were polymerized with 1,6-hexanediol, 1,4-butanediol, and neopentyl glycol, respectively, to produce two series of polyesters with reasonably high molecular weights (12-37 kg mol−1). The fully amorphous polyesters showed high thermal stability (Td,5 > 275 °C), tunable glass transition temperature (Tg ~ 36-75 °C), and moderately high mechanical stiffness. In addition, we have successfully developed and demonstrated a strategy for closed-loop chemical recycling of the polyesters through depolymerization using methanolysis, which allowed for the recovery of the native diester and diol monomers. The recovered monomers were subsequently repolymerized to produce a recycled polyester with properties comparable to the original one. (Less)
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author
; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Green Chemistry
volume
27
issue
20
pages
5770 - 5781
publisher
Royal Society of Chemistry
external identifiers
  • scopus:105003914635
ISSN
1463-9270
DOI
10.1039/D4GC05572A
language
English
LU publication?
yes
additional info
From the themed collection: Make polymers sustainable, why and how?
id
d2d59384-65f7-44cd-aa65-28e9f7dc04fb
date added to LUP
2023-11-09 19:41:03
date last changed
2025-05-21 09:20:24
@article{d2d59384-65f7-44cd-aa65-28e9f7dc04fb,
  abstract     = {{Utilizing building blocks derived from lignocellulose is an attractive strategy towards biobased aromatic polyesters. Here, we present the straightforward synthesis of three new asymmetric di-aromatic diester monomers by one-step reactions of lignin-derived hydroxybenzoates (methyl paraben, methyl vanillate and methyl syringate, respectively) with potentially sugar-based methyl 5-chloromethyl-2-furoate. The two diester monomers based on methyl paraben and methyl vanillate were polymerized with 1,6-hexanediol, 1,4-butanediol, and neopentyl glycol, respectively, to produce two series of polyesters with reasonably high molecular weights (12-37 kg mol<sup>−1</sup>). The fully amorphous polyesters showed high thermal stability (<i>T</i><sub>d,5</sub> &gt; 275 °C), tunable glass transition temperature (<i>T</i>g ~ 36-75 °C), and moderately high mechanical stiffness. In addition, we have successfully developed and demonstrated a strategy for closed-loop chemical recycling of the polyesters through depolymerization using methanolysis, which allowed for the recovery of the native diester and diol monomers. The recovered monomers were subsequently repolymerized to produce a recycled polyester with properties comparable to the original one.}},
  author       = {{Valsange, Nitin G. and Warlin, Niklas and Mankar, Smita V. and Rehnberg, Nicola and Zhang, Baozhong and Jannasch, Patric}},
  issn         = {{1463-9270}},
  language     = {{eng}},
  number       = {{20}},
  pages        = {{5770--5781}},
  publisher    = {{Royal Society of Chemistry}},
  series       = {{Green Chemistry}},
  title        = {{Closed-loop chemically recyclable aromatic polyesters using asymmetric dicarboxylates obtainable from lignocellulose}},
  url          = {{http://dx.doi.org/10.1039/D4GC05572A}},
  doi          = {{10.1039/D4GC05572A}},
  volume       = {{27}},
  year         = {{2025}},
}