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Synthesis and chemical recycling of biobased poly(acetal-ester)s with a non-cyclic acetal unit

Warlin, Niklas ; Subramaniyan, Sathiyaraj LU ; Garcia Gonzalez, Maria Nelly LU orcid ; N. L. de Menezes, Rafael LU orcid ; Mankar, Smita V. LU ; Valsange, Nitin LU ; Rehnberg, Nicola LU orcid ; Jannasch, Patric LU orcid and Zhang, Baozhong LU (2025) In Green Chemistry 27(9). p.2554-2564
Abstract
There is a high demand to design and develop recyclable biobased polymers using eco-friendly synthetic approaches. In this work, we present the facile synthesis of two dicarboxylate monomers with a central non-cyclic acetal unit (dimethyl 4,4'(methylenebis(oxy))dibenzoate and dimethyl 4,4'-(methylenebis(oxy))bis(3-methoxybenzoate)), using potentially biosourced methyl paraben and methyl vanillate. The synthetic parameters were evaluated by a cradle to gate life cycle greenhouse gas emissions aiming to understand the environmental impacts. The two monomers were subjected to melt polycondensation with three linear aliphatic diols (ethylene glycol, 1,4-butane diol, and 1,6-hexanediol ) with varied lengths and flexibility to yield six... (More)
There is a high demand to design and develop recyclable biobased polymers using eco-friendly synthetic approaches. In this work, we present the facile synthesis of two dicarboxylate monomers with a central non-cyclic acetal unit (dimethyl 4,4'(methylenebis(oxy))dibenzoate and dimethyl 4,4'-(methylenebis(oxy))bis(3-methoxybenzoate)), using potentially biosourced methyl paraben and methyl vanillate. The synthetic parameters were evaluated by a cradle to gate life cycle greenhouse gas emissions aiming to understand the environmental impacts. The two monomers were subjected to melt polycondensation with three linear aliphatic diols (ethylene glycol, 1,4-butane diol, and 1,6-hexanediol ) with varied lengths and flexibility to yield six polyesters with molecular weights (Mn) ranging from 10 – 19 kDa, tunable glass transition (Tg ~ 41 - 83 °C), and relatively high thermal stability. Most of the obtained biobased polyesters were amorphous, except for the polymer derived from butanediol and methyl paraben, which showed slow crystallization according to differential scanning calorimetry results. We discovered that the non-cyclic acetal bonds in the poly(acetal-ester)s could be selectively hydrolyzed under mild temperature (70 °C) by varying the acid concentration, offering a potential strategy for chemical recycling. (Less)
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author
; ; ; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Green Chemistry
volume
27
issue
9
pages
11 pages
publisher
Royal Society of Chemistry
external identifiers
  • scopus:85217227398
ISSN
1463-9270
DOI
10.1039/D4GC05778C
language
English
LU publication?
yes
id
621c8725-aed4-4310-ba8d-9f1dda2913ea
date added to LUP
2023-04-24 23:16:54
date last changed
2025-04-09 12:54:54
@article{621c8725-aed4-4310-ba8d-9f1dda2913ea,
  abstract     = {{There is a high demand to design and develop recyclable biobased polymers using eco-friendly synthetic approaches. In this work, we present the facile synthesis of two dicarboxylate monomers with a central non-cyclic acetal unit (dimethyl 4,4'(methylenebis(oxy))dibenzoate and dimethyl 4,4'-(methylenebis(oxy))bis(3-methoxybenzoate)), using potentially biosourced methyl paraben and methyl vanillate. The synthetic parameters were evaluated by a cradle to gate life cycle greenhouse gas emissions aiming to understand the environmental impacts. The two monomers were subjected to melt polycondensation with three linear aliphatic diols (ethylene glycol, 1,4-butane diol, and 1,6-hexanediol ) with varied lengths and flexibility to yield six polyesters with molecular weights (Mn) ranging from 10 – 19 kDa, tunable glass transition (<i>T</i><sub>g</sub> ~ 41 - 83 °C), and relatively high thermal stability. Most of the obtained biobased polyesters were amorphous, except for the polymer derived from butanediol and methyl paraben, which showed slow crystallization according to differential scanning calorimetry results. We discovered that the non-cyclic acetal bonds in the poly(acetal-ester)s could be selectively hydrolyzed under mild temperature (70 °C) by varying the acid concentration, offering a potential strategy for chemical recycling.}},
  author       = {{Warlin, Niklas and Subramaniyan, Sathiyaraj and Garcia Gonzalez, Maria Nelly and N. L. de Menezes, Rafael and Mankar, Smita V. and Valsange, Nitin and Rehnberg, Nicola and Jannasch, Patric and Zhang, Baozhong}},
  issn         = {{1463-9270}},
  language     = {{eng}},
  number       = {{9}},
  pages        = {{2554--2564}},
  publisher    = {{Royal Society of Chemistry}},
  series       = {{Green Chemistry}},
  title        = {{Synthesis and chemical recycling of biobased poly(acetal-ester)s with a non-cyclic acetal unit}},
  url          = {{http://dx.doi.org/10.1039/D4GC05778C}},
  doi          = {{10.1039/D4GC05778C}},
  volume       = {{27}},
  year         = {{2025}},
}