Exploring Acrylic Acid as an Oxirane Nucleophile: Direct Access to Poly(β‐Hydroxy Acrylates)

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Main Authors: Céline Montanari, Lukas Marcos Celada, Wenhao Zhang, Peter Olsén
Format: Artículo Open Access
Published: Wiley 2025
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author Céline Montanari
Lukas Marcos Celada
Wenhao Zhang
Peter Olsén
author_facet Céline Montanari
Lukas Marcos Celada
Wenhao Zhang
Peter Olsén
Céline Montanari
Lukas Marcos Celada
Wenhao Zhang
Peter Olsén
collection Wiley Open Access
contents Exploring Acrylic Acid as an Oxirane Nucleophile: Direct Access to Poly(β‐Hydroxy Acrylates) Céline Montanari Lukas Marcos Celada Wenhao Zhang Peter Olsén ChemSusChem The synthetic freedom to operate is highly dependent on the final application. In polymer science, scalable reactions, simple purification, and the ideal use of renewable and relevant precursors are relied on. This work explores the ring‐opening of oxiranes with acrylic acid (AA) toward β‐hydroxy acrylates; great care is given to the synthetic aspects of the transformation. In addition to its simplicity, and high yield (isolated yield 68%–87%), the methodology is scalable, atom‐economic, and associated with simple purification. Dependent on the initial oxirane, access to a wide range of polymeric properties with a modulus ranging from 0.3 to 630 MPa, strength from 0.3 to 19 MPa, and elongation‐at‐break from 3% to 170% is demonstrated. All four polymers explored are thermally stable above 250 °C and highly transparent. This work emphasizes the potential of AA as a nucleophile for direct access to monomers for a wide range of polymer applications. 10.1002/cssc.202500575 http://creativecommons.org/licenses/by/4.0/
doi_str_mv 10.1002/cssc.202500575
format Artículo Open Access
id wiley_oa_10_1002_cssc_202500575
institution Wiley Open Access
license_str_mv http://creativecommons.org/licenses/by/4.0/
publishDate 2025
publisher Wiley
record_format wiley_oa
spellingShingle Exploring Acrylic Acid as an Oxirane Nucleophile: Direct Access to Poly(β‐Hydroxy Acrylates)
Céline Montanari
Lukas Marcos Celada
Wenhao Zhang
Peter Olsén
ChemSusChem
Exploring Acrylic Acid as an Oxirane Nucleophile: Direct Access to Poly(β‐Hydroxy Acrylates) Céline Montanari Lukas Marcos Celada Wenhao Zhang Peter Olsén ChemSusChem The synthetic freedom to operate is highly dependent on the final application. In polymer science, scalable reactions, simple purification, and the ideal use of renewable and relevant precursors are relied on. This work explores the ring‐opening of oxiranes with acrylic acid (AA) toward β‐hydroxy acrylates; great care is given to the synthetic aspects of the transformation. In addition to its simplicity, and high yield (isolated yield 68%–87%), the methodology is scalable, atom‐economic, and associated with simple purification. Dependent on the initial oxirane, access to a wide range of polymeric properties with a modulus ranging from 0.3 to 630 MPa, strength from 0.3 to 19 MPa, and elongation‐at‐break from 3% to 170% is demonstrated. All four polymers explored are thermally stable above 250 °C and highly transparent. This work emphasizes the potential of AA as a nucleophile for direct access to monomers for a wide range of polymer applications. 10.1002/cssc.202500575 http://creativecommons.org/licenses/by/4.0/
title Exploring Acrylic Acid as an Oxirane Nucleophile: Direct Access to Poly(β‐Hydroxy Acrylates)
topic ChemSusChem
url https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cssc.202500575