Cargando…

Upgrading Polyurethanes into Functional Ureas through the Asymmetric Chemical Deconstruction of Carbamates

[Image: see text] The importance of systematic and efficient recycling of all forms of plastic is no longer a matter for debate. Constituting the sixth most produced polymer family worldwide, polyurethanes, which are used in a broad variety of applications (buildings, electronics, adhesives, sealant...

Descripción completa

Detalles Bibliográficos
Autores principales: Olazabal, Ion, González, Alba, Vallejos, Saúl, Rivilla, Iván, Jehanno, Coralie, Sardon, Haritz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9832924/
https://www.ncbi.nlm.nih.gov/pubmed/36643003
http://dx.doi.org/10.1021/acssuschemeng.2c05647
_version_ 1784868156984000512
author Olazabal, Ion
González, Alba
Vallejos, Saúl
Rivilla, Iván
Jehanno, Coralie
Sardon, Haritz
author_facet Olazabal, Ion
González, Alba
Vallejos, Saúl
Rivilla, Iván
Jehanno, Coralie
Sardon, Haritz
author_sort Olazabal, Ion
collection PubMed
description [Image: see text] The importance of systematic and efficient recycling of all forms of plastic is no longer a matter for debate. Constituting the sixth most produced polymer family worldwide, polyurethanes, which are used in a broad variety of applications (buildings, electronics, adhesives, sealants, etc.), are particularly important to recycle. In this study, polyurethanes are selectively recycled to obtain high value-added molecules. It is demonstrated that depolymerization reactions performed with secondary amines selectively cleave the C–O bond of the urethane group, while primary amines unselectively break C–O and C–N bonds. The selective cleavage of C–O bonds, catalyzed by an acid:base mixture, led to the initial polyol and a functional diurea in several hours to a few minutes for both model polyurethanes and commercial polyurethane foams. Different secondary amines were employed as nucleophiles to synthesize a small library of diureas obtained in good to excellent yields. This study not only targets the recovery of the initial polyol but also aims to form new diureas which are useful building blocks for the polymerization of innovative materials.
format Online
Article
Text
id pubmed-9832924
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-98329242023-01-12 Upgrading Polyurethanes into Functional Ureas through the Asymmetric Chemical Deconstruction of Carbamates Olazabal, Ion González, Alba Vallejos, Saúl Rivilla, Iván Jehanno, Coralie Sardon, Haritz ACS Sustain Chem Eng [Image: see text] The importance of systematic and efficient recycling of all forms of plastic is no longer a matter for debate. Constituting the sixth most produced polymer family worldwide, polyurethanes, which are used in a broad variety of applications (buildings, electronics, adhesives, sealants, etc.), are particularly important to recycle. In this study, polyurethanes are selectively recycled to obtain high value-added molecules. It is demonstrated that depolymerization reactions performed with secondary amines selectively cleave the C–O bond of the urethane group, while primary amines unselectively break C–O and C–N bonds. The selective cleavage of C–O bonds, catalyzed by an acid:base mixture, led to the initial polyol and a functional diurea in several hours to a few minutes for both model polyurethanes and commercial polyurethane foams. Different secondary amines were employed as nucleophiles to synthesize a small library of diureas obtained in good to excellent yields. This study not only targets the recovery of the initial polyol but also aims to form new diureas which are useful building blocks for the polymerization of innovative materials. American Chemical Society 2022-12-27 2023-01-09 /pmc/articles/PMC9832924/ /pubmed/36643003 http://dx.doi.org/10.1021/acssuschemeng.2c05647 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Olazabal, Ion
González, Alba
Vallejos, Saúl
Rivilla, Iván
Jehanno, Coralie
Sardon, Haritz
Upgrading Polyurethanes into Functional Ureas through the Asymmetric Chemical Deconstruction of Carbamates
title Upgrading Polyurethanes into Functional Ureas through the Asymmetric Chemical Deconstruction of Carbamates
title_full Upgrading Polyurethanes into Functional Ureas through the Asymmetric Chemical Deconstruction of Carbamates
title_fullStr Upgrading Polyurethanes into Functional Ureas through the Asymmetric Chemical Deconstruction of Carbamates
title_full_unstemmed Upgrading Polyurethanes into Functional Ureas through the Asymmetric Chemical Deconstruction of Carbamates
title_short Upgrading Polyurethanes into Functional Ureas through the Asymmetric Chemical Deconstruction of Carbamates
title_sort upgrading polyurethanes into functional ureas through the asymmetric chemical deconstruction of carbamates
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9832924/
https://www.ncbi.nlm.nih.gov/pubmed/36643003
http://dx.doi.org/10.1021/acssuschemeng.2c05647
work_keys_str_mv AT olazabalion upgradingpolyurethanesintofunctionalureasthroughtheasymmetricchemicaldeconstructionofcarbamates
AT gonzalezalba upgradingpolyurethanesintofunctionalureasthroughtheasymmetricchemicaldeconstructionofcarbamates
AT vallejossaul upgradingpolyurethanesintofunctionalureasthroughtheasymmetricchemicaldeconstructionofcarbamates
AT rivillaivan upgradingpolyurethanesintofunctionalureasthroughtheasymmetricchemicaldeconstructionofcarbamates
AT jehannocoralie upgradingpolyurethanesintofunctionalureasthroughtheasymmetricchemicaldeconstructionofcarbamates
AT sardonharitz upgradingpolyurethanesintofunctionalureasthroughtheasymmetricchemicaldeconstructionofcarbamates