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Green Synthesis of Novel Polyesterurethane Materials from Epoxides and Carbon Dioxide by New Set of One-Dimensional Coordination Polymer Catalyst
[Image: see text] Two novel polyesterurethane materials, PEU1 and PEU2, were synthesized via nontoxic and isocyanate-free route by simple conversion of two epoxides 1,2-epoxy-3-phenoxy propane (2) and styrene epoxide (3) utilizing CO(2). Epoxides 2 and 3 were converted to the respective cyclic carbo...
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2019
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6714527/ https://www.ncbi.nlm.nih.gov/pubmed/31497726 http://dx.doi.org/10.1021/acsomega.9b01922 |
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author | Kundu, Arunangshu De, Gobinda Chandra Ghosh, Sushobhan |
author_facet | Kundu, Arunangshu De, Gobinda Chandra Ghosh, Sushobhan |
author_sort | Kundu, Arunangshu |
collection | PubMed |
description | [Image: see text] Two novel polyesterurethane materials, PEU1 and PEU2, were synthesized via nontoxic and isocyanate-free route by simple conversion of two epoxides 1,2-epoxy-3-phenoxy propane (2) and styrene epoxide (3) utilizing CO(2). Epoxides 2 and 3 were converted to the respective cyclic carbonates 4 and 5 by a new set of cobalt-based catalyst 1a in the presence of 10 bar of CO(2) and 80 °C temperature without using cocatalyst tetrabutylammonium bromide (TBAB). The mechanistic pathway of the catalysis reaction for the cycloaddition of epoxides with CO(2) to generate the cyclic carbonates was investigated by several spectroscopic techniques and utilizing analogous zinc-based 1D coordination polymer 1b, which does not act as an efficient catalyst in the absence of TBAB. Cyclic carbonates 4 and 5 were converted to the respective polyesterurethanes PEU1 and PEU2 sequentially by first synthesizing the ring-opened diols 6 and 7 reacting with ethylenediamine and subsequently annealing the respective diols 6 and 7 at 120 °C in the presence of terepthalyl chloride and triethylamine. The polyesterurethanes PEU1 and PEU2 were characterized by multinuclear NMR and FTIR. PEU1 was also characterized by MALDI-TOF mass spectrometry. The thermal studies of PEU1 and PEU2 showed the stability up to 200–270 °C. The number-average and weight-average molecular weights were determined for PEU1 and PEU2 by GPC analysis. The weight-average molecular weight for PEU1 was found to be 5948 with a polydispersity of 1.1, and PEU2 showed the weight-average molecular weight as 4224 with a polydispersity of 1.06. |
format | Online Article Text |
id | pubmed-6714527 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-67145272019-09-06 Green Synthesis of Novel Polyesterurethane Materials from Epoxides and Carbon Dioxide by New Set of One-Dimensional Coordination Polymer Catalyst Kundu, Arunangshu De, Gobinda Chandra Ghosh, Sushobhan ACS Omega [Image: see text] Two novel polyesterurethane materials, PEU1 and PEU2, were synthesized via nontoxic and isocyanate-free route by simple conversion of two epoxides 1,2-epoxy-3-phenoxy propane (2) and styrene epoxide (3) utilizing CO(2). Epoxides 2 and 3 were converted to the respective cyclic carbonates 4 and 5 by a new set of cobalt-based catalyst 1a in the presence of 10 bar of CO(2) and 80 °C temperature without using cocatalyst tetrabutylammonium bromide (TBAB). The mechanistic pathway of the catalysis reaction for the cycloaddition of epoxides with CO(2) to generate the cyclic carbonates was investigated by several spectroscopic techniques and utilizing analogous zinc-based 1D coordination polymer 1b, which does not act as an efficient catalyst in the absence of TBAB. Cyclic carbonates 4 and 5 were converted to the respective polyesterurethanes PEU1 and PEU2 sequentially by first synthesizing the ring-opened diols 6 and 7 reacting with ethylenediamine and subsequently annealing the respective diols 6 and 7 at 120 °C in the presence of terepthalyl chloride and triethylamine. The polyesterurethanes PEU1 and PEU2 were characterized by multinuclear NMR and FTIR. PEU1 was also characterized by MALDI-TOF mass spectrometry. The thermal studies of PEU1 and PEU2 showed the stability up to 200–270 °C. The number-average and weight-average molecular weights were determined for PEU1 and PEU2 by GPC analysis. The weight-average molecular weight for PEU1 was found to be 5948 with a polydispersity of 1.1, and PEU2 showed the weight-average molecular weight as 4224 with a polydispersity of 1.06. American Chemical Society 2019-08-14 /pmc/articles/PMC6714527/ /pubmed/31497726 http://dx.doi.org/10.1021/acsomega.9b01922 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes. |
spellingShingle | Kundu, Arunangshu De, Gobinda Chandra Ghosh, Sushobhan Green Synthesis of Novel Polyesterurethane Materials from Epoxides and Carbon Dioxide by New Set of One-Dimensional Coordination Polymer Catalyst |
title | Green Synthesis of Novel Polyesterurethane Materials
from Epoxides and Carbon Dioxide by New Set of One-Dimensional Coordination
Polymer Catalyst |
title_full | Green Synthesis of Novel Polyesterurethane Materials
from Epoxides and Carbon Dioxide by New Set of One-Dimensional Coordination
Polymer Catalyst |
title_fullStr | Green Synthesis of Novel Polyesterurethane Materials
from Epoxides and Carbon Dioxide by New Set of One-Dimensional Coordination
Polymer Catalyst |
title_full_unstemmed | Green Synthesis of Novel Polyesterurethane Materials
from Epoxides and Carbon Dioxide by New Set of One-Dimensional Coordination
Polymer Catalyst |
title_short | Green Synthesis of Novel Polyesterurethane Materials
from Epoxides and Carbon Dioxide by New Set of One-Dimensional Coordination
Polymer Catalyst |
title_sort | green synthesis of novel polyesterurethane materials
from epoxides and carbon dioxide by new set of one-dimensional coordination
polymer catalyst |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6714527/ https://www.ncbi.nlm.nih.gov/pubmed/31497726 http://dx.doi.org/10.1021/acsomega.9b01922 |
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