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Synthesis of cyclic α-pinane carbonate – a potential monomer for bio-based polymers
This work reports the first known synthesis of α-pinane carbonate from an α-pinene derivative. Pinane carbonate is potentially useful as a monomer for poly(pinane carbonate), which would be a sustainable bio-based polymer. α-Pinene is a major waste product from the pulp and paper industries and the...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9192141/ https://www.ncbi.nlm.nih.gov/pubmed/35765421 http://dx.doi.org/10.1039/d1ra07943c |
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author | Eze, Valentine C. Rehman, Abdul Patel, Manthan Ahmad, Sajjad Harvey, Adam P. |
author_facet | Eze, Valentine C. Rehman, Abdul Patel, Manthan Ahmad, Sajjad Harvey, Adam P. |
author_sort | Eze, Valentine C. |
collection | PubMed |
description | This work reports the first known synthesis of α-pinane carbonate from an α-pinene derivative. Pinane carbonate is potentially useful as a monomer for poly(pinane carbonate), which would be a sustainable bio-based polymer. α-Pinene is a major waste product from the pulp and paper industries and the most naturally abundant monoterpene in turpentine oil. α-Pinene is routinely converted to pinene oxide and pinanediol, but no study has yet demonstrated the conversion of pinanediol into α-pinane carbonate. Here, α-pinane carbonate was synthesised via carboxylation of α-pinanediol with dimethyl carbonate under base catalysis using triazabicyclodecene guanidine (TBD). 81.1 ± 2.8% α-pinane carbonate yield was achieved at 98.7% purity. The produced α-pinane carbonate was a white crystalline solid with a melting point of 86 °C. It was characterised using FTIR, NMR, GCMS and a quadrupole time-of-flight (QTOF) mass spectrometer. The FTIR exhibited a C[double bond, length as m-dash]O peak at 1794 cm(−1) confirming the presence of a cyclic carbonate. GCMS showed that the α-pinane carbonate fragments with loss of CO(2), forming pinene epoxide. Base hydrolysis of the α-pinane carbonate using NaOH/ethanol/water regenerated the pinanediol with formations of Na(2)CO(3). |
format | Online Article Text |
id | pubmed-9192141 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-91921412022-06-27 Synthesis of cyclic α-pinane carbonate – a potential monomer for bio-based polymers Eze, Valentine C. Rehman, Abdul Patel, Manthan Ahmad, Sajjad Harvey, Adam P. RSC Adv Chemistry This work reports the first known synthesis of α-pinane carbonate from an α-pinene derivative. Pinane carbonate is potentially useful as a monomer for poly(pinane carbonate), which would be a sustainable bio-based polymer. α-Pinene is a major waste product from the pulp and paper industries and the most naturally abundant monoterpene in turpentine oil. α-Pinene is routinely converted to pinene oxide and pinanediol, but no study has yet demonstrated the conversion of pinanediol into α-pinane carbonate. Here, α-pinane carbonate was synthesised via carboxylation of α-pinanediol with dimethyl carbonate under base catalysis using triazabicyclodecene guanidine (TBD). 81.1 ± 2.8% α-pinane carbonate yield was achieved at 98.7% purity. The produced α-pinane carbonate was a white crystalline solid with a melting point of 86 °C. It was characterised using FTIR, NMR, GCMS and a quadrupole time-of-flight (QTOF) mass spectrometer. The FTIR exhibited a C[double bond, length as m-dash]O peak at 1794 cm(−1) confirming the presence of a cyclic carbonate. GCMS showed that the α-pinane carbonate fragments with loss of CO(2), forming pinene epoxide. Base hydrolysis of the α-pinane carbonate using NaOH/ethanol/water regenerated the pinanediol with formations of Na(2)CO(3). The Royal Society of Chemistry 2022-06-13 /pmc/articles/PMC9192141/ /pubmed/35765421 http://dx.doi.org/10.1039/d1ra07943c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Eze, Valentine C. Rehman, Abdul Patel, Manthan Ahmad, Sajjad Harvey, Adam P. Synthesis of cyclic α-pinane carbonate – a potential monomer for bio-based polymers |
title | Synthesis of cyclic α-pinane carbonate – a potential monomer for bio-based polymers |
title_full | Synthesis of cyclic α-pinane carbonate – a potential monomer for bio-based polymers |
title_fullStr | Synthesis of cyclic α-pinane carbonate – a potential monomer for bio-based polymers |
title_full_unstemmed | Synthesis of cyclic α-pinane carbonate – a potential monomer for bio-based polymers |
title_short | Synthesis of cyclic α-pinane carbonate – a potential monomer for bio-based polymers |
title_sort | synthesis of cyclic α-pinane carbonate – a potential monomer for bio-based polymers |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9192141/ https://www.ncbi.nlm.nih.gov/pubmed/35765421 http://dx.doi.org/10.1039/d1ra07943c |
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