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Hydrogen Peroxide Treatment of Softwood-Derived Poly(Ethylene Glycol)-Modified Glycol Lignin at Room Temperature

Recently, a large-scale production system of softwood-derived poly(ethylene glycol) (PEG)-modified glycol lignin (GL) was developed to produce high-quality lignin derivatives with substantially controlled chemical structures and attractive thermal properties. In this study, the further upgrading of...

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Detalles Bibliográficos
Autores principales: Nge, Thi Thi, Tobimatsu, Yuki, Takahashi, Shiho, Umezawa, Toshiaki, Yamada, Tatsuhiko
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9968004/
https://www.ncbi.nlm.nih.gov/pubmed/36838528
http://dx.doi.org/10.3390/molecules28041542
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author Nge, Thi Thi
Tobimatsu, Yuki
Takahashi, Shiho
Umezawa, Toshiaki
Yamada, Tatsuhiko
author_facet Nge, Thi Thi
Tobimatsu, Yuki
Takahashi, Shiho
Umezawa, Toshiaki
Yamada, Tatsuhiko
author_sort Nge, Thi Thi
collection PubMed
description Recently, a large-scale production system of softwood-derived poly(ethylene glycol) (PEG)-modified glycol lignin (GL) was developed to produce high-quality lignin derivatives with substantially controlled chemical structures and attractive thermal properties. In this study, the further upgrading of GL properties with carboxy functionalization was demonstrated through the room-temperature hydrogen peroxide (H(2)O(2)) treatment with the mass ratio of H(2)O(2) to GL, 1:1 and 1:3, for 7 d. The changes in the chemical structure, carboxy group content, molecular weight, and thermal properties of the insoluble portions of partially oxidized glycol lignins (OGLs) were then investigated. Nuclear magnetic resonance and thioacidolysis data revealed that the oxidative functionalization involved the cleavage of β–O–4 linkages and the oxidative cleavage of guaiacyl aromatic rings into muconic acid-type structures. This was validated by attenuated total reflectance-Fourier transform infrared (ATR-FTIR) spectroscopy and potentiometric titration. Overall, the results suggested that the varying outcomes of carboxy group content (0.81–2.04 mmol/g OGL) after 7-d treatment depended on the type of the GL origin having varying amounts of the retained native lignin structure (e.g., β–O–4 linkages), which were prepared from different source-wood-meal sizes and PEG molecular masses.
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spelling pubmed-99680042023-02-27 Hydrogen Peroxide Treatment of Softwood-Derived Poly(Ethylene Glycol)-Modified Glycol Lignin at Room Temperature Nge, Thi Thi Tobimatsu, Yuki Takahashi, Shiho Umezawa, Toshiaki Yamada, Tatsuhiko Molecules Article Recently, a large-scale production system of softwood-derived poly(ethylene glycol) (PEG)-modified glycol lignin (GL) was developed to produce high-quality lignin derivatives with substantially controlled chemical structures and attractive thermal properties. In this study, the further upgrading of GL properties with carboxy functionalization was demonstrated through the room-temperature hydrogen peroxide (H(2)O(2)) treatment with the mass ratio of H(2)O(2) to GL, 1:1 and 1:3, for 7 d. The changes in the chemical structure, carboxy group content, molecular weight, and thermal properties of the insoluble portions of partially oxidized glycol lignins (OGLs) were then investigated. Nuclear magnetic resonance and thioacidolysis data revealed that the oxidative functionalization involved the cleavage of β–O–4 linkages and the oxidative cleavage of guaiacyl aromatic rings into muconic acid-type structures. This was validated by attenuated total reflectance-Fourier transform infrared (ATR-FTIR) spectroscopy and potentiometric titration. Overall, the results suggested that the varying outcomes of carboxy group content (0.81–2.04 mmol/g OGL) after 7-d treatment depended on the type of the GL origin having varying amounts of the retained native lignin structure (e.g., β–O–4 linkages), which were prepared from different source-wood-meal sizes and PEG molecular masses. MDPI 2023-02-05 /pmc/articles/PMC9968004/ /pubmed/36838528 http://dx.doi.org/10.3390/molecules28041542 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Nge, Thi Thi
Tobimatsu, Yuki
Takahashi, Shiho
Umezawa, Toshiaki
Yamada, Tatsuhiko
Hydrogen Peroxide Treatment of Softwood-Derived Poly(Ethylene Glycol)-Modified Glycol Lignin at Room Temperature
title Hydrogen Peroxide Treatment of Softwood-Derived Poly(Ethylene Glycol)-Modified Glycol Lignin at Room Temperature
title_full Hydrogen Peroxide Treatment of Softwood-Derived Poly(Ethylene Glycol)-Modified Glycol Lignin at Room Temperature
title_fullStr Hydrogen Peroxide Treatment of Softwood-Derived Poly(Ethylene Glycol)-Modified Glycol Lignin at Room Temperature
title_full_unstemmed Hydrogen Peroxide Treatment of Softwood-Derived Poly(Ethylene Glycol)-Modified Glycol Lignin at Room Temperature
title_short Hydrogen Peroxide Treatment of Softwood-Derived Poly(Ethylene Glycol)-Modified Glycol Lignin at Room Temperature
title_sort hydrogen peroxide treatment of softwood-derived poly(ethylene glycol)-modified glycol lignin at room temperature
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9968004/
https://www.ncbi.nlm.nih.gov/pubmed/36838528
http://dx.doi.org/10.3390/molecules28041542
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