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A Complementary and Revised View on the N-Acylation of Chitosan with Hexanoyl Chloride

The modification of the biobased polymer chitosan is a broad and widely studied field. Herein, an insight into the hydrophobization of low-molecular-weight chitosan by substitution of amino functionalities with hexanoyl chloride is reported. Thereby, the influence of the pH of the reaction media was...

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Autores principales: Reis, Berthold, Gerlach, Niklas, Steinbach, Christine, Haro Carrasco, Karina, Oelmann, Marina, Schwarz, Simona, Müller, Martin, Schwarz, Dana
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8303196/
https://www.ncbi.nlm.nih.gov/pubmed/34356810
http://dx.doi.org/10.3390/md19070385
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author Reis, Berthold
Gerlach, Niklas
Steinbach, Christine
Haro Carrasco, Karina
Oelmann, Marina
Schwarz, Simona
Müller, Martin
Schwarz, Dana
author_facet Reis, Berthold
Gerlach, Niklas
Steinbach, Christine
Haro Carrasco, Karina
Oelmann, Marina
Schwarz, Simona
Müller, Martin
Schwarz, Dana
author_sort Reis, Berthold
collection PubMed
description The modification of the biobased polymer chitosan is a broad and widely studied field. Herein, an insight into the hydrophobization of low-molecular-weight chitosan by substitution of amino functionalities with hexanoyl chloride is reported. Thereby, the influence of the pH of the reaction media was investigated. Further, methods for the determination of the degree of substitution based on (1)H-NMR, FTIR, and potentiometric titration were compared and discussed regarding their accuracy and precision. (1)H-NMR was the most accurate method, while FTIR and the potentiometric titration, though precise and reproducible, underlie the influence of complete protonation and solubility issues. Additionally, the impact of the pH variation during the synthesis on the properties of the samples was investigated by Cd(2+) sorption experiments. The adjusted pH values during the synthesis and, therefore, the obtained degrees of substitution possessed a strong impact on the adsorption properties of the final material.
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spelling pubmed-83031962021-07-25 A Complementary and Revised View on the N-Acylation of Chitosan with Hexanoyl Chloride Reis, Berthold Gerlach, Niklas Steinbach, Christine Haro Carrasco, Karina Oelmann, Marina Schwarz, Simona Müller, Martin Schwarz, Dana Mar Drugs Article The modification of the biobased polymer chitosan is a broad and widely studied field. Herein, an insight into the hydrophobization of low-molecular-weight chitosan by substitution of amino functionalities with hexanoyl chloride is reported. Thereby, the influence of the pH of the reaction media was investigated. Further, methods for the determination of the degree of substitution based on (1)H-NMR, FTIR, and potentiometric titration were compared and discussed regarding their accuracy and precision. (1)H-NMR was the most accurate method, while FTIR and the potentiometric titration, though precise and reproducible, underlie the influence of complete protonation and solubility issues. Additionally, the impact of the pH variation during the synthesis on the properties of the samples was investigated by Cd(2+) sorption experiments. The adjusted pH values during the synthesis and, therefore, the obtained degrees of substitution possessed a strong impact on the adsorption properties of the final material. MDPI 2021-07-02 /pmc/articles/PMC8303196/ /pubmed/34356810 http://dx.doi.org/10.3390/md19070385 Text en © 2021 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
Reis, Berthold
Gerlach, Niklas
Steinbach, Christine
Haro Carrasco, Karina
Oelmann, Marina
Schwarz, Simona
Müller, Martin
Schwarz, Dana
A Complementary and Revised View on the N-Acylation of Chitosan with Hexanoyl Chloride
title A Complementary and Revised View on the N-Acylation of Chitosan with Hexanoyl Chloride
title_full A Complementary and Revised View on the N-Acylation of Chitosan with Hexanoyl Chloride
title_fullStr A Complementary and Revised View on the N-Acylation of Chitosan with Hexanoyl Chloride
title_full_unstemmed A Complementary and Revised View on the N-Acylation of Chitosan with Hexanoyl Chloride
title_short A Complementary and Revised View on the N-Acylation of Chitosan with Hexanoyl Chloride
title_sort complementary and revised view on the n-acylation of chitosan with hexanoyl chloride
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8303196/
https://www.ncbi.nlm.nih.gov/pubmed/34356810
http://dx.doi.org/10.3390/md19070385
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