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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Main Authors:	Berthold Reis, Niklas Gerlach, Christine Steinbach, Karina Haro Carrasco, Marina Oelmann, Simona Schwarz, Martin Müller, Dana Schwarz
Format:	Article
Language:	English
Published:	MDPI AG 2021-07-01
Series:	Marine Drugs
Subjects:	hexanoyl chitosan chitosan modification substitution degree pH variation
Online Access:	https://www.mdpi.com/1660-3397/19/7/385

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spelling	doaj-deaaba93801340878526e8c7e3e7d2642021-07-23T13:51:07ZengMDPI AGMarine Drugs1660-33972021-07-011938538510.3390/md19070385A Complementary and Revised View on the N-Acylation of Chitosan with Hexanoyl ChlorideBerthold Reis0Niklas Gerlach1Christine Steinbach2Karina Haro Carrasco3Marina Oelmann4Simona Schwarz5Martin Müller6Dana Schwarz7Leibniz-Institut fuer Polymerforschung Dresden e.V., Hohe Straße 6, 01069 Dresden, GermanyLeibniz-Institut fuer Polymerforschung Dresden e.V., Hohe Straße 6, 01069 Dresden, GermanyLeibniz-Institut fuer Polymerforschung Dresden e.V., Hohe Straße 6, 01069 Dresden, GermanyLeibniz-Institut fuer Polymerforschung Dresden e.V., Hohe Straße 6, 01069 Dresden, GermanyLeibniz-Institut fuer Polymerforschung Dresden e.V., Hohe Straße 6, 01069 Dresden, GermanyLeibniz-Institut fuer Polymerforschung Dresden e.V., Hohe Straße 6, 01069 Dresden, GermanyLeibniz-Institut fuer Polymerforschung Dresden e.V., Hohe Straße 6, 01069 Dresden, GermanyLeibniz-Institut fuer Polymerforschung Dresden e.V., Hohe Straße 6, 01069 Dresden, GermanyThe 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 <sup>1</sup>H-NMR, FTIR, and potentiometric titration were compared and discussed regarding their accuracy and precision. <sup>1</sup>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<sup>2+</sup> 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.https://www.mdpi.com/1660-3397/19/7/385hexanoyl chitosanchitosan modificationsubstitution degreepH variation
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Berthold Reis Niklas Gerlach Christine Steinbach Karina Haro Carrasco Marina Oelmann Simona Schwarz Martin Müller Dana Schwarz
spellingShingle	Berthold Reis Niklas Gerlach Christine Steinbach Karina Haro Carrasco Marina Oelmann Simona Schwarz Martin Müller Dana Schwarz A Complementary and Revised View on the N-Acylation of Chitosan with Hexanoyl Chloride Marine Drugs hexanoyl chitosan chitosan modification substitution degree pH variation
author_facet	Berthold Reis Niklas Gerlach Christine Steinbach Karina Haro Carrasco Marina Oelmann Simona Schwarz Martin Müller Dana Schwarz
author_sort	Berthold Reis
title	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_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_sort	complementary and revised view on the n-acylation of chitosan with hexanoyl chloride
publisher	MDPI AG
series	Marine Drugs
issn	1660-3397
publishDate	2021-07-01
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 <sup>1</sup>H-NMR, FTIR, and potentiometric titration were compared and discussed regarding their accuracy and precision. <sup>1</sup>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<sup>2+</sup> 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.
topic	hexanoyl chitosan chitosan modification substitution degree pH variation
url	https://www.mdpi.com/1660-3397/19/7/385
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A Complementary and Revised View on the N-Acylation of Chitosan with Hexanoyl Chloride

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