Single-Step Methylation of Chitosan Using Dimethyl Carbonate as a Green Methylating Agent

N,N,N-Trimethyl chitosan (TMC) is one chitosan derivative that, because of its improved solubility, has been studied for industrial and pharmaceutic applications. Conventional methods for the synthesis of TMC involve the use of highly toxic and harmful reagents, such as methyl iodide and dimethyl su...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Vol. 24; no. 21; p. 3986
Main Authors: Hemming, Ellen B., Masters, Anthony F., Perosa, Alvise, Selva, Maurizio, Maschmeyer, Thomas
Format: Journal Article
Language:English
Published: Switzerland MDPI AG 04.11.2019
MDPI
Subjects:
Cellulose
Chitosan - chemistry
dimethyl carbonate
Formates - chemistry
green methylating agents
ionic liquids
Ionic Liquids - chemistry
n-methylation
Polymers
Reagents
Solvents
trimethyl chitosan
dimethyl carbonate
N-methylation
green methylating agents
ionic liquids
trimethyl chitosan
ISSN:1420-3049, 1420-3049
Online Access:Get full text
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Summary:N,N,N-Trimethyl chitosan (TMC) is one chitosan derivative that, because of its improved solubility, has been studied for industrial and pharmaceutic applications. Conventional methods for the synthesis of TMC involve the use of highly toxic and harmful reagents, such as methyl iodide and dimethyl sulfate (DMS). Although the methylation of dimethylated chitosan to TMC by dimethyl carbonate (DMC, a green and benign methylating agent) was reported recently, it involved a formaldehyde-based procedure. In this paper we report the single-step synthesis of TMC from chitosan using DMC in an ionic liquid. The TMC synthesised was characterised by 1H NMR spectroscopy and a functionally meaningful degree of quaternisation of 9% was demonstrated after a 12-h reaction time.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules24213986