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

Hemming, Ellen B.; Masters, Anthony F.; Perosa, Alvise; Selva, Maurizio; Maschmeyer, Thomas

doi:10.3390/molecules24213986

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

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Thomas Maschmeyer

Laboratory of Advanced Catalysis for Sustainability, School of Chemistry, The University of Sydney, Sydney 2006, Australia

Department of Molecular Sciences and Nanosystems, Università Ca’ Foscari Venezia, Via Torino 155, 30172 Venezia Mestre, Italy

Authors to whom correspondence should be addressed.

Academic Editors: Rafael Luque and Luís Adriano Santos Do Nascimento

Molecules 2019, 24(21), 3986; https://doi.org/10.3390/molecules24213986

Received: 30 September 2019 / Revised: 28 October 2019 / Accepted: 31 October 2019 / Published: 4 November 2019

(This article belongs to the Special Issue Advances in Conversion of Biomass and Waste to Chemicals and Fuels)

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Abstract

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. View Full-Text

Keywords: trimethyl chitosan; green methylating agents; dimethyl carbonate; N-methylation; ionic liquids

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MDPI and ACS Style

Hemming, E.B.; Masters, A.F.; Perosa, A.; Selva, M.; Maschmeyer, T. Single-Step Methylation of Chitosan Using Dimethyl Carbonate as a Green Methylating Agent. Molecules 2019, 24, 3986. https://doi.org/10.3390/molecules24213986

AMA Style

Hemming EB, Masters AF, Perosa A, Selva M, Maschmeyer T. Single-Step Methylation of Chitosan Using Dimethyl Carbonate as a Green Methylating Agent. Molecules. 2019; 24(21):3986. https://doi.org/10.3390/molecules24213986

Chicago/Turabian Style

Hemming, Ellen B., Anthony F. Masters, Alvise Perosa, Maurizio Selva, and Thomas Maschmeyer. 2019. "Single-Step Methylation of Chitosan Using Dimethyl Carbonate as a Green Methylating Agent" Molecules 24, no. 21: 3986. https://doi.org/10.3390/molecules24213986

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

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