A mechanistic insight into the organocatalytic properties of imidazolium-based ionic liquids and a positive co-solvent effect on cellulose modification reactions in an ionic liquid

Ryohei Kakuchi; Ryo Ito; Shuhei Nomura; Hadi Abroshan; Kazuaki Ninomiya; Tomoyuki Ikai; Katsuhiro Maeda; Hyung J. Kim; Kenji Takahashi

doi:10.1039/C6RA28659C

A mechanistic insight into the organocatalytic properties of imidazolium-based ionic liquids and a positive co-solvent effect on cellulose modification reactions in an ionic liquid†

Ryohei Kakuchi,

^a Ryo Ito,^c Shuhei Nomura,^a Hadi Abroshan,^e Kazuaki Ninomiya,^b Tomoyuki Ikai,^cd Katsuhiro Maeda,*^cd Hyung J. Kim*^ef and Kenji Takahashi*^a

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* Corresponding authors

^a Faculty of Natural System, Institute of Science and Engineering, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
E-mail: ktkenji@staff.kanazawa-u.ac.jp
Tel: +81-76-234-4828

^b Institute for Frontier Science Initiative, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan

^c Graduate School of Natural Science and Technology, College of Science and Engineering, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
E-mail: maeda@se.kanazawa-u.ac.jp

^d Research Center for Sustainable Energy and Technology, College of Science and Engineering, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan

^e Department of Chemistry, Carnegie Mellon University, Pittsburgh, Pennsylvania 15213, USA
E-mail: hjkim@cmu.edu

^f School of Computational Sciences, Korea Institute for Advanced Study, Seoul 02455, Korea

Abstract

Detailed insights into the organocatalytic properties of imidazolium-based ionic liquids (Im-ILs) for transesterification of cellulose with isopropenyl acetate (IPA) are presented. According to model transesterification reactions and their computational analysis, acetate anions of Im-ILs play an essential role in the promotion of the reactions. Mechanistic considerations in the optimization of the protocol of IL-catalyzed transesterification reactions have enabled a significant improvement in reaction conditions and a positive co-solvent effect for cellulose modifications in an imidazolium acetate ionic liquid.

This article is part of the themed collection: Ionic Liquids: Editors collection for RSC Advances

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DOI: https://doi.org/10.1039/C6RA28659C
Article type: Paper
Submitted: 24 des. 2016
Accepted: 24 jan. 2017
First published: 31 jan. 2017
This article is Open Access

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RSC Adv., 2017,7, 9423-9430

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A mechanistic insight into the organocatalytic properties of imidazolium-based ionic liquids and a positive co-solvent effect on cellulose modification reactions in an ionic liquid

R. Kakuchi, R. Ito, S. Nomura, H. Abroshan, K. Ninomiya, T. Ikai, K. Maeda, H. J. Kim and K. Takahashi, RSC Adv., 2017, 7, 9423 DOI: 10.1039/C6RA28659C

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A mechanistic insight into the organocatalytic properties of imidazolium-based ionic liquids and a positive co-solvent effect on cellulose modification reactions in an ionic liquid†

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A mechanistic insight into the organocatalytic properties of imidazolium-based ionic liquids and a positive co-solvent effect on cellulose modification reactions in an ionic liquid

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