Issue 16, 2017
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RSC Advances

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, ORCID logo 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  

* 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.

Graphical abstract: 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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DOI
https://doi.org/10.1039/C6RA28659C
Article type
Paper
Submitted
24 Dec 2016
Accepted
24 Jan 2017
First published
31 Jan 2017
This article is Open Access
Creative Commons BY license

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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