Skip to content
Licensed Unlicensed Requires Authentication Published by De Gruyter July 27, 2018

A synergetic effect of ionic liquid and microwave irradiation on the acid-catalyzed direct conversion of cellulose into methyl glucopyranoside

  • Mafuyu Saito , Takao Kishimoto EMAIL logo , Masahiro Hamada , Noriyuki Nakajima and Daisuke Urabe
From the journal Holzforschung


Conversion of lignocellulose into useful chemicals is an important research topic in the area of biomass utilization. In this study, microcrystalline cellulose (MC) was dissolved in a mixed-solvent system containing the ionic liquid (IL) 1-allyl-3-methylimidazolium chloride ([Amim]Cl) and N-methyl-pyrrolidone (NMP), and the cellulose was directly converted into methyl glucoside (MG) by acid-catalyzed methanolysis aided by microwave irradiation (μWIr). Under moderate reaction temperature and pressure, and in the presence of acetyl chloride/methanol (in situ formed HCl) as an acid catalyst, MG was obtained in a 42% yield. In contrast, in the absence of either IL or μWIr, the MG yield was only 5 or 21%, respectively. Both μWIr and the dissolution of cellulose in IL were quite effective for the conversion of cellulose into MG.

Award Identifier / Grant number: JP16H04957

Funding statement: Part of this work was supported by JSPS, Funder Id: 10.13039/501100001691, KAKENHI Grant Number JP16H04957.


The authors are very grateful to Dr. Suzuki at Forest Products Research Institute, Toyama Prefectural Agricultural, Forestry and Fisheries Research Center in Japan, for the GC-MC analysis of the reaction products.

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Employment or leadership: None declared.

  3. Honorarium: None declared.


Azubuike, C.P., Rodríguez, H., Okhamafe, A.O., Rogers, R.D. (2012) Physicochemical properties of maize cob cellulose powders reconstituted from ionic liquid solution. Cellulose 19:425–433.10.1007/s10570-011-9631-ySearch in Google Scholar

Brandt, A., Graesvik, J., Hallett, J.P., Welton, T. (2013) Deconstruction of lignocellulosic biomass with ionic liquids. Green Chemistry 15:550–583.10.1039/c2gc36364jSearch in Google Scholar

Climent, M.J., Corma, A., Iborra, S., Martinez-Silvestre, S. (2016) Transformation of cellulose into nonionic surfactants using a one-pot catalytic process. Chem. Sus. Chem. 9:3492–3502.10.1002/cssc.201600977Search in Google Scholar PubMed

De la Hoz, A., Loupy, A. (Eds.) Microwave in Organic Synthesis (Wiley-VCH, Weinheim, Germany) 3rd edition, Vol. 1 and 2., 2012.10.1002/9783527651313Search in Google Scholar

Deng, W., Liu, M., Zhang, Q., Tan, X., Wang, Y. (2010) Acid-catalyzed direct transformation of cellulose into methyl glucosides in methanol at moderate temperature. Chem. Commum. 46:2668–2670.10.1039/b925723cSearch in Google Scholar PubMed

Dora, S., Bhaskar, T., Singh, B., Naik, D.V., Adhikari, D.K. (2012) Effective catalytic conversion of cellulose into high yields of methyl glucosides over sulfonated carbon based catalyst. Bioresour. Technol. 120:318–321.10.1016/j.biortech.2012.06.036Search in Google Scholar PubMed

Ishikawa, Y., Saka, S. (2001) Chemical conversion of cellulose as treated in supercritical methanol. Cellulose 8:189–195.10.1023/A:1013170020469Search in Google Scholar

Obermayer, D., Gutmann, B., Kappe, O. (2009) Microwave chemistry in silicon carbide reaction vials: separating thermal from nonthermal effects. Angew. Chemie. 48:8321–8324.10.1002/anie.200904185Search in Google Scholar PubMed

Peleteiro, S., Rivas, S., Alonso, J.L., Santos, V., Parajo, J.C. (2016) Furfural production using ionic liquids: a review. Bioresour. Technol. 202:181–191.10.1016/j.biortech.2015.12.017Search in Google Scholar PubMed

Qu, C., Kishimoto, T., Kishino, M., Hamada, M., Nakajima, N. (2011) Heteronuclear single-quantum coherence nuclear magnetic resonance (HSQC NMR) characterization of acetylated fir (Abies sachallnensis MAST) wood regenerated from ionic liquid. J. Agric. Food Chem. 59:5382–5389.10.1021/jf200498nSearch in Google Scholar PubMed

Qu, C., Kishimoto, T., Ogita, S., Hamada, M., Nakajima, N. (2012) Dissolution and acetylation of ball-milled birch (Betula platyphylla) and bamboo (Phyllostachys nigra) in the ionic liquid [Bmim]Cl for HSQC NMR analysis. Holzforschung 66:607–614.10.1515/hf.2011.186Search in Google Scholar

Qu, C., Kishimoto, T., Hamada, M., Nakajima, N. (2013a) Dissolution and acetylation of ball-milled lignocellulosic biomass in ionic liquids at room temperature: application to nuclear magnetic resonance analysis of cell-wall components. Holzforschung 67:25–32.10.1515/hf-2012-0037Search in Google Scholar

Qu, C., Kishimoto, T., Hamada, M., Nakajima, N. (2013b) Molecular weight distributions of acetylated lignocellulosic biomasses recovered from an ionic liquid system. Holzforschung 67:721–726.10.1515/hf-2012-0192Search in Google Scholar

Swatloski, R.P., Spear, S.K., Holbrey, J.D., Rogers, R.D. (2002) Dissolution of cellulose with ionic liquids. J. Am. Chem. Soc. 124:4974–4975.10.1021/ja025790mSearch in Google Scholar PubMed

Tao, J., Kishimoto, T., Suzuki, S., Hamada, M., Nakajima, N. (2016a) Superior cellulose-protective effects of cosolvent during enhanced dissolution in imidazolium ionic liquid. Holzforschung 70:519–525.10.1515/hf-2015-0116Search in Google Scholar

Tao, J., Kishimoto, T., Hamada, M., Nakajima, N. (2016b) Novel cellulose pretreatment solvent: phosphonium-based amino acid ionic liquid/cosolvent for enhanced enzymatic hydrolysis of cellulose. Holzforschung 70: 911–917.10.1515/hf-2016-0017Search in Google Scholar

Tao, J., Kishimoto, T., Hamada, M., Nakajima, N. (2017) Enzymatic synthesis of methyl β-D-glucoside directly from cellulose pretreated with biocompatible amino acid ionic liquid/cosolvent. Holzforschung 71:21–26.10.1515/hf-2016-0091Search in Google Scholar

Villandier, N., Corma, A. (2011) Transformation of cellulose into biodegradable alkyl glycosides by following two different chemical routes. Chem. Sus. Chem. 4:508–513.10.1002/cssc.201000371Search in Google Scholar PubMed

Wang, H., Gurau, G., Rogers, R.D. (2012) Ionic liquid processing of cellulose. Chem. Soc. Rev. 41:1519–1537.10.1039/c2cs15311dSearch in Google Scholar PubMed

Zhang, H., Wu, J., Zhang, J., He, J. (2005) 1-Allyl-3-methylimidazolium chloride room temperature ionic liquid: a new and powerful nonderivatizing solvent for cellulose. Macromolecules 38:8272–8277.10.1021/ma0505676Search in Google Scholar

Zhu, S., Guo, J., Wang, X., Wang, J., Fan, W. (2017) Alcoholysis: a promising technology for conversion of lignocellulose and platform chemicals. Chem. Sus. Chem. 10:2547–2559.10.1002/cssc.201700597Search in Google Scholar PubMed

Received: 2018-01-30
Accepted: 2018-06-27
Published Online: 2018-07-27
Published in Print: 2018-12-19

©2018 Walter de Gruyter GmbH, Berlin/Boston

Downloaded on 28.5.2023 from
Scroll to top button