Abstract
Recently, a method was presented for the dissolution and nuclear magnetic resonance analysis of cell wall components in lignocellulosic biomass, which involves cell wall ball-milling, dissolution in ionic liquids (ILs), in situ acetylation, and the recovery of acetylated materials. However, the dissolution in ILs and the relatively long ball-milling times may partially degrade the plant cell wall components. In the present study, the molecular weight (MW) distributions of acetylated biomasses from fir (Abies sachalinensis), birch (Betula platyphylla), and bamboo (Phyllostachys nigra) recovered from IL systems were examined by size exclusion chromatography. The effects of IL types, cosolvents, dissolution temperatures and times, and ball-milling times were evaluated. The MW of acetylated fir woods recovered from 1-allyl-3-methylimidazolium chloride at 30–80°C or from 1-butyl-3-methylimidazolium chloride at 100°C for 2 h were similar to those materials that were recovered from the N-methylimidazole/dimethyl sulfoxide system. In contrast, a significant decrease in MW was observed with 1-ethyl-3-methylimidazolium acetate ([Emim]OAc) even at 30°C. The degradation of cell wall components in [Emim]OAc was reduced to some extent in the presence of N,N-dimethylacetamide or pyridine. The MW decreased gradually with increased ball-milling time.
References
Bentivoglio, G., Röder, T., Fasching, M., Buchberger, M., Schottenberger, H., Sixta, H. (2006) Cellulose processing with chloride-based ionic liquids. Lenzinger Berichte. 86:154–161.Search in Google Scholar
Fort, D.A., Remsing, R.C., Swatloski, R.P., Moyna, P., Moyna, G., Rogers, R. D. (2007) Can ionic liquids dissolve wood? Processing and analysis of lignocellulosic materials with 1-n-butyl-3-methylimidazolium chloride. Green Chem. 9:63–69.10.1039/B607614ASearch in Google Scholar
Fujimoto, A., Matsumoto, Y., Chang, H.-M., Meshitsuka, G. (2005) Quantitative evaluation of milling effects on lignin structure during the isolation process of milled wood lignin. J. Wood Sci. 51:89–91.10.1007/s10086-004-0682-7Search in Google Scholar
Fukaya, Y., Hayashi, K., Wada, M., Ohno, H. (2008) Cellulose dissolution with polar ionic liquids under mild conditions: required factors for anions. Green Chem. 10:44–46.10.1039/B713289ASearch in Google Scholar
George, A., Tran, K., Morgan, T.J., Benke, P.I., Berrueco, C., Lorente, E., Wu, B.C., Keasling, J.D., Simmons, B.A., Holmes, B.M. (2011) The effect of ionic liquid cation and anion combinations on the macromolecular structures of lignins. Green Chem. 13:3375–3385.10.1039/c1gc15543aSearch in Google Scholar
Honglu, X., Tiejun, S. (2006) Wood liquefaction by ionic liquids. Holzforschung 60:509–512.10.1515/HF.2006.084Search in Google Scholar
Jia, S., Cox, B.J., Guo, X., Zhang, Z.C., Ekerdt, J.G. (2010) Decomposition of a phenolic lignin model compound over organic N-bases in an ionic liquid. Holzforschung 64:577–580.10.1515/hf.2010.075Search in Google Scholar
Kilpelainen, I., Xie, H., King, A., Granstrom, M., Heikkinen, S., Argyropoulos, D.S. (2007) Dissolution of wood in ionic liquid. J. Agric. Food Chem. 55:9142–9146.10.1021/jf071692eSearch in Google Scholar PubMed
Kubo, S., Hashida, K., Yamada, T., Hishiyama, S., Magara, K., Kishino, M., Ohno, H., Hosoya, S. (2008) A characteristic reaction of lignin in ionic liquids; glycelol type enol-ether as the primary decomposition product of β-O-4 model compound. J. Wood Chem. Technol. 28:84–96.Search in Google Scholar
Liebner, F., Patel, I., Ebner, G., Becker, E., Horix, M., Potthast, A., Rosenau, T. (2010) Thermal aging of 1-alkyl-3-methylimidazolium ionic liquids and its effect on dissolved cellulose. Holzforschung 64:161–166.10.1515/hf.2010.033Search in Google Scholar
Lu, F., Ralph, J. (2003) Non-degradative dissolution and acetylation of ball-milled plant cell walls: high-resolution solution-state NMR. Plant J. 35:535–544.10.1046/j.1365-313X.2003.01817.xSearch in Google Scholar PubMed
Lu, F., Ralph, J. (2011) Solution-state NMR of lignocellulosic biomass. J. Biobased Mater. Bioenergy 5:169–180.Search in Google Scholar
Nakamura, A., Miyafuji, H., Saka, S., Mori, M., Takahashi, H. (2010) Liquefaction behavior of Western red cedar and Japanese beech in the ionic liquid 1-ethyl-3-methylimidazolium chloride. Holzforschung 64:289–294.10.1515/hf.2010.042Search in Google Scholar
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., Ogita, S., Hamada, M., Nakajima N. (2013) Dissolution and acetylation of ball-milled lignocellulosic biomass in ionic liquids at room temperature: application to NMR analysis of cell-wall components. Holzforschung 67:25–32.10.1515/hf-2012-0037Search in Google Scholar
Schrems, M., Brandt, A., Welton, T., Liebner, F., Rosenau, T., Potthast, A. (2011) Ionic liquids as media for biomass processing: opportunities and restrictions. Holzforschung 65:527–533.10.1515/hf.2011.099Search in Google Scholar
Stasiewicz, M., Fojutowski, A., Kropacz, A., Pernak, J. (2008) 1-Alkoxymethyl-X- dimethylaminopyridinium-base ionic liquids in wood preservation. Holzforschung 62:309–317.10.1515/HF.2008.028Search in Google Scholar
Sun, N., Rahman, M., Qin, Y., Maxim, M.L., Rodriguez, H., Rogers, R.D. (2009) Complete dissolution and partial delignification of wood in the ionic liquid 1-ethyl-3-methyl- imidazolium acetate. Green Chem. 11:646–655.10.1039/b822702kSearch in Google Scholar
Viell, J., Marquardt, W. (2011) Disintegration and dissolution kinetics of wood chips in ionic liquids. Holzforschung 65:519–525.10.1515/hf.2011.072Search in Google Scholar
Yelle, D.J., Ralph, J., Frihart, C.R. (2008) Characterization of nonderivatized plant cell walls using high-resolution solution-state NMR spectroscopy. Magn. Reson. Chem. 46:508–517.Search in Google Scholar
Zoia, L., King, A.W.T., Argyropoulos, D.S. (2011) Molecular weight distributions and linkages in lignocellulosic materials derivatized from ionic liquid media. J. Agric. Food Chem. 53:829–838.10.1021/jf103615eSearch in Google Scholar PubMed
©2013 by Walter de Gruyter Berlin Boston
Articles in the same Issue
- Masthead
- Masthead
- Reviews
- Influence of the moisture content on the fracture characteristics of welded wood joint. Part 1: Mode I fracture
- Influence of the moisture content on the fracture characteristics of welded wood joint. Part 2: Mode II fracture
- Original Articles
- Molecular weight distributions of acetylated lignocellulosic biomasses recovered from an ionic liquid system
- Multivariate-parameter optimization of the alkaline peroxide mechanical pulp (APMP) process for larch (Larix gmelinii Rupr.) using Box-Behnken design
- Characterization of fiber development in high- and low-consistency refining of primary mechanical pulp
- Mechanical performance of yew (Taxus baccata L.) from a longbow perspective
- Predicting Douglas-fir wood density by artificial neural networks (ANN) based on progeny testing information
- The influence of lathe check depth and orientation on the bond quality of phenol-formaldehyde – bonded birch plywood
- Fire resistance of wood treated with various ionic liquids (ILs)
- Evaluation of cell wall reinforcement in feather keratin-treated waterlogged wood as imaged by synchrotron X-ray microtomography (μXRT) and TEM
- Drying of beech (Fagus sylvatica L.) timber in oscillation climates: drying time and quality
- Quantification of mobilized copper(II) levels in micronized copper-treated wood by electron paramagnetic resonance (EPR) spectroscopy
- Condensed conifer tannins as antifungal agents in liquid culture
- Meetings
- Meetings
Articles in the same Issue
- Masthead
- Masthead
- Reviews
- Influence of the moisture content on the fracture characteristics of welded wood joint. Part 1: Mode I fracture
- Influence of the moisture content on the fracture characteristics of welded wood joint. Part 2: Mode II fracture
- Original Articles
- Molecular weight distributions of acetylated lignocellulosic biomasses recovered from an ionic liquid system
- Multivariate-parameter optimization of the alkaline peroxide mechanical pulp (APMP) process for larch (Larix gmelinii Rupr.) using Box-Behnken design
- Characterization of fiber development in high- and low-consistency refining of primary mechanical pulp
- Mechanical performance of yew (Taxus baccata L.) from a longbow perspective
- Predicting Douglas-fir wood density by artificial neural networks (ANN) based on progeny testing information
- The influence of lathe check depth and orientation on the bond quality of phenol-formaldehyde – bonded birch plywood
- Fire resistance of wood treated with various ionic liquids (ILs)
- Evaluation of cell wall reinforcement in feather keratin-treated waterlogged wood as imaged by synchrotron X-ray microtomography (μXRT) and TEM
- Drying of beech (Fagus sylvatica L.) timber in oscillation climates: drying time and quality
- Quantification of mobilized copper(II) levels in micronized copper-treated wood by electron paramagnetic resonance (EPR) spectroscopy
- Condensed conifer tannins as antifungal agents in liquid culture
- Meetings
- Meetings