Raman microscopic analysis of wood after treatment with the ionic liquid, 1-ethyl-3-methylimidazolium chloride
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Toru Kanbayashi
Abstract
Japanese cedar (Cryptomeria japonica) was treated with the ionic liquid (IL) 1-ethyl-3-methylimidazolium chloride ([C2mim][Cl]), which is a solvent for cellulose, and the changes in the chemical components and their distribution in wood cell walls have been investigated by Raman microscopy. Raman spectra, recorded from various areas of the cell walls, showed that lignin in the compound middle lamellae (CML) and cell corners (CC) was resistant to the reaction with [C2mim][Cl], but its molecular structure changed partially. The reactivity of cellulose and hemicelluloses with [C2mim][Cl] was higher than that of lignin in the cell wall, and the cell wall structure was maintained even in an advanced state of the reactions. The effects of [C2mim]-[Cl] on cellulose and hemicelluloses in the cell wall were homogeneous, whereas that of lignin was inhomogeneous.
Acknowledgments
The authors wish to thank the Kyoto Municipal Institute of Industrial Technology and Culture for its assistance with the Raman microscopic analysis. This research was partly supported by a Grant-in-Aid for Scientific Research (c) (25450246) from JSPS, for which the authors are grateful.
References
Agarwal, U.P. (1998) Assignment of the photoyellowing-related 1675 cm-1 Raman/IR band to p-quinones and its implications to the mechanism of color reversion in mechanical pulps. J. Wood Chem. Technol. 18:381–402.Search in Google Scholar
Agarwal, U.P. (1999) An overview of Raman spectroscopy as applied to lignocellulosic materials. In: Advances in Lignocellulosics Characterization. Ed. Argyropoulos, D.S. TAPPI Press, Atlanta, GA. pp. 201–225.Search in Google Scholar
Agarwal, U.P., Atalla, R.H. (2000) Using Raman spectroscopy to identify chromophores in lignin-lignocellulosics. In: Lignin: Historical, Biological, and Materials Perspectives. Eds. Glasser, W.G., Northey, R.A., Schultz, T.P. ACS Symposium Series 742. American Chemical Society, Washington, DC. pp. 250–264.Search in Google Scholar
Agarwal, U.P., Ralph, S.A. (1997) FT-Raman spectroscopy of wood: identifying contributions of lignin and carbohydrate polymers in the spectrum of black spruce (Picea mariana). Appl. Spectrosc. 51:1648–1655.10.1366/0003702971939316Search in Google Scholar
Agarwal, U.P., Ralph, S.A. (2008) Determination of ethylenic residues in wood and TMP of spruce by FT-Raman spectroscopy. Holzforschung 62:667–675.10.1515/HF.2008.112Search in Google Scholar
Agarwal, U.P., McSweeny, J.D., Ralph, S.A. (2011) FT-Raman investigation of milled wood lignins: softwood, hardwood, and chemically modified black spruce lignins. J. Wood Chem. Technol. 31:324–344.10.1080/02773813.2011.562338Search in Google Scholar
Edwards, H.G.M., Farwell, D.W., Webster, D. (1997) FT Raman microscopy of untreated natural plant fibres. Spectrochim. Acta A 53:2383–2392.10.1016/S1386-1425(97)00178-9Search in Google Scholar
Fort, D.A., Remsing, R.C., Swatloski, R.P., Moyna, P., 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
Honglu, X., Tiejun, S. (2006) Wood liquefaction by ionic liquids. Holzforschung 60:509–512.10.1515/HF.2006.084Search in Google Scholar
Kanbayashi, T., Miyafuji, H. (2013) Morphological changes of Japanese beech treated with the ionic liquid, 1-ethyl-3-methylimidazolium chloride. J. Wood Sci. 59:410–418.10.1007/s10086-013-1343-5Search in Google Scholar
Kanbayashi, T., Miyafuji, H. (2014) Comparative study of morphological changes in hardwoods treated with the ionic liquid, 1-ethyl-3-methylimidazolium chloride. J. Wood Sci. 60:152–159.10.1007/s10086-014-1389-zSearch in Google Scholar
Kilpeläinen, I., Xie, H., King, A., Granstrom, M., Heikkinen, S., Argyropoulos, D.S. (2007) Dissolution of wood in ionic liquids. J. Agric. Food Chem. 55:9142–9148.10.1021/jf071692eSearch in Google Scholar PubMed
Miyafuji, H., Suzuki, N. (2012) Morphological changes in sugi (Cryptomeria japonica) wood after treatment with the ionic liquid, 1-ethyl-3-methylimidazolium chloride. J. Wood Sci. 58:222–230.10.1007/s10086-011-1245-3Search in Google Scholar
Miyafuji, H., Miyata, K., Saka, S. (2009) Reaction behavior of wood in an ionic liquid, 1-ethyl-3-methylimidazolium chloride. J. Wood Sci. 55:215–219.10.1007/s10086-009-1020-xSearch in Google Scholar
Nakamura, A., Miyafuji, H., Saka, S. (2010a) 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
Nakamura, A., Miyafuji, H., Saka, S. (2010b) Influence of reaction atmosphere on the liquefaction and depolymerization of wood in an ionic liquid, 1-ethyl-3-methylimidazolium chloride. J. Wood Sci. 56:256–261.10.1007/s10086-009-1081-xSearch in Google Scholar
Ohno, E., Miyafuji, H. (2013) Reaction behavior of cellulose in an ionic liquid, 1-ethyl-3-methylimidazolium chloride. J. Wood Sci. 59:221–228.10.1007/s10086-013-1322-xSearch in Google Scholar
Ou, R., Xie, Y., Wang, Q., Sui, S., Wolcott, M.P. (2013) Thermoplastic deformation of poplar wood plasticized by ionic liquids measured by a nonisothermal compression technique. Holzforschung 68:555–566.10.1515/hf-2013-0136Search in Google Scholar
Qu, C., Kishimoto, T., Hamada, M., Nakajima, N. (2013) 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
Schenzel, K., Fischer, S. (2001) NIR FT Raman spectroscopy – a rapid analytical tool for detecting the transformation of cellulose polymorphs. Cellulose 8:49–57.10.1023/A:1016616920539Search 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
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.Search in Google Scholar
Terashima, N., Fukushima, K. (1988) Heterogeneity in formation of lignin – XI: an autoradiographic study of the heterogeneous formation and structure of pine lignin. Wood Sci. Technol. 22:259–270.10.1007/BF00386021Search 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
Whiting, P., Goring, D.A.I. (1982) Chemical characterization of tissue fractions from the middle lamella and secondary wall of black spruce tracheids. Wood Sci. Technol. 16:261–267.Search in Google Scholar
Wiley, J.H., Atalla, R.H. (1987) Band assignments in the Raman spectra of celluloses. Carbohydr. Res. 160:113–129.Search in Google Scholar
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
©2015 by De Gruyter
Articles in the same Issue
- Frontmatter
- Original Articles
- Characterization of dissolved lignins from acetic acid Lignofibre (LGF) organosolv pulping and discussion of its delignification mechanisms
- Organic materials in black liquors of soda-AQ pulping of hot-water-extracted birch (Betula pendula) sawdust
- Effects of concentration and temperature on the rheological behavior of concentrated sodium lignosulfonate (NaLS) solutions
- Raman microscopic analysis of wood after treatment with the ionic liquid, 1-ethyl-3-methylimidazolium chloride
- Isolation and structural elucidation of norlignan polymers from the heartwood of Cryptomeria japonica
- Effect of ball milling on lignin polyesterification with ε-caprolactone
- Property enhancement of kenaf fiber composites by means of vacuum-assisted resin transfer molding (VARTM)
- Wood polypropylene composites prepared by thermally modified fibers at two extrusion speeds: mechanical and viscoelastic properties
- Numerical analysis of temperature profiles during thermal modification of wood: chemical reactions and experimental verification
- Fast online NIR technique to predict MOE and moisture content of sawn lumber
- Numerical study of the influence of veneer lathe checks on the elastic mechanical properties of laminated veneer lumber (LVL) made of beech
- Amination of pretreated ayous (Triplochiton scleroxylon) sawdust with two organosilanes: characterization, stability, and permselective property
- Damage evolution in wood – pattern recognition based on acoustic emission (AE) frequency spectra
- Mechanical stability of superhydrophobic epoxy/silica coating for better water resistance of wood
- Short Note
- Urea-formaldehyde resin penetration into Pinus radiata tracheid walls assessed by TEM-EDXS
- Obituary
- Professor Dr. Arnis Treimanis
Articles in the same Issue
- Frontmatter
- Original Articles
- Characterization of dissolved lignins from acetic acid Lignofibre (LGF) organosolv pulping and discussion of its delignification mechanisms
- Organic materials in black liquors of soda-AQ pulping of hot-water-extracted birch (Betula pendula) sawdust
- Effects of concentration and temperature on the rheological behavior of concentrated sodium lignosulfonate (NaLS) solutions
- Raman microscopic analysis of wood after treatment with the ionic liquid, 1-ethyl-3-methylimidazolium chloride
- Isolation and structural elucidation of norlignan polymers from the heartwood of Cryptomeria japonica
- Effect of ball milling on lignin polyesterification with ε-caprolactone
- Property enhancement of kenaf fiber composites by means of vacuum-assisted resin transfer molding (VARTM)
- Wood polypropylene composites prepared by thermally modified fibers at two extrusion speeds: mechanical and viscoelastic properties
- Numerical analysis of temperature profiles during thermal modification of wood: chemical reactions and experimental verification
- Fast online NIR technique to predict MOE and moisture content of sawn lumber
- Numerical study of the influence of veneer lathe checks on the elastic mechanical properties of laminated veneer lumber (LVL) made of beech
- Amination of pretreated ayous (Triplochiton scleroxylon) sawdust with two organosilanes: characterization, stability, and permselective property
- Damage evolution in wood – pattern recognition based on acoustic emission (AE) frequency spectra
- Mechanical stability of superhydrophobic epoxy/silica coating for better water resistance of wood
- Short Note
- Urea-formaldehyde resin penetration into Pinus radiata tracheid walls assessed by TEM-EDXS
- Obituary
- Professor Dr. Arnis Treimanis
