Comparative study of the topochemistry on delignification of Japanese beech (Fagus crenata) in subcritical phenol and subcritical water
Abstract
The delignification of Japanese beech (Fagus crenata) has been evaluated under conditions of subcritical phenol (230°C/1.2 MPa) and subcritical water (230°C/2.9 MPa). In the former, more than 90% of the original lignin was decomposed and removed, while in subcritical water, around half of the original lignin was left as insoluble residue. Ultraviolet (UV) microscopic images of the insoluble residues showed that the lignin in the secondary walls is decomposed and removed under both conditions. These images also revealed that the lignin in the compound middle lamella (CML) is resistant to subcritical water, but not to subcritical phenol. Results of alkaline nitrobenzene oxidation of the residual lignin confirmed these observations. Lignin in Japanese beech wood was phenolated by subcritical phenol, which was efficiently removed due to its high solubility in the reactant. It is obvious that CML is rich in condensed-type linkages facilitating rapid solvolysis by phenol. The topochemistry of the plant has a pronounced impact on its delignification behavior.
Acknowledgments:
This work was supported by the Japan Science and Technology Agency (JST) under the Advanced Low Carbon Technology Research and Development Program (ALCA), for which the authors are extremely grateful.
References
Ambrose, D. (1963) Critical temperatures of some phenols and other organic compounds. Trans. Faraday Soc. 59:1988–1993.10.1039/tf9635901988Suche in Google Scholar
Ando, H., Sakaki, T., Kokusho, T., Shibata, M., Uemura, Y., Hatate, Y. (2000) Decomposition behavior of plant biomass in hot-compressed water. Ind. Eng. Chem. Res. 39:3688–3693.10.1021/ie0000257Suche in Google Scholar
April, G.C., Kamal, M.M., Reddy, J.A., Bowers, G.H., Hansen, S.M. (1979) Delignification with aqueous-organic solvents southern yellow pine. Tappi 62:83–85.Suche in Google Scholar
Aulin-Erdtman, G., Sanden, R. (1968) Spectrographic contributions to lignin chemistry IX. Absorption properties of some 4-hydroxyphenyl, guaiacyl, and 4-hydroxy-3,5-dimethoxyphenyl type model compounds for hardwood lignins. Acta Chem. Scand. 22:1187–1209.10.3891/acta.chem.scand.22-1187Suche in Google Scholar
Baker, S.M. (1996) Rapid methoxyl analysis of lignins using gas chromatography. Holzforschung 50:573–574.Suche in Google Scholar
Brauns, F., Hibbert, H. (1933) Studies on lignin X: the identity and structure of spruce lignins prepared by different methods. J. Am. Chem. Soc. 55:4720–4727.10.1021/ja01338a070Suche in Google Scholar
Chen, C.L. (1992) Nitrobenzene and cupric oxide oxidations. In: Methods in Lignin Chemistry. Eds. Lin, S.Y., Dence, C.W. Springer, Berlin. pp. 301–312.10.1007/978-3-642-74065-7_21Suche in Google Scholar
Dence, C.W. (1992) The determination of lignin. In: Methods in Lignin Chemistry. Eds. Lin, S.Y., Dence, C.W. Springer, Berlin. pp. 33–39.10.1007/978-3-642-74065-7_3Suche in Google Scholar
Ehara, K., Saka, S., Kawamoto, H. (2002) Characterization of the lignin-derived products from wood as treated in supercritical water. J. Wood Sci. 48:320–325.10.1007/BF00831354Suche in Google Scholar
Erdocia, X., Prado, R., Corcuera, M.Á., Labidi, J. (2014) Influence of reaction conditions on lignin hydrothermal treatment. Front Energy Res. 2:1–7.10.3389/fenrg.2014.00013Suche in Google Scholar
Fergus, B.J., Goring, D.A.I. (1970) The location of guaiacyl and syringyl lignins in birch xylem tissue. Holzforschung 24:113–117.10.1515/hfsg.1970.24.4.113Suche in Google Scholar
Funaoka, M., Abe, I. (1989) Rapid separation of wood into carbohydrate and lignin with concentrated acid-phenol system. Tappi J 72:145–149.Suche in Google Scholar
Kratzl, K., Buchtela, K., Gratzl, J., Zauner, J., Ettingshausen, O. (1962) Lignin and plastics. the reaction of lignin with phenol and isocyanates. Tappi 45:113–119.Suche in Google Scholar
Lee, S.H., Ohkita, T. (2003) Rapid wood liquefaction by supercritical phenol. Wood Sci. Technol. 37:29–38.10.1007/s00226-003-0167-7Suche in Google Scholar
Lee, W.-J., Kang, C.-L., Chang, K.-C., Chen, Y.-C. (2012) Synthesis and properties of resol-type phenol-formaldehyde resins prepared from H2SO4- and HCl-catalyzed phenol-liquefied Cryptomeria japonica wood. Holzforschung 66:67–72.10.1515/HF.2011.121Suche in Google Scholar
Lee, Y.-Y., Lee, W.-J., Hsu, L.-Y., Hsieh, H.-M. (2014) Properties of molding plates made with various matrices impregnated with PF and liquefied wood-based PF resins. Holzforschung 68:37–43.10.1515/hf-2013-0029Suche in Google Scholar
Lin, L., Yao, Y., Yoshioka, M., Shiraishi, N. (1997a) Liquefaction mechanism of lignin in the presence of phenol at elevated temperature without catalysts Studies on β-O-4 lignin model compound. I. Structural Characterization of the Reaction Products. Holzforschung 51:316–324.10.1515/hfsg.1997.51.4.316Suche in Google Scholar
Lin, L., Yoshioka, M., Yao, Y., Shiraishi, N. (1997b) Liquefaction mechanism of lignin in the presence of phenol at elevated temperature without catalysts Studies on β-O-4 lignin model compound. II. Reaction Pathway. Holzforschung 51:325–332.10.1515/hfsg.1997.51.4.325Suche in Google Scholar
Liu, C., Wyman, C.E. (2003) The effect of flow rate of compressed hot water on xylan, lignin, and total mass removal from corn stover. Ind. Eng. Chem. Res. 42:5409–5416.10.1021/ie030458kSuche in Google Scholar
Mishra, G. (2012) Thermo-chemical conversion of Japanese beech by subcritical phenols to bio-fuels and bio-materials. Dissertation, Kyoto University, Japan, pp. 75–91.Suche in Google Scholar
Mishra, G., Saka, S. (2011a) Kinetic behavior of liquefaction of Japanese beech in subcritical phenol. Bioresour. Technol. 102:10946–10950.10.1016/j.biortech.2011.08.126Suche in Google Scholar PubMed
Mishra, G., Saka, S. (2011b) Liquefaction behaviors of Japanese beech as treated in subcritical phenol. In: Zero-Carbon Energy Kyoto 2010. Eds. Yao, T. Springer Japan, Tokyo. pp. 147–152.10.1007/978-4-431-53910-0_19Suche in Google Scholar
Mishra, G., Saka, S. (2012) Effects of various solvents on precipitation of phenolated products from Japanese beech as treated by subcritical phenol. In: Zero-Carbon Energy Kyoto 2011. Eds. Yao, T. Springer Japan, Tokyo. pp. 153–157.10.1007/978-4-431-54067-0_17Suche in Google Scholar
Mishra, G., Saka, S. (2013) Effects of water in water/phenol mixtures on liquefaction of Japanese beech as treated under subcritical conditions. Holzforschung 67:241–247.10.1515/hf-2012-0050Suche in Google Scholar
Phaiboonsilpa, N., Tamunaidu, P., Saka, S. (2011) Two-step hydrolysis of nipa (Nypa fruticans) frond as treated by semi-flow hot-compressed water. Holzforschung 65:659–666.10.1515/hf.2011.046Suche in Google Scholar
Rogalinski, T., Ingram, T., Brunner, G. (2008) Hydrolysis of lignocellulosic biomass in water under elevated temperatures and pressures. J. Supercrit. Fluids 47:54–63.10.1016/j.supflu.2008.05.003Suche in Google Scholar
Saisu, M., Sato, T., Watanabe, M., Adschiri, T., Arai, K. (2003) Conversion of lignin with supercritical water-phenol mixtures. Energy Fuels 17:922–928.10.1021/ef0202844Suche in Google Scholar
Saka, S., Goring, D.A.I. (1988) The distribution of lignin in white birch wood as determined by bromination with TEM-EDXA. Holzforschung 42:149–153.10.1515/hfsg.1988.42.3.149Suche in Google Scholar
Saka, S., Thomas, R.J., Gratzl, J.S., Abson, D. (1982) Topochemistry of delignification in Douglas-fir wood with soda, soda-anthraquinone and kraft pulping as determined by SEM-EDXA. Wood Sci. Technol. 16:139–153.10.1007/BF00351099Suche in Google Scholar
Sakakibara, A., Edashige, Y., Sano, Y., Hatakeyama, H. (1984) Solvolysis pulping with cresols-water system. Holzforschung 38:159–165.10.1515/hfsg.1984.38.3.159Suche in Google Scholar
Sano, Y., Sasaya, T. (1985) Studies on phenorganosolv pulping I. delignification of woods by modified organosolv pulping. Mokuzai Gakkaishi 31:836–842.Suche in Google Scholar
Sano, Y., Maeda, H., Sakashita, Y. (1989a) Pulping of wood at atmospheric pressure I., pulping of hardwoods with aqueous acetic acid containing a small amount of organic sulfonic acid. Mokuzai Gakkaishi 35:991–995.Suche in Google Scholar
Sano, Y., Endo, M., Sakashita, Y. (1989b) Solvolysis pulping of softwoods with aqueous cresols containing a small amount of acetic acid. Mokuzai Gakkaishi 35:807–812.Suche in Google Scholar
Schweers, W.H.M. (1974) Phenol pulping – a potential sulfur-free papermaking process. Chemtech. 4:490–493.Suche in Google Scholar
Schweers, W.H.M., Rechy, M. (1973) Über den Holzaufschluss mit Phenolen, 3. Mitt., Über den Aufschluss von Kiefern- und Buchenholz. Papier 27:36–639.Suche in Google Scholar
Takabe, K., Miyauchi, S., Tsunoda, R., Fukazawa, K. (1992) Distribution of guaiacyl and syringyl lignins in Japanese beech (Fagus crenata): Variation within an annual ring. IAWA J. 13:105–112.10.1163/22941932-90000561Suche in Google Scholar
Takada, M., Saka, S. (2015a) Characterization of lignin-derived products from Japanese cedar as treated by semi-flow hot-compressed water. J. Wood Sci. 61:299–307.10.1007/s10086-015-1464-0Suche in Google Scholar
Takada, M., Saka, S. (2015b) Comparative study on topochemistry of delignification from Japanese cedar and Japanese beech by hydrothermal treatment. J. Wood Sci. 61:602–607.10.1007/s10086-015-1501-zSuche in Google Scholar
Takagi, H., Wakai, M., Araki, H. (1989) Research and development of solvolysis pulping (3) cooking conditions and pulp properties. Japan Tappi J 43:1171–1178.10.2524/jtappij.43.1171Suche in Google Scholar
Tirtowidjojo, S., Sarkanen, K.V., Pla, F., McCarthy, J.L. (1988) Kinetics of organosolv delignification in batch- and flow-through reactors. Holzforschung 42:177–183.10.1515/hfsg.1988.42.3.177Suche in Google Scholar
Vega, A., Bao, M. (1993) Organosolv fractionation of ulex europaeus with dilute hydrochloric acid and phenol, two simple kinetic models for pre-hydrolysis and delignification. Wood Sci. Technol. 27:61–68.10.1007/BF00203411Suche in Google Scholar
Whiting, P., Goring, D.A.I. (1981) The topochemistry of delignification shown by pulping middle lamella and secondary wall tissue from black spruce wood. J. Wood Chem. Technol. 1:111–122.10.1080/02773818108085108Suche in Google Scholar
Yamazaki, J., Minami, E., Saka, S. (2006) Liquefaction of beech wood in various supercritical alcohols. J. Wood Sci. 52:527–532.10.1007/s10086-005-0798-4Suche in Google Scholar
Zhang, Q., Zhao, G., Chen, J. (2006) Effects of inorganic acid catalysts on liquefaction of wood in phenol. Front. Forestry China 2:214–218.10.1007/s11461-006-0002-zSuche in Google Scholar
Zhang, B., Huang, H.J., Ramaswamy, S. (2008) Reaction kinetics of the hydrothermal treatment of lignin. Appl. Biochem. Biotechnol. 147:119–131.10.1007/978-1-60327-526-2_46Suche in Google Scholar
©2016 Walter de Gruyter GmbH, Berlin/Boston
Artikel in diesem Heft
- Frontmatter
- Original Articles
- Preparation of prehydrolysis-TMPs with different severity factors and analysis of the pulps and byproducts
- Differences in solubility parameters and susceptibility to salting-out between softwood and hardwood lignosulfonates
- Modified sodium lignosulfonates (NaLS) with straight chain alcohols and their aggregation behavior and adsorption characteristics on solid surfaces
- Improved impregnation efficiency and pulp yield of softwood kraft pulp by high effective alkali charge in the impregnation stage
- Semitransparent, durable superhydrophobic polydimethylsiloxane/SiO2 nanocomposite coatings on varnished wood
- Comparative study of the topochemistry on delignification of Japanese beech (Fagus crenata) in subcritical phenol and subcritical water
- Characterisation of Postia placenta colonisation during 36 weeks in acetylated southern yellow pine sapwood at three acetylation levels including genomic DNA and gene expression quantification of the fungus
- Relation of transverse compression properties and the degree of brown rot biodeterioration of Pinus glabra in the soil block test
- Four-point bending strength of key-hole side-edge-notched western hemlock (Tsuga heterophylla) wood
- Determination of the elasto-plastic material characteristics of Norway spruce and European beech wood by experimental and numerical analyses
- Time dependence of the orthotropic compression Young’s moduli and Poisson’s ratios of Chinese fir wood
Artikel in diesem Heft
- Frontmatter
- Original Articles
- Preparation of prehydrolysis-TMPs with different severity factors and analysis of the pulps and byproducts
- Differences in solubility parameters and susceptibility to salting-out between softwood and hardwood lignosulfonates
- Modified sodium lignosulfonates (NaLS) with straight chain alcohols and their aggregation behavior and adsorption characteristics on solid surfaces
- Improved impregnation efficiency and pulp yield of softwood kraft pulp by high effective alkali charge in the impregnation stage
- Semitransparent, durable superhydrophobic polydimethylsiloxane/SiO2 nanocomposite coatings on varnished wood
- Comparative study of the topochemistry on delignification of Japanese beech (Fagus crenata) in subcritical phenol and subcritical water
- Characterisation of Postia placenta colonisation during 36 weeks in acetylated southern yellow pine sapwood at three acetylation levels including genomic DNA and gene expression quantification of the fungus
- Relation of transverse compression properties and the degree of brown rot biodeterioration of Pinus glabra in the soil block test
- Four-point bending strength of key-hole side-edge-notched western hemlock (Tsuga heterophylla) wood
- Determination of the elasto-plastic material characteristics of Norway spruce and European beech wood by experimental and numerical analyses
- Time dependence of the orthotropic compression Young’s moduli and Poisson’s ratios of Chinese fir wood