Startseite Naturwissenschaften Comparative study of the topochemistry on delignification of Japanese beech (Fagus crenata) in subcritical phenol and subcritical water
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Comparative study of the topochemistry on delignification of Japanese beech (Fagus crenata) in subcritical phenol and subcritical water

  • Masatsugu Takada , Yoshiki Tanaka , Eiji Minami und Shiro Saka EMAIL logo
Veröffentlicht/Copyright: 11. Mai 2016

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

Received: 2016-2-9
Accepted: 2016-4-11
Published Online: 2016-5-11
Published in Print: 2016-11-1

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