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Journal of Wood Science

Official Journal of the Japan Wood Research Society

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Application of the amount of oxygen consumption to the investigation of the oxidation mechanism of lignin during oxygen-alkali treatment

Journal of Wood Science volume 54, pages 62–67 (2008)Cite this article

Abstract

The dioxygen consumption by kraft lignin and several lignin model compounds during oxygen-alkali treatments were directly analyzed using a dioxygen fl owmeter. The average dioxygen consumption by 200 g of kraft lignin was about 3 moles. Because this value was as much as those obtained for monomeric phenolic lignin model compounds, guaiacol and vanillyl alcohol, it was postulated that not only phenolic but also nonphenolic moieties in kraft lignin are extensively oxidized. The dioxygen consumption by 0.5 moles (one equivalent of aromatic units) of a dimeric lignin model compound, guaiacylglycerol-β-guaiacyl ether (GG), was also similar to that for 1 mole of guaiacol and vanillyl alcohol, regardless of the type of the aromatic moiety, which supports the above postulation. The most plausible mechanism for the oxidation of nonphenolic moieties is the oxidation of side chains of residual β-O-4 substructures by active oxygen species. By this mechanism, nonphenolic moieties in kraft lignin and GG are converted into corresponding phenolic moieties, and the oxidation by dioxygen progresses.

References

  1. Chen C-L (1991) Lignin — occurrence in woody tissues, isolation, reactions, and structure. In: Levin M, Goldstein IS (eds) Wood structure and composition. Marcel Dekker, New York, pp 183–261

    Google Scholar 

  2. Tong G, Yokoyama T, Matsumoto Y, Meshitsuka G (2000) Analysis of progress of oxidation reaction during oxygen-alkali treatment of lignin 1: method and its application to lignin oxidation. J Wood Sci 46:32–39

    Article  CAS  Google Scholar 

  3. Tong G, Matsumoto Y, Meshitsuka G (2000) Analysis of progress of oxidation reaction during oxygen-alkali treatment of lignin 2: significance of oxidation reaction of lignin during oxygen delignification. J Wood Sci 46:371–375

    Article  CAS  Google Scholar 

  4. Eckert RC, Chang H-M, Tucker WP (1973) Oxidative degradation of phenolic lignin model compounds with oxygen and alkali. TAPPI 56:134–138

    CAS  Google Scholar 

  5. Gierer J, Imsgard F (1977) Studies on the autoxidation of t-butylsubstituted phenols in alkaline media 1: reaction of 4-t-butylguaiacol. Acta Chem Scand B31:537–545

    Article  CAS  Google Scholar 

  6. Johansson E, Ljunggren S (1994) The kinetics of lignin reactions during oxygen bleaching part 4: the reactivities of different lignin model compounds and the infl uence of metal ions on the rate of degradation. J Wood Chem Technol 14:507–525

    Article  CAS  Google Scholar 

  7. Li S, Lundquist K, Paulsson M (1995) Synthesis of guaiacylglycerol-β-guaiacyl ether. Acta Chem Scand 49:623–624

    Article  CAS  Google Scholar 

  8. Yokoyama T, Matsumoto Y, Meshitsuka G (1999) The role of peroxide species in carbohydrate degradation during oxygen bleaching III: effect of metal ions on the reaction selectivity between lignin and carbohydrate model compounds. J Pulp Pap Sci 22:J151–J154

    Google Scholar 

  9. Yokoyama T, Matsumoto Y, Yasumoto M, Meshitsuka G (1996) The role of peroxide species in carbohydrate degradation during oxygen bleaching II: effect of oxygen pressure on the degradation of lignin and carbohydrate model compounds and on the reaction selectivity. J Pulp Pap Sci 22:J151–J154

    Google Scholar 

  10. Yokoyama T, Matsumoto Y, Meshitsuka G (1999) Reaction selectivity of active oxygen species in oxygen-alkali bleaching. J Wood Chem Technol 19:187–202

    Article  CAS  Google Scholar 

  11. Yokoyama T, Matsumoto Y, Meshitsuka G (2005) Characterization of active oxygen species under oxygen-alkali bleaching conditions. Holzforschung 59:269–275

    Article  CAS  Google Scholar 

  12. Lautsch W, Plankenhorn E, Klink F (1940) Über die bildung des vanillins aus dem holz, dem lignin und der sulfitcelluloseablauge der fichte. Angew Chem 53:450–452

    Article  CAS  Google Scholar 

  13. Deineko IP, Nikol’skii SN, Zarubin MY (1983) Quantitative determination of oxygen consumption in oxygen pulping. Khimiya Drevesiny 1983:54–57

    Google Scholar 

  14. Capanema EA, Balakshin MY, Chen C-L, Gratzl JS, Kirkman AG (2001) Oxidative ammonolysis of technical lignins part 1: kinetics of the reaction under isothermal conditions at 130°C. Holzforschung 55:397–404

    CAS  Google Scholar 

  15. Capanema EA, Balakshin MY, Chen C-L, Gratzl JS, Kirkman AG (2001) Oxidative ammonolysis of technical lignins part 2: effect of oxygen pressure. Holzforschung 55:405–412

    CAS  Google Scholar 

  16. Capanema EA, Balakshin MY, Chen C-L, Gratzl JS, Kirkman AG (2002) Oxidative ammonolysis of technical lignins part 3: effect of temperature on the reaction rate. J Wood Chem Technol 26:5–20

    Google Scholar 

  17. Capanema EA, Balakshin MY, Chen C-L, Gratzl JS (2006) Oxidative ammonolysis of technical lignins part 4: effects of the ammonium hydroxide concentration and pH. Holzforschung 56:402–415

    Google Scholar 

  18. Miksche GE (1980) Lignin reactions in alkaline pulping processes. In: Gratzl JS, Nakano J, Singh RP (eds) Chemistry of delignification with oxygen, ozone, and peroxides. Uni, Tokyo, p 108

    Google Scholar 

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Authors and Affiliations

  1. Laboratory of Wood Chemistry, Department of Biomaterial Sciences, Graduate School of Agricultural and Life Sciences, the University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo, 113-8657, Japan

    Aiko Imai, Iori Tomoda, Tomoya Yokoyama, Yuji Matsumoto & Gyosuke Meshitsuka

  2. Department of Pulp and Paper Science, College of Chemical Engineering, Nanjing Forestry University, Nanjing, 210037, China

    Guolin Tong

Authors
  1. Aiko Imai
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  2. Iori Tomoda
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  3. Tomoya Yokoyama
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  4. Yuji Matsumoto
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  5. Gyosuke Meshitsuka
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  6. Guolin Tong
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Corresponding author

Correspondence to Tomoya Yokoyama.

Additional information

Part of this article was presented at the 13th International Symposium on Wood, Fiber, and Pulping Chemistry (13th ISWFPC), Auckland, New Zealand, May 2005

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Imai, A., Tomoda, I., Yokoyama, T. et al. Application of the amount of oxygen consumption to the investigation of the oxidation mechanism of lignin during oxygen-alkali treatment. J Wood Sci 54, 62–67 (2008). https://doi.org/10.1007/s10086-007-0906-8

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  • DOI: https://doi.org/10.1007/s10086-007-0906-8

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