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Fractionation of woody biomass with boiling aqueous acetic acid containing a small amount of mineral acid at atmospheric pressure: Reactivity of arylglycerol-β-aryl ethers in lignins with aqueous acetic acid containing H2SO4

Abstract

To characterize the mechanism of the reaction of lignin with aqueous acetic acid (AW) containing a small amount of H2SO4, guaiacylglycerol-β-guaiacyl ether (GOG), and guaiacylglycerol-β-syringol ether (GOS) were refluxed in 90% AW with 0.28% H2SO4 for 0–120 min. Reaction products and their silylated derivatives were characterized by analytical methods such as gas chromatography-mass spectrometry and nuclear magnetic resonance. When the model compounds were allowed to react at boiling temperature for 0 min (heat-up time 30 min), most of their primary alcohol groups and some of their secondary alcohol groups were acetylated, but their phenolic groups were not. About 90% of GOG was degraded, polymerized, or both during boiling for at least 15 min, yielding guaiacol and isocoumaran compounds (GOG-e and GOG-f) in addition to homovanillin (II) as guaiacylvinyl alcohol (I) and other minor products. GOS yielded syringol, homovanillin (II), and a novel compound (V) together with unknown products but not the corresponding isocoumaran compounds.

References

  1. 1.

    Sano Y, Nakamura M, Shimamoto S (1990) Pulping of wood at atmospheric pressure: II. Pulping of birch wood with aqueous acetic acid containing a small amount of sulfuric acid. Mokuzai Gakkaishi 36:207–211

    CAS  Google Scholar 

  2. 2.

    Sano Y, Uraki Y, Kubo S, Horisaki Y, Konno H (1996) Total utilization of woody biomass by acetic acid pulping at atmospheric presure (in Japanese). In: Proceedings of the 63rd pulp and paper research conference, pp 26–32

  3. 3.

    Sano Y, Shimamoto S (1995) Mild hydrogenolysis of acetic acid lignin. Mokuzai Gakkaishi 41:1006–1011

    CAS  Google Scholar 

  4. 4.

    Uraki Y, Kubo S, Nigo N, Sano Y (1995) Preparation of carbon fibers from organosoly lignin obtained by aqueous acetic acid pulping. Holzforschung 49:343–350

    CAS  Article  Google Scholar 

  5. 5.

    Uraki Y, Kubo S, Kurakami H, Sano Y (1997) Active carbon fibers from acetic acid lignin. Holzforschung 51:188–192

    CAS  Article  Google Scholar 

  6. 6.

    Nakamura M, Sano Y (1990) Production of lignin adhesives: resinification of acetic acid lignin (in Japanese). Proc Hokkaido Branch Jpn Wood Res Soc 22:68–73

    Google Scholar 

  7. 7.

    Kanai T, Sano Y, Sasaya T (1994) Preparation of highly efficient polymers from acetic acid lignin — preparation of cation ion: exchange resin (in Japanese). In: Abstracts of the 44th annual meeting of the Japan Wood Research Society, 59

  8. 8.

    Sano Y (1989) Reactivity of β-0–4 linkages in lignin during solvolysis pulping: degradation of β-0-4 lignin model compounds. Mokuzai Gakkaishi 35:813–819

    CAS  Google Scholar 

  9. 9.

    Mikshe GE (1966) Zur Synthese der beiden diastereomeren Formen des Guajacylglycerin-β-(2-methoxyphenyl)-athers und des Guajacylglycerins. Acta Chem Scand 20:1038–1043

    Article  Google Scholar 

  10. 10.

    Ede R, Brunow G, Poppius K (1988) Formic acid/peroxyformic acid pulping: Part 1. Reactions of β-aryl ether model compounds with formic acid. Nord Pulp Pap Res 3:119–123

    CAS  Article  Google Scholar 

  11. 11.

    Yasuda S, Ito N (1987) Behavior of lignin in organic pulping: I. Reaction of arylglycerol-β-aryl ethers with acetic acid. Mokuzai Gakkaishi 33:708–716

    CAS  Google Scholar 

  12. 12.

    Davis JL, Nakatubo F, Murakami K, Umezawa T (1987) Organic acid pulping of wood: IV. Reactions of arylglycerol-β-guaiacyl ethers. Mokuzai Gakkaishi 33:478–486

    CAS  Google Scholar 

  13. 13.

    Lundquist K (1970) Acid degradation of lignin: II. Separation and identification of low molecular weight phenols. Acta Chem Scand 24:889–907

    CAS  Article  Google Scholar 

  14. 14.

    Karlsson O, Lundquist K, Meuller S, Westid K (1988) On the acidolytic cleavage of arylglycerol β-aryl ethers. Acta Chem Scand 42:48–51

    Article  Google Scholar 

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Correspondence to Yoshihiro Sano.

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Sano, Y., Shimamoto, S., Enoki, M. et al. Fractionation of woody biomass with boiling aqueous acetic acid containing a small amount of mineral acid at atmospheric pressure: Reactivity of arylglycerol-β-aryl ethers in lignins with aqueous acetic acid containing H2SO4 . J Wood Sci 44, 217–221 (1998). https://doi.org/10.1007/BF00521966

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Key words

  • Fractionation of biomass
  • Atmospheric AcOH pulping
  • Degradation of β-Ethers
  • Sulfuric acid
  • Lignin model compounds