Skip to main content

Official Journal of the Japan Wood Research Society

Journal of Wood Science Cover Image

Characterization of the products resulting from ethylene glycol liquefaction of cellulose

Abstract

The composition of liquefied cellulose in the presence of ethylene glycol (EG) was studied. The liquefied products were fractionated and analyzed with highperformance liquid chromatography and nuclear magnetic resonance. EG-glucosides were detected as the only saccharides and 2-hydroxyethyl levulinate as the highly decomposed compound derived from cellulose. Quantitative analysis of the EG-glucosides and levulinic acid that comes from the levulinate shows the presence of the following mechanism in the EG-liquefaction of cellulose. First, cellulose is degraded and produces considerable amounts of EG-glucosides during the early stage of liquefaction. Then, when liquefaction is prolonged, the glucosides are decomposed, leading to a large quantity of levulinates.

References

  1. 1.

    Japan Wood Research Society (1995) From fossil resources to wood resources: the 40th anniversary conference of the Japan Wood Research Society, Tokyo, April 1995

  2. 2.

    Fierz-David HE (1925) The liquefaction of wood and some general remarks on the liquefaction of coal. Chem Ind Rev 44:942–944

    CAS  Google Scholar 

  3. 3.

    Appell HR, Fu YC, Illig EG, Steffgen FW, Miller RD (1971) Conversion of cellulosic waste to oil. Bureau of Mines Report of Investigations. Pittsburgh Energy Research Center, Pittsburgh, PA

    Google Scholar 

  4. 4.

    Ono H, Sudo K (1997) Japanese patent JP2611166

  5. 5.

    Shiraishi N, Shirakawa K, Kurimoto Y (2000) Japanese patent JP3012296

  6. 6.

    Kurimoto Y, Shirakawa K, Yoshioka M, Shiraishi N (1992) Liquefaction of untreated wood with polyhydric alcohols and its application to polyurethane forms. FRI (New Zealand) Bull 176:163–172

    CAS  Google Scholar 

  7. 7.

    Higashida R, Shirakawa K, Yoshioka M, Shiraishi N (1993) Biodegradation and photo degradation of polyurethane form prepared from liquefied wood. In: Abstracts of the 43rd annual meeting of the Japan Wood Research Society, p 184 (in Japanese)

  8. 8.

    Hibbert H, Rowley HJ (1930) Studies on lignin and related compounds. I. A new method for isolation of spruce wood lignin. Can J Res 2:357–363

    CAS  Article  Google Scholar 

  9. 9.

    Nakano J, Takatsuka C, Daima H (1976) Studies on alkalimethanol cooking Part 1. Behavior of dissolution of lignin and carbohydrate. TAPPI J 30:650–655

    CAS  Article  Google Scholar 

  10. 10.

    Nelson PJ (1977) Pulping of wood with glycol solutions of salicylic acid derivatives. Appita 31(1):29–32

    CAS  Google Scholar 

  11. 11.

    Thring RW, Chornet E (1990) Recovery of solvolytic lignin: effect of spent liquor/acid volume ratio, acid concentration and temperature. Biomass 23:289–305

    CAS  Article  Google Scholar 

  12. 12.

    Yamada T, Ono H, Ohara S, Yamaguchi A (1996) Characterization of the products resulting from direct liquefaction of cellulose. I. Identification of intermediates and the relevant mechanism in direct phenol liquefaction of cellulose in the presence of water. Mokuzai Gakkaishi 42:1098–1104

    CAS  Google Scholar 

  13. 13.

    Yao Y, Yoshioka M, Shiraishi N (1994) Soluble properties of liquefied biomass prepared in organic solvents. I. The soluble behavior of liquefied biomass in various diluents. Mokuzai Gakkaishi 40:176–184

    CAS  Google Scholar 

  14. 14.

    Japan Spectroscopic Co. (1983) High-pressure liquid Chlromatographic analyses of organic acids. Japanese patent JP59147262

  15. 15.

    Ono H (1992) Study of phnolated wood. II. Mechanism of phenolation in the presence of acid catalyst. In: Abstracts of the 42nd annual meeting of the Japan Wood Research Society, p 302 (in Japanese)

  16. 16.

    Azuma J, Koshijima T (1981)13C-NMR spectroscopy of carbohydrates. I.13C-NMR spectroscopy of cellulose and related carbohydrates. Wood Research Institute, Kyoto University, Uji Kyoto Japan, Wood Research and Technical Notes 16: 63–96

    Google Scholar 

  17. 17.

    Konno C, Hikono H (1976)13C nuclear magnetic resonance spectra of ethers and glycols. Tetrahedron 32:325–331

    CAS  Article  Google Scholar 

  18. 18.

    Angyal SJ (1972) Conformations of sugars. In: Pigman W, Horton D (eds.) The Carbohydrates. Chemistry and biochemistry, 2nd ed. Vol. IA, Academic Press, New York, pp 195–215

    Google Scholar 

  19. 19.

    Feather MS, Harris JF (1973) Dehydration reaction of carbohydrates. Adv Carbohydr Chem Biochem 28:161–224

    CAS  Article  Google Scholar 

  20. 20.

    The Merck Index No. 4153 formic acid (1989) The Merck index, centennial edition, 11th ed. Merck, Whitehouse Station, NJ, USA

Download references

Author information

Affiliations

Authors

Corresponding author

Correspondence to Tatsuhiko Yamada.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Yamada, T., Ono, H. Characterization of the products resulting from ethylene glycol liquefaction of cellulose. J Wood Sci 47, 458–464 (2001). https://doi.org/10.1007/BF00767898

Download citation

Key words

  • Liquefaction
  • Ethylene glycol
  • Wood
  • Cellulose
  • NMR