Skip to main content

Official Journal of the Japan Wood Research Society

Chemical analysis of the product in acid-catalyzed solvolysis of cellulose using polyethylene glycol and ethylene carbonate


Degradation and decomposition of cellulose were studied in an acid-catalyzed solvolysis treatment of biomass using polyethylene glycol (PEG) and ethylene carbonate (EC). The solvolysis reaction was followed by a typical reaction system of wood liquefaction that uses sulfuric acid catalyst at 140° or 150°C at atmospheric pressure. The methods of fractionation and chemical analysis of the degraded cellulose in the solvolyzed product are discussed. The solvolyzed product was separated into several fractions, and they were hydrolyzed to release glucose and levulinic acid to determine the quantity of glucosides and levulinates in the solvolysis product. The data clearly showed that the solvolysis reaction had the same mechanism when using PEG or EC. Degradation of cellulose leads to the formation of glucosides, which then decompose, resulting in a levulinic acid structure, and producing a water-insoluble fraction. The conversion rates of both glucosides and levulinates strongly depend on the reaction conditions of the solvolysis. In particular, EC promotes faster conversion of the reactions. The method discussed here is a chemical analytical technique for characterization of the products of wood liquefaction.


  1. Paszner L, Cho HJ (1989) Organosolv pulping — acidic catalysis options and their effect on fiber quality and delignification. TAPPI J 72:135–142

    CAS  Google Scholar 

  2. Gilarranz MA, Rodriguez F, Oliet M (2000) Lignin behavior during the autocatalyzed methanol pulping of Eucalyptus globulus — changes in molecular weight and functionality. Holzforschung 54:373–380

    Article  CAS  Google Scholar 

  3. Oliet M, Garcia J, Rodriguez F, Gilarrranz MA (2002) Solvent effects in autocatalyzed alcohol-water pulping comparative study between ethanol and methanol as delignifying agents. Chem Eng J 87:157–162

    Article  CAS  Google Scholar 

  4. Oliet M, Gilarranz MA, Dominguez JC, Alonso MV, Rodriguez F (2005) Ethanol-based pulping from Cynara cardunculus L. J Chem Technol Biotechnol 80:746–753

    Article  CAS  Google Scholar 

  5. Jimenez L, Rodriguez A, Diaz MJ, Lopez F, Ariza J (2004) Organosolv pulping of olive tree trimmings by use of ethylene glycol/ soda/water mixtures. Holzforschung 58:122–128

    Article  CAS  Google Scholar 

  6. Uraki Y, Sano Y (1999) Polyhydric alcohol pulping at atmospheric pressure: an effective method for organosolv pulping of softwoods. Holzforschung 53:411–415

    Article  CAS  Google Scholar 

  7. Sano Y, Shimamoto S (1995) Pulping of birchwood at atmospheric pressure with aqueous acetic acid containing small amounts of sulfuric acid and phenols. Mokuzai Gakkaishi 41:1006–1011

    CAS  Google Scholar 

  8. McDonough TJ (1993) The chemistry of organosolv delignification. TAPPI J 76:186–193

    CAS  Google Scholar 

  9. Yao Y, Yoshioka M, Shiraishi N (1993) Combined liquefaction of wood and starch in a polyethylene glycol-glycerin blended solvent. Mokuzai Gakkaishi 39:930–938

    CAS  Google Scholar 

  10. Ono H, Sudo K (1997) Japan Patent 2611166

  11. Shiraishi N, Shirakawa K, Kurimoto Y (2000) Japan Patent 3012296

  12. Kurimoto Y, Takeda M, Koizumi A, Yamauchi S, Doi S, Tamura Y (2000) Mechanical properties of polyurethane films prepared from liquefied wood with polymeric MDI. Bioresource Technol 74:151–157

    Article  CAS  Google Scholar 

  13. Lin L, Yoshioka M, Yao Y, Shiraishi N (1995) Preparation and properties of phenolated wood/phenol/formaldehyde cocondensed resin. J Appl Polym Sci 58:1297–1304

    Article  CAS  Google Scholar 

  14. Ono H, Yamada T, Hatano Y, Motohashi K (1996) Adhesives from waste paper by means of phenolation. J Adhesion 59:135

    Article  CAS  Google Scholar 

  15. Yamada T, Hosoya S, Ono H (2003) Acid catalyzed solvolysis of lignocellulosic waste for preparing useful chemicals. Proceedings of 12th International Symposium on Wood and Pulping Chemistry, Madison, USA, pp 235–238

  16. Yamada T, Ono H (2001) Characterization of the products resulting from ethylene glycol liquefaction of cellulose. J Wood Sci 47:458–464

    Article  CAS  Google Scholar 

  17. 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 

  18. Yamada T, Ono H (1999) Rapid liquefaction of lignocellulosic waste by using ethylene carbonate. Bioresource Technol 70:61–67

    Article  CAS  Google Scholar 

  19. Yamada T, Toyota S, Shimizu K, Ono H (2002) Japan Patent 3343564

  20. Garves K (1988) Acid-catalyzed degradation of cellulose in alcohols. J Wood Chem Technol 8:121–134

    Article  CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  23. Yamada T, Hu Y, Ono H (2001) Condensation reaction of degraded lignocellulose during wood liquefaction in the presence of polyhydric alcohols. J Adhesion Soc Jpn 37:471–478

    Article  CAS  Google Scholar 

  24. Bozell JJ, Moens L, Elliott DC, Wang Y, Neuenscwander GG, Fitzpatrick SW, Bilski RJ, Jarnefeld JL (2000) Production of levulinic acid and use as a platform chemical for derived products. Resour Conserv Recy 28:227–239

    Article  Google Scholar 

  25. Fitzpatrick SW (1997) Production of levulinic acid from carbohydrate-containing materials. US Patent 5608105

  26. Horvat J, Klaic B, Metelko B, Sunjic V (1986) Mechanism of levulinic acid formation in acid-catalyzed hydrolysis of 2-hydroxymethylfurane and 5-hydroxymethylfurane-2-carbaldehyde. Croat Chem Acta 59:429–438

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations


Corresponding author

Correspondence to Tatsuhiko Yamada.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yamada, T., Aratani, M., Kubo, S. et al. Chemical analysis of the product in acid-catalyzed solvolysis of cellulose using polyethylene glycol and ethylene carbonate. J Wood Sci 53, 487–493 (2007).

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI:

Key words