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Journal of Wood Science

Official Journal of the Japan Wood Research Society

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Catalytic pyrolysis of cellulose in sulfolane with some acidic catalysts

Journal of Wood Science volume 53, pages 127–133 (2007)Cite this article

A Correction to this article was published on 27 November 2018

Abstract

Catalytic pyrolysis of cellulose in sulfolane (tetramethylene sulfone) with sulfuric acid or polyphosphoric acid gave levoglucosenone, furfural, and 5-hydroxymethyl furfural (5-HMF) up to 42.2%, 26.9%, and 8.8% (as mol% yield based on the glucose unit), respectively. Pyrolysis behaviors of the intermediates indicated the conversion pathways, and the conversion: levoglucosenone → furfural was found to require water. The control of the water content in the pyrolysis medium was quite effective in controlling the product selectivity between levoglucosenone and furfural: mild vacuum conditions to remove the product water dramatically enhanced the levoglucosenone yield, while steam distillation conditions increased the furfural and 5-HMF yields.

References

  1. Kawamoto H, Hatanaka W, Saka S (2003) Thermochemical conversion of cellulose in polar solvent (sulfolane) into levoglucosan and other low molecular-weight substances. J Anal Appl Pyrolysis 70:303–313

    Article  CAS  Google Scholar 

  2. Kawamoto H, Murayam M, Saka S (2003) Pyrolysis behavior of levoglucosan as an intermediate in cellulose pyrolysis: polymerization into polysaccharide as a key reaction to carbonized product formation. J Wood Sci 49:469–473

    Article  CAS  Google Scholar 

  3. Kawamoto H, Saka S (2006) Heterogeneity in cellulose pyrolysis indicated from the pyrolysis in sulfolane. J Anal Appl Pyrolysis 76:280–284

    Article  CAS  Google Scholar 

  4. Tsuchiya Y, Sumi K (1970) Thermal decomposition products of cellulose. J Appl Polymer Sci 14:2003–2013

    Article  CAS  Google Scholar 

  5. Wodley FA (1971) Pyrolysis products of untreated and flame retardant-treated α-cellulose and levoglucosan. J Appl Polym Sci 15:835–851

    Article  CAS  Google Scholar 

  6. Lipska AE, McCasland GE (1971) Synergistic effect of benzydrylation and iodination of the flammability of alpha-cellulose. J Appl Polym Sci 15:419–435

    Article  CAS  Google Scholar 

  7. Halpern Y, Riffer R, Broido A (1973) Levoglucosenone (1,6-anhydro-3,4-dideoxy-δ3-β-d-pyranosen-2-one). Major product of the acid-catalyzed pyrolysis of cellulose and related carbohydrates. J Org Chem 38:204–209

    Article  CAS  Google Scholar 

  8. Broido A, Evett M, Hodges CC (1975) Yield of 1,6-anhydro-3, 4-dideoxy-β-d-glycerohex-3-enopyranos-2-ulose (levoglucosenone) on the acid-catalyzed pyrolysis of cellulose and 1,6-anhydro-b-d-glucopyranose (levoglucosan). Carbohydr Res 44:267–274

    Article  CAS  Google Scholar 

  9. Shafizadeh F, Furneaux RH, Stevenson TT, Cochran TG (1978) Acid-catalyzed pyrolytic synthesis and decomposition of 1,4:3,6-dianhydro-α-d-glucopyranose. Carbohydr Res 61:519–528

    Article  CAS  Google Scholar 

  10. Fung DPC (1976) Further investigation on the effect of phosphoric acid on the pyrolysis of cellulose. Wood Sci 9:55–57

    CAS  Google Scholar 

  11. Shafizadeh F, Chin PPS (1976) Pyrolytic production and decomposition of 1,6-anhydro-3,4-dideoxy-β-d-glycero-hex-3-enopyranos-2-ulose. Carbohydr Res 46:149–154

    Article  CAS  Google Scholar 

  12. Shafizadeh F, Chin PPS (1977) Preparation of 1,6-anhydro-3,4-dideoxy-β-d-glycero-hex-3-enopyranos-2-ulose (levoglucosenone) and some derivatives thereof. Carbohydr Res 58:79–87

    Article  CAS  Google Scholar 

  13. Dobele G, Rossinskaja G, Telysheva G, Meier D, Faix O (1999) Cellulose dehydration and depolymerization reactions during pyrolysis in the presence of phosphoric acid. J Anal Appl Pyrolysis 49:307–317

    Article  CAS  Google Scholar 

  14. Dobele G, Meier D, Faix O, Radtke S, Rossinskaja G, Telysheva G (2001) Volatile products of catalytic flash pyrolysis of celluloses. J Anal Appl Pyrolysis 58–59:453–463

    Article  Google Scholar 

  15. Dobele G, Dizhbite T, Rossinskaja G, Telysheva G, Meier D, Radtke S, Faix O (2003) Pre-treatment of biomass with phosphoric acid prior to fast pyrolysis: a promising method for obtaining 1,6-anhydrosaccharides in high yields. J Anal Appl Pyrolysis 68–69:197–211

    Article  Google Scholar 

  16. Witczak ZJ (1994) Levoglucosenone; past, present and further applications. In: Witczak ZJ (ed) Levoglucosenone and levoglucosans. ATL, Mount Prospect, IL, pp 3–16

    Google Scholar 

  17. Isobe M, Yamamoto N, Nishikawa T (1994) Levoglucosenone as chiral pool for synthesis. In: Witczak ZJ (ed) Levoglucosenone and levoglucosans. ATL, Mount Prospect, IL, pp 99–118

    Google Scholar 

  18. Streitwieser A Jr, Heathcock CH (1979) Introduction to organic chemistry (translation version in Japanese). Hirokawa, Tokyo, p 6 (appendix)

  19. Kato K, Komorita H (1968) Pyrolysis of cellulose. V. Isolation and identification of 3-deoxyglycosones produced from d-glucose, dxylose, and α-cellulose by heating. Agr Biol Chem 32:715–720

    CAS  Google Scholar 

  20. Houminer Y, Patai S (1967) Thermal decomposition of d-glucose labeled with carbon-14 at various positions. Tetrahedron Lett 8:1297–1300

    Article  Google Scholar 

  21. Arnett EM, Douty CF (1964) Solvent effects in organic chemistry. II. Sulfolane — a weakly basic aprotic solvent of high dielectric constant. J Am Chem Soc 86:409–412

    Article  CAS  Google Scholar 

  22. Gardiner D (1966) The pyrolysis of some hexoses and derived di-, tri-, and polysaccharides. J Chem Soc C 1473-1476

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Authors and Affiliations

  1. Department of Socio-Environmental Energy Science, Graduate School of Energy Science, Kyoto University, Yoshida Hon-machi, Sakyo-ku, Kyoto, 606-8501, Japan

    Haruo Kawamoto, Shinya Saito, Wataru Hatanaka & Shiro Saka

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  1. Haruo Kawamoto
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  2. Shinya Saito
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  3. Wataru Hatanaka
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  4. Shiro Saka
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Correspondence to Haruo Kawamoto.

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Kawamoto, H., Saito, S., Hatanaka, W. et al. Catalytic pyrolysis of cellulose in sulfolane with some acidic catalysts. J Wood Sci 53, 127–133 (2007). https://doi.org/10.1007/s10086-006-0835-y

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  • DOI: https://doi.org/10.1007/s10086-006-0835-y

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