Skip to main content
Journal of Wood Science

Official Journal of the Japan Wood Research Society

Download PDF
  • Original Article
  • Published:

Conversion of sulfuric acid lignin generated during bioethanol production from lignocellulosic materials into polyesters with ɛ-caprolactone

Journal of Wood Science volume 57, pages 214–218 (2011)Cite this article

Abstract

In this study, polyesters were prepared from sulfuric acid lignin (SAL) that was generated as a by-product during the production of bioethanol from lignocellulosic materials using ɛ-caprolactone (CL). Carboxylic groups were introduced into SAL by a hydrothermal reaction under alkali conditions. The acid form (-COOH) of the obtained polymer (HSAL) was dissolved into ɛ-caprolactone and the mixture was heated at 150°C for 12 h with ZnCl2 as a catalyst. The structure of the obtained polymer (PCL-HSAL) was proposed based on results of differential scanning calorimetric analysis, swelling tests, and dynamic mechanical thermal analysis. The hydroxyl group in HSAL participated in the ring-opening polymerization of CL. PCL-HSAL with a high HSAL content formed a three-dimensional network that did not dissolve in organic solvents and did not melt at high temperature. PCL-HSAL showed a high swelling property for a suitable ratio of CL to HSAL.

References

  1. Yasuda S, Tachi M, Takagi Y (1989) Phenolization of red pine sulfuric acid lignin and guaiacyl sulfuric acid lignin model in the presence of sulfuric acid catalyst. Mokuzai Gakkaishi 35:513–520

    CAS  Google Scholar 

  2. Yasuda S, Ito K, Hamaguchi E, Matsushita Y (1997) Ready chemical conversion of acid hydrolysis lignin into water-soluble lignosulfonate. I. Successive treatment of acid hydrolysis lignin by phenolation, hydroxymethylation and sulfonation. Mokuzai Gakkaishi 43:68–74

    CAS  Google Scholar 

  3. Matsushita Y, Yasuda S (2003) Preparation of anionic-exchange resins from pine sulfuric acid lignin, one of the acid hydrolysis lignins. J Wood Sci 49:423–429

    Article  CAS  Google Scholar 

  4. Matsushita Y, Yasuda S (2003) Reactivity of a condensed-type lignin model compound in the Mannich reaction and preparation of cationic surfactant from sulfuric acid lignin. J Wood Sci 49:166–171

    Article  CAS  Google Scholar 

  5. Matsushita Y, Iwatsuki A, Yasuda S (2004) Application of cationic polymer prepared from sulfuric acid lignin as a retention aid for usual rosin sizes to neutral papermaking. J Wood Sci 50:540–544

    Article  CAS  Google Scholar 

  6. Matsushita Y, Yasuda S (2005) Preparation and evaluation of lignosulfonates as a dispersant for gypsum paste from acid hydrolysis lignin. Bioresour Technol 96:465–470

    Article  CAS  PubMed  Google Scholar 

  7. Matsushita Y, Imai M, Tamura T, Fukushima K (2005) Preparation and evaluation of a dispersant for gypsum paste from acid hydrolysis lignin. J Appl Polym Sci 98:2508–2516

    Article  CAS  Google Scholar 

  8. Matsushita Y, Imai M, Iwatsuki A, Fukushima K (2008) Relationships between surface tension and industrial performance of water-soluble polymers prepared from acid hydrolysis lignin, a saccharification by-product from woody materials. Bioresour Technol 99:3024–3028

    Article  CAS  PubMed  Google Scholar 

  9. Tai S, Nakano J, Migita N (1966) Studies on utilization of lignin. II. Preparation of anion exchanger from wood hydrolysis lignin. Mokuzai Gakkaishi 12:108–112

    CAS  Google Scholar 

  10. Watanabe M, Meshitsuka G, Ishizu A (1992) Radical sulfonation of lignin. III. Application to various lignins. Mokuzai Gakkaishi 38:173–179

    CAS  Google Scholar 

  11. Matsushita Y, Inomata T, Hasegawa T, Fukushima K (2009) Solubilization and functionalization of sulfuric acid lignin generated during bioethanol production from woody biomass. Bioresour Technol 100:1024–1026

    Article  CAS  PubMed  Google Scholar 

  12. Hatakeyama H (2002) Thermal analysis of environmentally compatible polymers containing plant components in the main chain. J Therm Anal Cal 70:755–795

    Article  CAS  Google Scholar 

  13. Hatakeyama T, Izuta Y, Hirose S, Hatakeyama H (2002) Phase transitions of lignin-based polycaprolactones and their polyurethane derivatives. Polymer 43:1177–1182

    Article  CAS  Google Scholar 

  14. Hirose S, Hatakeyama T, Hatakeyama H (2005) Glass transition and thermal decomposition of epoxy resins from the carboxylic acid system consisting of ester-carboxylic acid derivatives of alcoholysis lignin and ethylene glycol with various dicarboxylic acids. Thermochem Acta 431:76–80

    Article  CAS  Google Scholar 

  15. Bonin C, D’Auria M, Emanuele L, Ferri R, Puccuariello R, Sabia ARJ (2005) Polyurethanes and polyesters from lignin. Appl Polym Sci 98:1451–1456

    Article  Google Scholar 

  16. Teramoto Y, Lee SH, Endo T (2009) Phase structure and mechanical property of blends of organosolv lignin alkyl esters with poly(ɛ-caprolactone). Polym J 41:219–227

    Article  CAS  Google Scholar 

  17. Cavalli G, Shooter AG, Pears DA, Steinke JHG (2003) Non-PEG-derived polyethers as solid supports. 1. Synthesis, swelling studies, and functionalization. J Comb Chem 5:637–644

    Article  CAS  Google Scholar 

  18. Chen CP, Ko BT, Lin SL, Hsu MY, Ting C (2006) Hydrophilic polymer supports grafted by poly(ethylene glycol) derivatives via atom transfer radical polymerization. Polymer 47:6630–6635

    Article  CAS  Google Scholar 

  19. de Oliveira W, Glasser WG (1994) Multiphase materials with lignin. 11. Starlike copolymers with caprolactone. Macromolecules 27:5–11

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Graduate School of Bioagricultural Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya, Aichi, 464-8601, Japan

    Yasuyuki Matsushita, Toyoki Inomata & Kazuhiko Fukushima

  2. Nagoya Municipal Industrial Research Institute, Nagoya, Aichi, 456-0058, Japan

    Yasuo Takagi

  3. EcoTopia Science Institute, Nagoya University, Nagoya, Aichi, 464-8601, Japan

    Tatsuya Hasegawa

Authors
  1. Yasuyuki Matsushita
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Toyoki Inomata
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yasuo Takagi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Tatsuya Hasegawa
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Kazuhiko Fukushima
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yasuyuki Matsushita.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Matsushita, Y., Inomata, T., Takagi, Y. et al. Conversion of sulfuric acid lignin generated during bioethanol production from lignocellulosic materials into polyesters with ɛ-caprolactone. J Wood Sci 57, 214–218 (2011). https://doi.org/10.1007/s10086-010-1158-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10086-010-1158-6

Key words