Advertisement

Journal of Wood Science

, Volume 64, Issue 6, pp 802–809 | Cite as

Characterization of lignin-derived products from various lignocellulosics as treated by semi-flow hot-compressed water

  • Masatsugu Takada
  • Harifara Rabemanolontsoa
  • Eiji Minami
  • Shiro Saka
Original Article
First Online:
  • 98 Downloads

Abstract

To elucidate the decomposition behaviors of lignin from different taxonomic groups, five different lignocellulosics were treated with hot-compressed water (230 °C/10 MPa/15 min) to fractionate lignins into water-soluble portions, precipitates, and insoluble residues. The lignin-derived products in each fraction were characterized and compared. The delignification of monocotyledons [nipa palm (Nypa fruticans) frond, rice (Oryza sativa) straw, and corn (Zea mays) cob] was more extensive than that achieved for Japanese cedar (Cryptomeria japonica, gymnosperm) and Japanese beech (Fagus crenata, dicotyledon angiosperm). The water-soluble portions contained lignin monomers like coniferyl alcohol and phenolic acids, while the precipitates contained higher molecular weight lignin with high content of ether-type linkages. Lignin in the insoluble residues was rich in condensed-type structures. In all five lignocellulosics, ether-type linkages were preferentially cleaved, while condensed-type lignin showed resistance to hot-compressed water. In the monocotyledons, lignin–carbohydrate complexes were cleaved and gave lignins that had higher molecular weights than those eluted from the woods. These differences would facilitate the delignification in monocotyledons. Such information provides useful information for efficient utilization of various lignocellulosics.

Keywords

Lignin Hot-compressed water Gymnosperms Angiosperms Monocotyledons 
This is a preview of subscription content, log in to check access.

Notes

Acknowledgements

This work was supported by the Japan Science and Technology Agency (JST) under the Advanced Low Carbon Technology Research and Development Program (ALCA) and Kakenhi (no. 16J11212), a Grant-in-Aid for Japan Society for the Promotion of Science (JSPS) Fellow, for which the authors are grateful.

Compliance with ethical standards

Conflict of interest

The authors declare no conflicts of interests associated with this manuscript.

References

  1. 1.
    Bröll D, Kaul C, Krämer A, Krammer P, Richter T, Jung M, Vogel H, Zehner P (1999) Chemistry in supercritical water. Angew Chem Int Ed 38:2998–3014CrossRefGoogle Scholar
  2. 2.
    Savage PE (1999) Organic chemical reactions in supercritical water. Chem Rev 99:603–621CrossRefPubMedGoogle Scholar
  3. 3.
    Garrote G, Domínguez H, Parajó JC (1999) Hydrothermal processing of lignocellulosic materials. Holz Als Roh Werkst 57:191–202CrossRefGoogle Scholar
  4. 4.
    Mosier N, Wyman C, Dale B, Elander R, Lee YY, Holtzapple M, Ladische M (2005) Features of promising technologies for pretreatment of lignocellulosic biomass. Bioresour Technol 96:673–686CrossRefPubMedGoogle Scholar
  5. 5.
    Ando H, Sakaki T, Kokusho T, Shibata M, Uemura Y, Hatate Y (2000) Decomposition behavior of plant biomass in hot-compressed water. Ind Eng Chem Res 39:3688–3693CrossRefGoogle Scholar
  6. 6.
    Sakaki T, Shibata M, Sumi T, Yasuda S (2002) Saccharification of cellulose using a hot-compressed water-flow reactor. Ind Eng Chem Res 41:661–665CrossRefGoogle Scholar
  7. 7.
    Liu C, Wyman CE (2003) The effect of flow rate of compressed hot water on xylan, lignin, and total mass removal from corn stover. Ind Eng Chem Res 42:5409–5416CrossRefGoogle Scholar
  8. 8.
    Lu X, Yamauchi K, Phaiboonsilpa N, Saka S (2009) Two-step hydrolysis of Japanese beech as treated by semi-flow hot-compressed water. J Wood Sci 55:367–375CrossRefGoogle Scholar
  9. 9.
    Phaiboonsilpa N, Yamauchi K, Lu X, Saka S (2010) Two-step hydrolysis of Japanese cedar as treated by semi-flow hot-compressed water. J Wood Sci 56:331–338CrossRefGoogle Scholar
  10. 10.
    Nakahara Y, Yamauchi K, Saka S (2014) MALDI-TOF/MS analyses of decomposition behavior of beech xylan as treated by semi-flow hot-compressed water. J Wood Sci 60:225–231CrossRefGoogle Scholar
  11. 11.
    Isikgor FH, Becer CR (2015) Lignocellulosic biomass: a sustainable platform for production of bio-based chemicals and polymers. Polym Chem 6:4497–4559CrossRefGoogle Scholar
  12. 12.
    Rabemanolotsoa H, Saka S (2016) Various pretreatments of lignocellulosics. Bioresour Technol 199:83–91CrossRefGoogle Scholar
  13. 13.
    Tanahashi M, Karina M, Tamabuchi K, Higuchi T (1989) Degradation mechanism of lignin accompanying steam explosions I. Mokuzai Gakkaishi 35:135–143Google Scholar
  14. 14.
    Tanahashi M (1990) Characterization and degradation mechanisms of wood components by steam explosion and utilization of exploded wood. Wood Res Bull Wood Res Inst Kyoto Univ 77:49–117Google Scholar
  15. 15.
    Li J, Henriksson G, Gellerstedt G (2007) Lignin depolymerisation/repolymerization and its critical role for delignification of aspen wood by steam explosion. Bioresour Technol 98:3061–3068CrossRefPubMedGoogle Scholar
  16. 16.
    Ehara K, Takada D, Saka S (2005) GC-MS and IR spectroscopic analyses of the lignin-derived products from softwood and hardwood treated in supercritical water. J Wood Sci 51:256–261CrossRefGoogle Scholar
  17. 17.
    Yokoyama C, Nishi K, Nakajima A, Seino K (1998) Thermolysis of organosolv lignin in supercritical water and supercritical methanol. Sekiyu Gakkaishi 41:243–250CrossRefGoogle Scholar
  18. 18.
    Saisu M, Sato T, Watanabe M, Adschiri T, Arai K (2003) Conversion of lignin with supercritical water–phenol mixtures. Energy Fuels 17:922–928CrossRefGoogle Scholar
  19. 19.
    Trajano HL, Engle N, Foston M, Ragauskas AJ, Tschaplinski TJ, Wyman CE (2013) The fate of lignin during hydrothermal pretreatment. Biotechnol Biofuels 6:110–125CrossRefPubMedGoogle Scholar
  20. 20.
    Chen X, Li H, Sun S, Cao X, Sun R (2016) Effect of hydrothermal pretreatment on the structural changes of alkaline ethanol lignin from wheat straw. Sci Rep 6:39354CrossRefPubMedGoogle Scholar
  21. 21.
    Samuel R, Cao S, Das BK, Hu F, Pu Y, Ragauskas AJ (2013) Investigation of the fate of poplar lignin during autohydrolysis pretreatment to understand the biomass recalcitrance. RSC Adv 3:5305–5309CrossRefGoogle Scholar
  22. 22.
    Yamauchi K, Phaiboonsilpa N, Kawamoto H, Saka S (2013) Characterization of lignin-derived products from Japanese beech wood as treated by two-step semi-flow hot-compressed water. J Wood Sci 59:149–154CrossRefGoogle Scholar
  23. 23.
    Takada M, Saka S (2015) Characterization of lignin-derived products from Japanese cedar as treated by semi-flow hot-compressed water. J Wood Sci 61:299–307CrossRefGoogle Scholar
  24. 24.
    Rabemanolontsoa H, Saka S (2013) Comparative study on chemical composition of various biomass species. RSC Adv 3:3946–3956CrossRefGoogle Scholar
  25. 25.
    Buranov AU, Mazza G (2008) Lignin in straw of herbaceous crops. Ind Crops Prod 28:237–259CrossRefGoogle Scholar
  26. 26.
    Rabemanolontsoa H, Ayada S, Saka S (2011) Quantitative method applicable for various biomass species to determine their chemical composition. Biomass Bioenerg 35:4630–4635CrossRefGoogle Scholar
  27. 27.
    Torre P, Aliakbarian B, Rivas B, Domínguez JM, Converti A (2008) Release of ferulic acid from corn cobs by alkaline hydrolysis. Biochem Eng J 40:500–506CrossRefGoogle Scholar
  28. 28.
    Chen C-L (1992) Nitrobenzene and cupric oxide oxidations. In: Lin SY, Dence CW (eds) Methods in lignin chemistry. Springer, Berlin, pp 301–321CrossRefGoogle Scholar
  29. 29.
    Takada M, Minami E, Yamauchi K, Kawamoto H, Saka S (2017) Characterization of the precipitated lignin from Japanese beech as treated by semi-flow hot-compressed water. Holzforschung 71:285–290CrossRefGoogle Scholar
  30. 30.
    Dence CW (1992) The determination of lignin. In: Lin SY, Dence CW (eds) Methods in lignin chemistry. Springer, Berlin, pp 33–58CrossRefGoogle Scholar
  31. 31.
    Gellerstedt G (1994) Gel permeation chromatography. In: Lin SY, Dence CW (eds) Methods in lignin chemistry. Springer, Berlin, pp 487–497Google Scholar
  32. 32.
    Higuchi T, Ito Y, Shimada M, Kawamura I (1967) Chemical properties of milled wood lignin of grasses. Phytochemistry 6:1551–1556CrossRefGoogle Scholar
  33. 33.
    Grabber J, Quideau S, Ralph J (1996) -Coumaroylated syringyl units in maize lignin implications for β-ether cleavage by thioacidolysis. Phytochem 43:1189–1194 p .CrossRefGoogle Scholar
  34. 34.
    Lu F, Karlen SD, Regner M, Kim H, Ralph SA, Sun RC, Kuroda K, Augustin MA, Mawson R, Sabarez H, Singh T, Jimenez-Monteon G, Zakaria S, Hill S, Harris PJ, Boerjan W, Wilkerson CG, Mansfield SD, Ralph J (2015) Naturally p-hydroxybenzoylated lignins in palms. Bioenergy Res 8:934–952CrossRefGoogle Scholar
  35. 35.
    Baucher M, Monties B, Van Montagu M, Boerjan W (1998) Biosynthesis and genetic engineering of lignin. Crit Rev Plant Sci 17:125–197CrossRefGoogle Scholar
  36. 36.
    Lapierre C, Pollet B, Rolando C (1995) New insights into the molecular architecture of hardwood lignins by chemical degradative methods. Res Chem Intermed 21:397–412CrossRefGoogle Scholar
  37. 37.
    Lapierre C (1993) Application of new methods for the investigation of lignin structure. In: Jung HG, Buxton DR, Hatfield RD, Ralph J (eds) Forage cell wall structure and digestility. American Society of Agronomy, Madison, pp 133–166Google Scholar
  38. 38.
    Billa E, Tollier MT, Monties B (1996) Characterization of the monomeric composition of in situ wheat straw lignins by alkaline nitrobenzene oxidation: effect of temperature and reaction time. J Sci Food Agric 72:250–256CrossRefGoogle Scholar
  39. 39.
    Billa E, Koukios EG, Monties B (1998) Investigation of lignins structure in cereal crops by chemical degradation methods. Polym Degrad Stab 59:71–75CrossRefGoogle Scholar
  40. 40.
    Lam TB, Iiyama K, Stone BA (1992) Cinnamic acid bridges wheat and between cell wall polymers in phalaris internodes. Phytochemistry 31:1179–1183CrossRefGoogle Scholar
  41. 41.
    Lam TBT, Iiyama K, Stone BA (1990) Distribution of free and combined phenolic acids in wheat internodes. Phytochemistry 29:429–433CrossRefGoogle Scholar
  42. 42.
    Ehara K, Saka S, Kawamoto H (2002) Characterization of the lignin-derived products from wood as treated in supercritical water. J Wood Sci 48:320–325CrossRefGoogle Scholar

Copyright information

© The Japan Wood Research Society 2018

Authors and Affiliations

  • Masatsugu Takada
    • 1
  • Harifara Rabemanolontsoa
    • 1
  • Eiji Minami
    • 1
  • Shiro Saka
    • 1
  1. 1.Department of Socio-environmental Energy Science, Graduate School of Energy ScienceKyoto UniversityKyotoJapan

Personalised recommendations

Cite article

Buy options