Abstract
Biomass refers to biological materials that can be used as fuel or for the production of chemicals. Globally, ever growing demand of energy and concerns for the environment have prompted researchers to develop convenient and efficient ways for converting wood biomass into valuable chemicals, bio-fuels and useful biomaterials. In this context, ionic liquid has the potential to play a major role. Ionic liquids, considered as green solvents, have been found capable of dissolving wood biomass, and the dissolution process can be enhanced in a number of ways, like heating, microwave treatment, addition of acids etc. The anionic part of ionic liquid plays an important role in this process coupled with hydrogen bond basicity (β) property of ionic liquid, which has a significant effect on wood biomass dissolution. This paper reviews the applications of ionic liquids for the dissolution, fractionation and regeneration of wood biomass. It is also related to the processing of cellulose and wood biomass, preparation of cellulose and wood biomass derivatives and composites.
Zusammenfassung
Als Biomasse werden biologische Stoffe bezeichnet, die für die Energieerzeugung oder die Herstellung von Chemikalien verwendet werden. Der weltweit stetig zunehmende Energiebedarf und steigendes Umweltbewusstsein haben bewirkt, dass Wissenschaftler praktische und effiziente Verfahren zur Umwandlung von Biomasse in wertvolle Chemikalien, Biotreibstoffe und brauchbare Biomaterialien entwickeln. In diesem Zusammenhang könnten ionische Flüssigkeiten eine große Rolle spielen. Ionische Flüssigkeiten gelten als umweltfreundliche Lösungsmittel und sind in der Lage, Holzbiomasse aufzulösen. Dieser Auflösungsprozess kann auf verschiedene Art und Weise, wie zum Beispiel durch Erhitzung, Mikrowellenbehandlung, Zugabe von Säuren etc., verbessert werden. Der anionische Anteil der ionischen Flüssigkeit spielt dabei in Verbindung mit der Wasserstoffbrückenbasizität (β) der ionischen Flüssigkeit, die einen signifikanten Einfluss auf die Auflösung der Holzbiomasse hat, eine große Rolle. Diese Studie gibt einen Überblick über die Verwendung der ionischen Flüssigkeit zur Auflösung, Fraktionierung und Gewinnung von Holzbiomasse. Daneben wird auch auf die Verarbeitung von Zellulose und Holzbiomasse sowie die Herstellung von Zellulose und anderen Holzbiomasseprodukten sowie Verbundwerkstoffen eingegangen.
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References
Abbott PA, Bell JT, Handa S, Stoddart B (2005) O-Acetylation of cellulose and monosaccharides using a zinc-based ionic liquid. Green Chem 7:705–707
Alder E (1977) Lignin chemistry-past, present and future. Wood Sci Technol 11:169–218
Aldous L, Silvester DS, Pitner WR, Compton RG, Lagunas MC, Hardacre C (2007) Voltammetric studies of gold, protons, and [HCl2]– in ionic liquids. J Phys Chem C 111:8496
Argyropoulos DS (2008) Use of lignocellulosics solvated in ionic liquids for production of biofuels. US Patent 2008/0190013 A1
Bagheri M, Rodríguez H, Swatloski RP, Spear KS, Daly TD, Rogers RD (2008) Ionic liquid-based preparation of cellulose—dendrimer films as solid supports for enzyme immobilization. Biomacromolecules 9:381–387
Barthel S, Heinze T (2006) Acylation and carbanilation of cellulose in ionic liquids. Green Chem 8:301–306
Browning LB (1975) The chemistry of wood. Krieger, Huntington
Chandra RP, Bura R, Mabee WE, Berlin A, Pan X, Saddler JN (2007) Substrate pretreatment: the key to effective enzymatic hydrolysis of lignocellulosics. Adv Biochem Eng Biotechnol 108:67–93
Crowhurst L, Mawdsley RP, Perez-Arlandis MJ, Salter AP, Welton T (2003) Solvent-solute interaction in ionic liquids. Chem Chem Phys 5:2790–2794
Dadi PA, Varanasi S, Schall AC (2006) Enhancement of cellulose saccharification kinetics using an ionic liquid pretreatment step. Biotechnol Bioeng 95:904–910
Earle MJ, Seddon KR (2000) Ionic liquids: Green solvents for the future. Pure Appl Chem 72:1391–1398
Edye LA, Doherty SOW (2008) Fractionation of lignocellulosic materials. World Intellectual Property Organization Patent WO/2008/095252 A1
Egorov MV, Smirnova VS, Formanovsky AA, Pletnev IV (2007) Dissolution of cellulose in ionic liquids as a way to obtain test materials for metal-ion detection. Anal Bioanal Chem 387:2263–2269
Erdmenger T, Haensch C, Hoogenboom R, Schubert SU (2007) Homogeneous tritylation of cellulose in 1-butyl-3-methylimidazoliumchloride. Macromol Biosci 7:440–445
Fort DA, Remsing RC, Swatloski RP, Moyna P, Moyna G, Rogers RD (2007) Can ionic liquids dissolve wood? Processing and analysis of lignocellulosic materials with 1-n-butyl-3-methylimidazolium chloride Green Chem 9:63–69
Fukaya Y, Sugimoto A, Ohno H (2006) Superior solubility of polysaccharides in low viscosity, polar, and halogen-free 1,3-dialkylimidazolium formates. Biomacromolecules 7:3295–3297
Galbe M, Zacchi G (2007) Pretreatment of lignocellulosic materials for efficient bioethanol production. Adv Biochem Eng Biotechnol 108:41–65
Graenacher C (1934) Cellulose solution. US Patent 1943176
Guo LY, Shi TJ, Li Z, Duan YP (2008a) Solubility of two kinds of imidazolium ionic liquids for fir powder. J Chem Ind Eng 59:1299–1304
Guo LY, Shi TJ, Li Z, Duan YP, Wang YG (2008b) Synthesis of novel and functionalized ionic liquid [HeEIM]Cl and its solubility for cotton fibre. Chem J Chin Univ 29:1901–1907
Hornby AS (2000) Oxford advanced learner’s dictionary of current English, 6th edn. Oxford University Press, Oxford
Kilpelainen I, Xie H, King A, Granstrom M, Heikkinen S, Argyropoulos DS, et al. (2007) Dissolution of wood in ionic liquids. Agric Food Chem 55:9142–9148
Klemn D, Heublein B, Fink PH, Bohn A (2005) Cellulose: Fascinating biopolymer and sustainable raw material. Angew Chem Int Ed 44:3358–3393
Kohler S, Heinze T (2007) Efficient synthesis of cellulose furoates in 1-N-butyl-3-methylimidazolium chloride. Cellulose 14:489–495
Lee SH, Doherty TV, Linhardt RJ, Dordick JS (2009) Ionic liquid-mediated selective extraction of lignin from wood leading to enhanced enzymatic cellulose hydrolysis. Biotechnol Bioeng 102:1368–1376
Li B, Asikkala J, Filpponen I, Argyropoulos DS (2010) Factors affecting wood dissolution and regeneration of ionic liquids. Ind Eng Chem Res 49:2477–2484
Li C, Wang Q, Zhao KZ (2008) Acid ionic liquid: An efficient system for hydrolysis of lignocelluloses. Green Chem 10:177–182
Li C, Knierim B, Manisseri C, Arora R, Scheller HV, Auer M, Vogel KP, Simmons BA, Singh S (2010) Comparison of dilute acid and ionic liquid pretreatment of switch grasses: Biomass recalcitrance, delignification and enzymatic saccharification. Bioresour Technol 101:4900–4906
Li RX (2005) Green solvents: synthesis and application of ionic liquids. China Chemical Industry Press, Beijing, pp 298–300
Luo HM, Li QY, Zhou RC (2005) Study on the dissolubility of the cellulose in the functionalized ionic liquid. Polym Mater Sci Eng 21(2):233–235
Miyafuji H, Miyata K, Saka S (2009) Reaction behavior of wood in an ionic liquid, 1-ethyl-3-methylimidazolium chloride. J Wood Sci 55:215–219
Muldoon JM, Gordon MC, Dunkin RI (2001) Investigations of solvent-solute interactions in room temperature ionic liquids using solvatochromic dyes. J Chem Soc Perkin Trans 2:433–436
Muldoon JM, Aki KV, Anderson LJ, Dixon KJ, Brennecke FJ (2007) Improving carbon dioxide solubility in ionic liquids. J Phys Chem B 111(30):9001–9009
Nakamura A, Miyafuji H, Saka S (2010) Influence of reaction atmosphere on the liquefaction and depolymerization of wood in an ionic liquid, 1-ethyl-3-methylimidazolium chloride. J Wood Sci. doi:10.1007/s10086-009-1081-x
Ohno H, Fukaya Y (2009) Task specific ionic liquids for cellulose. Chem Lett 38:2–7
Ohno H, Fukumoto K (2007) Amino acid ionic liquids. Acc Chem Res 40:1122–1129
Paun C, Barklie J, Goodrich P, Gunaratne HQN, McKeown A, Parvulescu VI, Hardacre C (2007) Supported and liquid phase task specific ionic liquids for base catalysed Knoevenagel reactions. J Mol Catal A 269:64
Poole SK, Shetty HP, Poole FC (1989) Chromatographic and spectroscopic studies of the solvent properties of a new series of room-temperature liquid tetraalkylammonium sulfonates. Anal Chim Acta 218:241
Rayne S, Mazza G (2007) Rapid dissolution of lignocellulosic plant materials in ionic liquids. Nat Prec 637:7–15
Ren LJ, Sun CR, Liu FC, Cao NZ, Luo W (2007) Acetylation of wheat straw hemicelluloses in ionic liquid using iodine as a catalyst. Carbohydr Polym 70:406–414
Rowell RM (1984) The chemistry of solid wood. Advances in chemistry series, vol 207. American Chemical Society, Washington
Sarkanen KV, Ludwig CH (1971) Lignin: occurrence, formation, structure reactions. Wiley-Interscience, New York
Shipovskov S, Nimal Gunaratne QH, Seddon KR, Stephens G (2008) Catalytic activity of laccases in aqueous solutions of ionic liquids. Green Chem 10:806–810
Singh S, Simmons BA, Voge KP (2009) Visualization of biomass solubilization and cellulose regeneration during ionic liquid pretreatment of switchgrass. Biotechnol Bioeng 104(1):68–75
Sjostrom E (1981) Wood chemistry: fundamentals and applications. Academic Press, New York
Sun N, Swatloski RP, Maxim LM, Rahman M, Harland MG, Haque A, Spear KS, Daly TD, Rogers RD (2008) Magnetite-embedded cellulose fibers prepared from ionic liquid. J Mater Chem 18:283–290
Sun N, Rahman M, Qin Y, Maxim ML, Rodriguez RH, Rogers RD (2009) Complete dissolution and partial delignification of wood in the ionic liquid 1-ethyl-3-methylimidazolium acetate. Green Chem 11:646–655
Sun Y, Cheng J (2002) Hydrolysis of lignocellulosic materials for ethanol production: a review. Bioresour Technol 83:1–11
Swatloski RP, Rogers RD, Spear KS (2002) Dissolution of cellulose in ionic liquid. J Am Chem Soc 124:4974–4975
Swatloski RP, Rogers RD, Holbery DJ (2003) Dissolution and processing of cellulose using ionic liquids, 11/30/04. US Patent No 6,824,599 B2; International Application PCT/US02/31404; International Publication Number WO 03/029329 A2
Swatloski RP, Rogers RD, Moyna G (2006) Mechanism of cellulose dissolution in the ionic liquid 1-n-butyl-3-methylimidazolium chloride: a 13C and 35/37Cl NMR relaxation study on model systems. Chem Commun 28:1271–1273
Takegawa A, Murakami M, Kaneko Y, Kadokawa J (2010) Preparation of chitin/cellulose composite gels and films with ionic liquids. Carbohydr Polym 79:85–90
Tan SSY, MacFarlane DR, Upfal J, Edye LA, Doherty WOS, Patti AF, Pringle JM, Scott JL (2009) Extraction of lignin from lignocellulose at atmospheric pressure using alkylbenzenesulfonate ionic liquid. Green Chem 11:339–345
Turner BM, Spear KS, Huddleston KJ Holbrey DJ, Rogers RD (2003) Ionic liquid-induced inactivation and unfolding of cellulase from trichoderma reesei. Green Chem 5:443–447
Turner BM, Spear KS, Holbrey DJ, Rogers RD (2004) Production of bioactive cellulose films reconstituted from ionic liquids. Biomacromolecules 5:1379–1384
Venkataramanan NS, Matsui K, Kawanami H, Ikushima Y (2007) Green synthesis of titania nanowire composites on natural cellulose fibers. Green Chem 9:698
Vesa M, Reijo A (2005) Dissolution method for lignocellulosic materials. World Intellectual Property Organization Patent WO 017001 A1
Wu J, Zhang J, Zhang H, He J, Ren Q, Guo M (2007) Homogeneous acetylation of cellulose in a new ionic liquid. Biomacromolecules 5(2):266–268
Xie H, Shi T (2009) Liquefaction of wood (Metasequoia glyptostroboides) in allyl alkyl imidazolium ionic liquids. Wood Sci Technol 44:119–128
Xie H, Li S, Zhang S (2005) Ionic liquids as novel solvents for the dissolution and blending of wool keratin fibers. Green Chem 7:606–608
Xie H, King A, Kilpelainen I, Granstrom M, Argyropoulos DS (2007) Thorough chemical modification of wood-based lignocellulosic materials in ionic liquids. Biomacromolecules 8:3740–3748
Xie H, King A, Jarvi P, Karesoja M, Kilpelainen I, Granstrom M, Argyropoulos DS (2009) Highly compatible wood thermoplastic composites from lignocellulosic material modified in Ionic liquids: Preparation and thermal properties. J Appl Polym Sci 111:2468–2476
Yang Q, Xing H, Cao Y, Su B, Yang Y, Ren Q (2009) Selective separation of tocopherol homologues by liquid-liquid extraction using ionic liquids. Ind Eng Chem Res 48:6417–6422
Zhang H, Wu J, Zhang J, He J (2005) 1-allyl-3-methylimidazolium chloride room temperature ionic liquid: a new and powerful nonderivatizing solvent for cellulose. Macromolecules 38:8272–8277
Zhang Q, Li Z, Zhang J, Zhang S, Zhu L, Yang J, Zhang X, Deng Y (2007) Physicochemical properties of nitrile-functionalized ionic liquids. J Phys Chem B 111:2864–2872
Zhao H Jones CL, Baker GA, Olubajo O Xia S, Person VN (2009) Regenerating cellulose from ionic liquids for an accelerated enzymatic hydrolysis. J Biotechnol 139:47–54
Zhao BH, Song AG, Olubajo Z, Crittle O, Peters T (2008) Design enzyme-compatible ionic liquids that can dissolve carbohydrates. Green Chem 10:696–705
Acknowledgements
This work was supported by Ionic Liquid Laboratory, Department of Chemical Engineering, Universiti Teknologi PETRONAS, Malaysia.
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Muhammad, N., Man, Z. & Bustam Khalil, M.A. Ionic liquid—a future solvent for the enhanced uses of wood biomass. Eur. J. Wood Prod. 70, 125–133 (2012). https://doi.org/10.1007/s00107-011-0526-2
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DOI: https://doi.org/10.1007/s00107-011-0526-2