Application of ionic liquids for effective use of woody biomass

Journal of Wood Science

Volumn 61, Issue 4, 2015, Pages 343-350

  Miyafuji, Hisashi ^a  

^a KYOTO PREFECTURAL UNIVERSITY   (Japan)

Author keywords

Biorefinery; Cellulose; Ionic liquid; Preservation; Woody biomass

Indexed keywords

CELLULOSE; DECAY (ORGANIC); ENZYMATIC HYDROLYSIS; FIRE RESISTANCE; INDICATORS (CHEMICAL); LIGNIN; REFINING; WOOD CHEMICALS; WOOD PRESERVATION;

BIOREFINERIES; DECAY RESISTANCE; HIGH SOLUBILITY; LOW VISCOSITY; PRESERVATION; PROCESSING TECHNOLOGIES; REACTION SOLVENTS; WOOD POLYMERS; WOOD PROCESSING; WOODY BIOMASS;

IONIC LIQUIDS;

EID: 84938748989     PISSN: 14350211     EISSN: 16114663     Source Type: Journal    
DOI: 10.1007/s10086-015-1489-4     Document Type: Article

References (99)

1. Wasserscheid P (2003) Potential to apply ionic liquids in industry. In: Rogers RD et al (eds) Green industrial applications of ionic liquids. Kluwer Academic Publishers, Netherlands, pp 29–47
2. Cybulski J, Wiśniewska A, Kulig-Adamiak A, Lewicka L, Cieniecka-Rosłonkiewicz A, Kita K, Fojutowski A, Nawrot J, Materna K, Pernak J (2008) Long-alkyl-chain quaternary ammonium lactate based ionic liquids. Chem A Eur J 14:9035–9311
3. Pernak J, Zabielska-Matejuk J, Kropacz A, Foksowicz J (2004) Ionic liquids in wood preservation. Holzforschung 58:286–291
4. Stasiewicz M, Fojutowski A, Kropacz A, Pernak J (2008) 1-Alkoxymethyl-x-dimethylaminopyridinium-based ionic liquids in wood preservation. Holzforschung 62:309–317
5. Miyafuji H, Fujiwara Y (2013) Fire resistance of wood treated with various ionic liquids (ILs). Holzforschung 67:787–793
6. Swatloski RP, Spear SK, Holbrey JD, Rogers RD (2002) Dissolution of cellulose with ionic liquids. J Am Chem Soc 124:4974–4975
7. Pinkert A, Marsh KN, Pang S, Staiger MP (2009) Ionic liquids and their interaction with cellulose. Chem Rev 109:6712–6728
8. Cuissinat C, Navard P, Heinze T (2008) Swelling and dissolution of cellulose. Part IV: free floating cotton and wood fibers in ionic liquids. Carbohyd Poly 72:590–596
9. Vitz J, Erdmenger T, Haensch C, Schubert U (2009) Extended dissolution studies of cellulose in imidazolium based ionic liquids. Green Chem 11:417–424
10. Zavrel M, Bross D, Funke M, Büchs J, Spiess AC (2009) High-throughput screening for ionic liquids dissolving (lingo-)cellulose. Bioresour Technol 100:2580–2587
11. Xu A, Wang J, Wang H (2010) Effects of anionic structure and lithium salts addition on the dissolution of cellulose in 1-butyl-3-methylimidazolium-based ionic liquid solvent systems. Green Chem 12:268–275
12. Lan W, Liu C, Yue F, Sun R, Kennedy JF (2011) Ultrasound-assisted dissolution of cellulose in ionic liquid. Carbohyd Polym 86:672–677
13. 13C NMR studies of cellulose and cellulose oligomers in ionic liquid solution. Chem Commun 2005:1557–1559
14. 35/37Cl NMR relaxation study on model systems. Chem Comm 2006:1271–1273
15. Remsing RC, Harnandez G, Swatroski RP, Massefski WW, Rogers RD, Moyna G (2008) Solvation of carbohydrates in N,N′-dialkylimidazolium ionic liquids: a multinuclear NMR spectroscopy study. J Phys Chem B 112:11071–11078
16. Youngs TGA, Holbrey JD, Deetlefts M, Nieuwenhuyzen M, Gomes MFC, Hardacre C (2006) A molecular dynamics study of glucose solvation in the ionic liquid 1,3-dimethylimidazolium chloride. Chem Phys Chem 7:2279–2281
17. Youngs TGA, Hardacre C, Holbrey JD (2007) Glucose solvation by the ionic liquid 1,3-dimethylimidazolium chloride: a simulation study. J Phys Chem B 111:13765–13774
18. Liu H, Sale KL, Holmes BM, Simmons BA, Singh S (2010) Understanding the interactions of cellulose with ionic liquids: a molecular dynamics study. J Phys Chem B 114:4293–4301
19. 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
20. Fukaya Y, Hayashi K, Wada M, Ohno H (2008) Cellulose dissolution with polar ionic liquids under mild conditions: required factors for anion. Green Chem 10:44–46
21. Ebner G, Schiehser S, Potthast A, Rosenau T (2008) Side reaction of cellulose with common 1-alkyl-3-methylimidazolium-based ionic liquids. Tetrahedron Lett 49:7322–7324
22. Kilpelainen I, Xie H, King A, Granstrom M, Heikkinen S, Argyropoulos DS (2007) Dissolution of wood in ionic liquids. J Agric Food Chem 55:9142–9148
23. Guo L, Zhang M (2010) Comparative studies on synthesis of imidazole ionic liquids and their solubility for wood by microwave. Adv Mater Res 113–114:1744–1748
24. Sun N, Rahman M, Qin Y, Maxim ML, Rodríguez H, Rogers RD (2009) Complete dissolution and partial delignification of wood in the ionic liquid 1-ethyl-3-methylimidazolium acetate. Green Chem 11:646–655
25. Chen C, Li J (2010) Synthesis of ionic liquid and its application in Duabanga grandiflora wood powder as green solvent. Adv Mater Res 113–114:407–411
26. Nakamura A, Miyafuji H, Saka S (2010) Liquefaction behavior of western red cedar and Japanese beech in the ionic liquid, 1-ethyl-3-methylimidazolium chloride. Holzforschung 64:289–294
27. Li W, Sun N, Stoner B, Jiang X, Lu X, Rogers RD (2011) Rapid dissolution of lignocellulosic biomass in ionic liquids using temperatures above the glass transition of lignin. Green Chem 13:2038–2047
28. Mäki-Arvela P, Anugwom I, Virtanen P, Sjöholm R, Mikkola JP (2010) Dissolution of lignocellulosic materials and its constituents using ionic liquids. A review. Ind Crops Prod 32:175–201
29. Fort DA, Remsing RC, Swatloski RP, Moyna P, Moyn 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
30. Miyafuji H, Miyata K, Saka S, Umeda F, Mori M (2009) Reaction behavior of wood in an ionic liquid, 1-ethyl-3-methylimidazolium chloride. J Wood Sci 55:215–219
31. Wang X, Li H, Cao Y, Tang Q (2011) Cellulose extraction from wood chip in an ionic liquid 1-allyl-3-methylimidazolium chloride (AmimCl). Bioresour Technol 102:7959–7965
32. Casas A, Oliet M, Alonso MV, Godríguez F (2012) Dissolution of Pinus radiata and Eucalyptus globulus woods in ionic liquids under microwave radiation: lignin regeneration and characterization. Sep Purif Technol 97:115–122
33. Miyafuji H, Suzuki N (2011) Observation by light microscope of sugi (Cryptomeria japonica) treated with the ionic liquid 1-ethyl-3-methylimidazolium chloride. J Wood Sci 57:459–461
34. Miyafuji H, Suzuki N (2012) Morphological changes in sugi (Cryptomeria japonica) wood after treatment with the ionic liquid, 1-ethyl-3-methylimidazolium chloride. J Wood Sci 58:222–230
35. Kanbayashi T, Miyafuji H (2013) Morphological changes of Japanese beech treated with the ionic liquid, 1-ethyl-3-methylimidazolium chloride. J Wood Sci 59:410–418
36. Kanbayashi T, Miyafuji H (2014) Comparative study of morphological changes in hardwoods treated with the ionic liquid, 1-ethyl-3-methylimidazolium chloride. J Wood Sci 60:152–159
37. Viell J, Marquardt W (2011) Disintegration and dissolution kinetics of wood chips in ionic liquids. Holzforschung 65:519–525
38. Kanbayashi T, Miyafuji H (2015) Raman microscopic analysis of wood after treatment with the ionic liquid, 1-ethyl-3-methylimidazolium chloride. Holzforschung 69:273–279
39. Zhang X, Ma J, Ji Z, Yang GH, Zhou X, Xu F (2014) Using confocal raman microscopy to real-time monitor poplar cell wall swelling and dissolution during ionic liquid pretreatment. Microsc Res Tech 77:609–618
40. Heinze T, Schwikal K, Barthal S (2005) Ionic liquids as reaction medium in cellulose functionalization. Macromolecular Biosci 5:520–525
41. Barthel S, Heinze T (2006) Acylation and carbanilation of cellulose in ionic liquids. Green Chem 8:301–306
42. Wu J, Zhang J, Zhang H, He J, Ren Q, Guo M (2004) Homogeneous acetylation of cellulose in a new ionic liquid. Biomacromolecules 5:266–268
43. Liu CF, Sun RC, Zhang AP, Ren JL, Wang XA, Qin MH, Chao ZN, Luo W (2007) Homogeneous modification of sugarcane bagasse cellulose with succinic anhydride using a ionic liquid as reaction medium. Carbohyd Res 342:919–926
44. Liu CF, Sun RC, Zhang AP, Qin MH, Ren JL, Wang XA (2007) Preparation and characterization of phthalated cellulose derivatives in room-temperature ionic liquid without catalysts. J Agric Food Chem 55:2399–2406
45. Mikkola JP, Kirilin A, Tuuf JC, Pranovich A, Holmbom B, Kustov LM, Murzin DY, Salmi T (2007) Ultrasound enhancement of cellulose processing in ionic liquids: from dissolution towards functionalization. Green Chem 9:1229–1237
46. Zhang J, Wu J, Cao Y, Sang S, Zhang J, He J (2009) Synthesis of cellulose benzoates under homogeneous conditions in an ionic liquid. Cellulose 16:299–308
47. Liu CF, Zhang AP, Li WY, Yue FX, Sun RC (2009) Homogeneous modification of cellulose in ionic liquid with succinic anhydride using n-bromosuccinimide as a catalyst. J Agric Food Chem 57:1814–1820
48. Liu CF, Zhang AP, Li WY, Yue FX, Sun RC (2010) Succinoylation of cellulose catalyzed with iodine in ionic liquid. Ind Crop Prod 31:363–369
49. 2 film in ionic liquid dissolving cellulose. Microporous Mesoporous Mater 95:26–30
50. Murakami M, Kaneko Y, Kadokawa J (2007) Preparation of cellulose-polymerized ionic liquid composite by in situ polymerization of polymerizable ionic liquid in cellulose-dissolving solution. Carbohyd Polym 69:378–381
51. Zhang H, Wang Z, Zhang Z, Wu J, Zhang J, He J (2007) Regenerated-cellulose/multiwalled-carbon-nanotube composite fibers with enhanced mechanical properties prepared with the ionic liquid 1-allyl-3-methylimidazolium chloride. Adv Mater 19:698–704
52. Kadokawa J, Murakami M, Kaneko Y (2008) A facile method for preparation of composites composed of cellulose and polystyrene-type polymeric ionic liquid using a polymerizable ionic liquid. Comp Sci Technol 68:493–498
53. Hameed N, Guo Q (2010) Blend films of natural wool and cellulose prepared from an ionic liquid. Cellulose 17:803–813
54. Yuan T, Sun S, Xu F, Sun R (2010) Homogeneous esterification of poplar wood in an ionic liquid under mild conditions: characterization and properties. J Agric Food Chem 58:11302–11310
55. 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
56. Xie H, Jarvi P, Karesoja M, King A, Kilpelainen I, Argyropoulos DS (2009) Highly compatible wood thermoplastic composites from lignocellulosica material modified in ionic liquids: preparation and thermal propertied. J Appl Poly Sci 111:2468–2476
57. Dadi AP, Varanasai S, Schall CA (2006) Enhancement of cellulose saccharification kinetics using an ionic liquid pretreatment step. Biotechnol Bioeng 95:904–910
58. Dadi AP, Varanasai S, Schall CA (2007) Mitigation of cellulose recalcitrance to enzymatic hydrolysis by ionic liquid pretreatment. Appl Biochem Biotechnol 136:407–421
59. Kuo CH, Lee CK (2009) Enhancement of enzymatic saccharification of cellulose by cellulose dissolution pretreatment. Carbohyd Poly 77:41–46
60. Lee SM, Doherty TV, Linhardt RJ, Dordick JS (2008) Ionic liquid-mediated selective extraction of lignin from wood leading to enhanced enzymatic cellulose hydrolysis. Biotechnol Bioeng 102:1368–1376
61. Lin B, Asikkala J, Filpponen I, Argyropoulos DS (2010) Factors affecting wood dissolution and regeneration of ionic liquids. Ind Eng Chem Res 49:2477–2484
62. Samayam IP, Schall CA (2010) Saccharification of ionic liquid pretreated biomass with commercial enzyme mixtures. Bioresour Technol 101:3561–3566
63. Çetinkol ÖP, Dibble DC, Cheng G, Kent MS, Knierim B, Auer M, Wemmer AE, Pelton JG, Melnichenko YB, Ralph J, Simmons BA, Holmes BM (2010) Understanding the impact of ionic liquid pretreatment on eucalyptus. Biofuels 1:33–46
64. Wang Y, Radosevich M, Hayes D, Labbé N (2010) Compatible ionic liquid–cellulase system for hydrolysis of lignocellulosic biomass. Biotechnol Bioeng 108:1042–1048
65. Cheng G, Varanasi P, Li C, Liu H, Melnichenko YB, Simmons BA, Kent MS, Singh S (2011) Transition of cellulose crystalline structure and surface morphology of biomass as a function of ionic liquid pretreatment and its relation to enzymatic hydrolysis. Biomacromolecules 12:933–941
66. Labbé N, Kline LM, Moens L, Kin K, Kim PC, Hayes DG (2012) Activation of lignocellulosic biomass by ionic liquid for biorefinery fraction. Bioresour Technol 104:701–707
67. Uju Shoda Y, Nakamoto A, Goto M, Tokuhara W, Noritake Y, Katahira S, Ishida N, Nakashima K, Ogino C, Kamiya N (2012) Short time ionic liquids pretreatment on lignocellulosic biomass to enhance enzymatic saccharification. Bioresour Technol 103:446–452
68. Torr KM, Love KT, Çetinkol ÖP, Donaldson LA, George A, Holmes BM, Simmons BA (2012) The impact of ionic liquid pretreatment on the chemistry and enzymatic digestibility of Pinus radiata compression wood. Green Chem 14:778–787
69. Cox BJ, Ekerdt JG (2013) Pretreatment of yellow pine in an acidic ionic liquid: extraction of hemicellulose and lignin to facilitate enzymatic digestion. Bioresour Technol 134:59–65
70. Kamiya N, Matsushita Y, Hanaki M, Nakashima K, Narita M, Goto M, Takahashi H (2008) Enzymatic in situ saccharification of cellulose in aqueous-ionic liquid media. Biotechnol Lett 30:1037–1040
71. Datta S, Holmes B, Park JI, Chen Z, Dibble DC, Hadi M, Blanch HW, Simmons BA, Sapra R (2010) Ionic liquid tolerant hyperthermophilic cellulose for biomass pretreatment and hydrolysis. Green Chem 12:338–345
72. Bose S, Armstrong DW, Petrich JW (2010) Enzyme-catalyzed hydrolysis of cellulose in ionic liquids: a green approach toward the production of biofuels. J Phys Chem B 114:8221–8227
73. Yang F, Li L, Li Q, Tan W, Liu W, Xian M (2010) Enhancement of enzymatic in situ saccharification of cellulose in aqueous-ionic liquid media by ultrasonic intensification. Carbohyd Polym 81:311–316
74. Feng D, Li L, Yang F, Tan W, Zhao G, Zou H, Xian M, Zhang Y (2011) Separation of ionic liquid [Mmim][DMP] and glucose from enzymatic hydrolysis mixture of cellulose using alumina column chromatography. Appl Microbiol Biotechnol 91:399–405
75. Abels C, Thimm K, Wulfhorst H, Spiess AC, Wessling M (2013) Membrane-based recovery of glucose from enzymatic hydrolysis of ionic liquid pretreated cellulose. Bioresour Technol 149:58–64
76. Yokoo T, Miyafuji H (2014) Reaction behavior of wood in an ionic liquid, 1-ethylpyridinium bromide. J Wood Sci 60:339–345
77. 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 56:256–261
78. Ohno E, Miyafuji H (2013) Reaction behavior of cellulose in an ionic liquid, 1-ethyl-3-methylimidazolium chloride. J Wood Sci 59:221–228
79. Ohno E, Miyafuji H (2014) Decomposition of cellulose in an ionic liquid, 1-ethyl-3-methylimidazolium chloride. J Wood Sci 60:428–437
80. Ohno E, Miyafuji H (2014) Production of disaccharides from glucose by treatment with an ionic liquid, 1-ethyl-3-methylimidazolium chloride. J Wood Sci 61:65–170
81. Miyata A, Miyafuji H (2014) Reaction behavior of cellulose in various pyridinium-based ionic liquids. J Wood Sci 60:438–445
82. Cox BJ, Ekerdt JG (2012) Depolymerization of oak wood lignin under mild conditions using the acidic ionic liquid 1-H-3-methylimidazolium chloride as both solvent and catalyst. Bioresour Technol 118:584–588
83. Kubo S, HashidaK Yamada T, Hishiyama S, Magara K, Kishino M, Ohno H, Hosoya S (2008) A characteristic reaction of lignin in ionic liquids; glycerol type enol-ether as the primary decomposition product of β-O-4 model compounds. J Wood Chem Technol 28:84–96
84. Binder JB, Gray MJ, White JF, Zhang ZC, Holladay JE (2009) Reaction of lignin model compounds in ionic liquids. Biomass Bioenergy 33:1122–1130
85. Jia S, Cox BJ, Guo X, Zhang ZC, Ekerdt JG (2010) Cleaving theβ-O-4 bonds of lignin model compounds in an acidic ionic liquid, 1-H-3-methylimidazolium chloride: an optional strategy for the degradation of lignin. Chem Sus Chem 3:1078–1084
86. Miyafuji H (2013) Liquefaction of wood by ionic liquid treatment. In: Kadokawa J (ed) Ionic liquids–new aspect for the future–. InTech, Croatia, pp 299–314
87. Vanoye L, Fanselow M, Holbrey JD, Atkins MP, Seddon KR (2009) Kinetic model for the hydrolysis of lignocellulosic biomass in the ionic liquid, 1-ethyl-3-methylimidazolium chloride. Green Chem 11:390–396
88. Li C, Zhao ZK (2007) Efficient acid-catalyzed hydrolysis of cellulose in ionic liquid. Adv Synth Catal 349:1847–1850
89. Li C, Wang Q, Zhao ZK (2008) Acid in ionic liquid: an efficient system for hydrolysis of lignocellulose. Green Chem 10:177–182
90. Amarasekara AS, Owereh OS (2009) Hydrolysis and decomposition of cellulose in Brönsted acidic ionic liquids under mild conditions. Ind Eng Chem Res 48:10152–10155
91. Dee SJ, Bell AT (2011) A study of the acid-catalyzed hydrolysis of cellulose dissolved in ionic liquids and factors influencing the dehydration of glucose and the formation of humins. Chem Sus Chem 4:1166–1173
92. Xie H, Shi T (2010) Liquefaction of wood (Metasequoiaglyptostroboides) in allyl alkyl imidazolium ionic liquids. Wood Sci Technol 44:119–128
93. Sievers C, Valenzuela-Olarte MB, Marzialetti T, Musin I, Agrawal PK, Jones CW (2009) Ionic-liquid-phase hydrolysis of pine wood. Ind Eng Chem Res 48:1277–1286
94. Lin B, Filpponen I, Argyropoulos DS (2010) Acidolysis of wood in ionic liquids. Ind Eng Chem Res 49:3129–3136
95. Zhang Z, Zhao ZK (2010) Microwave-assisted conversion of lignocellulosic biomass into furans in ionic liquid. Bioresour Technol 101:1111–1114
96. Zhang Y, Du H, Qian X, Chen EYX (2010) Ionic liquid–water mixtures: enhanced Kw for efficient cellulosic biomass conversion. Energy Fuels 24:2410–2417
97. Chidambaram M, Bell AT (2010) A two-step approach for the catalytic conversion of glucose to 2,5-dimethylfuran in ionic liquids. Green Chem 12:1253–1262
98. Rinaldi R, Palkovits R, Schüth F (2008) Depolymerization of cellulose using solid catalysts in ionic liquids. Angew Chem Int Ed 47:8047–8050
99. Watanabe H (2010) The study of factors influencing the depolymerisation of cellulose using a solid catalyst in ionic liquids. Carbohyd Polym 80:1168–1171