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Ionic Liquids pp 311-339 | Cite as

Ionic Liquids in Biomass Processing

Chapter
First Online:
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 290)

Abstract

Ionic liquids have been studied for their special solvent properties in a wide range of processes, including reactions involving carbohydrates such as cellulose and glucose. Biomass is a widely available and renewable resource that is likely to become an economically viable source of starting materials for chemical and fuel production, especially with the price of petroleum set to increase as supplies are diminished. Biopolymers such as cellulose, hemicellulose and lignin may be converted to useful products, either by direct functionalisation of the polymers or depolymerisation to monomers, followed by microbial or chemical conversion to useful chemicals. Major barriers to the effective conversion of biomass currently include the high crystallinity of cellulose, high reactivity of carbohydrates and lignin, insolubility of cellulose in conventional solvents, as well as heterogeneity in the native lignocellulosic materials and in lignin itself. This combination of factors often results in highly heterogeneous depolymerisation products, which make efficient separation difficult. Thus the extraction, depolymerisation and conversion of biopolymers will require novel reaction systems in order to be both economically attractive and environmentally benign. The solubility of biopolymers in ionic liquids is a major advantage of their use, allowing homogeneous reaction conditions, and this has stimulated a growing research effort in this field. This review examines current research involving the use of ionic liquids in biomass reactions, with perspectives on how it relates to green chemistry, economic viability, and conventional biomass processes.

Keywords

Biomass Cellulose Hemicellulose Ionic liquids Lignin 

Abbreviations

[Amim]

1-Allyl-3-methylimidazolium

[C2mim]

1-Ethyl-3-methylimidazolium

[C4mim]

1-Butyl-3-methylimidazolium

[DBU]

1,8-Diazabicyclo 5.4.0 undec-7-enium

[dca]

Dicyanamide

[BF4]

Tetrafluoroborate

[PF6]

Hexafluorophosphate

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Notes

Acknowledgements

The Australian Sugar Research and Development Corporation and the Centre for Green Chemistry at Monash University are gratefully acknowledged for their financial support.

References

  1. 1.
    Daily G, Dasgupta P, Bolin B, Crosson P, Du Guerny J, Ehrlich P, Folke C, Jansson AM, Jansson B-O, Kautsky N, Kinzig A, Levin S, Maler K-G, Pinstrup-Andersen P, Siniscalco D, Walker B (1998) Science 281:1291CrossRefGoogle Scholar
  2. 2.
    Hoegh-Guldberg O, Mumby PJ, Hooten AJ, Steneck RS, Greenfield P, Gomez E, Harvell CD, Sale PF, Edwards AJ, Caldeira K, Knowlton N, Eakin CM, Iglesias-Prieto R, Muthiga N, Bradbury RH, Dubi A, Hatziolos ME (2007) Science 318:1737CrossRefGoogle Scholar
  3. 3.
    Okkerse C, van Bekkum H (1999) Green Chem 1:107CrossRefGoogle Scholar
  4. 4.
    Shannon MA, Bohn PW, Elimelech M, Georgiadis JG, Marinas BJ, Mayes AM (2008) Nature 452:301CrossRefGoogle Scholar
  5. 5.
    Vorosmarty CJ, Green P, Salisbury J, Lammers RB (2000) Science 289:284CrossRefGoogle Scholar
  6. 6.
    Emission Trading Scheme (EU ETS), European Commission (2008) http://ec.europa.eu/environment/climat/emission.htm
  7. 7.
    Department of Climate Change, Australian Government (2008) Carbon Pollution Reduction Scheme Green Paper, Department of Climate Change, Australian Government, http://www.climatechange.gov.au/greenpaper/index.html
  8. 8.
    Kyoto Protocol to the United Nations Framework Convention on Climate Change: Annex B (1997) http://unfccc.int/kyoto_protocol/items/2830.php
  9. 9.
    Foley JA (2005) Science 310:627CrossRefGoogle Scholar
  10. 10.
    Ham B (2007) Science 318:1396CrossRefGoogle Scholar
  11. 11.
    Hansen J (2007) How can we avert dangerous climate change? Los Alamos National Laboratory, Preprint Archive, Physics, http://arxiv.org/abs/0706.3720
  12. 12.
    Hansen J, Sato M, Ruedy R, Kharecha P, Lacis A, Miller R, Nazarenko L, Lo K, Schmidt GA, Russell G, Aleinov I, Bauer S, Baum E, Cairns B, Canuto V, Chandler M, Cheng Y, Cohen A, Del Genio A, Faluvegi G, Fleming E, Friend A, Hall T, Jackman C, Jonas J, Kelley M, Kiang NY, Koch D, Labow G, Lerner J, Menon S, Novakov T, Oinas V, Perlwitz J, Perlwitz J, Rind D, Romanou A, Schmunk R, Shindell D, Stone P, Sun S, Streets D, Tausnev N, Thresher D, Unger N, Yao M, Zhang S (2007) Atmos Chem Phys 7:2287CrossRefGoogle Scholar
  13. 13.
    Kerr RA (2008) Science 319:153Google Scholar
  14. 14.
    Spratt D, Sutton P (2008) Climate code red. Scribe Publications, MelbourneGoogle Scholar
  15. 15.
    Walker G (2006) Nature 441:802CrossRefGoogle Scholar
  16. 16.
    Flannery T (2005) The weather makers: the history and future impact of climate change. The Text Publishing Company, MelbourneGoogle Scholar
  17. 17.
    Anastas PT, Lankey RL (2002) In: Lankey RL, Anastas PT (eds) Advancing sustainability through green chemistry and engineering. ACS Symp Ser 823:1Google Scholar
  18. 18.
    Anastas PT (1998) Green chemistry, theory and practice. Oxford University Press, OxfordGoogle Scholar
  19. 19.
    Clark JH (2007) J Chem Technol Biotechnol 82:603CrossRefGoogle Scholar
  20. 20.
    Ragauskas AJ, Williams CK, Davison BH, Britovsek G, Cairney J, Eckert CA, Frederick WJ Jr, Hallett JP, Leak DJ, Liotta CL, Mielenz JR, Murphy R, Templer R, Tschaplinski T (2006) Science 311:484CrossRefGoogle Scholar
  21. 21.
    Zhang YHP (2008) J Ind Microbiol Biotechnol 35:367CrossRefGoogle Scholar
  22. 22.
    Chang MCY (2007) Curr Opin Chem Biol 11:677CrossRefGoogle Scholar
  23. 23.
    National Renewable Energy Laboratory (2008) What is a biorefinery? National Renewable Energy Laboratory, http://www.nrel.gov/biomass/biorefinery.html
  24. 24.
    Crutzen PJ, Mosier AR, Smith KA, Winiwarter W (2008) Atmos Chem Phys 8:389CrossRefGoogle Scholar
  25. 25.
    Ebeling J, Yasue M (2008) Philos Trans R Soc B 363:1917CrossRefGoogle Scholar
  26. 26.
    Searchinger T, Heimlich R, Houghton RA, Dong F, Elobeid A, Fabiosa J, Tokgoz S, Hayes D, Yu T-H (2008) Science 319:1238CrossRefGoogle Scholar
  27. 27.
    (2001) Kirk–Othmer encyclopedia of chemical technology. Wiley, New YorkGoogle Scholar
  28. 28.
    Werpy T, Peterson G (2004) Top value added chemicals from biomass, volume 1 – results of screening for potential candidates from sugars and synthesis gas. U.S. Department of EnergyGoogle Scholar
  29. 29.
    Lichtenthaler FW (2007) In: Tundo P (ed) Methods and reagents for green chemistry. Wiley, New Jersey, p 23CrossRefGoogle Scholar
  30. 30.
    Carole TM, Pellegrino J, Paster MD (2004) Appl Biochem Biotechnol 113/116:871CrossRefGoogle Scholar
  31. 31.
    Huber GW, Iborra S, Corma A (2006) Chem Rev 106:4044CrossRefGoogle Scholar
  32. 32.
    Buchanan BB, Gruissem W, Jones RL (2000) Biochemistry and molecular biology of plants. American Society of Plant Biologists, Rockville, MDGoogle Scholar
  33. 33.
    Brunow G (2006) In: Kamm B, Gruber PR, Kamm M (eds) Biorefineries – industrial processes and products, vol 2. Wiley, Weinheim, p 151Google Scholar
  34. 34.
    Berlin A, Balakshin M, Gilkes N, Kadla J, Maximenko V, Kubo S, Saddler J (2006) J Biotechnol 125:198CrossRefGoogle Scholar
  35. 35.
    Pan X, Xie D, Gilkes N, Gregg DJ, Saddler JN (2005) Appl Biochem Biotechnol 121/124:1069CrossRefGoogle Scholar
  36. 36.
    Huang H-J, Ramaswamy S, Tschirner UW, Ramarao BV (2008) Sep Purif Technol 62:1CrossRefGoogle Scholar
  37. 37.
    Palmqvist E, Hahn-Hagerdal B (2000) Bioresour Technol 74:25CrossRefGoogle Scholar
  38. 38.
    Thielemans W, Can E, Morye SS, Wool RP (2002) J Appl Polym Sci 83:323CrossRefGoogle Scholar
  39. 39.
    Pye EK (2006) In: Kamm B, Gruber PR, Kamm M (eds) Biorefineries – industrial processes and products, vol 2. Wiley, Weinheim, p 165Google Scholar
  40. 40.
    Brunow G, Kilpelainen I, Sipila J, Syrjanen K, Karhunen P, Setala H, Rummakko Pet al (1998) In: Lewis NG, Sarkanen S (eds) Lignin and lignan biosynthesis. ACS Symp Ser 697:131Google Scholar
  41. 41.
    Navarro RM, Pena MA, Fierro JLG (2007) Chem Rev 107:3952CrossRefGoogle Scholar
  42. 42.
    Elliott DC, Beckman D, Bridgwater AV, Diebold JP, Gevert SB, Solantausta Y (1991) Energ Fuels 5:399CrossRefGoogle Scholar
  43. 43.
    Faith WL (1945) J Ind Eng Chem 37:9CrossRefGoogle Scholar
  44. 44.
    Lee YY, Iyer P, Torget RW (1999) Adv Biochem Eng Biotechnol 65:93Google Scholar
  45. 45.
    Hayes DJ, Fitzpatrick S, Hayes MHB, Ross JRH (2006) In: Kamm B, Gruber PR, Kamm M (eds) Biorefineries – industrial processes and products, vol 1. Wiley, Weinheim, p 139Google Scholar
  46. 46.
    Smook GA (2002) Handbook for pulp & paper technologists. Angus Wilde Publications, VancouverGoogle Scholar
  47. 47.
    Wegener G (1992) Ind Crops Prod 1:113CrossRefGoogle Scholar
  48. 48.
    Zhang Y-HP, Ding S-Y, Mielenz JR, Cui J-B, Elander RT, Laser M, Himmel ME, McMillan JR, Lynd LR (2007) Biotechnol Bioeng 97:214CrossRefGoogle Scholar
  49. 49.
    Delmas M (2008) Chem Eng Technol 31:792CrossRefGoogle Scholar
  50. 50.
    McKee RH (1943) US Patent 2 308 564Google Scholar
  51. 51.
    McKee RH (1954) Pulp Paper Mag Can 55:64Google Scholar
  52. 52.
    McKee RH (1960) Paper Ind 42:255Google Scholar
  53. 53.
    Procter AR (1971) Pulp Paper Mag Can 72:67Google Scholar
  54. 54.
    Bland DE (1976) Research Review – Australia, Commonwealth Scientific and Industrial Research Organization, Division of Chemical Technology, p 27Google Scholar
  55. 55.
    Shanmugam KT, Ingram LO (2008) J Mol Microbiol Biotechnol 15:8CrossRefGoogle Scholar
  56. 56.
    Zhang PYH, Himmel ME, Mielenz JR (2006) Biotechnol Adv 24:452CrossRefGoogle Scholar
  57. 57.
    Himmel ME, Ding S-Y, Johnson DK, Adney WS, Nimlos MR, Brady JW, Foust TD (2007) Science 315:804CrossRefGoogle Scholar
  58. 58.
    Lee S (2007) In: Lee S, Speight JG, Loyalka SK (eds) Handbook of alternative fuel technologies. Taylor & Francis Group, Boca Raton, p 343CrossRefGoogle Scholar
  59. 59.
    Yang S-T (2007) In: Yang S-T (ed) Bioprocessing for value-added products from renewable resources: new technologies and applications. Elsevier BV, Oxford, p 1CrossRefGoogle Scholar
  60. 60.
    Henstra AM, Sipma J, Rinzema A, Stams AJM (2007) Curr Opin Biotechnol 18:200CrossRefGoogle Scholar
  61. 61.
    Brown RC (2006) In: Kamm B, Gruber PR, Kamm M (eds) Biorefineries – industrial processes and products, vol 1. Wiley, Weinheim, p 227Google Scholar
  62. 62.
    Wasserscheid P, Keim W (2000) Angew Chem Int Ed 39:3772Google Scholar
  63. 63.
    Holbrey JD, Rogers RD (2008) In: Wasserscheid P, Welton T (eds) Ionic liquids in synthesis, 2nd edn, vol 1. Wiley, Weinheim, p 57Google Scholar
  64. 64.
    Fox DM, Gilman JW, Morgan AB, Shields JR, Maupin PH, Lyon RE, De Long HC, Trulove PC (2008) Ind Eng Chem Res 47:6327CrossRefGoogle Scholar
  65. 65.
    Smiglak M, Reichert WM, Holbrey JD, Wilkes JS, Sun L, Thrasher JS, Kirichenko K, Singh S, Katritzky AR, Rogers RD (2006) Chem Comm 2554Google Scholar
  66. 66.
    Boesmann A, Schulz PS, Wasserscheid P (2007) Monatsh Chem 138:1159CrossRefGoogle Scholar
  67. 67.
    Bonhote P, Dias A-P, Armand M, Papageorgiou N, Kalyanasundaram K, Graetzel M (1996) Inorg Chem 35:1168CrossRefGoogle Scholar
  68. 68.
    Carter EB, Culver SL, Fox PA, Goode RD, Ntai I, Tickell MD, Traylor RK, Hoffman NW, Davis JH Jr (2004) Chem Comm 630Google Scholar
  69. 69.
    Nockemann P, Thijs B, Driesen K, Janssen CR, Van Hecke K, Van Meervelt L, Kossmann S, Kirchner B, Binnemans K (2007) J Phys Chem B 111:5254CrossRefGoogle Scholar
  70. 70.
    MacFarlane DR, Seddon KR (2007) Aust J Chem 60:3CrossRefGoogle Scholar
  71. 71.
    Earle MJ, Esperanca JMSS, Gilea MA, Canongia Lopes JN, Rebelo LPN, Magee JW, Seddon KR, Widegren JA (2006) Nature 439:831CrossRefGoogle Scholar
  72. 72.
    Kreher UP, Rosamilia AE, Raston CL (2004) Molecules 9:387CrossRefGoogle Scholar
  73. 73.
    Rosamilia AE, Strauss CR, Scott JL (2007) Pure Appl Chem 79:1869CrossRefGoogle Scholar
  74. 74.
    Wasserscheid P (2006) Nature 439:797CrossRefGoogle Scholar
  75. 75.
    Fraser KJ, Izgorodina EI, Forsyth M, Scott JL, MacFarlane DR (2007) Chem Comm 3817Google Scholar
  76. 76.
    Scammells PJ, Scott JL, Singer RD (2005) Aust J Chem 58:155CrossRefGoogle Scholar
  77. 77.
    Baranyai KJ, Deacon GB, MacFarlane DR, Pringle JM, Scott JL (2004) Aust J Chem 57:145CrossRefGoogle Scholar
  78. 78.
    Glenn AG, Jones PB (2004) Tetrahedron Lett 45:6967CrossRefGoogle Scholar
  79. 79.
    Ngo HL, LeCompte K, Hargens L, McEwen AB (2000) Thermochim Acta 357/358:97CrossRefGoogle Scholar
  80. 80.
    Freire MG, Neves CMSS, Carvalho PJ, Gardas RL, Fernandes AM, Marrucho IM, Santos LMNBF, Coutinho JAP (2007) J Phys Chem B 111:13082CrossRefGoogle Scholar
  81. 81.
    Huddleston JG, Visser AE, Reichert WM, Willauer HD, Broker GA, Rogers RD (2001) Green Chem 3:156CrossRefGoogle Scholar
  82. 82.
    Olivier-Bourbigou H, Vallee C (2005) In: Cornils B, Herrmann WA, Horvath IT, Leitner W, Mecking S, Olivier-Bourbigou H, Vogt D (eds) Multiphase homogeneous catalysis, vol 2. Wiley, Weinheim, p 413CrossRefGoogle Scholar
  83. 83.
    Earle MJ, Seddon KR (2000) Pure Appl Chem 72:1391CrossRefGoogle Scholar
  84. 84.
    Rogers RD, Seddon Kenneth R (2003) Science 302:792CrossRefGoogle Scholar
  85. 85.
    Seddon KR (1997) J Chem Technol Biotechnol 68:351CrossRefGoogle Scholar
  86. 86.
    MacFarlane DR, Pringle JM, Johansson KM, Forsyth SA, Forsyth M (2006) Chem Comm 1905Google Scholar
  87. 87.
    Sheldon R (2001) Chem Comm 2399Google Scholar
  88. 88.
    Boon JA, Levisky JA, Pflug JL, Wilkes JS (1986) J Org Chem 51:480CrossRefGoogle Scholar
  89. 89.
    Earle M (2008) In: Wasserscheid P, Welton T (eds) Ionic liquids in synthesis, 2nd edn, vol 1. Wiley, Weinheim, p 292Google Scholar
  90. 90.
    Earle MJ, Seddon KR, Adams CJ, Roberts G (1998) Chem Comm 2097Google Scholar
  91. 91.
    Sahoo S, Joseph T, Halligudi SB (2006) J Mol Cat A Chem 244:179CrossRefGoogle Scholar
  92. 92.
    Yin D, Li C, Li B, Tao L, Yin D (2005) Adv Synth Catal 347:137CrossRefGoogle Scholar
  93. 93.
    Xu J-M, Liu B-K, Wu W-B, Qian C, Wu Q, Lin X-F (2006) J Org Chem 71:3991CrossRefGoogle Scholar
  94. 94.
    Ranu BC, Jana R (2006) Eur J Org Chem 3767Google Scholar
  95. 95.
    Ranu BC, Banerjee S, Jana R (2006) Tetrahedron 63:776CrossRefGoogle Scholar
  96. 96.
    Wasserscheid P (2003) In: Rogers RD, Seddon Kenneth R, Volkov S (eds) NATO science series, II: mathematics, physics and chemistry, vol 92. Kluwer, Dordrecht, p 29Google Scholar
  97. 97.
    Wasserscheid P, Hilgers C, Gordon CM, Muldoon MJ, Dunkin IR (2001) Chem Comm 1186Google Scholar
  98. 98.
    Holbrey JD, Seddon KR (1999) J Chem Soc Dalton Trans 2133Google Scholar
  99. 99.
    Forsyth S (2003) Novel organic salts, novel organic salts. PhD Thesis, Monash UniversityGoogle Scholar
  100. 100.
    Jastorff B, Stoermann R, Ranke J, Moelter K, Stock F, Oberheitmann B, Hoffmann W, Hoffmann J, Nuechter M, Ondruschka B, Filser J (2003) Green Chem 5:136CrossRefGoogle Scholar
  101. 101.
    Docherty KM, Hebbeler SZ, Kulpa CF Jr (2006) Green Chem 8:560CrossRefGoogle Scholar
  102. 102.
    Frade RFM, Matias A, Branco LC, Afonso CAM, Duarte CMM (2007) Green Chem 9:873CrossRefGoogle Scholar
  103. 103.
    Ranke J, Stolte S, Stoermann R, Arning J, Jastorff B (2007) Chem Rev 107:2183CrossRefGoogle Scholar
  104. 104.
    Kralisch D, Reinhardt D, Kreisel G (2007) Green Chem 9:1308CrossRefGoogle Scholar
  105. 105.
    Kralisch D, Stark A, Koersten S, Kreisel G, Ondruschka B (2005) Green Chem 7:301CrossRefGoogle Scholar
  106. 106.
    Holbrey JD (2004) Chim Oggi 22:35Google Scholar
  107. 107.
    Holbrey JD, Seddon Kenneth R (1999) Clean Prod Proc 1:223Google Scholar
  108. 108.
    Maase M (2005) In: Cornils B, Herrmann WA, Horvath IT, Leitner W, Mecking S, Olivier-Bourbigou H, Vogt D (eds) Multiphase homogeneous catalysis, vol 2. Wiley, Weinheim, p 560Google Scholar
  109. 109.
    Maase M (2008) In: Wasserscheid P, Welton T (eds) Ionic liquids in synthesis, 2nd edn, vol 2. Wiley, Weinheim, p 663Google Scholar
  110. 110.
    Plechkova NV, Seddon KR (2008) Chem Soc Rev 37:123CrossRefGoogle Scholar
  111. 111.
    Olivier-Bourbigou H, Favre F (2008) In: Wasserscheid P, Welton T (eds) Ionic liquids in synthesis, 2nd edn, vol 2. Wiley, Weinheim, p 464Google Scholar
  112. 112.
    Olivier-Bourbigou H, Hugues F (2003) In: Rogers RD, Seddon Kenneth R, Volkov S (eds) NATO science series, II: mathematics, physics and chemistry, vol 92, p 67Google Scholar
  113. 113.
    Forsyth SA, MacFarlane DR, Thomson RJ, von Itzstein M (2002) Chem Comm 714Google Scholar
  114. 114.
    Kimizuka N, Nakashima T (2001) Langmuir 17:6759CrossRefGoogle Scholar
  115. 115.
    Kimizuka N, Nakashima T (2002) Foundation for Scientific Technology Promotion, Japan, JP Patent 2002/003478Google Scholar
  116. 116.
    Liu Q, Janssen MHA, van Rantwijk F, Sheldon RA (2005) Green Chem 7:39CrossRefGoogle Scholar
  117. 117.
    Swatloski RP, Rogers RD, Holbrey JD (2003) University of Alabama, USA, WO Patent 03/029329Google Scholar
  118. 118.
    Swatloski RP, Spear SK, Holbrey JD, Rogers RD (2002) J Am Chem Soc 124:4974CrossRefGoogle Scholar
  119. 119.
    Youngs TGA, Hardacre C, Holbrey JD (2007) J Phys Chem B 111:13765CrossRefGoogle Scholar
  120. 120.
    Zhang H, Wu J, Zhang J, He J (2005) Macromolecules 38:8272CrossRefGoogle Scholar
  121. 121.
    Ren Q, Wu J, Zhang J, He JS (2003) Acta Polym Sin 3:448Google Scholar
  122. 122.
    Zhang J, Ren Q, He J (2004) Inst. of Chemistry, Chinese Academy of Sciences, Peop. Rep. China, CN Patent 1491974Google Scholar
  123. 123.
    Hermanutz F, Gaehr F, Uerdingen E, Meister F, Kosan B (2008) Macromol Symp 262:23CrossRefGoogle Scholar
  124. 124.
    Fukaya Y, Hayashi K, Wada M, Ohno H (2008) Green Chem 10:44CrossRefGoogle Scholar
  125. 125.
    Fukaya Y, Sugimoto A, Ohno H (2006) Biomacromolecules 7:3295CrossRefGoogle Scholar
  126. 126.
    Remsing RC, Swatloski RP, Rogers RD, Moyna G (2006) Chem Comm 1271Google Scholar
  127. 127.
    Fort DA, Remsing RC, Swatloski RP, Moyna P, Moyna G, Rogers RD (2007) Green Chem 9:63CrossRefGoogle Scholar
  128. 128.
    Kilpelainen I, Xie H, King A, Granstrom M, Heikkinen S, Argyropoulos DS (2007) J Agric Food Chem 55:9142CrossRefGoogle Scholar
  129. 129.
    Myllymaeki V, Aksela R (2005) Kemira Oyj, Finland, WO Patent 2005/017001Google Scholar
  130. 130.
    Pu YQ, Jiang N, Ragauskas AJ (2007) J Wood Chem Technol 27:23CrossRefGoogle Scholar
  131. 131.
    D’Andola G, Szarvas L, Massonne K, Stegmann V (2008) BASF, Germany, WO Patent 2008/043837Google Scholar
  132. 132.
    Wu Y, Sasaki T, Irie S, Sakurai K (2008) Polymer 49:2321CrossRefGoogle Scholar
  133. 133.
    Hecht SE, Niehoff RL, Narasimhan K, Neal CW, Forshey PA, Phan DV, Brooker ADM, Combs KH (2006) Procter & Gamble, USA, WO Patent 2006/116126Google Scholar
  134. 134.
    Zhu S, Wu Y, Chen Q, Yu Z, Wang C, Jin S, Ding Y, Wu G (2006) Green Chem 8:325CrossRefGoogle Scholar
  135. 135.
    Heinze T, Liebert T (2001) Prog Polym Sci 26:1689CrossRefGoogle Scholar
  136. 136.
    Wu J, Zhang J, Zhang H, He J, Ren Q, Guo M (2004) Biomacromolecules 5:266CrossRefGoogle Scholar
  137. 137.
    Moens L, Khan N (2003) In: Rogers RD, Seddon Kenneth R, Volkov S (eds) NATO science series, II: mathematics, physics and chemistry, vol 92. Kluwer, Dordrecht, p 157Google Scholar
  138. 138.
    Li C, Wang Q, Zhao ZK (2008) Green Chem 10:177CrossRefGoogle Scholar
  139. 139.
    Massonne K, D’Andola G, Stegmann V, Mormann W, Wezstein M, Leng W (2007) BASF, Germany, WO Patent 2007/101811Google Scholar
  140. 140.
    Lewkowski J (2001) ARKIVOC [online computer file – http://www.arkat-usa.org/], vol 2, p 17
  141. 141.
    Moreau C, Finiels A, Vanoye L (2006) J Mol Cat A Chem 253:153Google Scholar
  142. 142.
    Zhao H, Holladay JE, Brown H, Zhang ZC (2007) Science 316:1597CrossRefGoogle Scholar
  143. 143.
    Zhao H, Holladay JE, Zhang ZC (2008) Batelle Memorial Institute, US Patent 2008/033187Google Scholar
  144. 144.
    Van Rantwijk F, Sheldon RA (2007) Chem Rev 107:2757CrossRefGoogle Scholar
  145. 145.
    Cantone S, Hanefeld U, Basso A (2007) Green Chem 9:954CrossRefGoogle Scholar
  146. 146.
    Kaar JL, Jesionowski AM, Berberich JA, Moulton R, Russell AJ (2003) J Am Chem Soc 125:4125CrossRefGoogle Scholar
  147. 147.
    Kaftzik N, Neumann S, Kula M-R, Kragl U (2003) ACS Symp Ser 856:206CrossRefGoogle Scholar
  148. 148.
    Kim M-J, Choi MY, Lee JK, Ahn Y (2003) J Mol Catal B: Enzym 26:115CrossRefGoogle Scholar
  149. 149.
    Madeira Lau R, van Rantwijk F, Seddon KR, Sheldon RA (2000) Org Lett 2:4189CrossRefGoogle Scholar
  150. 150.
    Galletti P, Moretti F, Samori C, Tagliavini E (2007) Green Chem 9:987CrossRefGoogle Scholar
  151. 151.
    Turner MB, Spear SK, Huddleston JG, Holbrey JD, Rogers RD (2003) Green Chem 5:443CrossRefGoogle Scholar
  152. 152.
    Kamiya N, Matsushita Y, Hanaki M, Nakashima K, Narita M, Goto M, Takahashi H (2008) Biotechnol Lett 30:1037CrossRefGoogle Scholar
  153. 153.
    Balensiefer T (2008) BASF, Germany, WO Patent 2008/090156Google Scholar
  154. 154.
    Balensiefer T, Brodersen J, D’Andola G, Massonne K, Freyer S, Stegmann V (2008) BASF, Germany, WO Patent 2008/090155Google Scholar
  155. 155.
    Kuhad RC, Kuhar S, Kapoor M, Sharma KK, Singh A (2007) In: Kuhad RC, Singh A (eds) Lignocellulose biotechnology: future prospects. Anshan, Tunbridge Wells, p 3Google Scholar
  156. 156.
    Kumar A, Jain N, Chauhan SMS (2007) Synlett 411Google Scholar
  157. 157.
    Shipovskov S, Gunaratne HQN, Seddon KR, Stephens G (2008) Green Chem 10:806CrossRefGoogle Scholar
  158. 158.
    Zhou G-P, Zhang Y, Huang X-R, Shi C-H, Liu W-F, Li Y-Z, Qu Y-B, Gao P-J (2008) Colloids Surf B 66:146CrossRefGoogle Scholar
  159. 159.
    Barthel S, Heinze T (2006) Green Chem 8:301CrossRefGoogle Scholar
  160. 160.
    Heinze T, Schwikal K, Barthel S (2005) Macromol Biosci 5:520CrossRefGoogle Scholar
  161. 161.
    Cao Y, Wu J, Meng T, Zhang J, He J, Li H, Zhang Y (2007) Carbohydr Polym 69:665CrossRefGoogle Scholar
  162. 162.
    Schlufter K, Schmauder H-P, Dorn S, Heinze T (2006) Macromol Rapid Commun 27:1670CrossRefGoogle Scholar
  163. 165.
    Buchanan CM, Buchanan NL (2008) Eastman Chemical Co., USA, WO Patent 2008/100569Google Scholar
  164. 164.
    Buchanan CM, Buchanan NL (2008) Eastman Chemical Co., USA, WO Patent 2008/100577Google Scholar
  165. 165.
    Buchanan CM, Buchanan NL, Hembre RT, Lambert JL (2008) Eastman Chemical Co., USA, WO Patent 2008/100566Google Scholar
  166. 166.
    Myllymaeki V, Aksela R (2005) Kemira Oyj, Finland, WO Patent 2005/054298Google Scholar
  167. 167.
    Liu CF, Sun RC, Zhang AP, Ren JL (2007) Carbohydr Polym 68:17CrossRefGoogle Scholar
  168. 168.
    Liu C-F, Sun R-C, Zhang A-P, Qin M-H, Ren J-L, Wang X-A (2007) J Agric Food Chem 55:2399CrossRefGoogle Scholar
  169. 169.
    Scheibel JJ, Kenneally CJ, Menkhaus JA, Seddon KR, Chwala P (2007) Procter and Gamble, USA, US Patent 2007/225190Google Scholar
  170. 170.
    Massonne K, Stegmann V, D’Andola G, Mormann W, Wezstein M, Leng W (2007) BASF, Germany; Universitaet Siegen, WO Patent 2007/147813Google Scholar
  171. 171.
    Liu CF, Sun RC, Zhang AP, Ren JL, Wang XA, Qin MH, Chao ZN, Luo W (2007) Carbohydr Res 342:919CrossRefGoogle Scholar
  172. 172.
    Erdmenger T, Haensch C, Hoogenboom R, Schubert US (2007) Macromol Biosci 7:440CrossRefGoogle Scholar
  173. 173.
    Granstroem M, Kavakka J, King A, Majoinen J, Maekelae V, Helaja J, Hia S, Virtanen T, Maunu S-L, Argyropoulos DS, Kilpelaeinen Iet al (2008) Cellulose 15:481CrossRefGoogle Scholar
  174. 174.
    Holbrey JD, Chen J, Turner MB, Swatloski RP, Spear SK, Rogers RD (2005) In: Brazel CS, Rogers RD (eds) Ionic liquids in polymer systems. ACS Symp Ser 913:71Google Scholar
  175. 175.
    Holbrey JD, Swatloski RP, Chen J, Daly D, Rogers RD (2005) University of Alabama, USA, WO Patent 2005/098546Google Scholar
  176. 176.
    Poplin JH, Swatloski RP, Holbrey JD, Spear SK, Metlen A, Gratzel M, Nazeeruddin MK, Rogers RD (2007) Chem Comm 2025Google Scholar
  177. 177.
    Sun N, Swatloski RP, Maxim ML, Rahman M, Harland AG, Haque A, Spear SK, Daly DT, Rogers RD (2008) J Mater Chem 18:283CrossRefGoogle Scholar
  178. 178.
    Swatloski RP, Holbrey JD, Weston JL, Rogers RD (2006) Chimica Oggi 24:31Google Scholar
  179. 179.
    Turner MB, Spear SK, Holbrey JD, Daly DT, Rogers RD (2005) Biomacromolecules 6:2497CrossRefGoogle Scholar
  180. 180.
    Egorov VM, Smirnova SV, Formanovsky AA, Pletnev IV, Zolotov YA (2007) Anal Bioanal Chem 387:2263CrossRefGoogle Scholar
  181. 181.
    Kadokawa J-I, Murakami M-A, Kaneko Y (2008) Compos Sci Technol 68:493CrossRefGoogle Scholar
  182. 182.
    Dadi AP, Schall CA, Varanasi S (2007) Appl Biochem Biotechnol 137/140:407CrossRefGoogle Scholar
  183. 183.
    Sheldrake GN, Schleck D (2007) Green Chem 9:1044CrossRefGoogle Scholar
  184. 184.
    Argyropoulos D (2008) North Carolina State University, USA, US Patent 2008/0185112Google Scholar
  185. 185.
    Massonne K, D’Andola G, Stegmann V, Mormann W, Wezstein M, Leng W (2007) BASF, Germany, WO Patent 2007/101813Google Scholar
  186. 186.
    Massonne K, D’Andola G, Stegmann V, Mormann W, Wezstein M, Leng W, Freyer S (2007) BASF, Germany, WO Patent 2007/101812Google Scholar
  187. 187.
    Correia P (2008) WO Patent 2008/053284Google Scholar
  188. 188.
    Guo X, Zheng Y, Zhou B (2008) Shanghai University, Peop. Rep. China, CN Patent 101235312Google Scholar
  189. 189.
    Gurin MH (2007) US Patent 2007/161095Google Scholar
  190. 190.
    Ji J, Yu F, Ai N, Ji D, Xu Z, Yu Y (2007) Zhejiang University of Technology, Peop. Rep. China, CN Patent 101085924Google Scholar
  191. 191.
    Edye LA, Doherty WOS (2008) Queensland University of Technology, Australia, WO Patent 2008/095252Google Scholar
  192. 192.
    Upfal J, MacFarlane DR, Forsyth SA (2005) Viridian Chemicals, Australia, WO Patent 2005/017252Google Scholar
  193. 193.
    Maase M, Huttenloch O (2005) BASF, Germany, WO Patent 2005/061416Google Scholar
  194. 194.
    Maase M, Massonne K, Halbritter K, Noe R, Bartsch M, Siegel W, Stegmann V, Flores M, Huttenloch O, Becker M (2003) BASF, Germany, WO Patent 2003/062171Google Scholar
  195. 195.
    Volland M, Seitz V, Maase M, Flores M, Papp R, Massonne K, Stegmann V, Halbritter K, Noe R, Bartsch M, Siegel W, Becker M, Huttenloch O (2003) BASF, Germany, WO Patent 2003/062251Google Scholar
  196. 196.
    Huddleston JG, Willauer Heather D, Swatloski Richard P, Visser AE, Rogers RD (1998) Chem Comm 1765Google Scholar
  197. 197.
    Visser AE, Swatloski RP, Reichert WM, Davis JH Jr, Rogers RD, Mayton R, Sheff S, Wierzbicki A (2001) Chem Comm 135Google Scholar
  198. 198.
    Webb PB, Kunene TE, Cole-Hamilton DJ (2005) Green Chem 7:373CrossRefGoogle Scholar
  199. 199.
    Webb PB, Sellin MF, Kunene TE, Williamson S, Slawin AMZ, Cole-Hamilton DJ (2003) J Am Chem Soc 125:15577CrossRefGoogle Scholar
  200. 200.
    Jessop PG, Stanley RR, Brown RA, Eckert CA, Liotta CL, Ngo TT, Pollet P (2003) Green Chem 5:123CrossRefGoogle Scholar
  201. 201.
    Visser AE, Swatloski RP, Rogers RD (2000) Green Chem 2:1CrossRefGoogle Scholar
  202. 202.
    Riisager A, Fehrmann R, Berg RW, van Hal R, Wasserscheid P (2005) Phys Chem Chem Phys 7:3052CrossRefGoogle Scholar
  203. 203.
    Gutowski KE, Broker GA, Willauer HD, Huddleston JG, Swatloski RP, Holbrey JD, Rogers RD (2003) J Am Chem Soc 125:6632CrossRefGoogle Scholar
  204. 204.
    Wu B, Zhang YM, Wang HP (2008) J Chem Eng Data 53:983CrossRefGoogle Scholar
  205. 205.
    Blanchard LA, Hancu D, Beckman EJ, Brennecke JF (1999) Nature 399:28CrossRefGoogle Scholar
  206. 206.
    Kreher UP, Rosamilia AE, Raston CL, Scott JL, Strauss CR (2003) Org Lett 5:3107CrossRefGoogle Scholar
  207. 207.
    Beste YA, Schoenmakers H, Arlt W, Seiler M, Jork C (2005) BASF, Germany, WO Patent 2005/016484Google Scholar
  208. 208.
    Ge Y, Zhang L, Yuan X, Geng W, Ji J (2008) J Chem Thermodyn 40:1248CrossRefGoogle Scholar
  209. 209.
    Rinaldi R, Palkovits R, Schuth F (2008) Angew Chem Int Ed 47 : 8047CrossRefGoogle Scholar
  210. 210.
    Sievers C, Valenzuela-Olarte MB, Marzialetti T, Musin I, Agrawal PK, Jones CW (2009) Ind Eng Chem Res 48:1277CrossRefGoogle Scholar
  211. 211.
    Tan SSY, MacFarlane DR, Upfal J, Edye LA, Doherty WOS, Patti AF, Pringle JM, Scott JL (2009) Green chem 11:339CrossRefGoogle Scholar

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Authors and Affiliations

  1. 1.School of ChemistryMonash UniversityClaytonAustralia

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