Biocatalysis and Biomass Conversion in Alternative Reaction Media

Chemistry - A European Journal

Volumn 22, Issue 37, 2016, Pages 12984-12999

  Sheldon, Roger A ^a,b  

^a UNIVERSITY OF THE WITWATERSRAND   (South Africa)

^b DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

biocatalysis; biomass; deep eutectic solvents; green chemistry; ionic liquids

Indexed keywords

AMINES; BIOCATALYSTS; BIOCONVERSION; BIODIESEL; CATALYSIS; EUTECTICS; HYDROGEN BONDS; IONIC LIQUIDS; LIPASES; MIXING; NEGATIVE IONS; POSITIVE IONS; SACCHARIFICATION; SALTS; SOLVENTS;

BIOCATALYSIS; BIODIESEL PRODUCTION; DEEP EUTECTIC SOLVENTS; ENVIRONMENTALLY ACCEPTABLE; GREEN CHEMISTRY; HEXAFLUOROPHOSPHATES; HYDROGEN BOND DONORS; PROTIC IONIC LIQUIDS;

BIOMASS;

EID: 84985015814     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201601940     Document Type: Review

References (258)

1. A. Tao, R. J. Kazlaukas, Biocatalysis for Green Chemistry and Chemical Process Development, Wiley, Hoboken, New Jersey, 2011.
2. R. Wohlgemuth, Curr. Opin. Biotechnol. 2010, 21, 713–724;
3. J.-M. Choi, S.-S. Han, H.-S. Kim, Biotechnol. Adv. 2015, 33, 1443–1454.
4. G. W. Huisman, S. J. Collier, Curr. Opin. Chem. Biol. 2013, 17, 284–292.
5. J. H. Kastle, A. S. Loevenhart, Am. Chem. J. 1900, 24, 491–525;
6. E. A. Sym, Biochem. Z. 1933, 258, 304–324;
7. E. A. Sym, Enzymologia 1937, 2, 107–109.
8. A. Zaks, A. M. Klibanov, Science 1984, 224, 1249–1251.
9. G. Carrea, S. Riva, Organic Synthesis with Enzymes in Non-Aqueous Media, Wiley-VCH, Weinheim, 2008.
10. J. S. Dordick, Enzyme Microb. Technol. 1989, 11, 194–211.
11. Y. L. Khmelnitsky, S. H. Welch, D. S. Clark, J. S. Dordick, Biotechnol. Bioeng. 1994, 58, 1063.
12. Handbook of Green Chemistry: Green Solvents, Vol. 6 (Eds.: P. Wasserscheid, A. Stark), Wiley-VCH, Weinheim, 2009;
13. J. P. Hallett, Chem. Rev. 2011, 111, 3508–3576.
14. R. A. Sheldon, Chem. Commun. 2001, 299–309;
15. T. Welton, Coord. Chem. Rev. 2004, 248, 2459–2477;
16. V. I. Pârvulescu, C. Hardacre, Chem. Rev. 2007, 107, 2615–2665;
17. H. Olivier-Bourbigou, L. Magna, D. Morvan, Appl. Catal. A 2010, 373, 1–56;
18. D. Betz, P. Altmann, M. Cokoja, W. A. Herrmann, F. E. Kuehn, Coord. Chem. Rev. 2011, 255, 1518–1540;
19. Z. S. Qureshi, K. M. Deshmukh, B. M. Bhanage, Clean Technol. Environ. Policy 2014, 16, 1487–1513;
20. H. P. Steinrück, P. Wasserscheid, Catal. Lett. 2015, 145, 380–397.
21. S. G. Cull, J. D. Holbrey, V. Vargas-Mora, K. R. Seddon, G. J. Lye, Biotechnol. Bioeng. 2000, 69, 227–233.
22. M. Erbeldinger, A. J. Mesiano, A. J. Russell, Biotechnol. Prog. 2000, 16, 1129–1131.
23. R. Madeira Lau, F. van Rantwijk, K. R. Seddon, R. A. Sheldon, Org. Lett. 2000, 2, 4189–4191.
24. Selected examples:
25. Ionic Liquids in Biotransformations and Organocatalysis (Ed.: P. Dominguez de Maria), Wiley, Hoboken, 2012;
26. R. A. Sheldon in Catalysis in Ionic Liquids: from Catalyst Synthesis to Application (Eds.: C. Hardacre, V. Parvulescu), RSC, Cambridge, UK, 2014, pp. 20–43;
27. F. van Rantwijk, R. A. Sheldon, Chem. Rev. 2007, 107, 2757–2585;
28. M. Moniruzzaman, N. Kamiya, K. Nakashima, M. Goto, Biochem. Eng. J. 2010, 48, 295–314;
29. F. J. Hernández-Fernández, A. P. De Los Ríos, L. J. Lozano-Blanco, C. Godinez, J. Chem. Technol. Biotechnol. 2010, 85, 1423–1435;
30. S. H. Ha, Y.-M. Koo, Korean J. Chem. Eng. 2011, 28, 2095–2101;
31. M. K. Potdar, G. F. Kelso, L. Schwarz, C. Zhang, M. T. W. Hearne, Molecules 2015, 20, 16788–16816.
32. R. P. Gaisberger, M. H. Fechter, H. Griengl, Tetrahedron: Asymmetry 2004, 15, 2959–2963.
33. S. Park, R. J. Kazlauskas, J. Org. Chem. 2001, 66, 8395–8401;
34. M. Eckstein, M. Villela Filho, A. Liese, U. Kragl, Chem. Commun. 2004, 1084–1085;
35. K. W. Kim, B. Song, M. Y. Choi, M. J. Kim, Org.Lett. 2001, 3, 1507–1509;
36. S. H. Schöfer, N. Kaftzik, P. Wasserscheid, U. Kragl, Chem. Commun. 2001, 425–426;
37. T. Itoh, E. Akasaki, K. Kudo, S. Shirakami, Chem. Lett. 2001, 262–263.
38. P. Lozano, T. de Diego, J.-P. Guegan, M. Vaultier, J. L. Iborra, Biotechnol. Bioeng. 2001, 75, 563–569;
39. P. Lozano, T. De Diego, D. Carrie, M. Vaultier, J. L. Iborra, Biotechnol. Lett. 2001, 23, 1529–1533;
40. J. R. Martín, M. Nus, J. V. Sinisterra Gago, J. M. Sánchez-Montero, J. Mol. Catal. B 2008, 52–53, 162–167.
41. D. Coleman, N. Gathergood, Chem. Soc. Rev. 2010, 39, 600–637.
42. S. Stolte, M. Matzke, J. Arning, A. Böschen, W. R. Pitner, U. Welz-Biermann, B. Jastorff, J. Ranke, Green Chem. 2007, 9, 1170–1179;
43. R. F. M. Frade, C. A. M. Afonso, Hum. Exp. Toxicol. 2010, 29, 1038–1054;
44. S. Bruzzone, C. Chiappe, S. E. Focardi, C. Pretti, M. Renzi, Chem. Eng. J. 2011, 175, 17–23;
45. T. P. Thuy Pham, C. W. Cho, Y. S. Chun, Water Res. 2010, 44, 352–372.
46. R. A. Sheldon, Green Chem. 2007, 9, 1273–1283 and references therein.
47. M. Deetlefs, K. R. Seddon, Green Chem. 2010, 12, 17–30.
48. G. Imperato, B. König, C. Chiappe, Eur. J. Org. Chem. 2007, 1049–1058.
49. S. T. Handy, Chemistry 2003, 9, 2938–2944.
50. C. Chiappe, A. Marra, A. Mele, Top.Curr. Chem. 2010, 295, 177–195.
51. K. Fukumoto, M. Yoshizawa, H. Ohno, J. Am. Chem. Soc. 2005, 127, 2398–2399.
52. X. Chen, X. Li, A. Hu, F. Wang, Tetrahedron: Asymmetry 2008, 19, 1–14.
53. Y. Fukaya, Y. Iizuka, K. Sekikawa, H. Ohno, Green Chem. 2007, 9, 1155–1157.
54. Y. Yu, X. Lu, Q. Zhou, K. Dong, H. Yao, S. Zhang, Chem. Eur. J. 2008, 14, 11174–11182.
55. M. Petkovic, J. L. Ferguson, H. Q. Nimal Gunaratne, R. Ferreira, M. C. Leitão, K. R. Seddon, L. P. N. Rebelo, C. S. Pereira, Green Chem. 2010, 12, 643–649.
56. X.-D. Hou, Q.-P. Liu, T. J. Smith, N. Li, M.-H. Zong, PLOS One 2013, 8, e59145.
57. S. Pavlovica, A. Ziemanis, E. Gziboska, M. Klavins, P. Mekss, Green Sustainable Chem. 2011, 1, 103–110.
58. J. H. Davis, Jr., Chem. Lett. 2004, 33, 1072–1077;
59. S. Tang, G. A. Baker, H. Zhao, Chem. Soc. Rev. 2012, 41, 4030–4066.
60. A. P. de los Ríos, F. van Rantwijk, R. A. Sheldon, Green Chem. 2012, 14, 1584–1588.
61. T. L. Greaves, C. J. Drummond, Chem. Rev. 2008, 108, 206–237.
62. C. Pretti, C. Chiappe, I. Baldetti, S. Brunini, G. Monni, L. Intorre, Ecotoxicol. Environ. Saf. 2009, 72, 1170–1176.
63. L. Chen, G. F. Mullen, M. Le Roch, C. G. Cassity, N. Gouault, H. Y. Fadamiro, R. E. Barletta, R. A. O′Brien, R. E. Sykora, A. C. Stenson, K. N. West, H. E. Horne, J. M. Hendrich, K. R. Xiang, J. H. Davis, Jr., Angew. Chem. Int. Ed. 2014, 53, 11762–11765;
64. Angew. Chem. 2014, 126, 11956–11959.
65. L. Chen, M. Sharifzadeh, N. MacDowell, T. Welton, N. Shah, J. P. Hallett, Green Chem. 2014, 16, 3098–3106.
66. R. Madeira Lau, M. J. Sorgedrager, G. Carrea, F. van Rantwijk, F. Secundo, R. A. Sheldon, Green Chem. 2004, 6, 483–487;
67. F. van Rantwijk, F. Secundo, R. A. Sheldon, Green Chem. 2006, 8, 282–286.
68. R. A. Sheldon, R. Madeira Lau, M. J. Sorgedrager, F. Van Rantwijk, K. R. Seddon, Green Chem. 2002, 4, 147–151.
69. M. B. Turner, S. K. Spear, J. G. Huddleston, J. D. Holbrey, R. D. Rogers, Green Chem. 2003, 5, 443–447.
70. A. J. Walker, N. C. Bruce, Chem. Commun. 2004, 2570;
71. A. J. Walker, N. C. Bruce, Tetrahedron 2004, 60, 561–568.
72. T. Maruyama, H. Yamamura, T. Kotani, N. Kamiya, M. Goto, Org. Biomol. Chem. 2004, 2, 1239–1244.
73. H. Zhao, C. L. Jones, J. V. Cowins, Green Chem. 2009, 11, 1128–1138.
74. H. Zhao, G. A. Baker, Z. Song, O. Olubajo, T. Crittle, D. Peters, Green Chem. 2008, 10, 696–705;
75. H. Zhao, G. A. Baker, Z. Song, O. Olubajo, L. Zandesr, S. M. Campbell, J. Mol. Catal. B 2009, 57, 149–157.
76. Z. Guo, B. Chen, R. L. Murillo, T. Tan, X. Xu, Org. Biomol. Chem. 2006, 4, 2772–2776;
77. B. Chen, Z. Guo, T. Tan, X. Xu, Biotechnol. Bioeng. 2008, 99, 18–29.
78. D. Das, A. Dasgupta, P. K. Das, Tetrahedron Lett. 2007, 48, 5635–5639.
79. A. A. Papadopoulou, A. Tzani, D. Alivertis, M. H. Katsoura, A. C. Polydera, A. Detsi, H. Stamatis, Green Chem. 2016, 18, 1147–1158.
80. A. J. Kotlewska, F. van Rantwijk, R. A. Sheldon, I. W. C. E. Arends, Green Chem. 2011, 13, 2154–2160; see also:
81. A. Drożdż, K. Erfurt, R. Bielas, A. Chrobok, New J. Chem. 2015, 39, 1315–1321.
82. R. A. Sheldon, Appl. Microbiol. Biotechnol. 2011, 92, 467–477;
83. R. A. Sheldon, S. van Pelt, S. Kanbak-Aksu, J. Rasmussen, M. H. A. Janssen, Aldrichimica Acta 2013, 46, 81–93;
84. S. Talekar, A. Joshi, G. Joshi, P. Kamat, R. Haripurkar, S. Kambale, RSC Adv. 2013, 3, 12485–12511;
85. M. del Pilar Guauque Torres, M. L. Foresti, M. L. Ferreira, AMB express 2013, 3, 25.
86. A. R. Toral, A. P. De Los Rios, F. J. Hernandez, M. H. A. Janssen, R. Schoevaart, F. van Rantwijk, R. A. Sheldon, Enzyme Microb. Technol. 2007, 40, 1095–1099;
87. P. Hara, U. Hanefeld, L. T. Kanerva, Green Chem. 2009, 11, 250–256;
88. S. Shah, M. N. Gupta, Bioorg. Med. Chem. Lett. 2007, 17, 921–924.
89. J.-Q. Lai, Z.-L. Hub, R. A. Sheldon, Z. Yang, Process Biochem. 2012, 47, 2058–2063.
90. C. Vafiadi, E. Topakas, V. R. Nahmias, C. B. Faulds, P. Christakopoulos, J. Biotechnol. 2009, 139, 124–129.
91. C. Y. Yu, P. Wei, X. F. Li, M. H. Zong, W. Y. Lou, Ind. Eng. Chem. Res. 2014, 53, 7923–7930.
92. L. A. Blanchard, D. Hancu, E. J. Beckman, J. F. Brennecke, Nature 1999, 399, 28–29.
93. C. Cadena, J. L. Anthony, J. K. Shah, T. I. Morrow, J. F. Brennecke, E. J. Maginn, J. Am. Chem. Soc. 2004, 126, 5300–5308.
94. P. Lozano, T. De Diego, D. Carrié, M. Vaultier, J. L. Iborra, Chem. Commun. 2002, 692–693;
95. M. T. Reetz, W. Wiesenhofer, G. Francio, W. Leitner, Chem. Commun. 2002, 992–993;
96. P. Lozano, T. De Diego, D. Carrié, M. Vaultier, J. L. Iborra, Biotechnol. Prog. 2003, 19, 380–382;
97. M. T. Reetz, W. Wiesenhofer, G. Francio, W. Leitner, Adv. Synth. Catal. 2003, 345, 1221;
98. P. Lozano, E. Garcia-Verdugo in Ionic Liquids in Biotransformations and Organocatalysis (Ed.: P. Dominguez de Maria), Wiley, New York, 2012, Chapter 4.
99. M. D. Bermejo, A. J. Kotlewska, L. J. Florusse, M. J. Cocero, F. van Rantwijk, C. J. Peters, Green Chem. 2008, 10, 1049–1054.
100. P. Lozano, E. Garcıa-Verdugo, N. Karbass, K. Montague, T. De Diego, M. I. Burguete, S. V. Luis, Green Chem. 2010, 12, 1803–1810.
101. P. Lozano, E. Garcia-Verdugo, R. Piamtongkam, N. Karbass, T. De Diego, M. I. Burguete, S. V. Luis, J. L. Iborra, Adv. Synth. Catal. 2007, 349, 1077–1084.
102. A. P. Abbott, G. Capper, D. L. Davies, R. K. Rasheed, V. Tambyrajah, Chem. Commun. 2003, 70–71;
103. A. P. Abbott, D. Boothby, G. Capper, D. L. Davies, R. K. Rasheed, J. Am. Chem. Soc. 2004, 126, 9142–9147;
104. E. L. Smith, A. P. Abbott, K. S. Ryder, Chem. Rev. 2014, 114, 11060–11082;
105. C. Ruß, B. König, Green Chem. 2012, 14, 2969–2982;
106. Q. Zhang, K. De Oliveira Vigier, S. Royer, F. Jérôme, Chem. Soc. Rev. 2012, 41, 7108–7146.
107. For a recent review of the use of DESs in organic synthesis see: D. A. Alonso, A. Baeza, R. Chinchilla, G. Guillena, I. M. Pastor, D. J. Ramon, Eur. J. Org. Chem. 2016, 612–632.
108. M. Francisco, A. van den Bruinhorst, M. C. Kroon, Angew. Chem. Int. Ed. 2013, 52, 3074–3085;
109. Angew. Chem. 2013, 125, 3152–3163.
110. O. S. Hammond, D. T. Bowron, K. J. Edler, Green Chem. 2016, 18, 2736–2744.
111. A. P. Abbott, R. C. Harris, K. S. Ryder, C. D′Agostino, L. F. Gladden, M. D. Mantle, Green Chem. 2011, 13, 82–90.
112. A. Hayyan, F. S. Mjalli, I. M. Al Nashef, Y. M. Al-Wahaibi, T. Al-Wahaibi, M. Ali Hashim, J. Mol. Liq. 2013, 178, 137–141.
113. Z. Maugeri, P. Dominguez de Maria, RSC Adv. 2012, 2, 421–425.
114. Y. H. Choi, J. Van Spronsen, Y. Dai, M. Verberne, F. Hollmann, I. W. C. E. Arends, G.-J. Witkamp, R. Verpoorte, Plant Physiol. 2011, 156, 1701–1705.
115. Y. Dai, J. Van Spronsen, G. J. Witkamp, R. Verpoorte, Y. H. Choi, Anal. Chim. Acta 2013, 766, 61–68.
116. A. Paiva, R. Craveiro, I. Aroso, M. Martins, R. L. Reis, A. R. C. Duarte, ACS Sustainable Chem. Eng. 2014, 2, 1063–1071.
117. J. T. Gorke, F. Srienc, R. Kazlauskas, Chem. Commun. 2008, 1235–1237.
118. H. Monhemi, M. R. Housaindokht, A. A. Moosavi-Movahedi, M. R. Bozorgmehr, Phys. Chem. Chem. Phys. 2014, 16, 14882–14895.
119. N. Guajardo, C. R. Müller, R. Schrebler, C. Carlesi, P. Dominguez de Maria, ChemCatChem 2016, 8, 1020–1027.
120. E. Durand, J. Lecomte, B. Barea, G. Piombo, E. Dubreucq, P. Villeneuve, Process Biochem. 2012, 47, 2081–2089;
121. E. Durand, J. Lecomte, P. Villeneuve, Eur. J. Lipid Sci. Technol. 2013, 115, 379–385;
122. B. Kleiner, U. Schörken, Eur. J. Lipid Sci. Technol. 2015, 117, 167–177;
123. M. Cvjetko Bubalo, A. J. Tušek, M. Vinković, K. Radošević, V. G. Srček, I. R. Redovniković, J. Mol. Catal. B 2015, 122, 188–198;
124. E. Durand, J. Lecomte, B. Baréa, E. Dubreucq, R. Lortie, P. Villeneuve, Green Chem. 2013, 15, 2275–2282;
125. A. Petrenz, P. Dominguez de Maria, A. Ramanathan, U. Hanefeld, M. B. Ansorge-Scumacher, S. Kara, J. Mol. Catal. B 2015, 114, 42–49;
126. C. R. Müller, I. Meiners, P. Dominguez de Maria, RSC Adv. 2014, 4, 46097–46101.
127. H. Zhao, G. A. Baker, S. Holmes, J. Mol. Catal. B 2011, 72, 163–167;
128. Z. Maugeri, W. Leitner, P. Dominguez de Maria, Eur. J. Org. Chem. 2013, 4223–4228.
129. D. Lindberg, M. de La Fuenta Revenga, M. Widersten, J. Biotechnol. 2010, 147, 169–171.
130. B.-P. Wu, Q. Wen, H. Xu, Z. Yang, J. Mol. Catal. B 2014, 101, 101–107;
131. A. A. Papadopoulou, E. Efstathiadou, M. Patila, A. C. Polydera, H. Stamatis, Ind. Eng. Chem. Res. 2016, 55, 5145–5151.
132. Z. Maugeri, P. Dominguez de Maria, J. Mol. Catal. B 2014, 107, 120–123.
133. K. Hult, P. Berglund, Trends Biotechnol. 2007, 25, 231–238.
134. D. González-Martínez, V. Gotor, V. Gotor-Fernández, Eur. J. Org. Chem. 2016, 1513–1519;
135. X. Tian, S. Zhang, L. Zheng, J. Microbiol. Biotechnol. 2016, 26, 80–88;
136. B. N. Borse, V. S. Borude, S. R. Shukla, Curr. Chem. Lett. 2012, 1, 59–68.
137. D. Gamenara, G. Seoane, P. Saénz Mendez, P. Dominguez de Maria, Redox Biocatalysis: Fundamentals and Applications, Wiley, Hoboken, NJ, 2012.
138. Y. Ni, J.-H. Xu, Biotechnol. Adv. 2012, 30, 1279–1288;
139. G.-W. Zheng, J.-H. Xu, Curr. Opin. Biotechnol. 2011, 22, 784–792;
140. G. W. Huisman, J. Liang, A. Krebber, Curr. Opin. Chem. Biol. 2010, 14, 122–129;
141. J. C. Moore, D. J. Pollard, B. Kosjek, P. N. Devine, Acc. Chem. Res. 2007, 40, 1412–1419;
142. S. M. A. De Wildeman, T. Sonke, H. E. Schoemaker, O. May, Acc. Chem. Res. 2007, 40, 1260–1266.
143. S. Rodríguez, M. M. Kayser, J. D. Stewart, J. Am. Chem. Soc. 2001, 123, 1547–1555.
144. Z. Maugeri, P. Dominguez de Maria, ChemCatChem 2014, 6, 1535–1537.
145. C. R. Müller, I. Lavandera, V. Gotor-Fernandez, P. Dominguez de Maria, ChemCatChem 2015, 7, 2654–2659.
146. S. Mao, L. Yu, S. Ji, X. Liu, F. Lu, J. Chem. Technol. Biotechnol. 2016, 91, 1099–1104.
147. M. J. Earle, N. V. Plechkova, K. R. Seddon, Pure Appl. Chem. 2009, 81, 2045–2057.
148. H. Zhao, G. A. Baker, J. Chem. Technol. Biotechnol. 2013, 88, 3–12.
149. H. Zhao, G. A. Baker, S. Holmes, Org. Biomol. Chem. 2011, 9, 1908–1916;
150. H. Zhao, C. Zhang, T. D. Crittle, J. Mol. Catal. B 2013, 85–86, 243–247.
151. Z.-L. Huang, B.-P. Wu, Q. Wen, T.-X. Yang, Z. Yang, J. Chem. Technol. Biotechnol. 2014, 89, 1975–1981.
152. B. Kleiner, P. Fleischer, U. Schörken, Process Biochem. 2015, DOI: 10.1016/j.procbio.2015.10.016.
153. Y.-G. Shi, J.-R. Li, Y.-H. Chu, J. Chem. Technol. Biotechnol. 2011, 86, 1457–1468.
154. A. M. Gumel, M. S. M. Annuar, T. Heidelberg, Y. Chisti, Process Biochem. 2011, 46, 2079–2090.
155. M. Woudenberg-van Oosterom, F. van Rantwijk, R. A. Sheldon, Biotechnol. Bioeng. 1996, 49, 328–333.
156. D. R. Macfarlane, J. Golding, S. Forsyth, M. Forsyth, G. B. Deacon, Chem. Commun. 2001, 1430–1431.
157. Q. Liu, M. H. A. Janssen, F. Van Rantwijk, R. A. Sheldon, Green Chem. 2005, 7, 39–42.
158. N. Li, D. Ma, M.-H. Zong, J. Biotechnol. 2008, 133, 103–109;
159. X.-F. Li, W.-Y. Lou, T. J. Smith, M.-H. Zong, H. Wu, J.-F. Wang, Green Chem. 2006, 8, 538–544.
160. M. E. Zakrzewska, E. Bogel-Lukasik, R. Bogel-Lukasik, Energy Fuels 2010, 24, 737–745.
161. S. Murugesan, R. J. Linhardt, Curr. Org. Synth. 2005, 2, 437–451.
162. N. Galonde, K. Nott, A. Debuigne, M. Deleu, C. Jerome, M. Paquot, J.-P. Wathelet, J. Chem. Technol. Biotechnol. 2012, 87, 451–471 and references therein.
163. F. Ganske, U. T. Bornscheuer, Org. Lett. 2005, 7, 3097–3098;
164. S. W. Chang, J. F. Shaw, New Biotechnol. 2009, 26, 109–116;
165. Z. Yang, Z.-L. Huang, Catal. Sci. Technol. 2012, 2, 1767–1775.
166. S. H. Lee, D. T. Dang, S. H. Ha, W.-J. Chang, Y.-M. Koo, Biotechnol. Bioeng. 2008, 99, 1–8.
167. C. Graenacher, US Patent 1943176, 1934, Society of Chemical Industry, Basel.
168. R. P. Swatloski, S. K. Spear, J. D. Holbrey, R. D. Rogers, J. Am. Chem. Soc. 2002, 124, 4974–4975.
169. Y. Fukaya, K. Hayashi, M. Wada, H. Ohno, Green Chem. 2008, 10, 44–46.
170. M. Abe, Y. Fukaya, H. Ohno, Green Chem. 2010, 12, 1274–1280.
171. M. Abe, S. Yamanaka, H. Yamada, T. Yamada, H. Ohno, Green Chem. 2015, 17, 4432–4438;
172. M. Abe, T. Yamada, H. Ohno, RSC Adv. 2014, 4, 17136–17140.
173. Q. Xu, J. F. Kennedy, L. Liu, Carbohydr. Polym. 2008, 72, 113–121.
174. Y. Wu, T. Sasaki, S. Irie, K. Sakurai, Polymer 2008, 49, 2321–2327.
175. M. Sharma, C. Mukesh, D. Mondal, K. Prasad, RSC Adv. 2013, 3, 18149–185155.
176. R. A. Sheldon, Green Chem. 2014, 16, 950–963.
177. S.-T. Yang, H. A. El-Enshasy, N. Thongchul, Bioprocessing Technologies Biorefinery for Sustainable Production of Fuels, Chemicals and Polymers, Wiley, Hoboken, 2013;
178. Catalytic Process Development for Renewable Materials (Eds.: P. Imhof, J. C. van der Waal), Wiley-VCH, Weinheim, 2013;
179. P. Gallezot, Chem. Soc. Rev. 2012, 41, 1538–1558.
180. E. F. Sousa-Aguiar, L. Gorenstin Appel, P. Costa Zonetti, A. do Couto Fraga, A. Azevedo Bicudo, I. Fonseca, Catal. Today 2014, 234, 13–23.
181. E. De Jong, A. Higson, P. Walsh, M. Wellisch, Biofuels Bioprod. Biorefin. 2012, 6, 606–624.
182. C. O. Tuck, E. Perez, I. T. Horvath, R. A. Sheldon, M. Poliakoff, Science 2012, 337, 695–699.
183. J. P. Lange, Biofuels Bioprod. Biorefin. 2007, 1, 39–48.
184. U. Bornscheuer, K. Buchholz, J. Seibel, Angew. Chem. Int. Ed. 2014, 53, 10876–10893;
185. Angew. Chem. 2014, 126, 11054–11073.
186. H. Rabemanolontsoa, S. Saka, Bioresour. Technol. 2016, 199, 83–91;
187. P. Kumar, D. M. Barrett, M. J. Delwiche, P. Stroeve, Ind. Eng. Chem. Res. 2009, 48, 3713–3729;
188. V. Menon, M. Rao, Prog. Energy Combust. Sci. 2012, 38, 522–550;
189. P. Alvira, E. Tomas-Pejo, M. Ballesteros, M. J. Negro, Bioresour. Technol. 2010, 101, 4851–4861.
190. X. Zhao, K. Cheng, D. Liu, Appl. Microbiol. Biotechnol. 2009, 82, 815–827;
191. J. Wildschut, A. T. Smit, J. H. Reith, W. J. J. Huijgen, Bioresour. Technol. 2013, 135, 58–66;
192. J. Viell, A. Harwardt, J. Seiler, W. Marquardt, Bioresour. Technol. 2013, 150, 89–97.
193. For an excellent review, see A. Brandt, J. Gräsvik, J. P. Hallett, T. Welton, Green Chem. 2013, 15, 550–583.
194. P. Domínguez de María, J. Chem. Technol. Biotechnol. 2014, 89, 11–18;
195. T. Vancov, A.-S. Alston, T. Brown, S. McIntosh, Renewable Energy 2012, 45, 1–6;
196. G. Cevasco, C. Chiappe, Green Chem. 2014, 16, 2375–2385;
197. Ionic Liquids in the Biorefinery Concept: Challenges and Perspectives (Ed.: R. Bogel-Lukasic), RSC Green Chemistry Series, No. 36, Royal Society of Chemistry, London, 2016;
198. Production of Biofuels and Chemicals with Ionic Liquids (Eds.: Z. Fang, R. L. Smith, X. Qi), Springer, Dordrecht, 2014.
199. M. Perez-Sanchez, M. Sandoval, M. J. Hernaiz, P. Domínguez de María, Curr. Org. Chem. 2013, 17, 1188–1199.
200. D. A. Fort, R. C. Remsing, R. P. Swatloski, P. Moyna, G. Moyna, R. D. Rogers, Green Chem. 2007, 9, 63–69;
201. N. Sun, M. Rahman, Y. Qin, M. L. Maxim, H. Rodriguez, R. D. Rogers, Green Chem. 2009, 11, 646–655;
202. M. Zavrel, D. Bross, M. Funke, J. Büchs, A. C. Spiess, Bioresour. Technol. 2009, 100, 2580–2587;
203. J.-K. Xu, Y.-C. Sun, R.-C. Sun, ACS Sustainable Chem. Eng. 2014, 2, 1035–1042;
204. V. P. Soudham, D. G. Raut, I. Anugwom, T. Brandberg, C. Larsson, J.-P. Mikkola, Biotechnol. Biofuels 2015, 8, 135;
205. J. Gräsvik, S. Winestrand, M. Normark, L. J. Jönsson, J. P. Mikkola, BMC Biotechnol. 2014, 14, 34.
206. Y. Cao, H. Li, Y. Zhang, J. He, J. Appl. Polym. Sci. 2010, 116, 547–554.
207. Q. Li, Y. He, M. Xian, G. Jun, X. Ju, J. Yang„ L. Li, Bioresour. Technol. 2009, 100, 3570–3575.
208. W. Li, N. Sun, B. Stoner, X. Jiang, X. Lu, R. D. Rogers, Green Chem. 2011, 13, 2038–2047;
209. Z. Wang, L. Li, K. Xiao, J. Wu, Bioresour. Technol. 2009, 100, 1687–1690.
210. R. Rinaldi, Angew. Chem. Int. Ed. 2014, 53, 8559–8560;
211. Angew. Chem. 2014, 126, 8699–8701;
212. S. Morales-delaRosa, J. M. Campos-Martin, J. L. G. Fierro, Chem. Eng. J. 2012, 181–182, 538–541;
213. J. Long, X. Li, B. Guo, F. Wang, Y. Yu, L. Wang, Green Chem. 2012, 14, 1935–1941.
214. S. P. Magalhães da Silva, A. M. da Costa Lopes, L. B. Roseiro, R. Bogel-Łukasik, RSC Adv. 2013, 3, 16040–16050;
215. A. M. da Costa Lopes, K. G. João, D. F. Rubik, E. Bogel-Łukasik, L. C. Duarte, J. Andreaus, R. Bogel-Łukasik, Bioresour. Technol. 2013, 142, 198–208.
216. J. Viell, H. Wulfhorst, T. Schmidt, U. Commandeur, R. Fischer, A. Spiess, W. Marquardt, Bioresour. Technol. 2013, 146, 144–151.
217. J. Shi, J. M. Gladden, N. Sathitsuksanoh, P. Kambam, L. Sandoval, D. Mitra, S. Zhang, A. George, S. W. Singer, B. A. Simmons, S. Singh, Green Chem. 2013, 15, 2579–2589.
218. Z. Qiu, G. M. Aita, M. S. Walker, Bioresour. Technol. 2012, 117, 251–256.
219. N. L. Mai, S. H. Ha, Y.-M. Koo, Process Biochem. 2014, 49, 1144–1151.
220. E. C. Achinivu, R. M. Howard, G. Li, H. Gracz, W. A. Henderson, Green Chem. 2014, 16, 1114–1119.
221. M. Ungurean, Z. Csanádi, L. Gubicza, F. Peter, Bioresources 2014, 9, 6100–6116.
222. S. Datta, B. Holmes, J. I. Park, Z. Chen, D. C. Dibble, M. Hadi, H. W. Blanch, B. A. Simmons, R. Sapra, Green Chem. 2010, 12, 338–345.
223. S. Dalal, A. Sharma, M. N. Gupta, Chem. Cent. J. 2007, 1, 16–20;
224. P. O. Jones, P. T. Vasudevan, Biotechnol. Lett. 2010, 32, 103;
225. B. Li, S. Dong, X. Xie, Z. Xu, L. Li, Adv. Mater. Res. 2012, 581–582, 257–260;
226. S. Jamwal, G. S. Chauhan, J.-H. Ahn, N. S. Reddy, RSC Adv. 2016, 6, 25485–25491.
227. K. Periyasamy, L. Santhalembi, G. Mortha, M. Aurousseau, S. Subramanian, RSC Adv. 2016, 6, 32849–32857.
228. L. Sutarlie, K.-L. Yang, J. Colloid Interface Sci. 2013, 411, 76–81.
229. K. J. Khorshidi, H. Lenjannezhadian, M. Jamalan, M. Zeinalid, J. Chem. Technol. Biotechnol. 2016, 91, 539–546; see also
230. R. A. Sheldon, M. J. Sorgedrager, B. Kondor, (CLEA Technologies B.V), WO 2012/023847A2 and US 2013/0196407A1 and NL 1038098, 2012.
231. A. Bhattacharya, B. I. Pletschke, Enzyme Microb. Technol. 2014, 61–62, 17–27.
232. J. Xu, X. Liu, J. He, L. Hu, B. Dai, B. Wu, J. Chem. Technol. Biotechnol. 2015, 90, 57–63.
233. K. Nakashima, K. Yamaguchi, N. Tanguchi, S. Arai, R. Yamada, S. Katahira, N. Ishida, H. Takahasshi, C. Ogino, A. Kondo, Green Chem. 2011, 13, 2948–2953.
234. M. T. Clough, K. Geyer, P. A. Hunt, S. Son, U. Vagt, T. Welton, Green Chem. 2015, 17, 231–243.
235. X.-D. Hou, N. Li, M.-H. Zong, Bioresour. Technol. 2013, 136, 469–474.
236. N. Sun, R. Parthasarathi, A. M. Socha, J. Shi, S. Zhang, V. Stavila, K. L. Sale, B. A. Simmons, S. Singh, Green Chem. 2014, 16, 2546–2557.
237. P. Verdía, A. Brandt, J. P. Hallett, M. J. Ray, T. Welton, Green Chem. 2014, 16, 1617–1627;
238. A. Brandt, M. J. Ray, T. Q. To, D. J. Leak, R. J. Murphy, T. Welton, Green Chem. 2011, 13, 2489–2499.
239. A. George, A. Brandt, K. Tran, S. M. S. Nizan, S. Zahari, D. Klein-Marcuschamer, N. Sun, N. Sathitsuksanoh, J. Shi, V. Stavila, R. Parthasari, S. Singh, B. M. Holmes, T. Welton, B. A. Simmons, J. P. Hallett, Green Chem. 2015, 17, 1728–1734.
240. A. A. N. Gunny, D. Arbain, E. M. Nashef, P. Jamal, Bioresour. Technol. 2015, 181, 297–302.
241. C. Lehmann, F. Sibilla, Z. Maugeri, W. R. Streit, P. Domínguez de María, R. Martinez, U. Schwaneberg, Green Chem. 2012, 14, 2719–2726.
242. S. Xia, G. A. Baker, S. Ravula, H. Zhao, RSC Adv. 2014, 4, 10586–10596.
243. N. A. M. Nor, W. A. W. Mustapha, O. Hassa, Procedia Chem. 2016, 18, 147–154.
244. A. Procentese, E. Johnson, V. Orr, A. Garruto Campanile, J. A. Wood, A. Marzocchella, L. Rehmann, Bioresour. Technol. 2015, 192, 31–36.
245. M. Jablonský, A. Škulcová, L. Kamenská, M. Vrška, J. Šima, Bioresources 2015, 10, 8039–8047.
246. M. Francisco, A. van den Bruinhorst, M. C. Kroon, Green Chem. 2012, 14, 2153–2157.
247. M. C. Kroon, M. F. Casal, A. Van den Bruinhorst, Technische Universiteit Eindhoven, WO 2013/153203A1.
248. A. K. Kumar, B. S. Parikh, M. Pravakar, Environ. Sci. Pollut. Res. 2015, 23, 9265–9275.
249. J. J. Bozell, G. R. Petersen, Green Chem. 2010, 12, 539–554.
250. Biorefineries: Industrial Processes and Products (Eds.: B. Kamm, P. R. Gruber, M. Kamm), Wiley-VCH, Weinheim, 2006.
251. R.-J. van Putten, J. C. van der Waal, E. de Jong, C. B. Rasrendra, H. J. Heeres, J. G. de Vries, Chem. Rev. 2013, 113, 1499–1597.
252. T. Ståhlberg, W. Fu, J. M. Woodley, A. Riisager, ChemSusChem 2011, 4, 451–458;
253. M. Dashtban, A. Gilbert, P. Fatehi, RSC Adv. 2014, 4, 2037–2050;
254. Y.-B. Yi, J.-W. Lee, C.-H. Chung, Curr. Org. Chem. 2014, 18, 1149–1158.
255. S. Hu, Z. Zhang, Y. Zhou, B. Han, H. Fan, W. Li, J. Song, Green Chem. 2008, 10, 1280–1283.
256. F. Goursaud, M. Berchel, J. Guilbot, N. Legros, L. Lemiègre, J. Marcilloux, J. Plusquelleca, T. Benvegnu, Green Chem. 2008, 10, 310–320.
257. K. De Oliveira Vigier, A. Benguerba, J. Barrault, F. Jérôme, Green Chem. 2012, 14, 285–289.
258. F. Liu, F. Boissou, A. Vignault, L. Lemée, S. Marinkovic, B. Estrine, K. De Oliveira Vigier, F. Jérôme, RSC Adv. 2014, 4, 28836–28841.