Ionic liquid-mediated formation of 5-hydroxymethylfurfural-A promising biomass-derived building block

Chemical Reviews

Volumn 111, Issue 2, 2011, Pages 397-417

  Zakrzewska, Małgorzata E ^a   Bogel Łukasik, Ewa ^a   Bogel Łukasik, Rafał ^a,b  

^a UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^b LABORATÓRIO NACIONAL DE ENERGIA E GEOLOGIA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMASS; CHLORINE COMPOUNDS; IONIC LIQUIDS;

AQUEOUS PROCESS; BUILDING BLOCKES; CHEMICAL PRETREATMENTS; IONIC ADDITIVES; LEAVING GROUPS; LIGNOCELLULOSIC BIOMASS; MICRO-CRYSTALLINE CELLULOSE; PHYSICAL STRUCTURES;

CELLULOSE;

EID: 78649512635     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr100171a     Document Type: Article

References (120)

1. Piebalgs, A. European Commissioner of Energy, Commission Speech, July 2007.
2. Dalai, A. K.; Bassi, A. Energy Fuels 2010, 24, 4627.
3. Saha, B. D. J. Ind. Microbiol. Biotechnol 2003, 30, 279.
4. Girio, F. M.; Fonseca, C.; Carvalheiro, F.; Duarte, L. C.; Marques, S.; Bogel-Łukasik, R. Bioresour. Technol. 2010, 101, 4775.
5. Röper, H. Starch 2002, 54, 89.
6. Lichtenthaler, F. W. In Methods and Reagents for Green Chemistry: An Introduction; Tundo, P., Perosa, A., Zecchini, F., Eds.; John Wiley & Sons, Inc.: New Jork, 2007; p 23.
7. Boisen, A.; Christensen, T. B.; Fu, W.; Gorbanev, Y. Y.; Hansen, T. S.; Jensen, J. S.; Klitgaard, S. K.; Pedersen, S.; Riisager, A.; Ståhlberg, T.; Woodley, J. M. Chem. Eng. Res. Des. 2009, 1318.
8. www.chemistryinnovation.co.uk/FROPTOP.
9. Werpy, T. A.; Petersen, G. Top value added chemicals from biomass; U.S. Department of Energy (DOE), Golden, CO, DOE/GO-1020041992, 2004.
10. Lichtenthaler, F. W. Acc. Chem. Res. 2002, 35, 728.
11. Bicker, M.; Kaiser, D.; Ott, L.; Vogel, H. J. Supercrit. Fluids 2005, 36, 118.
12. Lichtenthaler, F. W.; Cuny, E.; Martin, D.; Rönninger, S. In Carbohydrates as Organic Raw Materials; Lichtenthaler, F. W., Ed.; VCH Publishers: Weinheim/NewYork, 1991; p 214.
13. Lichtenthaler, F. W.; Cuny, E.; Martin, D.; Rönninger, S. In Carbohydrates as Organic Raw Materials; Lichtenthaler, F. W., Ed.; VCH Publishers: Weinheim/NewYork, 1991; p 80.
14. Koch, H.; Pein, J. Polym. Bull. 1985, 13, 525.
15. Huber, G. W.; Chheda, J. N.; Barrett, C. J.; Dumesic, J. A. Science 2005, 308, 1446.
16. Metzger, J. O. Angew. Chem., Int. Ed. 2006, 45, 696-698; Production of Liquid Hydrocarbons from Biomass.
17. Chheda, J. N.; Dumesic, J. A. Catal. Today 2007, 123, 59.
18. Mehdi, H.; Fábos, V.; Tuba, R.; Bodor, A.; Mika, L. T.; Horváth, I. T. Top. Catal. 2008, 48, 49.
19. Kunkes, E. L.; Simonetti, D. A.; West, R. M.; Serrano-Ruiz, J. C.; Gärtner, C. A.; Dumesic, J. A. Science 2008, 322, 417.
20. Lewkowski, J. Arkivoc 2001, (i), 17.
21. Corma, A.; Iborea, S.; Velty, A. Chem. Rev. 2007, 107, 2411.
22. Chheda, J. N.; Huber, G. W.; Dumesic, J. A. Angew. Chem., Int. Ed. 2007, 46, 7164.
23. Moreau, C.; Belgacem, M. N.; Gandini, A. Top. Catal. 2004, 27, 11.
24. Kuster, B. M. F. Starch 1990, 42, 314.
25. Hu, S.; Zhang, Z.; Song, J.; Zhou, X.; Han, B. Green Chem. 2009, 11, 1746.
26. Yong, G.; Zhang, Y.; Ying, J. Y. Angew. Chem., Int. Ed, 2008, 47, 9345.
27. Sievers, C.; Musin, I.; Marzialetti, T.; Valenzuela-Olaite, M. B.; Agrawal, P. K.; Jones, C. W. ChemSusChem 2009, 2, 665.
28. Binder, J. B.; Raines, R. T. J. Am. Chem. Soc. 2009, 131, 1979.
29. Lifka, J.; Stark, A.; Ondraschka, B. Reactions in Ionic LiquidsDehydration of Carbohydrates to 5-Hydroxymethylfurfural; International Conference on Renewable Resources and Biorefinieries, Rotterdam, The Netherlands, June 2008.
30. Lima, S.; Neves, P.; Antunes, M. M.; Pillinger, M.; Ignatyev, N.; Valente, A. A. Appl. Catal. A 2009, 363, 93.
31. Zhao, H.; Holladay, J. E.; Brown, H.; Zhang, Z. C. Science 2007, 316, 1597.
32. Tong, X.; Li, Y. ChemSusChem 2010, 3, 350.
33. Zhang, Y.; Chan, J. Y. G. U. S. Patent 2009/0313889, 2009.
34. Zhao, H.; Holladay, J. E.; Zhang, Z. C. WO Patent 2008/019219 A1, 2008.
35. Qi, X.; Watanabe, M.; Aida, T. M.; Smith, R. L., Jr. Catal. Commun. 2008, 9, 2244.
36. Chheda, J. N.; Román-Leshkov, Y.; Dumesic, J. A. Green Chem. 2007, 9, 342.
37. Chan, J. Y. G.; Zhang, Y. ChemSusChem 2009, 2, 731.
38. Qi, X.; Watanabe, M.; Aida, T. M.; Smith, R. L., Jr. Green Chem. 2009, 11, 1327.
39. Qi, X.; Watanabe, M.; Aida, T. M.; Smith, R. L., Jr. ChemSusChem 2009, 2, 944.
40. Hu, S.; Zhang, Z.; Zhou, Y.; Han, B.; Fan, H.; Li, W.; Song, J.; Xie, Y. Green Chem. 2008, 10, 1280.
41. Bao, Q.; Qiao, K.; Tomida, D.; Yokoyama, C. Catal. Commun. 2008, 9, 1383.
42. Moreau, C.; Finiels, A.; Vanoye, L. J. Mol. Catal. A: Chem. 2006, 253, 165.
43. Lansalot-Matras, C.; Moreau, C. Catal. Commun. 2003, 4, 517.
44. Qi, X.; Watanabe, M.; Aida, T. M.; Smith, R. L., Jr. Green Chem. 2008, 10, 799.
45. Dumesic, J. A.; Román-Leshkov, Y.; Chheda, J. N. U. S. Patent 2008/ 0033188, 2008.
46. Román-Leshkov, Y.; Chheda, J. N.; Dumesic, J. A. Science 2006, 312, 1933.
47. Li, C.; Zhang, Z.; Zhao, Z. K. Tetrahedron Lett. 2009, 50, 5403.
48. Degirmenci, V.; Pidko, E. A.; Hensen, E. J. M. Dehydration of Glucose into HMF by Lewis Acidic Metal Chlorides: Development of a Heterogeneous MECLX/Ionic Liquid SBA-15 Catalyst; 21st North American Catalysis Society Meeting, San Francisco, CA, June, 2009.
49. Ståhlberg, T.; Sørensen, M. G.; Riisager, A. Green Chem. 2010, 12, 321.
50. Tyrlik, S. K.; Szerszeñ, D.; Olejnik, M.; Danikiewicz, W. Carbohydr. Res. 1999, 315, 268.
51. Frenzel, S.; Peters, S.; Rose, T.; Kunz, M. In Sustainable solutions for modern economies; Höfer, R., Ed.; RSC Publishing: Cambridge, 2009; p 264.
52. Chun, J.-A.; Lee, J.-W.; Yi, Y.-B.; Hong, S.-S.; Chung, Ch.-H. Korean J. Chem. Eng. 2010, 27, 930.
53. Vanoye, L.; Fanselow, M.; Holbrey, J. D.; Atkins, M. P.; Seddona, K. S. Green Chem. 2009, 11, 390.
54. Hu, S.; Zhang, Z.; Zhou, Y.; Song, J.; Fan, H.; Han, B. Green Chem. 2009, 11, 873.
55. Su, Y.; Brown, H. M.; Huang, X.; Zhou, X.-.D.; Amonette, J. E.; Zhang, Z. C. Appl. Catal. A 2009, 361, 117.
56. Zhang, Z.; Zhao, Z. K. Bioresour. Technol. 2010, 101, 1111.
57. Zhang, Z.; Zhao, Z. K. Carbohydr. Res. 2009, 344, 2069.
58. Li, B.; Filpponen, I.; Argyropoulos, D. S. Ind. Eng. Chem. Res. 2010, 49, 3126.
59. Sievers, C.; Valenzuela-Olarte, M. B.; Marzialetti, T.; Musin, I.; Agrawal, P. K.; Jones, C. W. Ind. Eng. Chem. Res. 2009, 48, 1277.
60. Robyt, J. F. Essentials of Carbohydrate Chemistry; Springer: New York, 1998.
61. Carlini, C.; Giuttari, M.; Galletti, A. M. R.; Sbrana, G.; Armaroli, T.; Busca, G. Appl. Catal. A 1999, 183, 295.
62. Armaroli, T.; Busca, G.; Carlini, C.; Giuttari, M.; Galletti, A. M. R.; Sbrana, G. J. Mol. Catal., A: Chem. 2000, 151, 233.
63. Carlini, C.; Patrono, P.; Galletti, A. M. R.; Sbrana, G. Appl. Catal., A 2004, 275, 111.
64. Ishida, H.; Seri, K. J. Mol. Catal. A: Chem. 1996, 112, L163.
65. Van Dam, H. E.; Kieboom, A. P. G.; Van Bekkum, H. Starch 1986, 38, 95.
66. Nakamura, Y.; Morikawa, S. Bull. Chem. Soc. Jpn. 1980, 53, 3705.
67. Rigal, L.; Goreichon, J. P.; Gaset, A.; Heughebaert, J. C. Biomass 1985, 7, 27.
68. Musau, R. M.; Munavu, R. M. Biomass 1987, 13, 67.
69. Bonner, W. A.; Roth, M. R. J. Am. Chem. Soc. 1959, 81, 5454.
70. Seri, K.; Inoue, Y.; Ishida, H. Chem. Lett. 2000, 22.
71. Smythe, B. M.; Moye, C. J. U.S. Patent 003290263, 1965.
72. Brown, D. W.; Floyd, A. J.; Kinsman, R. G.; Roshan-Ali, Y. J. Chem. Technol, Biotechnol. 1982, 32, 920.
73. West, R. M.; Liu, Z. Y.; Peter, M.; Gartner, C. A.; Dumesic, J. A. J. Mol. Catal. A: Chem. 2008, 296, 18.
74. Román-Leshkov, Y.; Barrett, C. J.; Liu, Z. Y.; Dumesic, J. A. Nature 2007, 447, 982.
75. Moreau, C.; Durand, R.; Razigade, S.; Duhamet, J.; Faugeras, P.; Rivalier, P.; Ros, P.; Avignon, G. Appl. Catal. A: Gen. 1996, 145, 211.
76. Seri, K.; Inoue, Y.; Ishida, H. Bull. Chem. Soc. Jpn. 2001, 74, 1145.
77. Asghari, F. S.; Yoshida, H. Carbohydr. Res. 2006, 341, 2379.
78. Asghari, F. S.; Yoshida, H. Ind. Eng. Chem. Res. 2006, 45, 2163.
79. Asghari, F. S.; Yoshida, H. Ind. Eng. Chem. Res. 2007, 46, 7703.
80. Li, Y.; Lu, X.; Yuan, L.; Liu, X. Biomass Bioenergy 2009, 33, 1182.
81. Antal, M. J., Jr.; Mok, W. S. L.; Richards, G. N. Carbohydr. Res. 1990, 199, 91.
82. Watanabe, M.; Aizawa, Y.; Iida, T.; Aida, T. M.; Levy, C.; Sue, K.; Inomata, H. Carbohydr. Res. 2005, 340, 1925.
83. Watanabe, M.; Aizawa, Y.; lida, T.; Nishimura, R.; Inomata, H. Appl. Catal. A 2005, 295, 150.
84. Bicker, M.; Endres, S.; Ott, L.; Vogel, H. J. Mol. Catal. A: Chem. 2005, 239, 151.
85. Bicker, M.; Hirth, J.; Vogel, H. Green Chem. 2003, 5, 280.
86. Lifka, J.; Ondraschka, B.; Stark, A. DE 102008009933-A1, 2009.
87. Zhang, Y.; Du, H.; Qian, X.; Chen, E. Y.-X. Energy Fuels 2010, 24, 2410.
88. Qi, X.; Watanabe, M.; Aida, T. M.; Smith, R. L., Jr. Ind. Eng. Chem. Res. 2008, 47, 9234.
89. Vlachos, D. G.; Caratzoulas, S. Chem. Eng. Sci. 2010, 65, 18.
90. Zakrzewska, M. E.; Bogel-Łukasik, E.; Bogel-Łukasik, R. Energy Fuels 2010, 24, 737.
91. Paulechka, Y. U.; Kabo, G. J.; Blokhin, A. V.; Vydrov, O. A.; Magee, J. W.; Frenkel, M. J. Chem. Eng. Data 2003, 48, 457.
92. Domañska, U.; Bogel-łukasik, R. J. Phys. Chem. B 2005, 109, 12124.
93. Ngo, H. L.; LeCompte, K.; Hargens, L.; McEwen, A. B. Thermochim. Acta 2000, 357, 97.
94. Pretti, C.; Chiappe, C.; Baldetti, I.; Branini, S.; Monni, G.; Intorre, L. Ecotoxicol Environ. Saf. 2009, 72, 1170.
95. http://www.il-eco.uft.uni-bre.men.de/.
96. Huddleston, J. G.; Visser, A. E.; Reichert, W. M.; Willauer, H. D.; Broker, G. A.; Rogers, R. D. Green Chem. 2001, 3, 156.
97. Reichardt, C. Green Chem. 2005, 7, 339.
98. Bogel-Łukasik, E.; Domañska, U. Green Chem. 2004, 6, 299.
99. Domañska, U.; Bogel-Łukasik, E.; Bogel-Łukasik, R. J. Phys. Chem. B 2003, 107, 1858.
100. Domañska, U.; Marciniak, A.; Bogel-Łukasik, R. In Ionic Liquids IIIA: Fundamentals, Progress, Challenges and Opportunities, Properties and Structure; Rogers, R. D., Seddon, K. R., Eds.; ACS Publications: Washington, DC, 2005; p 256.
101. Bogel-Łukasik, R.; Matkowska, D.; Zakrzewska, M. E.; BogelŁukasik, E.; Hofman, T. Fluid Phase Equilib. 2010, 295, 111.
102. Trindade, C. A. S.; Visak, Z. P.; Bogel-Łukasik, R.; Bogel-Łukasik, E.; Nunes da Ponte, M. Ind. Eng. Chem, Res. 2010, 49, 4850.
103. Roth, M. J. Chromatogr., A 2009, 1216, 1861.
104. Bogel-Łukasik, R.; Najdanovic-Visak, V.; Barreiros, S.; Nunes da Ponte, M. Ind. Eng. Chem. Res. 2008, 47, 4473.
105. Fayet, C.; Gelas, J. Carbohydr. Res. 1983, 122, 59.
106. Qian, X.; Nimlos, M. R.; Davis, M.; Johnson, D. K.; Himmel, M. E. Carbohydr. Res. 2005, 340, 2319.
107. Perez Locas, C.; Yaylayan, V. A. J. Agric. Food Chem. 2008, 56, 6717.
108. Defaye, J.; Gadelle, A. Carbohydr. Res. 1985, 136, 53.
109. Swatloski, R. P.; Spear, S. K.; Holbrey, J. D.; Rogers, R. D. J. Am. Chem. Soc. 2002, 124, 4974.
110. Bogel-Łukasik, R.; Lourenco, N. M. T.; Vidinha, P.; Gomes da Silva, M. D. R.; Afonso, C. A. M.; Nunes da Ponte, M.; Barreiros, S. Green Chem. 2008, 10, 243.
111. Bogel-Łukasik, R. Monatsh. Chem. 2007, 138, 1137.
112. Bogel-Łukasik, E.; Santos, S.; Bogel-Łukasik, R.; Nunes da Ponte, M. J. Supercrit Fluids 2010, 54, 210.
113. Bogel-Łukasik, E.; Gomes da Silva, M.; Nogueira, I. D.; BogelŁukasik, R.; Nunes da Ponte, M. Green Chem. 2009, 11, 1847.
114. Fan, X.; Qu, Y.; Wang, Y.; Zhang, X.; Wang, J. Tetrahedron Lett. 2010, 51, 2123.
115. Palma, M.; Taylor, L. T. J. Agric. Food Chem. 2001, 49, 628.
116. Minutes of the Biochemical platform workshop; EERA Workshop on Next Generation Biofuels for Transport, Brussels, Belgium, April, 2010.
117. Domañska, U.; Bogel-Łukasik, R. Fluid Phase Equilib. 2005, 233, 220.
118. Domañska, U.; Bogel-Łukasik, E.; Bogel-Łukasik, R. Chem.-Eur. J. 2003, 9, 3033.
119. Bogel-Łukasik, R.; Matkowska, D.; Bogel-Łukasik, E.; Hofman, T. Fluid Phase Equilib. 2010, 295, 168.
120. Earle, M. J.; Frohlich, U.; Huq, S.; Katdare, S.; Łukasik, R. M.; Bogel, E.; Plechkova, N. V. WO Patent 2006/072785 A2, 2006.