From Lignocellulosic Biomass to Furans via 5-Acetoxymethylfurfural as an Alternative to 5-Hydroxymethylfurfural

ChemSusChem

Volumn 8, Issue 7, 2015, Pages 1179-1188

  Kang, Eun Sil ^a   Hong, Yeon Woo ^a   Chae, Da Won ^a   Kim, Bora ^b   Kim, Baekjin ^b,c   Kim, Yong Jin ^b,c   Cho, Jin Ku ^b,c   Kim, Young Gyu ^a  

^a Seoul National University   (South Korea)

^b Korea Institute of Industrial Technology   (South Korea)

^c University of Science and Technology (UST)   (South Korea)

Author keywords

biomass; furan derivatives; reaction mechanisms; renewable resources; synthesis design

Indexed keywords

AROMATIC COMPOUNDS; CHEMICAL STABILITY; ORGANIC POLLUTANTS; SYNTHESIS (CHEMICAL);

2 ,5-FURANDICARBOXYLIC ACIDS; 5 HYDROXYMETHYL FURFURALS; FURAN DERIVATIVES; ISOLATION AND PURIFICATION; LIGNOCELLULOSIC BIOMASS; REACTION MECHANISM; RENEWABLE RESOURCE; SYNTHESIS DESIGN;

BIOMASS;

5-ACETOXYMETHYLFURFURAL; 5-HYDROXYMETHYLFURFURAL; ACETIC ACID DERIVATIVE; FURFURAL; LIGNIN; LIGNOCELLULOSE;

ANALOGS AND DERIVATIVES; BIOMASS; CHEMICAL PHENOMENA; CHEMISTRY; ISOLATION AND PURIFICATION; SYNTHESIS;

ACETATES; BIOMASS; FURALDEHYDE; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LIGNIN;

EID: 84926649070     PISSN: 18645631     EISSN: 1864564X     Source Type: Journal    
DOI: 10.1002/cssc.201403252     Document Type: Article

References (84)

1. A. J. Ragauskas, C. K. Williams, B. H. Davison, G. Britovsek, J. Cairney, C. A. Eckert, W. J. Frederick, J. P. Hallett, D. J. Leak, C. L. Liotta, J. R. Mielenz, R. Murphy, R. Templer, T. Tschaplinski, Science 2006, 311, 484-489.
2. L. Petrus, M. A. Noordermeer, Green Chem. 2006, 8, 861-867;
3. J. N. Chheda, G. W. Huber, J. A. Dumesic, Angew. Chem. Int. Ed. 2007, 46, 7164-7183;
4. Angew. Chem. 2007, 119, 7298-7318;
5. R. Rinaldi, F. Schuth, ChemSusChem 2009, 2, 1096-1107.
6. T. Werpy, G. Petersen, Top Value Added Chemicals from Biomass, Vol. I: Results of Screening for Potential Candidates from Sugars and Synthesis Gas, NREL/TP-510-35523, National Renewable Energy Laboratory, Golden, CO, 2004;
7. Y. Román-Leshkov, C. J. Barrett, Z. Y. Liu, J. A. Dumesic, Nature 2007, 447, 982-985.
8. M. E. Zakrzewska, E. Bogel-Łukasik, R. Bogel-Łukasik, Chem. Rev. 2011, 111, 397-417.
9. H. Zhao, J. E. Holladay, H. Brown, Z. C. Zhang, Science 2007, 316, 1597-1600;
10. J. N. Chheda, Y. Román-Leshkov, J. A. Dumesic, Green Chem. 2007, 9, 342-350;
11. J. B. Binder, R. T. Raines, J. Am. Chem. Soc. 2009, 131, 1979-1985;
12. M. Moliner, Y. Román-Leshkov, M. E. Davis, Proc. Natl. Acad. Sci. USA 2010, 107, 6164-6168;
13. B. Kim, J. Jeong, D. Lee, S. Kim, H. J. Yoon, Y. S. Lee, J. K. Cho, Green Chem. 2011, 13, 1503-1506;
14. F. Yang, Q. Liu, X. Bai, Y. Du, Bioresour. Technol. 2011, 102, 3424-3429;
15. V. Choudhary, S. H. Mushrif, C. Ho, A. Anderko, V. Nikolakis, N. S. Marinkovic, A. I. Frenkel, S. I. Sandler, D. G. Vlachos, J. Am. Chem. Soc. 2013, 135, 3997-4006.
16. J. Lewkowski, ARKIVOC 2001, 1, 17-54;
17. 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.
18. B. F. M. Kuster, H. S. van der Baan, Carbohydr. Res. 1977, 54, 165-176;
19. B. F. M. Kuster, Carbohydr. Res. 1977, 54, 177-183;
20. B. F. M. Kuster, H. M. G. Temmink, Carbohydr. Res. 1977, 54, 185-191;
21. H. E. Van Dam, A. P. G. Kieboom, H. Van Bekkum, Starch/Stärke 1986, 38, 95-101;
22. C. Moreau, R. Durand, S. Razigade, J. Duhamet, P. Faugeras, P. Rivalier, P. Ros, G. Avignon, Appl. Catal. A 1996, 145, 211-224;
23. T. S. Hansen, J. M. Woodley, A. Riisager, Carbohydr. Res. 2009, 344, 2568-2572;
24. J. Zhang, E. Weitz, ACS Catal. 2012, 2, 1211-1218.
25. S. K. R. Patil, C. R. F. Lund, Energy Fuels 2011, 25, 4745-4755.
26. M. Mascal, E. B. Nikitin, ChemSusChem 2009, 2, 423-426.
27. M. Mascal, E. B. Nikitin, Angew. Chem. Int. Ed. 2008, 47, 7924-7926;
28. Angew. Chem. 2008, 120, 8042-8044;
29. M. Mascal, E. B. Nikitin, ChemSusChem 2009, 2, 859-861.
30. F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Part A: Structure and Mechanisms, 5th ed., Springer, New York, 2007, Chap. 4.
31. M. Mascal, E. B. Nikitin, Green Chem. 2010, 12, 370-373.
32. B. F. M. Kuster, Starch/Stärke 1990, 42, 314-321.
33. G. J. M. Gruter, F. Dautzenberg, (Avantium International B.V.), WO 2007/104514, 2007;
34. G. J. M. Gruter, F. Dautzenberg, J. Purmova, (Avantium International B.V.) WO 2007/104515, 2007;
35. G. J. M. Gruter, L. E. Manzer, A. S. V. De Sousa Dias, F. Dautzenberg, J. Purmova, (Furanix Technologies B.V.) WO 2009/030512, 2009;
36. G. J. M. Gruter, F. Dautzenberg, (Furanix Technologies B.V.), US 2009/131690, 2009;
37. G. J. M. Gruter, L. E. Manzer, (Furanix Technologies B.V.), US 2010/0058650, 2010;
38. G. J. M. Gruter, (Furanix Technologies B.V.) US 2010/0083565, 201;
39. G. J. M. Gruter, L. E. Manzer, (Furanix Technologies B.V.), US 2010/0218415, 2010;
40. G. J. M. Gruter, (Furanix Technologies B.V.), US 2010/0218416, 2010.
41. C. Janzowski, V. Glaab, E. Samimi, J. Schlatter, G. Eisenbrand, Food Chem. Toxicol. 2000, 38, 801.
42. J. K. Kim, S. W. Kim, K. O. Oh, S. Y. Ko, J. Y. Kim, B. E. Lee, B. T. Kim, Y. S. Lee, Y. K. Min, N. K. Park, (Oscotec Inc.; Korea research institute of chemical technology), WO 2004/037804, 2004;
43. J. K. Kim, S. W. Kim, K. O. Oh, J. Y. Kim, B. E. Lee, B. T. Kim, Y. S. Lee, Y. K. Min, N. K. Park, US 2008/0221205, 2008;
44. J. B. Zheng, J. Li, R. Wen, J. Y. Li, H. L. Dai, Q. Shen, CN 101775008 A 20100714, 2010;
45. H. L. Dai, Q. Shen, J. B. Zheng, J. Y. Li, R. Wen, J. Li, Lett. Org. Chem. 2011, 8, 526-530.
46. T. Eggeman, D. Verser, Appl. Biochem. Biotechnol. 2006, 129-132, 361-381.
47. Q. Li, D. Wang, Y. Wu, W. L. Li, Y. J. Zhang, J. M. Xing, Z. G. Su, Sep. Purif. Technol. 2010, 72, 294-300;
48. F. L. Zhou, C. W. Wang, J. Wei, J. Membr. Sci. 2013, 429, 243-251.
49. A. S. Kertes, C. King, Biotechnol. Bioeng. 1986, 28, 269-282;
50. E. Alkaya, S. Kaptan, L. Ozkan, S. Uludag-Demirer, G. N. Demirer, Chemosphere 2009, 77, 1137-1142.
51. J. Dakka, Y. Sasson, K. Khawaled, G. Bram, A. Loupy, J. Chem. Soc. Chem. Commun. 1991, 853-854.
52. G. D. Yadav, M. M. Sharma, Ind. Eng. Chem. Process Des. Dev. 1981, 20, 385-390.
53. M. Brasholz, K. von Känel, C. H. Hornung, S. Saubern, J. Tsanaktsidis, Green Chem. 2011, 13, 1114-1117.
54. P. H. Toy, Y. Lam, Solid-Phase Organic Synthesis: Concepts, Strategies, and Applications, 1st ed., Wiley, Chichester, 2012, Chap. 3.
55. The Merck Index, 12th ed. (Eds.:, S. Budavari, M.J. O'Neil, A. Smith, P.E. Heckelman, J.F. Kinneary,), Merck, Rahway, 1996, p. 830;
56. Solubility Information, Sigma-Aldrich, available from http://www.sigmaaldrich.com/united-kingdom/technical-services/solubility.html (accessed December 2014).
57. R. E. Jones, H. B. Lange, (Merck & Co, Inc.), US 2994645, 1961;
58. R. H. Hunter, (Atlas Chemical Industries, Inc.), US 3201331, 1965.
59. D. Reichert, M. Sarich, F. Merz, (Evonik Degussa GmbH), EP 1958944, 2008.
60. G. Yi, S. P. Teong, X. Li, Y. Zhang, ChemSusChem 2014, 7, 2131-2135.
61. L. Lai, Y. Zhang, ChemSusChem 2011, 4, 1745-1748;
62. J. Jeong, C. A. Antonyraj, S. Shin, S. Kim, B. Kim, K. Y. Lee, J. K. Cho, J. Ind. Eng. Chem. 2013, 19, 1106-1111;
63. B. Kim, J. Jeong, D. Moon, C. A. Antonyraj, Y. Kim, B. Kim, S. Shin, S. Kim, K. Y. Lee, J. K. Cho, Ind. Eng. Chem. Res. 2014, 53, 4633-4641.
64. A. Gandini, M. N. Belgacem, Prog. Polym. Sci. 1997, 22, 1203-1379;
65. C. Moreau, M. N. Belgacem, A. Gandini, Top. Catal. 2004, 27, 11-30;
66. A. Gandini, Macromolecules 2008, 41, 9491-9504.
67. E. I. Leupold, M. Wiesner, M. Schlingmann, K. Kapp, (Hoechst AG), EP 0356703, 1993;
68. K. Yutaka, T. Miura, S. Eritate, T. Komuro, US 2011/0092720, 2011;
69. Y. Y. Gorbanev, S. K. Klitgaard, J. M. Woodley, C. H. Christensen, A. Riisager, ChemSusChem 2009, 2, 672-675;
70. N. K. Gupta, S. Nishimura, A. Takagaki, K. Ebitani, Green Chem. 2011, 13, 824-827;
71. S. E. Davis, L. R. Houk, E. C. Tamargo, A. K. Datye, R. J. Davis, Catal. Today 2011, 160, 55-60.
72. A. J. Sanborn, E. J. Howard, US 2009/156841, 2009;
73. A. J. Sanborn, (Archer Daniels Midland Company), WO 2010/132740, 2010;
74. C. M. Diego, M. A. Dam, G. J. M. Gruter, (Furanix Technologies B.V.), WO 2011/43661, 2011;
75. M. E. Janka, D. M. Lange, M. C. Morrow, B. R. Bowers, K. R. Parker, A. Shaikh, L. R. Partin, J. C. Jenkins, P. Moody, T. E. Shanks, C. E. Sumner, Jr., (Eastman Chemical Company), US 2012/302768, 2012;
76. M. E. Janka, D. M. Lange, M. C. Morrow, B. R. Bowers, K. R. Parker, A. Shaikh, L. R. Partin, C. E. Sumner Jr., (Eastman Chemical Company), US 2012/302770, 2012;
77. M. E. Janka, D. M. Lange, M. C. Morrow, B. R. Bowers, K. R. Parker, A. Shaikh, L. R. Partin, C. E. Sumner, Jr., (Eastman Chemical Company), US 2012/302771, 2012;
78. A. Shaikh, M. E. Janka, D. M. Lange, M. C. Morrow, B. R. Bowers, K. R. Parker, L. R. Partin, J. C. Jenkins. Moody, T. E. Shanks, C. E. Sumner, Jr., (Eastman Chemical Company), US 2012/302772, 2012;
79. M. E. Janka, D. M. Lange, M. C. Morrow, B. R. Bowers, K. R. Parker, A. Shaikh, L. R. Partin, J. C. Jenkins, (Eastman Chemical Company), US 2012/302773, 2012;
80. M. E. Janka, K. R. Parker, A. Shaikh, L. R. Partin, (Eastman Chemical Company), US 2014/0066639, 2014
81. R. Frank, R. Jostock, H. Schick, F. Theil, O. Groeger, R. Kudick, H. Sonnenschein, B. Henkel, (Gruenenthal GmbH), WO 2006/122772, 2006.
82. K. Heyns, H. Paulsen, Angew. Chem. 1957, 69, 600-608.
83. E. S. Kang, D. W. Chae, B. Kim, Y. G. Kim, J. Ind. Eng. Chem. 2012, 18, 174-177, and references therein;
84. S. Subbiah, S. P. Simeonov, J. M. S. S. Esperança, L. P. N. Rebelo, C. A. M. Afonso, Green Chem. 2013, 15, 2849-2853.