Insights into the interplay of lewis and Brønsted acid catalysts in glucose and fructose conversion to 5-(hydroxymethyl)furfural and levulinic acid in aqueous media

Journal of the American Chemical Society

Volumn 135, Issue 10, 2013, Pages 3997-4006

  Choudhary, Vinit ^a   Mushrif, Samir H ^b   Ho, Christopher ^a   Anderko, Andrzej ^c   Nikolakis, Vladimiros ^a   Marinkovic, Nebojsa S ^a   Frenkel, Anatoly I ^d   Sandler, Stanley I ^a   Vlachos, Dionisios G ^a  

^a UNIVERSITY OF DELAWARE   (United States)

^b Nanyang Technological University   (Singapore)

^c OLI SYSTEMS INC   (United States)

^d YESHIVA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CAR-PARRINELLO MOLECULAR DYNAMICS SIMULATIONS; COMPLEX INTERACTION; COORDINATION SPHERE; EQUILIBRIUM CONCENTRATION; EXTENDED X-RAY ABSORPTION FINE STRUCTURES; GLUCOSE ISOMERIZATION; LEWIS ACID CATALYSTS; MODERATE TEMPERATURE;

ALDEHYDES; CATALYSTS; EXTENDED X RAY ABSORPTION FINE STRUCTURE SPECTROSCOPY; FRUCTOSE; FURFURAL; GLUCOSE; HYDROLYSIS; ISOMERIZATION; ISOMERS; METHANOL; MOLECULAR DYNAMICS; MOLECULES; ORGANIC ACIDS;

CHROMIUM COMPOUNDS;

5 (HYDROXYMETHYL)FURFURAL; BRONSTED ACID; FRUCTOSE; FURFURAL; GLUCOSE; LEVULINIC ACID; LEWIS ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTAL STRUCTURE; ISOMERIZATION; KINETICS; MOLECULAR DYNAMICS; SPECIES DIFFERENTIATION; X RAY ABSORPTION SPECTROSCOPY;

ACIDS; CATALYSIS; FRUCTOSE; FURALDEHYDE; GLUCOSE; LEVULINIC ACIDS; MOLECULAR DYNAMICS SIMULATION; WATER;

EID: 84875001637     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3122763     Document Type: Article

References (76)

1. Schmidt, L. D.; Dauenhauer, P. J. Nature 2007, 447, 914
2. Alonso, D. M.; Bond, J. Q.; Dumesic, J. A. Green Chem. 2010, 12, 1493
3. Climent, M. J.; Corma, A.; Iborra, S. Green Chem. 2011, 13, 520
4. Vlachos, D. G.; Caratzoulas, S. Chem. Eng. Sci. 2010, 65, 18
5. Stocker, M. Angew. Chem., Int. Ed. 2008, 47, 9200
6. Lewkowski, J. Arkivoc 2001, 2
7. James, O. O.; Maity, S.; Usman, L. A.; Ajanaku, K. O.; Ajani, O. O.; Siyanbola, T. O.; Sahu, S.; Chaubey, R. Energy Environ. Sci. 2010, 3, 1833
8. Kuster, B. F. M. Starch-Starke 1990, 42, 314
9. Zakrzewska, M. E.; Bogel-Lukasik, E.; Bogel-Lukasik, R. Chem. Rev. 2011, 111, 397
10. Rackemann, D. W.; Doherty, W. O. S. Biofuels, Bioprod. Biorefin. 2011, 5, 198
11. Peng, L.; Lin, L.; Li, H. Prog. Chem. 2012, 24, 801
12. Serrano-Ruiz, J. C.; West, R. M.; Durnesic, J. A. In Annual Review of Chemical and Biomolecular Engineering; Annual Reviews: Palo Alto, CA, Prausnitz, J. M.; Doherty, M. F.; Segalman, M. A., Eds.; 2010; Vol. 1, p 79.
13. Vandam, H. E.; Kieboom, A. P. G.; Vanbekkum, H. Starch-Starke 1986, 38, 95
14. Roman-Leshkov, Y.; Chheda, J. N.; Dumesic, J. A. Science 2006, 312, 1933
15. Rigal, L.; Gaset, A.; Gorrichon, J. P. Ind. Eng. Chem. Prod. Res. Dev. 1981, 20, 719
16. Chuntanapum, A.; Yong, T. L. K.; Miyake, S.; Matsumura, Y. Ind. Eng. Chem. Res. 2008, 47, 2956
17. Bicker, M.; Hirth, J.; Vogel, H. Green Chem. 2003, 5, 280
18. Brown, D. W.; Floyd, A. J.; Kinsman, R. G.; Roshanali, Y. J. Chem. Technol. Biotechnol. 1982, 32, 920
19. Moreau, C.; Durand, R.; Razigade, S.; Duhamet, J.; Faugeras, P.; Rivalier, P.; Ros, P.; Avignon, G. Appl. Catal., A 1996, 145, 211
20. Kruger, J. S.; Nikolakis, V.; Vlachos, D. G. Curr. Opin. Chem. Eng. 2012, 1, 312
21. Choudhary, V.; Burnett, R. I.; Vlachos, D. G.; Sandler, S. I. J. Phys. Chem. C 2012, 116, 5116
22. Zhao, H.; Holladay, J. E.; Brown, H.; Zhang, Z. C. Science 2007, 316, 1597
23. Mascal, M.; Nikitin, E. B. Chemsuschem 2009, 2, 423
24. Lew, C. M.; Rajabbeigi, N.; Tsapatsis, M. Ind. Eng. Chem. Res. 2012, 51, 5364
25. Boisen, A.; Christensen, T. B.; Fu, W.; Gorbanev, Y. Y.; Hansen, T. S.; Jensen, J. S.; Klitgaard, S. K.; Pedersen, S.; Riisager, A.; Stahlberg, T.; Woodley, J. M. Chem. Eng. Res. Des. 2009, 87, 1318
26. Chheda, J. N.; Roman-Leshkov, Y.; Dumesic, J. A. Green Chem. 2007, 9, 342
27. Asghari, F. S.; Yoshida, H. Ind. Eng. Chem. Res. 2006, 45, 2163
28. Bicker, M.; Kaiser, D.; Ott, L.; Vogel, H. J. Supercrit. Fluids 2005, 36, 118
29. Shimizu, K.; Uozumi, R.; Satsuma, A. Catal. Commun. 2009, 10, 1849
30. Qi, X. H.; Watanabe, M.; Aida, T. M.; Smith, R. L. Ind. Eng. Chem. Res. 2008, 47, 9234
31. Qi, X. H.; Watanabe, M.; Aida, T. M.; Smith, R. L. Catal. Commun. 2009, 10, 1771
32. Wang, F. F.; Shi, A. W.; Qin, X. X.; Liu, C. L.; Dong, W. S. Carbohydr. Res. 2011, 346, 982
33. Zhang, Z. H.; Liu, B.; Zhao, Z. B. Carbohydr. Polym. 2012, 88, 891
34. Shi, C.; Zhao, Y.; Xin, J.; Wang, J.; Lu, X.; Zhang, X.; Zhang, S. Chem. Commun. 2012, 48, 4103
35. Jadhav, A. H.; Kim, H.; Hwang, I. T. Catal. Commun. 2012, 21, 96
36. Torres, A. I.; Tsapatsis, M.; Daoutidis, P. Comput. Chem. Eng. 2012, 42, 130
37. Hu, S.; Zhang, Z.; Song, J.; Zhou, Y.; Han, B. Green Chem. 2009, 11, 1746
38. Yong, G.; Zhang, Y. G.; Ying, J. Y. Angew. Chem., Int. Ed. 2008, 47, 9345
39. Sievers, C.; Musin, I.; Marzialetti, T.; Olarte, M. B. V.; Agrawal, P. K.; Jones, C. W. Chemsuschem 2009, 2, 665
40. Binder, J. B.; Raines, R. T. J. Am. Chem. Soc. 2009, 131, 1979
41. Ohara, M.; Takagaki, A.; Nishimura, S.; Ebitani, K. Appl. Catal., A 2010, 383, 149
42. Rasrendra, C.; Soetedjo, J.; Makertihartha, I.; Adisasmito, S.; Heeres, H. Top. Catal. 2012, 55, 543
43. Dutta, S.; De, S.; Alam, M. I.; Abu-Omar, M. M.; Saha, B. J. Catal. 2012, 288, 8
44. Moliner, M.; Roman-Leshkov, Y.; Davis, M. E. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 6164
45. Roman-Leshkov, Y.; Moliner, M.; Labinger, J. A.; Davis, M. E. Angew. Chem., Int. Ed. 2010, 49, 8954
46. Choudhary, V.; Pinar, A. B.; Sandler, S. I.; Vlachos, D. G.; Lobo, R. F. ACS Catal. 2011, 1, 1724
47. Nikolla, E. N. E.; Roman-Leshkov, Y.; Moliner, M.; Davis, M. E. ACS Catal. 2011, 1, 408
48. Rasrendra, C. B.; Makertihartha, I. G. B. N.; Adisasmito, S.; Heeres, H. J. Top. Catal. 2010, 53, 1241
49. Efremov, A.; Pervyshina, G.; Kuznetsov, B. Chem. Nat. Compd. 1998, 34, 182
50. Peng, L.; Lin, L.; Zhang, J.; Zhuang, J.; Zhang, B.; Gong, Y. Molecules 2010, 15, 5258
51. Tyrlik, S. K.; Szerszen, D.; Kurzak, B.; Bal, K. Starch-Starke 1995, 47, 171
52. Tyrlik, S. K.; Szerszen, D.; Olejnik, M.; Danikiewicz, W. J. Mol. Catal. A: Chem. 1996, 106, 223
53. De, S.; Dutta, S.; Saha, B. Green Chem. 2011, 13, 2859
54. Pagan-Torres, Y. J.; Wang, T.; Gallo, J. M. R.; Shanks, B. H.; Dumesic, J. A. ACS Catal. 2012, 2, 930
55. Newville, M. J. Synchrotron Radiat. 2001, 8, 322
56. Ravel, B.; Newville, M. J. Synchrotron Radiat. 2005, 12, 537
57. Zabinsky, S. I.; Rehr, J. J.; Ankudinov, A.; Albers, R. C.; Eller, M. J. Phys. Rev. B 1995, 52, 2995
58. Wang, P. M.; Anderko, A.; Young, R. D. Fluid Phase Equilib. 2002, 203, 141
59. Wang, P.; Springer, R. D.; Anderko, A.; Young, R. D. Fluid Phase Equilib. 2004, 222, 11
60. Wang, P.; Anderko, A.; Springer, R. D.; Young, R. D. J. Mol. Liq. 2006, 125, 37
61. Kosinski, J. J.; Wang, P.; Springer, R. D.; Anderko, A. Fluid Phase Equilib. 2007, 256, 34
62. Laio, A.; Gervasio, F. L. Rep. Prog. Phys. 2008, 71
63. Patil, S. K. R.; Heltzel, J.; Lund, C. R. F. Energy Fuels 2012, 26, 5281
64. Horvat, J.; Klaic, B.; Metelko, B.; Sunjic, V. Croat. Chem. Acta 1986, 59, 429
65. Choudhary, V.; Sandler, S. I.; Vlachos, D. G. ACS Catal. 2012, 2, 2022
66. Weingarten, R.; Tompsett, G. A.; Conner, W. C., Jr.; Huber, G. W. J. Catal. 2011, 279, 174
67. Nikbin, N.; Caratzoulas, S.; Vlachos, D. G. Chemcatchem 2012, 4, 504
68. Asghari, F. S.; Yoshida, H. Ind. Eng. Chem. Res. 2007, 46, 7703
69. Roman-Leshkov, Y.; Dumesic, J. A. Top. Catal. 2009, 52, 297
70. Bailar, J. C.; Eméleus, H. J.; Nyholm, R; Trotman-Dickenson, A. F., Eds. Comprehensive Inorganic Chemistry; Pergamon Press: Oxford, 1973; Vol. 3.
71. Pechova, A.; Pavlata, L. Vet. Med. (Prague, Czech Repub.) 2007, 52, 1
72. Bermejo-Deval, R.; Assary, R. S.; Nikolla, E.; Moliner, M.; Roman-Leshkov, Y.; Hwang, S.-J.; Palsdottir, A.; Silverman, D.; Lobo, R. F.; Curtiss, L. A.; Davis, M. E. Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 9727
73. Choudhary, V.; Caratzoulas, S.; Vlachos, D. G. Carbohydr. Res. 2013, 368, 89
74. Boronat, M.; Concepcion, P.; Corma, A.; Renz, M.; Valencia, S. J. Catal. 2005, 234, 111
75. Tai, Z.; Zhang, J.; Wang, A.; Zheng, M.; Zhang, T. Chem. Commun. 2012, 48, 7052
76. Bennett, B. C.; Yeager, M. Structure 2010, 18, 657