The Alpha-Bet(a) of Salty Glucose Pyrolysis: Computational Investigations Reveal Carbohydrate Pyrolysis Catalytic Action by Sodium Ions

ACS Catalysis

Volumn 5, Issue 1, 2015, Pages 192-202

  Mayes, Heather B ^a   Nolte, Michael W ^b   Beckham, Gregg T ^c   Shanks, Brent H ^b,d   Broadbelt, Linda J ^a  

^a Northwestern University   (United States)

^b Iowa State University of Science and Technology   (United States)

^c NATIONAL RENEWABLE ENERGY LABORATORY   (United States)

^d IOWA STATE UNIVERSITY   (United States)

Author keywords

5 HMF; biofuels; biomass; cellulose; dehydration; inorganic salts; kinetics; transition state stabilization

Indexed keywords

ALKALINITY; BIOFUELS; BIOMASS; CELLULOSE; CHEMICAL REACTIONS; COMPUTATION THEORY; COST EFFECTIVENESS; DEHYDRATION; DENSITY FUNCTIONAL THEORY; ELECTRONIC STRUCTURE; ENZYME KINETICS; GLUCOSE; METAL IONS; PYROLYSIS; REACTION KINETICS; SALTS;

5 HYDROXYMETHYL FURFURALS; 5-HMF; CHEMICAL TRANSFORMATIONS; COMPUTATIONAL INVESTIGATION; INORGANIC SALTS; REACTION RATE COEFFICIENTS; THERMAL DECOMPOSITION REACTION; TRANSITION STATE STABILIZATION;

CRACKING (CHEMICAL);

EID: 84927761754     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs501125n     Document Type: Article

References (82)

1. Huber, G. W.; Iborra, S.; Corma, A. Chem. Rev. 2006, 106, 4044 - 4098 10.1021/cr068360d
2. Ragauskas, A. J.; Williams, C. K.; Davison, B. H.; Britovsek, G.; Cairney, J.; Eckert, C. A.; Frederick, W. J., Jr.; Hallett, J. P.; Leak, D. J.; Liotta, C. L.; Mielenz, J. R.; Murphy, R.; Templer, R.; Tschaplinski, T. Science 2006, 311, 484 - 489 10.1126/science.1114736
3. Pauly, M.; Keegstra, K. Plant J. 2008, 54, 559 - 568 10.1111/j.1365-313X.2008.03463.x
4. Alonso, D. M.; Bond, J. Q.; Dumesic, J. A. Green Chem. 2010, 12, 1493 - 1513 10.1039/c004654j
5. Chundawat, S. P.; Beckham, G. T.; Himmel, M. E.; Dale, B. E. Annu. Rev. Chem. Biomol. Eng. 2011, 2, 121 - 145 10.1146/annurev-chembioeng-061010-114205
6. Sheldon, R. A. Green Chem. 2014, 16, 950 - 963 10.1039/c3gc41935e
7. Evans, R. J.; Milne, T. A. Energy Fuels 1987, 1, 311 - 319 10.1021/ef00004a001
8. Bridgwater, A. V.; Peacocke, G. V. C. Renew. Sust. Energy Rev. 2000, 4, 1 - 73 10.1016/S1364-0321(99)00007-6
9. Serrano-Ruiz, J. C.; Dumesic, J. A. Energy Environ. Sci. 2011, 4, 83 - 99 10.1039/c0ee00436g
10. Czernik, S.; Bridgwater, A. Energy Fuels 2004, 18, 590 - 598 10.1021/ef034067u
11. Branca, C.; Di Blasi, C.; Elefante, R. Energy Fuels 2006, 20, 2253 - 2261 10.1021/ef0601059
12. Mohan, D.; Pittman, C. U.; Steele, P. H. Energy Fuels 2006, 20, 848 - 889 10.1021/ef0502397
13. Ringer, M.; Putsche, V.; Scahill, J. Large-Scale Pyrolysis Oil Production: A Technology Assessment and Economic Analysis; National Renewable Energy Laboratory: Golden, CO, 2006.
14. Di Blasi, C. Prog. Energy Combust. Sci. 2008, 34, 47 - 90 10.1016/j.pecs.2006.12.001
15. Briodo, A.; Nelson, M. A. Combust. Flame 1975, 24, 263 - 268 10.1016/0010-2180(75)90156-X
16. Bradbury, A. G. W.; Sakai, Y.; Shafizadeh, F. J. Appl. Polym. Sci. 1979, 23, 3271 - 3280 10.1002/app.1979.070231112
17. Ranzi, E.; Cuoci, A.; Faravelli, T.; Frassoldati, A.; Migliavacca, G.; Pierucci, S.; Sommariva, S. Energy Fuels 2008, 22, 4292 - 4300 10.1021/ef800551t
18. Authier, O.; Ferrer, M.; Khalfi, A.-E.; Lédé, J. Int. J. Chem. Reactor Eng. 2010, 8, A78 10.2202/1542-6580.2115
19. Lin, T.; Goos, E.; Riedel, U. Fuel Process. Technol. 2013, 115, 246 - 253 10.1016/j.fuproc.2013.03.048
20. Patwardhan, P. R.; Satrio, J. A.; Brown, R. C.; Shanks, B. H. J. Anal. Appl. Pyrolysis 2009, 86, 323 - 330 10.1016/j.jaap.2009.08.007
21. Patwardhan, P. R.; Dalluge, D. L.; Shanks, B. H.; Brown, R. C. Bioresour. Technol. 2011, 102, 5265 - 5269 10.1016/j.biortech.2011.02.018
22. Paulsen, A. D.; Mettler, M. S.; Dauenhauer, P. J. Energy Fuels 2013, 27, 2126 - 2134 10.1021/ef302117j
23. Paine, J. B., III; Pithawalla, Y. B.; Naworal, J. D. J. Anal. Appl. Pyrolysis 2008, 82, 10 - 41 10.1016/j.jaap.2008.01.002
24. Paine, J. B., III; Pithawalla, Y. B.; Naworal, J. D. J. Anal. Appl. Pyrolysis 2008, 82, 42 - 69 10.1016/j.jaap.2007.12.005
25. Paine, J. B., III; Pithawalla, Y. B.; Naworal, J. D. J. Anal. Appl. Pyrolysis 2008, 83, 37 - 63 10.1016/j.jaap.2008.05.008
26. Mayes, H. B.; Broadbelt, L. J. J. Phys. Chem. A 2012, 116, 7098 - 7106 10.1021/jp300405x
27. Seshadri, V.; Westmoreland, P. R. J. Phys. Chem. A 2012, 116, 11997 - 12013 10.1021/jp3085099
28. Mayes, H. B.; Broadbelt, L. J.; Beckham, G. T. J. Am. Chem. Soc. 2014, 136, 1008 - 1022 10.1021/ja410264d
29. Vinu, R.; Broadbelt, L. J. Energy Environ. Sci. 2012, 5, 9808 - 9826 10.1039/c2ee22784c
30. Zhou, X.; Nolte, M. W.; Mayes, H. B.; Shanks, B. H.; Broadbelt, L. J. Ind. Eng. Chem. Res. 2014, 53, 13274 - 13289 10.1021/ie502259w
31. Zhou, X.; Nolte, M. W.; Shanks, B. H.; Broadbelt, L. J. Ind. Eng. Chem. Res. 2014, 53, 13290 - 13301 10.1021/ie502260q
32. Shafizadeh, F. J. Anal. Appl. Pyrolysis 1982, 3, 283 - 305 10.1016/0165-2370(82)80017-X
33. Sekiguchi, Y.; Shafizadeh, F. J. Appl. Polym. Sci. 1984, 29, 1267 - 1286 10.1002/app.1984.070290421
34. Evans, R. J.; Milne, T. A. Energy Fuels 1987, 1, 123 - 137 10.1021/ef00002a001
35. Richards, G. N. J. Anal. Appl. Pyrolysis 1987, 10, 251 - 255 10.1016/0165-2370(87)80006-2
36. Várhegyi, G.; Antal, M. J., Jr.; Szekely, T.; Till, F.; Jakab, E. Energy Fuels 1988, 2, 267 - 272 10.1021/ef00009a007
37. Piskorz, J.; Radlein, D. S. A. G.; Scott, D. S.; Czernik, S. J. Anal. Appl. Pyrolysis 1989, 16, 127 - 142 10.1016/0165-2370(89)85012-0
38. Ponder, G. R.; Richards, G. N. Carbohydr. Res. 1993, 244, 341 - 359 10.1016/0008-6215(83)85012-5
39. Antal, M. J., Jr.; Varhegyi, G. Ind. Eng. Chem. Res. 1995, 34, 703 - 717 10.1021/ie00042a001
40. Sanders, E. B.; Goldsmith, A. I.; Seeman, J. I. J. Anal. Appl. Pyrolysis 2003, 66, 29 - 50 10.1016/S0165-2370(02)00104-3
41. Shimada, N.; Kawamoto, H.; Saka, S. J. Anal. Appl. Pyrolysis 2008, 81, 80 - 87 10.1016/j.jaap.2007.09.005
42. Patwardhan, P. R.; Satrio, J. A.; Brown, R. C.; Shanks, B. H. Bioresour. Technol. 2010, 101, 4646 - 4655 10.1016/j.biortech.2010.01.112
43. Shaik, S. M.; Sharratt, P. N.; Tan, R. B. J. Anal. Appl. Pyrolysis 2013, 104, 234 - 242 10.1016/j.jaap.2013.07.010
44. Yu, Y.; Liu, D.; Wu, H. Energy Fuels 2014, 28, 245 - 253 10.1021/ef401483u
45. Ponder, G. R.; Richards, G. N.; Stevenson, T. T. J. Anal. Appl. Pyrolysis 1992, 22, 217 - 229 10.1016/0165-2370(92)85015-D
46. Scott, D. S.; Paterson, L.; Piskorz, J.; Radlein, D. J. Anal. Appl. Pyrolysis 2001, 57, 169 - 176 10.1016/S0165-2370(00)00108-X
47. Richards, G. N.; Zheng, G. J. Anal. Appl. Pyrolysis 1991, 21, 133 - 146 10.1016/0165-2370(91)80021-Y
48. Ponder, G. R.; Richards, G. N. Carbohydr. Res. 1993, 244, 27 - 47 10.1016/0008-6215(93)80003-W
49. Lédé, J. J. Anal. Appl. Pyrolysis 2012, 94, 17 - 32 10.1016/j.jaap.2011.12.019
50. Julien, S.; Chornet, E.; Tiwari, P. K.; Overend, R. P. J. Anal. Appl. Pyrolysis 1991, 19, 81 - 104 10.1016/0165-2370(91)80036-8
51. Saddawi, A.; Jones, J. M.; Williams, A. Fuel Process. Technol. 2012, 104, 189 - 197 10.1016/j.fuproc.2012.05.014
52. Nimlos, M. R.; Blanksby, S. J.; Ellison, G. B.; Evans, R. J. J. Anal. Appl. Pyrolysis 2003, 66, 3 - 27 10.1016/S0165-2370(02)00103-1
53. Mayes, H. B.; Nolte, M. W.; Beckham, G. T.; Shanks, B. H.; Broadbelt, L. J. ACS Sustainable Chem. Eng. 2014, 2, 1461 - 1473 10.1021/sc500113m
54. Radlein, D. S. T. A. G.; Grinshpun, A.; Piskorz, J.; Scott, D. S. J. Anal. Appl. Pyrolysis 1987, 12, 39 - 49 10.1016/0165-2370(87)80013-X
55. Piskorz, J.; Majerski, P.; Radlein, D.; Vladars-Usas, A.; Scott, D. S. J. Anal. Appl. Pyrolysis 2000, 56, 145 - 166 10.1016/S0165-2370(00)00089-9
56. Wang, S.; Guo, X.; Liang, T.; Zhou, Y.; Luo, Z. Bioresour. Technol. 2012, 104, 722 - 728 10.1016/j.biortech.2011.10.078
57. Mettler, M. S.; Paulsen, A. D.; Vlachos, D. G.; Dauenhauer, P. J. Green Chem. 2012, 14, 1284 - 1288 10.1039/c2gc35184f
58. Mayes, H. B.; Tian, J.; Nolte, M. W.; Shanks, B. H.; Beckham, G. T.; Gnanakaran, S.; Broadbelt, L. J. J. Phys. Chem. B 2014, 118, 1990 - 2000 10.1021/jp409481f
59. Paine, J. B., III; Pithawalla, Y. B.; Naworal, J. D.; Thomas, C. E., Jr. J. Anal. Appl. Pyrolysis 2007, 80, 297 - 311 10.1016/j.jaap.2007.03.007
60. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09 Revision C.01; Gaussian, Inc.: Wallingford, CT, 2010.
61. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215 - 241 10.1007/s00214-007-0310-x
62. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650 - 654 10.1063/1.438955
63. Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys. 1984, 80, 3265 - 3269 10.1063/1.447079
64. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999 - 3093 10.1021/cr9904009
65. Cattoir, F. R.; Parks, G. S. J. Phys. Chem. 1929, 33, 879 - 882 10.1021/j150300a007
66. Chan, R. K.; Pathmanathan, K.; Johari, G. P. J. Phys. Chem. 1986, 90, 6358 - 6362 10.1021/j100281a059
67. Calkins, C. R. TAPPI J. 1950, 33, 278 - 285
68. Glendening, E. D.; Landis, C. R.; Weinhold, F. WIREs Comput. Mol. Sci. 2012, 2, 1 - 42 10.1002/wcms.51
69. Glendening, E.; Badenhoop, J. K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Landis, C. R.; Weinhold, F. NBO 6.0; Theoretical Chemistry Institute: Madison, WI, 2013.
70. Hratchian, H. P.; Schlegel, H. B. J. Chem. Phys. 2004, 120, 9918 - 9924 10.1063/1.1724823
71. Hratchian, H. P.; Schlegel, H. B. In Theory and Applications of Computational Chemistry: The First Forty Years; Dykstra, C. E., Frenking, G., Kim, K. S., Scuseria, G., Eds.; Elsevier Science: Elsevier, Amsterdam, 2005; pp 195 - 249.
72. Hratchian, H. P.; Schlegel, H. B. J. Chem. Theory Comput. 2005, 1, 61 - 69 10.1021/ct0499783
73. Collins, M. A. Theor. Chem. Acc. 2002, 108, 313 - 324 10.1007/s00214-002-0383-5
74. Merrick, J. P.; Moran, D.; Radom, L. J. Phys. Chem. A 2007, 111, 11683 - 11700 10.1021/jp073974n
75. Moore, J. W.; Pearson, R. G. Kinetics and Mechanism, 3rd ed.; Wiley: New York, 1981; pp 159 - 172.
76. Mettler, M. S.; Vlachos, D. G.; Dauenhauer, P. J. Energy Environ. Sci. 2012, 5, 7797 - 7809 10.1039/c2ee21679e
77. Broadbelt, L. J.; Pfaendtner, J. AIChE J. 2005, 51, 2112 - 2121 10.1002/aic.10599
78. Yang, C.-y.; Lu, X.-s.; Lin, W.-g.; Yang, X.-m.; Yao, J.-z. Chem. Res. Chinese U. 2006, 22, 524 - 532 10.1016/S1005-9040(06)60155-4
79. Mamleev, V.; Bourbigot, S.; Le Bras, M.; Yvon, J. J. Anal. Appl. Pyrolysis 2009, 84, 1 - 17 10.1016/j.jaap.2008.10.014
80. Pauling, L. Chem. Eng. News 1946, 24, 1375 - 1377 10.1021/cen-v024n010.p1375
81. Herschlag, D.; Jencks, W. P. J. Am. Chem. Soc. 1990, 112, 1942 - 1950 10.1021/ja00161a046
82. Pregel, M. J.; Dunn, E. J.; Nagelkerke, R.; Thatcher, G. R. J.; Buncel, E. Chem. Soc. Rev. 1995, 24, 449 - 455 10.1039/cs9952400449