Unraveling the reactions that unravel cellulose

Journal of Physical Chemistry A

Volumn 116, Issue 26, 2012, Pages 7098-7106

  Mayes, Heather B ^a   Broadbelt, Linda J ^a  

^a Northwestern University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST DESIGNS; CONCERTED REACTIONS; COST-EFFICIENT; DENSITY FUNCTIONAL THEORY METHODS; GLYCOSIDIC BOND; IMPLICIT SOLVENTS; IONIC INTERMEDIATES; LEVOGLUCOSAN; PRIMARY REACTION; PROCESS MODELING; RENEWABLE ENERGIES; THERMAL PROCESS; TRANSPORTATION FUELS;

DECOMPOSITION; DENSITY FUNCTIONAL THEORY;

CELLULOSE;

CELLULOSE; FREE RADICAL; SOLVENT;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HYDROGEN BOND; QUANTUM THEORY;

CELLULOSE; FREE RADICALS; HYDROGEN BONDING; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; QUANTUM THEORY; SOLVENTS;

EID: 84863618360     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp300405x     Document Type: Article

References (72)

1. Huber, G. W.; Iborra, S.; Corma, A. Chem. Rev. 2006, 106, 4044-4098
2. Bridgwater, A. V.; Meier, D.; Radlein, D. Org. Geochem. 1999, 30, 1479-1493
3. Elliott, D. C. Energy Fuels 2007, 21, 1792-1815
4. Mohan, D.; Pittman, C. U., Jr.; Steele, P. H. Energy Fuels 2006, 20, 848-889
5. Di Blasi, C. Prog. Energy Combust. Sci. 2008, 34, 47-90
6. Byrne, G. A.; Gardiner, D.; Holmes, F. H. J. Appl. Chem. 1966, 16, 81-88
7. Broido, A.; Nelson, M. A. Combust. Flame 1975, 24, 263-268
8. Bradbury, A. G. W.; Sakai, Y.; Shafizadeh, F. J. Appl. Polym. Sci. 1979, 23, 3271-3280
9. Agrawal, R. K. Can. J. Chem. Eng. 1988, 66, 403-412
10. Diebold, J. P. Biomass Bioenergy 1994, 7, 75-85
11. Antal, M. J., Jr.; Varhegyi, G. Ind. Eng. Chem. Res. 1995, 34, 703-717
12. Várhegyi, G.; Antal, M. J., Jr.; Jakab, E.; Szabó, P. J. Anal. Appl. Pyrolysis 1997, 42, 73-87
13. Ranzi, E.; Cuoci, A.; Faravelli, T.; Frassoldati, A.; Migliavacca, G.; Pierucci, S.; Sommariva, S. Energy Fuels 2008, 22, 4292-4300
14. Authier, O.; Ferrer, M.; Khalfi, A.-E.; Lédé, J. Int. J. Chem. React. Eng. 2010, 8, A78
15. Ivanov, V. I.; Golova, O. P.; Pakhomov, A. M. Russ. Chem. Bull. 1956, 5, 1295-1296
16. Shafizadeh, F. J. Anal. Appl. Pyrolysis 1982, 3, 283-305
17. Lakshmanan, C. M.; Gal-or, B.; Hoelscher, H. E. Ind. Eng. Chem. Prod. Res. Dev. 1969, 8, 261-267
18. Lomax, J. A.; Commandeur, J. M.; Arisz, P. W.; Boon, J. J. J. Anal. Appl. Pyrolysis 1991, 19, 65-79
19. Patwardhan, P. R.; Satrio, J. A.; Brown, R. C.; Shanks, B. H. J. Anal. Appl. Pyrolysis 2009, 86, 323-330
20. Irvine, J. C.; Oldham, J. W. H. J. Chem. Soc., Faraday Trans. 1921, 119, 1744-1759
21. Kislitsyn, A. N.; Rodionova, Z. M.; Savinykh, V. I.; Gusev, A. V. Zh. Prikl. Khim. (Leningrad) 1971, 44, 2518-2524
22. Pakhomov, A. M. Russ. Chem. Bull. 1958, 6, 1525-1527
23. Gardiner, D. J. Chem. Soc. C 1966, 1473-1476
24. Kato, K. Agric. Biol. Chem. 1967, 31, 657-663
25. Ponder, G. R.; Richards, G. N.; Stevenson, T. T. J. Anal. Appl. Pyrolysis 1992, 22, 217-229
26. Shen, D. K.; Gu, S. Bioresour. Technol. 2009, 100, 6496-6504
27. Golova, O. P.; Andrievskaya, E. A.; Pakhomov, A. M.; Merlis, N. M. Russ. Chem. Bull. 1957, 6, 399-401
28. Kilzer, F. J.; Broido, A. Pyrodynamics 1965, 2, 151-163
29. Molton, P. M.; Demmitt, T. F. Reaction Mechanisms in Cellulose Pyrolysis: A Literature Review; Battelle, Pacific Northwest Laboratories: Richland, WA, 1977
30. Assary, R. S.; Curtiss, L. A. ChemCatChem 2012, 4, 200-205
31. Hosoya, T.; Nakao, Y.; Sato, H.; Kawamoto, H.; Sakaki, S. J. Org. Chem. 2009, 74, 6891-6894
32. Frisch, M. J. Gaussian 09, Revision B.01; Gaussian, Inc.: Wallingford, CT, 2010.
33. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3093
34. Calkins, C. R. TAPPI 1950, 33, 278-285
35. Csonka, G. I.; French, A. D.; Johnson, G. P.; Stortz, C. A. J. Chem. Theory Comput. 2009, 5, 679-692
36. Curtiss, L. A.; Redfern, P. C.; Raghavachari, K. Chem. Phys. Lett. 2010, 499, 168-172
37. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. J. Chem. Theory Comput. 2006, 2, 364-382
38. Wodrich, M. D.; Corminboeuf, C.; Schreiner, P. R.; Fokin, A. A.; von Ragué Schleyer, P. Org. Lett. 2007, 9, 1851-1854
39. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241
40. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
41. Boese, A. D.; Martin, J. M. L. J. Chem. Phys. 2004, 121, 3405-3416
42. Pople, J. A.; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. 1976, 10, 1-19
43. Merrick, J. P.; Moran, D.; Radom, L. J. Phys. Chem. A 2007, 111, 11683-11700
44. Hratchian, H. P.; Schlegel, H. B. J. Chem. Phys. 2004, 120, 9918-9924
45. 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: New York, 2005; pp 195-249.
46. Hratchian, H. P.; Schlegel, H. B. J. Chem. Theory Comput. 2005, 1, 61-69
47. Collins, M. A. Theor. Chem. Acc. 2002, 108, 313-324
48. Seeger, R.; Pople, J. A. J. Chem. Phys. 1977, 66, 3045-3050
49. Bauernschmitt, R.; Ahlrichs, R. J. Chem. Phys. 1996, 104, 9047-9052
50. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553-566
51. Simon, S.; Duran, M.; Dannenberg, J. J. J. Chem. Phys. 1996, 105, 11024-11031
52. Pfaendtner, J.; Yu, X.; Broadbelt, L. J. Theor. Chem. Acc. 2007, 118, 881-898
53. Moore, J. W.; Pearson, R. G. Kinetics and Mechanism, 3 rd ed.; John Wiley and Sons: New York, 1981.
54. Truong, T. N.; Duncan, W. T.; Tirtowidjojo, M. Phys. Chem. Chem. Phys. 1999, 1, 1061-1065
55. Hong, X.; Sun, H.; Law, C. K. Comput. Theor. Chem. 2011, 963, 357-364
56. Chu, S. S. C.; Jeffrey, G. A. Acta Crystallogr., Sect. B 1968, 24, 830-838
57. Strati, G. L.; Willett, J. L.; Momany, F. A. Carbohydr. Res. 2002, 337, 1833-1849
58. Nishiyama, Y.; Langan, P.; Chanzy, H. J. Am. Chem. Soc. 2002, 124, 9074-9082
59. Momany, F. A.; Schnupf, U. Carbohydr. Res. 2011, 346, 619-630
60. Matthews, J. F.; Bergenstråhle, M.; Beckham, G. T.; Himmel, M. E.; Nimlos, M. R.; Brady, J. W.; Crowley, M. F. J. Phys. Chem. B 2011, 115, 2155-2166
61. Zhang, X.; Li, J.; Yang, W.; Blasiak, W. Energy Fuels 2011, 25, 3739-3746
62. Kraka, E.; Wu, A.; Cremer, D. J. Phys. Chem. A 2003, 107, 9008-9021
63. Tranter, R. S.; Klippenstein, S. J.; Harding, L. B.; Giri, B. R.; Yang, X.; Kiefer, J. H. J. Phys. Chem. A 2010, 114, 8240-61
64. Bianciotto, M.; Barthelat, J.-C.; Vigroux, A. J. Am. Chem. Soc. 2002, 124, 7573-7587
65. Beste, A.; Buchanan, A. C., III J. Org. Chem. 2009, 74, 2837-2841
66. Kim, S.; Chmely, S. C.; Nimlos, M. R.; Bomble, Y. J.; Foust, T. D.; Paton, R. S.; Beckham, G. T. J. Phys. Chem. Lett. 2011, 2, 2846-2852
67. Parthasarathi, R.; Bellesia, G.; Chundawat, S. P. S.; Dale, B. E.; Langan, P.; Gnanakaran, S. J. Phys. Chem. A 2011, 115, 14191-14202
68. Nimlos, M. R.; Blanksby, S. J.; Ellison, G. B.; Evans, R. J. J. Anal. Appl. Pyrolysis 2003, 66, 3-27
69. Temelso, B.; Sherrill, C. D.; Merkle, R. C.; Freitas, R. A., Jr. J. Phys. Chem. A 2006, 110, 11160-11173
70. Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2008, 4, 1849-1868
71. Beste, A.; Buchanan, A. C.; Britt, P. F.; Hathorn, B. C.; Harrison, R. J. J. Mol. Struct.: THEOCHEM 2008, 851, 232-241
72. Antal, M. J., Jr.; Várhegyi, G.; Jakab, E. Ind. Eng. Chem. Res. 1998, 37, 1267-1275