Challenges in the Computation of Rate Constants for Lignin Model Compounds

Rate Constant Calculation for Thermal Reactions: Methods and Applications

Volumn , Issue , 2011, Pages 191-238

  Beste, Ariana ^a   Buchanan, A C ^a  

^a OAK RIDGE NATIONAL LABORATORY   (United States)

Author keywords

Computation of rate constants, lignin model compounds; Relative rate constants and error cancellation; Thermal decomposition of O 4 model compounds

Indexed keywords

EID: 84887197483     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118166123.ch7     Document Type: Chapter

References (98)

1. http://www.cfo.doe.gov/budget/10budget/Content/Highlights/FY2010Highligh ts.pdf.
2. R. Rinaldi and F. Schu€th, Energy Environ. Sci. 2, 610 (2009).
3. http://archive.greenpeace.org/climate/arctic99/reports/wildlife.html.
4. D. Mohan, C.U. Pittman, Jr., and P.H. Steele, Energy Fuels 20, 848 (2006).
5. E.C. Petrou and C.P. Pappis, Energy Fuels 23, 1055 (2009).
6. M. Sto€cker, Angew. Chem. Int. Ed. 47, 9200 (2008).
7. J.N. Chheda, G.W. Huber, and J.A. Dumesic, Angew. Chem. Int. Ed. 46, 7164 (2007).
8. S. Czernik and A.V. Bridgwater, Energy Fuels 18, 590 (2004).
9. G.W. Huber, S. Iborra, and A. Corma, Chem. Rev. 106, 4044 (2006).
10. http://en.wikipedia.org/wiki/File:Lignin_structure.svg.
11. E. Dorrestijn, L.J.J. Laarhoven, I.W.C.E. Arends, and P. Mulder, J. Anal. Appl. Pyrolysis 54, 153 (2000).
12. J.C. del Río, A.T. Martínez, and A. Gutiérrez, J. Anal. Appl. Pyrolysis 79, 33 (2007).
13. M. Kleinert and T. Barth, Chem. Eng. Technol. 31, 736 (2008).
14. P.J.M. Suhas Carrott and M.M.L. Ribeiro Carrott, Bioresour. Technol. 98, 2301 (2007).
15. S. Baumlin, F. Broust, F. Bazer-Bachi, T. Bourdeaux, O. Herbinet, F.T. Ndiaye, M. Ferrer, and J. Lédé, Int.J. Hydrogen Energy 31, 2179 (2006).
16. C. Fushimi, K. Araki, Y. Yamaguchi, and A. Tsutsumi, Ind. Eng. Chem. Res. 42, 3929 (2003).
17. E.A. Borges da Silva, M. Zabkova, J.D. Arau'jo, C.A. Cateto, M.F. Barreiro, M.N. Belgacem, and A.E. Rodrigues, Chem. Eng. Res. Des. 87, 1276 (2009).
18. H. Priefert, J. Rabenhorst, and A. Steinbu€chel, Appl. Microbiol. Biotechnol. 56, 296 (2001).
19. D. Ferdous, A.K. Dalai, S.K. Bej, and R.W. Thring, Energy Fuels 16, 1405 (2002).
20. S.Wang, K.Wang, Q. Liu,Y. Gu, Z. Luo, K. Cen, and T. Fransson, Biotechnol. Adv. 27, 562 (2009).
21. T. Faravelli, A. Frassoldati, G. Migliavacca, and E. Ranzi, Biomass Bioenergy 34, 290 (2010).
22. C. Fargues, Á. Mathias, and A. Rodrigues, Ind. Eng. Chem. Res. 35, 28 (1996).
23. G.X. Wu and M. Heitz, J. Wood Chem. Technol. 15, 189 (1995).
24. A. Oasmaa, R. Alén, and D. Meier, Bioresour. Technol. 45, 189 (1993).
25. G. Gellerstedt, J. Li, I. Eide, M. Kleinert, and T. Barth, Energy Fuels 22, 4240 (2008).
26. K. Miura, Energy and Fuels 9, 302 (1995).
27. M.T. Klein and P.S. Virk, Energy Fuels 22, 2175 (2008).
28. Z.H. Craig, A. Bennett, M.T. Klein, and P.S. Virk, Energy Fuels 24, 58 (2010).
29. J.B. Binder,M.J. Gray, J.F. White, C. Zhang, and J.E. Holladay, Biomass Bioenergy 33, 1122 (2009).
30. K. Kuroda and A. Nakagawa-izumi, Org. Geochem. 37, 665 (2006).
31. K. Kuroda, A. Nakagawa-izumi, T. Ashitani, and K. Fujita, J. Anal. Appl. Pyrolysis 86, 185 (2009).
32. H. Kawamoto, S. Horigoshi, and S. Saka, J. Wood Sci. 53, 168 (2007).
33. P.F. Britt, A.C. Buchanan, III, and E.A. Malcolm, J. Org. Chem. 60, 6523 (1995).
34. P.F. Britt, A.C. Buchanan, III, M.J. Cooney, and D.R. Martineau, J. Org. Chem. 65, 1376 (2000).
35. M.K. Kidder, P.F. Britt, A.L. Chaffee, and A.C. Buchanan, III, Chem. Commun. 1, 52 (2007).
36. P.F. Britt, A.C. Buchanan, III, and E.A. Malcolm, Energy Fuels 14, 1314 (2000).
37. P.F. Britt, M.K. Kidder, and A.C. Buchanan, III, Energy Fuels 21, 3102 (2007).
38. P.H. Kandanarachchi, T. Autrey, and J.A. Franz, J. Org. Chem. 67, 7937 (2002).
39. T.C. Drage, C.H. Vane, and G.D. Abbott, Org. Geochem. 33, 1523 (2002).
40. R. Katahira, H. Kamitakahara, T. Takano, and F. Nakatsubo, J. Wood Sci. 52, 255 (2006).
41. H. Kawamoto, M. Ryoritani, and S. Saka, J. Anal. Appl. Pyrolysis 81, 88 (2008).
42. T. Watanabe, H. Kawamoto, and S. Saka, Holzforschung 63, 424 (2009).
43. E. Dorrestijn, M. Kranenburg, M.V. Ciriano, and P. Mulder, J. Org. Chem. 64, 3012 (1999).
44. K.E. Gilbert and J.J. Gajewski, J. Org. Chem. 47, 4899 (1982).
45. M.T. Klein and P.S. Virk, Ind. Eng. Chem. Fundam. 22, 35 (1983).
46. R. Brežný, V. Mihalov, and V. Kováčik, Holzforschung 37, 199 (1983).
47. H. Kawamoto, S. Horigoshi, and S. Saka, J. Wood Sci. 53, 268 (2007).
48. K. Kuroda, J. Anal. Appl. Pyrolysis 35, 53 (1995).
49. M. Bietti, G. Ercolani, and M. Salamone, J. Org. Chem. 72, 4515 (2007).
50. M. Smeu and G.A. DiLabio, J. Org. Chem. 72, 4520 (2007).
51. T. Elder, Biomacromolecules 8, 3619 (2007).
52. C. Agache and V.I. Popa, Monatshefte Chem. 137, 55 (2006).
53. K. Kato, K. Endo, D. Matsumoto, T. Ida, K. Saito, K. Fukushima, and N. Kato, Appl. Surf. Sci. 255, 1040 (2008).
54. L. Petridis and J.C. Smith, J. Comp. Chem. 30, 457 (2008).
55. B. Durbeej, Y.-N. Wang, and L.A. Eriksson, Lect. Notes Comput. Sci. 2565, 137 (2003).
56. M. Shigematsu and H. Masamoto, J. Wood Sci. 54, 308 (2008).
57. C. Martínez, M. Sedano, J. Mendoza, R. Herrera, J.G. Rutiaga, and P. Lo'pez, J. Mol. Graph. Model. 28, 196 (2009).
58. C. Martínez, J.L. Rivera, R. Herrera, J.L. Rico, N. Flores, J.G. Rutiaga, and P. Lo'pez, J. Mol. Model. 14, 77 (2008).
59. G. da Silva and J.W. Bozzelli, J. Phys. Chem. A 111, 7987 (2007).
60. I. Shavitt and R.J. Bartlett, Many-Body Methods in Chemistry and Physics, Cambridge University Press, New York (2009).
61. R.G. Parr and W. Yang, Density-Functional Theory of Atoms and Molecules, Oxford University Press, New York (1989).
62. A.G. Vandeputte, M.K. Sabbe, M.-F. Reyniers, V. Van Speybroeck, M. Waroquier, and G.B. Marin, J. Chem. Phys. A 111, 11771 (2007).
63. J. Sun, Y. Tang, H. Sun, Y. Pan, X. Jia, X. Pan, and R.Wang, Mol. Phys. 106, 1379 (2008).
64. X. Yang, Annu. Rev. Phys. Chem. 58, 433 (2007).
65. D.G. Truhlar and B.C. Garrett, Acc. Chem. Res. 13, 440 (1980).
66. D.G. Truhlar and B.C. Garrett, Ann. Rev. Phys. Chem. 35, 159 (1984).
67. J.B. Anderson, J. Chem. Phys. 58, 4684 (1973).
68. R.T. Skodje and D.G. Truhlar, J. Phys. Chem. 85, 624 (1981).
69. B.C. Garrett, T. Joseph, T.N. Truong, and D.G. Truhlar, Chem. Phys. 136, 271 (1989).
70. B.C. Garrett, D.G. Truhlar, R.S. Grev, and A.W. Magnuson, J. Phys. Chem. 84, 1730 (1980).
71. W.H. Miller, J. Chem. Phys. 61, 1823 (1974).
72. W.H. Miller, J. Chem. Phys. 62, 1899 (1975).
73. M. Thoss and H. Wang, Annu. Rev. Phys. Chem. 55, 299 (2004).
74. N. Makri, J. Phys. Chem. A 108, 806 (2004).
75. N.E. Henriksen and F.Y. Hansen, Theories of Molecular Reaction Dynamics, Oxford University Press, New York (2008).
76. J.E. House, Principles of Chemical Kinetics, 2nd edition, Academic Press (2007).
77. D.A. McQuarrie and J.D. Simon, Molecular Thermodynamics, University Science Books, Sausalito, CA (1999).
78. A. Beste, Chem. Phys. Lett. 493, 200 (2010).
79. A. Beste, A.C. Buchanan, III, P.F. Britt, B.C. Hathorn, and R.J. Harrison, J. Phys. Chem. A 111, 12118 (2007).
80. A.D. Isaacson and D.G. Truhlar, J. Chem. Phys. 76, 1380 (1982).
81. P.Y. Ayala and H.B. Schlegel, J. Chem. Phys. 108, 2314 (1998).
82. A. Chakraborty and D.G. Truhlar, J. Chem. Phys. 124, 184310 (2006).
83. D.G. Truhlar and A.D. Isaacson, J. Chem. Phys. 94, 357 (1991).
84. R.Q. Topper and D.G. Truhlar, J. Chem. Phys. 97, 3647 (1992).
85. M.B. Hansen, O. Christiansen, D. Toffoli, and J. Kongsted, J. Chem. Phys. 128, 174106 (2008).
86. E.P. Wigner, Phys. Rev. 40, 749 (1932).
87. J.G. Kirkwood, Phys. Rev. 44, 31 (1933).
88. P. Linz and R.L.C. Wang, Exploring Numerical Methods: An Introduction to Scientific Computing Using MATLAB, Jones and Bartlett Publishers, Sudbury, MA (2003).
89. J.M. Younker, Qinetic, Pennsylvania State University, Pennsylvania (2010).
90. A. Beste, A.C. Buchanan, III, and R.J. Harrison, J. Phys. Chem. A 112, 4982 (2008).
91. A. Beste and A.C. Buchanan, III, Energy Fuels 24, 2857 (2010).
92. A. Beste and A.C. Buchanan, III, J. Org. Chem. 74, 2837 (2090).
93. E.J. Bylaska et al., NWChem, A Computational Chemistry Package for Parallel Computers, Version 5.1, Pacific Northwest National Laboratory, Richland, WA (2007).
94. A.D. Becke, J. Chem. Phys. 98, 5648 (1993).
95. C. Lee, W. Yang, and R.G. Parr, Phys. Rev. B 37, 785 (1988).
96. Y. Zhao and D.G. Truhlar, Acc. Chem. Res. 41, 157 (2008).
97. The best experimental rate constant for a reference reaction (2-allylbenzyl radical abstracting hydrogen from meta-xylene;
98. J.A. Franz et al., J. Org. Chem. 51, 1446 (1986)) has an error of 0.7 kcal/mol in the activation energy and 0.4 in log A. The group additivity parameters have errors associated with them also. An overall estimate of the errors in the experimental values is 1-2 kcal/mol for the activation energies and 2.5 for ln A.