ReaxFF study of the oxidation of lignin model compounds for the most common linkages in softwood in view of carbon fiber production

Journal of Physical Chemistry A

Volumn 118, Issue 5, 2014, Pages 803-814

  Beste, Ariana ^a,b  

^a Oak Ridge National Laboratory   (United States)

^b OAK RIDGE NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84893855192     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp410454q     Document Type: Article

References (71)

1. Tuck, C. O.; Pérez, E.; Horváth, I. T.; Sheldon, R. A.; Poliakoff, M. Valorization of Biomass: Deriving More Value from Waste Science 2012, 337, 695-699
2. Menon, V.; Rao, M. Trends in Bioconversion of Lignocellulose: Biofuels, Plattform Chemicals & Biorefinery Concept Prog. Energy Combust. Sci. 2012, 38, 522-550
3. Fitzpatrick, M.; Champagne, P.; Cunningham, M. F.; Whitney, R. A. A Biorefinery Processing Perspective: Treatment of Lignocellulosic Materials for the Production of Value-Added Products Bioresour. Technol. 2010, 101, 8915-8922
4. Mohan, D.; Pittman, C. U., Jr.; Steele, P. H. Pyrolysis of Wood/Biomass for Bio-Oil: A Critical Review Energy Fuels 2006, 20, 848-889
5. Caldeira-Pires, A.; da Luz, S. M.; Palma-Rojas, S.; Rodrigues, T. O.; Silverio, V. C.; Vilela, F.; Barbosa, P. C.; Alves, A. M. Sustainability of the Biorefinery Industry for Fuel Production Energies 2013, 6, 329-350
6. Yuan, T.-Q.; Xu, F.; Sun, R.-C. Role of Lignin in a Biorefinery: Separation Characterization and Valorization J. Chem. Technol. Biotechnol. 2013, 88, 346-352
7. Baker, D. A.; Rials, T. G. Recent Advances in Low-Cost Carbon Fiber Manufacture from Lignin J. Appl. Polym. Sci. 2013, 130, 713-728
8. Frank, E.; Hermanutz, F.; Buchmeiser, M. R. Carbon Fibers: Precursors, Manufacturing, and Properties Macromol. Mater. Eng. 2012, 297, 493-501
9. Warren, C. D.; Paulauskas, F. L.; Baker, F. S.; Eberle, C. C.; Naskar, A. Development of Commodity Grade, Lower Cost Carbon Fiber-Commercial Applications SAMPE J. 2009, 45, 24-36
10. Hunt, M. A.; Saito, T.; Brown, R. H.; Kumbhar, A. S.; Naskar, A. K. Patterned Functional Carbon Fibers from Polyethylene Adv. Mater. 2012, 24, 2386-2389
11. Younker, J. M.; Saito, T.; Hunt, M. A.; Naskar, A. K.; Beste, A. Pyrolysis Pathways of Sulfonated Polyethylene, an Alternative Carbon Fiber Precursor J. Am. Chem. Soc. 2013, 135, 6130-6141
12. Norberg, I.; Nordström, Y.; Drougge, R.; Gellerstedt, G.; Sjöholm, E. A New Method for Stabilizing Softwood Kraft Lignin Fibers for Carbon Production J. Appl. Polym. Sci. 2013, 128, 3824-3830
13. Awal, A.; Sain, M. Characterization of Soda Hardwood Lignin ad the Formation of Lignin Fibers by Melt Spinning J. Appl. Polym. Sci. 2013, 129, 2765-2771
14. Qin, W.; Kadla, J. F. Carbon Fibers Based on Pyrolytic Lignin J. Appl. Polym. Sci. 2012, 126, 203-212
15. Baker, D. A.; Gallego, N. C.; Baker, F. S. On the Characterization and Spinning of an Organic-Purified Lignin Toward the Manufacture of Low-Cost Carbon Fiber J. Appl. Polym. Sci. 2012, 124, 227-234
16. Qin, W.; Kadla, J. F. Effect of Organoclay Reinforcement on Lignin-Based Carbon Fibers Ind. Eng. Chem. Res. 2011, 50, 12548-12555
17. Kubo, S.; Kadla, J. F. Lignin-Based Carbon Fibers: Effect of Synthetic Polymer Blending on Fiber Properties J. Polym. Environ. 2005, 13, 97-105
18. Dorrestijn, E.; Laarhoven, L. J. J.; Arends, I. W. C. E.; Mulder, P. The Occurence and Reactivity of Phenoxyl Linkages in Lignin and Low Rank Coal J. Anal. Appl. Pyrol. 2000, 54, 153-192
19. Braun, J. L.; Holtman, K. M.; Kadla, J. F. Lignin-Based Carbon Fibers: Oxidative Thermostabilization of Kraft Lignin Carbon 2005, 43, 385-394
20. Wu, X.; Fu, J.; Lu, X. Kinetics and Mechanism of Hydrothermal Decomposition of Lignin Model Compounds Ind. Eng. Chem. Res. 2013, 52, 5016-5022
21. Chu, S.; Subrahmanyam, A. V.; Hubert, G. W. The Pyrolysis Chemistry of a β-O-4 Type Oligomeric Lignin Model Compound Green Chem. 2013, 15, 125-136
22. Holmelid, B.; Kleinert, M.; Barth, T. Reactivity and Reaction Pathways in Thermochemical Treatment of Selected Lignin-Like Model Compounds under Hydrogen Rich Conditions J. Anal. Appl. Pyrol. 2012, 98, 37-44
23. Britt, P. F.; Buchanan, A. C., III; Malcolm, E. A. Thermolysis of Phenethyl Phenyl Ether: A Model for Ether Linkages in Lignin and Low Rank Coal J. Org. Chem. 1995, 60, 6523-6536
24. Kim, S.; Chmely, S. C.; Nimlos, M. R.; Bomble, Y. J.; Foust, T. D.; Paton, R. S.; Beckham, G. T. Computational Study of Bond Dissociation Enthalpies for a Large Range of Native and Modified Lignins J. Phys. Chem. Lett. 2011, 2, 2846-2852
25. Parthasarathi, R.; Romero, R. A.; Redondo, A.; Gnanakaran, S. Theoretical Study of the Remarkably Diverse Linkages in Lignin J. Phys. Chem. Lett. 2011, 2, 2660-2666
26. Cho, D. W.; Parthasarathi, R.; Pimentel, A. S.; Maestas, G. D.; Park, H. J.; Yoon, U. C.; Dunaway-Mariano, D.; Gnanakaran, S.; Langan, P.; Mariano, P. S. Nature and Kinetic Analysis of Carbon-Carbon Bond Fragmentation Reactions of Cation Radicals Derived from SET-Oxidation of Lignin Model Compounds J. Org. Chem. 2010, 75, 6549-6562
27. Jarvis, M. W.; Daily, J. W.; Carstensen, H.-H.; Dean, A. M.; Sharma, S.; Dayton, D. C.; Robichaud, D. J.; Nimlos, M. R. Direct Detection of Products from Pyrolysis of 2-Phenethyl Phenyl Ether J. Phys. Chem. A 2011, 115, 428-438
28. Elder, T. A Computational Study of Pyrolysis Reactions of Lignin Model Compounds Holzforschung 2010, 64, 435-440
29. Elder, T. Bond Dissociation Enthalpies of a Dibenzodioxocin Lignin Model Compound Energy Fuels 2013, 27, 4785-4790
30. Gardrat, C.; Ruggiero, R.; Rayez, M.-T.; Rayez, J.-C.; Castellan, A. Experimental and Theoretical Studies of the Thermal Degradation of a Phenolic Dibenzodioxin Lignin Model Wood Sci. Technol. 2013, 47, 27-41
31. Beste, A.; Buchanan, A. C., III. Computational Study of Bond Dissociation Enthalpies for Lignin Model Compounds. Substituent Effects in Phenethyl Phenyl Ethers J. Org. Chem. 2009, 74, 2837-2841
32. Younker, J. M.; Beste, A.; Buchanan, A. C., III. Computational Study of Bond Dissociation Enthalpies for Substituted β-O-4 Lignin Model Compounds ChemPhysChem 2011, 12, 3556-3565
33. Younker, J. M.; Beste, A.; Buchanan, A. C., III. Computational Study of Bond Dissociation Enthalpies for Lignin Model Compounds: β-5 Arylcoumaran Chem. Phys. Lett. 2012, 545, 100-106
34. Sangha, A. K.; Parks, J. M.; Standaert, R. F.; Ziebell, A.; Davis, M.; Smith, J. C. Radical Coupling Reactions in Lignin Sythesis: A Density Functional Theory Study J. Phys. Chem. B 2012, 116, 4760-4768
35. Durbeej, B.; Eriksson, L. A. A Density Functional Theory Study of Conferyl Alcohol Intermonomeric Cross Linkages in Lignin-Three-Dimensional Structures, Stabilities and the Thermodynamic Control Hypothesis Holzforschung 2003, 57, 150-164
36. Durbeej, B.; Eriksson, L. A. Formation of β-O-4 Lignin Models-A Theoretical Study Holzforschung 2003, 57, 466-478
37. Shigematsu, M.; Masamoto, H. Solvent Effects on the Electronic State of Monolignol Radicals as Predicted by Molecular Orbital Calculations J. Wood Sci. 2008, 54, 308-311
38. Martínez, C.; Rivera, J. L.; Herrera, R.; Rico, J. L.; Flores, N.; Rutiaga, J. G.; López, P. Evaluation of the Chemical Reactivity in Lignin Precursors Using the Fukui Function J. Mol. Model 2008, 14, 77-91
39. Elder, T. Quantum Chemical Determination of Young's Modulus of Lignin. Calculations on a β-O-4 Model Compound Biomacromolecules 2007, 8, 3619-3627
40. Watts, H. D.; Mohamed, M. N. A.; Kubicki, J. D. Comparison of Multistandard and TMS-Standard Calculated NMR Shifts for Coniferyl Alcohol and Application of the Multistandard Method to Lignin Dimers J. Phys. Chem. B 2011, 115, 1958-1970
41. Mostaghni, F.; Teimouri, A.; Mirshokraei, S. A. Synthesis, Spectroscopic Characterization and DFT Calculations of β-O-4 Type Lignin Model Compounds Spectrochim. Acta, Part A 2013, 110, 430-436
42. Janesko, B. G. Modeling Interactions Between Lignocellulose and Ionic Liquids Using DFT-D Phys. Chem. Chem. Phys. 2011, 13, 11393-11401
43. Ji, W.; Ding, Z.; Liu, J.; Song, Q.; Xia, X.; Gao, H.; Wang, H.; Gu, W. Mechanism of Lignin Dissolution and Regeneration in Ionic Liquid Energy Fuels 2012, 26, 6393-6403
44. β Bond in β-O-4 Linakge of Lignin to Transition Metals Using a Relativistic Pseudopotential-Based ccCA-ONIOM Method ChemPhysChem 2011, 12, 3320-3330
45. Elder, T.; Bozell, J. J.; Cedeno, D. The Effect of Axial Ligand on the Oxidation of Syringyl Alcohol by Co(Salen) Adducts Phys. Chem. Chem. Phys. 2013, 15, 7328-7337
46. Beste, A.; Buchanan, A. C., III. Substituent Effects on the Reaction Rates of Hydrogen Abstraction in the Pyrolysis of Phenethyl Phenyl Ethers Energy Fuels 2010, 24, 2857-2867
47. Beste, A.; Buchanan, A. C., III. Kinetic Analysis of the Phenyl-Shift Reaction in β-O-4 Lignin Model Compounds: A Computational Study J. Org. Chem. 2011, 76, 2195-2203
48. Beste, A.; Buchanan, A. C., III; Britt, P. F.; Hathorn, B. C.; Harrison, R. J. Kinetic Analysis of the Pyrolysis of Phenethyl Phenyl Ether: Computational Prediction of α/β-Selectivities J. Phys. Chem. A 2007, 111, 12118-12126
49. Beste, A.; Buchanan, A. C., III; Harrison, R. J. Computational Prediction of α/β-Selectivities in the Pyrolysis of Oxygen-Substituted Phenethyl Phenyl Ethers J. Phys. Chem. A 2008, 112, 4982-4988
50. Beste, A.; Buchanan, A. C., III. Computational Investigation of the Pyrolysis Product Selectivity for α-Hydroxy Phenethyl Phenyl Ether and Phenethyl Phenyl Ether: Analysis of Substituent Effects and Reactant Conformer Selection J. Phys. Chem. A 2013, 117, 3235-3242
51. Beste, A.; Buchanan, A. C., III. Kinetic Simulation of the Thermal Degradation of Phenethyl Phenyl Ether, a Model Compound for the β-O-4 Linkage in Lignin Chem. Phys. Lett. 2012, 550, 19-24
52. Beste, A.; Buchanan, A. C., III. Role of Carbon-Carbon Phenyl Migration in the Pyrolysis Mechanism of β-O-4 Lignin Model Compounds: Phenethyl Phenyl Ether and α-Hydroxy Phenethyl Phenyl Ether J. Phys. Chem. A 2012, 116, 12242-12248
53. Petridis, L.; Schulz, R.; Smith, J. C. Simulation Analysis of the Temperature Dependence of Lignin Structure and Dynamics J. Am. Chem. Soc. 2011, 133, 20277-20287
54. Petridis, L.; Smith, J. C. A Molecular Mechanics Force Field for Lignin J. Comput. Chem. 2009, 30, 457-467
55. van Duin, A. C. T.; Dasgupta, S.; Lorant, F.; Goddard, W. A., III. ReaxFF: A Reactive Force Field for Hydrocarbons J. Phys. Chem. A 2001, 105, 9396-9409
56. Chenoweth, K.; van Duin, A. C. T.; Goddard, W. A., III. ReaxFF Reactive Force Field for Molecular Dynamics Simulations of Hydrocarbon Oxidation J. Phys. Chem. A 2008, 112, 1040-1053
57. Guo, F.; Cheng, X.; Zhang, H. ReaxFF Molecular Dynamics Study of Initial Mechanism of JP-10 Combustion Combust. Sci. Technol. 2012, 184, 1233-1243
58. Chenoweth, K.; van Duin, A. C. T.; Dasgupta, S.; Goddard, W. A., III. Initiation Mechanism and Kinetics of Pyrolysis and Combustion of JP-10 Hydrocarbon Jet Fuel J. Phys. Chem. A 2009, 113, 1740-1746
59. Liu, L.; Bai, C.; Sun, H.; Goddard, W. A., III. Mechanism and Kinetics for the Initial Steps of Pyrolysis and Combustion of 1,6-Dicyclopropane-2,4- hexyne from ReaxFF Reactive Dynamics J. Phys. Chem. A 2011, 115, 4941-4950
60. en Jiang, D.; van Duin, A. C. T.; Goddard, W. A., III; Dai, S. Simulating the Initial Stage of Phenolic Resin Carbonization via the ReaxFF Reactive Force Field J. Phys. Chem. A 2009, 113, 6891-6894
61. Sharma, R. K.; Hajaligol, M. R. Effect of Pyrolysis Conditions on the Formation of Polycyclic Aromatic Hydrocarbons (PAHs) from Polyphenolic Compounds J. Anal. Appl. Pyrol. 2003, 66, 123-144
62. Wornat, M. J.; Ledesma, E. B.; Marsh, N. D. Polycyclic Aromatic Hydrocarbons from the Pyrolysis of Catechol (ortho-Dihydroxybenzene), a Model Fuel Representative of Entities in Tobacco, Coal, and Lignin Fuel 2001, 80, 1711-1726
63. Fitzpatrick, E. M.; Jones, J. M.; Pourkashanian, M.; Ross, A. B.; Williams, A.; Bartle, K. D. Mechanistic Aspects of Soot Formation from the Combustion of Pine Wood Energy Fuels 2008, 22, 3771-3778
64. Jarvis, M. W.; Haas, T. J.; Donohoe, B. S.; Daily, J. W.; Gaston, K. R.; Frederick, W. J.; Nimlos, M. R. Elucidation of Biomass Pyrolysis Products Using a Laminar Entrained Flow Reactor and Char Particle Imaging Energy Fuels 2011, 25, 324-336
65. McGrath, T. E.; Wooten, J. B.; Chan, W. G.; Hajaligol, M. R. Formation of Polycyclic Aromatic Hydrocarbons from Tobacco: The Link between Low Temperature Residual Solid (Char) and PAH Formation Food Chem. Toxicol. 2007, 45, 1039-1050
66. Dobele, G.; Domburg, G.; Rossinskaya, G.; Brez̆ny, R. Thermocatalytic Transformations of Lignin Model Compounds Thermochim. Acta 1985, 93, 413-416
67. Sazanov, Y. N.; Gribanov, A. V. Thermochemistry of Lignin Russ. J. Appl. Chem. 2010, 83, 175-194
68. Plimpton, S. Fast Parallel Algorithms for Short-Range Molecular Dynamics J. Comput. Phys. 1995, 117, 1-19
69. Zheng, M.; Li, X.; Guo, L. Algorithms of GPU-Enabled Reactive Force Field (ReaxFF) Molecular Dynamics J. Mol. Graph. Modell. 2013, 41, 1-11
70. Humphrey, W.; Dalke, A.; Schulten, K. VMD-Visual Molecular Dynamics J. Mol. Graph. 1996, 14, 33-38
71. Britt, P. F.; Buchanan, A. C., III; Cooney, M. J.; Martineau, D. R. Flash Vacuum Pyrolysis of Methoxy-Substituted Lignin Model Compounds J. Org. Chem. 2000, 65, 1376-1389