Multiscale molecular modeling can be an effective tool to aid the development of biomass conversion technology: A perspective

Chemical Engineering Science

Volumn 121, Issue , 2015, Pages 217-235

  Mushrif, Samir H ^a   Vasudevan, Vallabh ^a   Krishnamurthy, Chethana B ^a   Venkatesh, Boddu ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

Ab initio molecular dynamics; Biomass conversion; Density functional theory; Molecular mechanics; Pyrolysis; Solvent effects

Indexed keywords

BIOCONVERSION; CATALYSIS; DENSITY FUNCTIONAL THEORY; MOLECULAR DYNAMICS; MOLECULAR MECHANICS; MOLECULAR MODELING; PYROLYSIS; QUANTUM THEORY; REACTION KINETICS; SOLVENTS;

AB INITIO MOLECULAR DYNAMICS; BIOMASS CONVERSION; BIOMASS CONVERSION TECHNOLOGIES; CAR-PARRINELLO MOLECULAR DYNAMICS; CATALYTIC REACTION MECHANISM; MULTI-SCALE MOLECULAR MODELING; PHYSICOCHEMICAL CHARACTERISTICS; SOLVENT EFFECTS;

BIOMASS;

EID: 84921892357     PISSN: 00092509     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ces.2014.08.019     Document Type: Article

References (186)

1. Agarwal V., Dauenhauer P.J., et al. Ab initio dynamics of cellulose pyrolysis: nascent decomposition pathways at 327 and 600 degrees C. J. Am. Chem. Soc. 2012, 134(36):14958-14972.
2. Alonso D.M., Wettstein S.G., et al. Gamma-valerolactone, a sustainable platform molecule derived from lignocellulosic biomass. Green Chem. 2013, 15(3):584-595.
3. Anca-Couce A., Zobel N. Numerical analysis of a biomass pyrolysis particle model: solution method optimized for the coupling to reactor models. Fuel 2012, 97:80-88.
4. Anex R.P., Aden A., et al. Techno-economic comparison of biomass-to-transportation fuels via pyrolysis, gasification, and biochemical pathways. Fuel 2010, 89:S29-S35.
5. Assary R.S., Curtiss L.A. Theoretical studies for the formation of γ-valero-lactone from levulinic acid and formic acid by homogeneous catalysis. Chemical Physics Letters 2012, 541(0):21-26.
6. Assary R.S., Redfern P.C., et al. Predicted thermochemistry for chemical conversions of 5-hydroxymethylfurfural. Chem. Phys. Lett. 2010, 497(1-3):123-128.
7. Babu B.V., Chaurasia A.S. Heat transfer and kinetics in the pyrolysis of shrinking biomass particle. Chem. Eng. Sci. 2004, 59(10):1999-2012.
8. Babu B.V., Chaurasia A.S. Parametric study of thermal and thermodynamic properties on pyrolysis of biomass in thermally thick regime. Energy Convers. Manag. 2004, 45(1):53-72.
9. Bährle C., Custodis V., et al. In situ observation of radicals and molecular products during lignin pyrolysis. ChemSusChem 2014, 7:2022-2029. (n/a-n/a). 10.1002/cssc.201400079.
10. Balat M. Production of bioethanol from lignocellulosic materials via the biochemical pathway: a review. Energy Convers. Manag. 2011, 52(2):858-875.
11. Bergenstrahle M., Wohlert J., et al. Simulation studies of the insolubility of cellulose. Carbohydr. Res. 2010, 345(14):2060-2066.
12. Bermejo-Deval R., Assary R.S., et al. Metalloenzyme-like catalyzed isomerizations of sugars by Lewis acid zeolites. Proc. Natl. Acad. Sci. USA 2012, 109(25):9727-9732.
13. Bermejo-Deval R., Gounder R., et al. Framework and extraframework tin sites in zeolite beta react glucose differently. ACS Catal. 2012, 2(12):2705-2713.
14. Biarnés X., Pietrucci F., et al. METAGUI. A VMD interface for analyzing metadynamics and molecular dynamics simulations. Comput. Phys. Commun. 2012, 183(1):203-211.
15. Bilik V. Reactions of saccharides catalyzed by molybdate ions. II. Epimerization of d-glucose and d-mannose. Chem. Pap. 1972, 26:183-186.
16. Bilik V., Caplovic J. Reactions of saccharides catalyzed by molybdate ions. VII. Preparation of l-ribose, d-, and l-lyxose. Chem. Pap. 1973, 27(4):547-550.
17. Bilik V., Knezek I. Reactions of saccharides catalyzed by molybdate ions XL. Inhibition of the epimerization of aldoses. Chem. Pap. 1990, 44(1):89-96.
18. Bílik V., Petrus L. Selective transformation of 3-deoxy-d-arabino-hexose and 3-deoxy-d-ribo-hexose to 3-deoxy-d-erythro-hexulose. Collect. Czechoslov. Chem. Commun. 1978, 43:1159-1162.
19. Bilik V., Stancovik L. Reactions of saccharides catalyzed by molybdate ions. VI. Epimerization of aldotetroses. Chem. Pap. 1973, 27(4):544-546.
20. Bílik V., Petrus L., et al. Preparation of d-[U-14C]aldopentoses from any d-[U-14C]aldopentose. Collect. Czechoslov. Chem. Commun. 1978, 43:1163-1166.
21. Bilik V., Petrus L., et al. Reactions of saccharides catalyzed by molybdate ions. XXI. Preparation of some ω-deoxyaldoses. Chem. Pap. 1978, 32(3):372-377.
22. Bilik V., Petrus L., et al. Reactions of saccharides catalyzed by molybdate ions. XV Mechanism of the epimerization reaction. Chem. Pap. 1975, 29(5):690-693.
23. Binder J.B., Raines R.T. Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals. J. Am. Chem. Soc. 2009, 131(5):1979-1985.
24. BioEneregyTechnologyOffice, 2013. Biochemical Conversion: Using Enzymes, Microbes, and Catalysts to Make Fuels and Chemicals. US Department of Energy, Energy Efficieny and Renewable Energy (BioEneregy Technologies Office), USA.
25. Di Blasi C. Heat, momentum and mass transport through a shrinking biomass particle exposed to thermal radiation. Chem. Eng. Sci. 1996, 51(7):1121-1132.
26. Blasi D. Kinetic and heat transfer control in the slow and flash pyrolysis of solids. Ind. Eng. Chem. Res. 1996, 35:37-46.
27. Blondeau J., Jeanmart H. Biomass pyrolysis at high temperatures: prediction of gaseous species yields from an anisotropic particle. Biomass Bioenergy 2012, 41:107-121.
28. Brandt A., Gräsvik J., et al. Deconstruction of lignocellulosic biomass with ionic liquids. Green Chem. 2013, 15(3):550.
29. Bridgwater A.V. Review of fast pyrolysis of biomass and product upgrading. Biomass Bioenergy 2012, 38(0):68-94.
30. Bussi G., Laio A., et al. Equilibrium free energies from nonequilibrium metadynamics. Phys. Rev. Lett. 2006, 96(9).
31. Cai L., Liu Y., et al. Impact of hydrogen bonding on inclusion layer of urea to cellulose: study of molecular dynamics simulation. Polymer 2012, 53(5):1124-1130.
32. Caputo A.C., Palumbo M., et al. Economics of biomass energy utilization in combustion and gasification plants: effects of logistic variables. Biomass Bioenergy 2005, 28(1):35-51.
33. Car R., Parrinello M. Unified approach for molecular-dynamics and density-functional theory. Phys. Rev. Lett. 1985, 55(22):2471-2474.
34. Caratzoulas S., Vlachos D.G. Converting fructose to 5-hydroxymethylfurfural: a quantum mechanics/molecular mechanics study of the mechanism and energetics. Carbohydr. Res. 2011, 346(5):664-672.
35. Chaurasia A.S., Kulkarni B.D. Most sensitive parameters in pyrolysis of shrinking biomass particle. Energy Convers. Manag. 2007, 48(3):836-849.
36. Chen M., Bomble Y.J., et al. Molecular dynamics simulations of the interaction of glucose with imidazole in aqueous solution. Carbohydr. Res. 2012, 349:73-77.
37. Chheda J.N., Huber G.W., et al. Liquid-Phase catalytic processing of biomass-derived oxygenated hydrocarbons to fuels and chemicals. Angew. Chem. Int. Ed. 2007, 46(38):7164-7183.
38. Chiaramonti D., Oasmaa A., et al. Power generation using fast pyrolysis liquids from biomass. Renew. Sustain. Energy Rev. 2007, 11(6):1056-1086.
39. Choudhary V., Pinar A.B., et al. Comparison of homogeneous and heterogeneous catalysts for glucose-to-fructose isomerization in aqueous media. ChemSusChem 2013, 6(12):2369-2376.
40. Choudhary V., Pinar A.B., et al. Xylose isomerization to xylulose and its dehydration to furfural in aqueous media. ACS Catal. 2011, 1(12):1724-1728.
41. Choudhary V., Burnett R.I., et al. Dehydration of glucose to 5-(hydroxymethyl)furfural and anhydroglucose: thermodynamic insights. J. Phys. Chem. C 2012, 116(8):5116-5120.
42. Choudhary V., Caratzoulas S., et al. Insights into the isomerization of xylose to xylulose and lyxose by a Lewis acid catalyst. Carbohydr. Res. 2013, 368:89-95.
43. Choudhary V., Mushrif S.H., et al. 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. J. Am. Chem. Soc. 2013, 135(10):3997-4006.
44. Climent M.J., Corma A., et al. Converting carbohydrates to bulk chemicals and fine chemicals over heterogeneous catalysts. Green Chem. 2011, 13(3):520-540.
45. Cole A.C., Jensen J.L., et al. Novel Brønsted acidic ionic liquids and their use as dual solvent-catalysts. J. Am. Chem. Soc. 2002, 124(21):5962-5963.
46. Collard F.-X., Blin J. A review on pyrolysis of biomass constituents: mechanisms and composition of the products obtained from the conversion of cellulose, hemicelluloses and lignin. Renew. Sustain. Energy Rev. 2014, 38(0):594-608.
47. Comba P., Kerscher M. Computation of structures and properties of transition metal compounds. Coord. Chem. Rev. 2009, 253(5-6):564-574.
48. Couhert C., Commandre J.-M., et al. Is it possible to predict gas yields of any biomass after rapid pyrolysis at high temperature from its composition in cellulose, hemicellulose and lignin?. Fuel 2009, 88(3):408-417.
49. Cybulsk A., Kuster B.F.M., et al. The kinetics of the molybdate-catalysed epimerization d-glucose and d-mannose in aqueous solutions. J. Mol. Catal. 1991, 68:87-103.
50. Dahl S., Logadottir A., et al. Electronic factors in catalysis: the volcano curve and the effect of promotion in catalytic ammonia synthesis. Appl. Catal. A: General 2001, 222(1-2):19-29.
51. Dauenhauer P.J., Colby J.L., et al. Reactive boiling of cellulose for integrated catalysis through an intermediate liquid. Green Chem. 2009, 11(10):1555-1561.
52. Davis S.E., Zope B.N., et al. On the mechanism of selective oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over supported Pt and Au catalysts. Green Chem. 2011.
53. Deeth R.J. The ligand field molecular mechanics model and the stereoelectronic effects of d and s electrons. Coord. Chem. Rev. 2001, 212:11-34.
54. Deeth R.J., Anastasi A., et al. Molecular modelling for transition metal complexes: dealing with d-electron effects. Coord. Chem. Rev. 2009, 253(5-6):795-816.
55. Dellago C., Bolhuis P.G., et al. Transition path sampling and the calculation of rate constants. J. Chem. Phys. 1998, 108(5):1964-1977.
56. Ding Z.-D., Chi Z., et al. Theoretical and experimental investigation on dissolution and regeneration of cellulose in ionic liquid. Carbohydr. Polym. 2012, 89(1):7-16.
57. Domínguez de María P. Recent trends in (ligno)cellulose dissolution using neoteric solvents: switchable, distillable and bio-based ionic liquids. J. Chem. Technol. Biotechnol. 2014, 89(1):11-18.
58. Dong H., Nimlos M.R., et al. The effects of water on β-d-xylose condensation reactions. J. Phys. Chem. A 2009, 113(30):8577-8585.
59. Dufour A., Ouartassi B., et al. Modelling intra-particle phenomena of biomass pyrolysis. Chem. Eng. Res. Des. 2011, 89(10):2136-2146.
60. van Duin A.C.T., Dasgupta S., et al. ReaxFF: a reactive force field for hydrocarbons. J. Phys. Chem. A 2001, 105(41):9396-9409.
61. Ensing B., Laio A., et al. New approach to efficiently explore the free energy surface, trace the reaction pathways and converge the free energy barriers. Abstr. Pap. Am. Chem. Soc. 2005, 229. (U767-U767).
62. Ensing B., Laio A., et al. A recipe for the computation of the free energy barrier and the lowest free energy path of concerted reactions. J. Phys. Chem. B 2005, 109(14):6676-6687.
63. Faradjian A.K., Elber R. Computing time scales from reaction coordinates by milestoning. J. Chem. Phys. 2004, 120(23):10880-10889.
64. Feng S., Voth G.a. Molecular dynamics simulations of imidazolium-based ionic liquid/water mixtures: alkyl side chain length and anion effects. Fluid Phase Equilib. 2010, 294(1-2):148-156.
65. Fleming K.L., Pfaendtner J. Characterizing the catalyzed hydrolysis of β-1,4 glycosidic bonds using density functional theory. J. Phys. Chem. A 2013, 117(51):14200-14208.
66. Fort D.A., Remsing R.C., et al. Can ionic liquids dissolve wood? Processing and analysis of lignocellulosic materials with 1-n-butyl-3-methylimidazolium chloride. Green Chem. 2007, 9(1):63-69.
67. Frost D.S., Machas M., et al. Molecular dynamics studies on the adaptability of an ionic liquid in the extraction of solid nanoparticles. Langmuir: ACS J. Surf. Coll. 2012, 28(39):13924-13932.
68. Fukuoka A., Dhepe P.L. Catalytic conversion of cellulose into sugar alcohols. Angew. Chem. 2006, 118(31):5285-5287.
69. Gallo J.M.R., Alonso D.M., et al. Production and upgrading of 5-hydroxymethylfurfural using heterogeneous catalysts and biomass-derived solvents. Green Chem. 2013, 15(1):85-90.
70. Garcia-Perez M., Wang X.S., et al. Fast pyrolysis of oil mallee woody biomass: effect of temperature on the yield and quality of pyrolysis products. Ind. Eng. Chem. Res. 2008, 47(6):1846-1854.
71. Guan J., Cao Q., et al. The mechanism of glucose conversion to 5-hydroxymethylfurfural catalyzed by metal chlorides in ionic liquid: a theoretical study. Comput. Theor. Chem. 2011, 963(2-3):453-462.
72. Gunther W.R., Duong Q., et al. Catalytic consequences of borate complexation and pH on the epimerization of l-arabinose to l-ribose in water catalyzed by Sn-Beta zeolite with borate salts. J. Mol. Catal. A: Chemical 2013, 379:294-302.
73. Gunther W.R., Wang Y., et al. Sn-Beta zeolites with borate salts catalyse the epimerization of carbohydrates via an intramolecular carbon shift. Nat. Commun. 2012, 3:1109.
74. Guo N., Caratzoulas S., et al. A perspective on the modeling of biomass processing. Energy Environ. Sci. 2012, 5(5):6703-6716.
75. Hagge M.J., Bryden K.M. Modeling thermally thick pyrolysis of wood. Chem. Eng. Sci. 2002, 57:2811-2823.
76. Hamann D.R., Schluter M., et al. Norm-conserving pseudopotentials. Phys. Rev. Lett. 1979, 43(20):1494-1497.
77. Haseli Y., van Oijen J.A., et al. Modeling biomass particle pyrolysis with temperature-dependent heat of reactions. J. Anal. Appl. Pyrolysis 2011, 90(2):140-154.
78. Haseli Y., van Oijen J.A., et al. Numerical study of the conversion time of single pyrolyzing biomass particles at high heating conditions. Chem. Eng. J. 2011, 169(1-3):299-312.
79. Haseli Y., van Oijen J.A., et al. Predicting the pyrolysis of single biomass particles based on a time and space integral method. J. Anal. Appl. Pyrolysis 2012, 96:126-138.
80. Haseli Y., van Oijen J.A., et al. A simplified pyrolysis model of a biomass particle based on infinitesimally thin reaction front approximation. Energy Fuels 2012, 26(6):3230-3243.
81. Heinen A.W., Peters J.A., et al. The combined hydrolysis and hydrogenation of inulin catalyzed by bifunctional Ru/C. Carbohydr. Res. 2001, 330(3):381-390.
82. Henkelman G., Jonsson H. Improved tangent estimate in the nudged elastic band method for finding minimum energy paths and saddle points. J. Chem. Phys. 2000, 113(22):9978-9985.
83. Heo H.S., Park H.J., et al. Influence of operation variables on fast pyrolysis of Miscanthus sinensis var. purpurascens. Bioresour. Technol. 2010, 101(10):3672-3677.
84. Hohenberg P., Kohn W. Inhomogeneous electron gas. Phys. Rev. B 1964, 136(3B):B864-&..
85. 2O/cellulose molar ratios, temperatures, times, and different ILs on the production of monosaccharides and 5-hydroxymethylfurfural (HMF). Catal. Today 2011, 174(1):65-69.
86. Huang J., Li X., et al. Theoretical studies on pyrolysis mechanism of guaiacol as lignin model compound. J. Renew. Sustain. Energy 2013, 5(4):043112.
87. Huang J., Liu C., et al. Theoretical studies on pyrolysis mechanism of xylopyranose. Comput. Theor. Chem. 2012, 1001:44-50.
88. Huang X., Liu C., et al. Theory studies on pyrolysis mechanism of phenethyl phenyl ether. Comput. Theor. Chem. 2011, 976(1-3):51-59.
89. Huo F., Liu Z., et al. Cosolvent or antisolvent? A molecular view of the interface between ionic liquids and cellulose upon addition of another molecular solvent. J. Phys. Chem. B 2013, 117(39):11780-11792.
90. Iannuzzi M., Laio A., et al. Efficient exploration of reactive potential energy surfaces using Car-Parrinello molecular dynamics. Phys. Rev. Lett. 2003, 90(23).
91. Jadhav A.H., Kim H., et al. Efficient selective dehydration of fructose and sucrose into 5-hydroxymethylfurfural (HMF) using dicationic room temperature ionic liquids as a catalyst. Catal. Commun. 2012, 21:96-103.
92. Jensen F., Norrby P.O. Transition states from empirical force fields. Theor. Chem. Accounts 2003, 109(1):1-7.
93. Ji N., Zhang T., et al. Direct catalytic conversion of cellulose into ethylene glycol using nickel-promoted tungsten carbide catalysts. Angew. Chem. Int. Ed. 2008, 47(44):8510-8513.
94. Ju F., VanderVelde D., et al. Molybdenum-based polyoxometalates as highly active and selective catalysts for the epimerization of aldoses. ACS Catal. 2014, 4(5):1358-1364.
95. Kandziolka M.V., Kidder M.K., et al. Aromatic-hydroxyl interaction of an alpha-aryl ether lignin model-compound on SBA-15, present at pyrolysis temperatures. Phys. Chem. Chem. Phys. 2014.
96. Kayser H., Rodriguez-Ropero F., et al. Mechanistic comparison of saccharide depolymerization catalyzed by dicarboxylic acids and glycosidases. RSC Adv. 2013, 3(24):9273-9278.
97. Kislenko S.A., Samoylov I.S., et al. Molecular dynamics simulation of the electrochemical interface between a graphite surface and the ionic liquid [BMIM][PF6]. Phys. Chem. Chem. Phys. 2009, 11(27):5584-5590.
98. Kohn W., Sham L.J. Self-consistent equations including exchange and correlation effects. Phys. Rev. 1965, 140(4A):1133-&..
99. Kosan B., Michels C., et al. Dissolution and forming of cellulose with ionic liquids. Cellulose 2008, 15(1):59-66.
100. Laio A., Gervasio F.L. Metadynamics: a method to simulate rare events and reconstruct the free energy in biophysics, chemistry and material science. Rep. Prog. Phys. 2008, 71(12).
101. Laio A., Parrinello M. Escaping free-energy minima. Proc. Natl. Acad. Sci. USA 2002, 99(20):12562-12566.
102. Laio, A., Parrinello, M., 2006. Computing Free Energies and Accelerating Rare Events with Metadynamics. Computer Simulations in Condensed Matter Systems: From Materials to Chemical Biology, vol. 1. Springer, Berlin, Heidelberg, pp. 315-347.
103. Laio A., Rodriguez-Fortea A., et al. Assessing the accuracy of metadynamics. J. Phys. Chem. B 2005, 109(14):6714-6721.
104. Lange J.-p., Solutions S.G. Lignocellulose conversion: an introduction to chemistry. Biofuels Bioprod. Biorefining 2007, 1:39-48.
105. Lateef H., Grimes S., et al. Separation and recovery of cellulose and lignin using ionic liquids: a process for recovery from paper-based waste. J. Chem. Technol. Biotechnol. 2009, 84(12):1818-1827.
106. Li, K., Jia, X., et al., 2014. Highly efficient and easily recyclable ionic liquid-based polyoxometalate catalysts for bio-lubricant production: experimental and theoretical studies (submitted for publication).
107. Liang X., Montoya A., et al. Local site selectivity and conformational structures in the glycosidic bond scission of cellobiose. J. Phys. Chem. B 2011, 115(36):10682-10691.
108. Lima S., Antunes M.M., et al. Ionic liquids as tools for the acid-catalyzed hydrolysis/dehydration of saccharides to furanic aldehydes. ChemCatChem 2011, 3(11):1686-1706.
109. Lin Y., Cho J., et al. Reaction-transport model for the pyrolysis of shrinking cellulose particles. Chem. Eng. Sci. 2012, 74:160-171.
110. Lin Y.-C., Huber G.W. The critical role of heterogeneous catalysis in lignocellulosic biomass conversion. Energy Environ. Sci. 2009, 2(1):68-80.
111. Liu B., Cheng L., et al. Effects of van der Waals density functional corrections on trends in furfural adsorption and hydrogenation on close-packed transition metal surfaces. Surf. Sci. 2014, 622:51-59.
112. Liu B., Zhang Z., et al. Microwave-assisted catalytic conversion of cellulose into 5-hydroxymethylfurfural in ionic liquids. Chem. Eng. J. 2013, 215-216:517-521.
113. Liu C.-Z., Wang F., et al. Ionic liquids for biofuel production: opportunities and challenges. Appl. Energy 2012, 92:406-414.
114. Liu D., Chen E.Y.X. Polymeric ionic liquid (PIL)-supported recyclable catalysts for biomass conversion into HMF. Biomass Bioenergy 2013, 48:181-190.
115. Liu Z., Zhang F.-S. Effects of various solvents on the liquefaction of biomass to produce fuels and chemical feedstocks. Energy Convers. Manag. 2008, 49(12):3498-3504.
116. Marx, D., Hutter, J., 2000. Ab-initio molecular dynamics: theory and implementation. In: Grotendorst, J. (Ed.), Modern Methods and Algorithms of Quantum Chemistry Proceedings, vol. 1. John von Neumann Institute for Computing, Forschungszentrum Jülich, pp. 301-449.
117. Mayes H.B., Broadbelt L.J. Unraveling the reactions that unravel cellulose. J. Phys. Chem. A 2012, 116(26):7098-7106.
118. Mayes H.B., Nolte M.W., et al. The alpha-bet(a) of glucose pyrolysis: computational and experimental investigations of 5-hydroxymethylfurfural and levoglucosan formation reveal implications for cellulose pyrolysis. ACS Sustain. Chem. Eng. 2014, 2(6):1461-1473.
119. Mettler M.S., Vlachos D.G., et al. Top ten fundamental challenges of biomass pyrolysis for biofuels. Energy Environ. Sci. 2012, 7797-7809.
120. Mettler M.S., Mushrif S.H., et al. Revealing pyrolysis chemistry for biofuels production: conversion of cellulose to furans and small oxygenates. Energy Environ. Sci. 2012, 5(1):5414-5424.
121. Mettler M.S., Paulsen A.D., et al. The chain length effect in pyrolysis: bridging the gap between glucose and cellulose. Green Chem. 2012, 14(5):1284.
122. Mettler M.S., Paulsen A.D., et al. Pyrolytic conversion of cellulose to fuels: levoglucosan deoxygenation via elimination and cyclization within molten biomass. Energy Environ. Sci. 2012, 5(7):1-6.
123. Meyer B. The pseudopotential planewave approach. Computational Nanoscience: Do It Yourself!, vol. 31 2006, 1-13. John von Neumann Institute for Computing, Forschungszentrum Jülich. J. Grotendorst, S. Blügel, D. Marx (Eds.).
124. Miron R.A., Fichthorn K.A. Multiple-time scale accelerated molecular dynamics: addressing the small-barrier problem. Phys. Rev. Lett. 2004, 93(12).
125. Moliner M., Roman-Leshkov Y., et al. Tin-containing zeolites are highly active catalysts for the isomerization of glucose in water. Proc. Natl. Acad. Sci. USA 2010, 107(14):6164-6168.
126. Mushrif S.H., Caratzoulas S., et al. Understanding solvent effects in the selective conversion of fructose to 5-hydroxymethyl-furfural: a molecular dynamics investigation. Phys. Chem. Chem. Phys. 2012, 14(8):2637-2644.
127. Mushrif S.H., Varghese J.J., et al. Insights into the Cr (III) catalyzed isomerization mechanism of glucose to fructose in the presence of water using ab initio molecular dynamics. Phys. Chem. Chem. Phys. 2014, 16:19564-19572. 10.1039/c4cp02095b.
128. Nikbin N., Caratzoulas S., et al. A first principles-based microkinetic model for the conversion of fructose to 5-hydroxymethylfurfural. ChemCatChem 2012, 4(4):504-511.
129. Nikolakis V., Mushrif S.H., et al. Fructose-water-dimethylsulfoxide interactions by vibrational spectroscopy and molecular dynamics simulations. J. Phys. Chem. B 2012, 116(36):11274-11283.
130. Nikolla E., Román-Leshkov Y., et al. "One-Pot" synthesis of 5-(hydroxymethyl)furfural from carbohydrates using tin-beta zeolite. ACS Catal. 2011, 1(4):408-410.
131. Norrby P.O., Brandt P. Deriving force field parameters for coordination complexes. Coord. Chem. Rev. 2001, 212:79-109.
132. Okano T., Qiao K., et al. Dehydration of fructose to 5-hydroxymethylfurfural (HMF) in an aqueous acetonitrile biphasic system in the presence of acidic ionic liquids. Appl. Catal. A: General 2013, 451:1-5.
133. Okekunle P.O., Watanabe H., et al. Effect of biomass size and aspect ratio on intra-particle tar decomposition during wood cylinder pyrolysis. J. Therm. Sci. Technol. 2012, 7(1):1-15.
134. Olsson, C., Westman, G., 2013. Direct dissolution of cellulose: background, means and applications. In: Theo van de Ven, Louis Godbout (Eds), Cellulose - Fundamental Aspects, InTech, Chapters published August 28, 2013 under CC BY 3.0 license, pp. 376, (ISBN 978-953-51-1183-2). http://dx.doi.org/10.5772/2705.
135. Ozbay N., Pütün A.E., et al. Bio-oil production from rapid pyrolysis of cottonseed cake: product yields and compositions. Int. J. Energy Res. 2006, 30(7):501-510.
136. Paine Iii J.B., Pithawalla Y.B., et al. Carbohydrate pyrolysis mechanisms from isotopic labeling: Part 2. The pyrolysis of d-glucose: general disconnective analysis and the formation of C1 and C2 carbonyl compounds by electrocyclic fragmentation mechanisms. J. Anal. Appl. Pyrolysis 2008, 82(1):10-41.
137. Pastore G., Smargiassi E., et al. Theory of abinitio molecular-dynamics calculations. Phys. Rev. A 1991, 44(10):6334-6347.
138. Payne M.C., Teter M.P., et al. Iterative minimization techniques for abinitio total-energy calculations - molecular-dynamics and conjugate gradients. Rev. Mod. Phys. 1992, 64(4):1045-1097.
139. Peters B. Validation of a numerical approach to model pyrolysis of biomass and assessment of kinetic data. Fuel 2011, 90(6):2301-2314.
140. Qi X., Watanabe M., et al. Synergistic conversion of glucose into 5-hydroxymethylfurfural in ionic liquid-water mixtures. Bioresour. Technol. 2012, 109:224-228.
141. Qian X., Liu D. Free energy landscape for glucose condensation and dehydration reactions in dimethyl sulfoxide and the effects of solvent. Carbohydr. Res. 2014, 388:50-60.
142. Qian X., Wei X. Glucose isomerization to fructose from ab initio molecular dynamics simulations. J. Phys. Chem. B 2012, 116(35):10898-10904.
143. Qu Y.-S., Song Y.-L., et al. Alkaline ionic liquids as catalysts: a novel and green process for the dehydration of carbohydrates to give 5-hydroxymethylfurfural. Ind. Eng. Chem. Res. 2012, 51(40):13008-13013.
144. Rai N., Caratzoulas S., et al. Role of silanol group in Sn-beta zeolite for glucose isomerization and epimerization reactions. ACS Catal. 2013, 3(10):2294-2298.
145. Remler D.K., Madden P.A. Molecular-dynamics without effective potentials via the Car-Parrinello approach. Mol. Phys. 1990, 70(6):921-966.
146. Román-Leshkov Y., Chheda J.N., et al. Phase modifiers promote efficient production of hydroxymethylfurfural from fructose. Science 2006, 312(5782):1933-1937.
147. Roman-Leshkov Y., Moliner M., et al. Mechanism of glucose isomerization using a solid lewis acid catalyst in water. Angew. Chem.-Int. Ed. 2010, 49(47):8954-8957.
148. Russo M.F., van Duin A.C.T. Atomistic-scale simulations of chemical reactions: bridging from quantum chemistry to engineering. Nucl. Instrum. Methods Phys. Res. Sect. B: Beam Interact. Mater. Atoms 2011, 269(14):1549-1554.
149. Sadhukhan A.K., Gupta P., et al. Modelling and experimental studies on pyrolysis of biomass particles. J. Anal. Appl. Pyrolysis 2008, 81(2):183-192.
150. Sadhukhan A.K., Gupta P., et al. Modelling of pyrolysis of large wood particles. Bioresour. Technol. 2009, 100(12):3134-3139.
151. Sarangi S.S., Raju S.G., et al. Molecular dynamics simulations of ionic liquid-vapour interfaces: effect of cation symmetry on structure at the interface. Phys. Chem. Chem. Phys. 2011, 13(7):2714-2722.
152. Schrodinger E. An undulatory theory of the mechanics of atoms and molecules. Phys. Rev. 1926, 28(6):1049-1070.
153. Seshadri V., Westmoreland P.R. Concerted reactions and mechanism of glucose pyrolysis and implications for cellulose kinetics. J. Phys. Chem. A 2012, 116(49):11997-12013.
154. Sharma A., Pareek V., et al. A phenomenological model of the mechanisms of lignocellulosic biomass pyrolysis processes. Comput. Chem. Eng. 2014, 60:231-241.
155. Shen J., Wang X.-S., et al. Effects of particle size on the fast pyrolysis of oil mallee woody biomass. Fuel 2009, 88(10):1810-1817.
156. Sreekanth M., Leckner B. Transient thermal behaviour of a cylindrical wood particle during devolatilization in a bubbling fluidized bed. Fuel Process. Technol. 2008, 89(9):838-850.
157. Ståhlberg T., Rodriguez-Rodriguez S., et al. Metal-free dehydration of glucose to 5-(hydroxymethyl)furfural in ionic liquids with boric acid as a promoter. Chem. - A Eur. J. 2011, 17(5):1456-1464.
158. Swatloski R.P., Spear S.K., et al. Dissolution of cellose with ionic liquids. J. Am. Chem. Soc. 2002, 124(18):4974-4975.
159. Tanase T., Shimizu F., et al. Novel C-2 epimerization of aldoses promoted by nickel(II) diamine complexes, involving a stereospecific pinacol-type 1,2-carbon shift. Inorg. Chem. 1988, 27(23):4085-4094.
160. Tong X., Li Y. Efficient and selective dehydration of fructose to 5-hydroxymethylfurfural catalyzed by Brønsted-acidic ionic liquids. ChemSusChem 2010, 3(3):350-355.
161. Torres A.I., Daoutidis P., et al. Continuous production of 5-hydroxymethylfurfural from fructose: a design case study. Energy Environ. Sci. 2010, 3(10):1560-1572.
162. Torrie G.M., Valleau J.P. Non-physical sampling distributions in Monte-Carlo free-energy estimation - umbrella sampling. J. Comput. Phys. 1977, 23(2):187-199.
163. Tsai W.T., Lee M.K., et al. Fast pyrolysis of rice husk: product yields and compositions. Bioresour. Technol. 2007, 98(1):22-28.
164. Tsuzuki S., Shinoda W., et al. Molecular dynamics simulations of ionic liquids: cation and anion dependence of self-diffusion coefficients of ions. J. Phys. Chem. B 2009, 113(31):10641-10649.
165. Uzun B.B., Pütün A.E., et al. Fast pyrolysis of soybean cake: product yields and compositions. Bioresour. Technol. 2006, 97(4):569-576.
166. Vasiliu M., Guynn K., et al. Prediction of the thermodynamic properties of key products and intermediates from biomass. J. Phys. Chem. C 2011, 115(31):15686-15702.
167. Vasiliu M., Jones A.J., et al. Prediction of the thermodynamic properties of key products and intermediates from biomass. II. J. Phys. Chem. C 2012, 116(39):20738-20754.
168. Verdeguer P., Merat N., et al. Oxydation catalytique du HMF en acide 2,5-furane dicarboxylique. J. Mol. Catal. 1993, 85(3):327-344.
169. Vinu R., Broadbelt L.J. A mechanistic model of fast pyrolysis of glucose-based carbohydrates to predict bio-oil composition. Energy Environ. Sci. 2012, 5(12):9808.
170. Wang S., Guo X., et al. Influence of the interaction of components on the pyrolysis behavior of biomass. J. Anal. Appl. Pyrolysis 2011, 91(1):183-189.
171. Wang S., Ru B., et al. Degradation mechanism of monosaccharides and xylan under pyrolytic conditions with theoretic modeling on the energy profiles. Bioresour Technol 2013, 143:378-383.
172. Weinan E., Ren W.Q., et al. Finite temperature string method for the study of rare events. J. Phys. Chem. B 2005, 109(14):6688-6693.
173. Xiong R., Sandler S.I., et al. Molecular screening of alcohol and polyol adsorption onto MFI-type zeolites. Langmuir 2012, 28(9):4491-4499.
174. Yan N., Zhao C., et al. One-step conversion of cellobiose to C6-alcohols using a ruthenium nanocluster catalyst. J. Am. Chem. Soc. 2006, 128(27):8714-8715.
175. Yang G., Pidko E.A., et al. The mechanism of glucose isomerization to fructose over Sn-BEA zeolite: a periodic density functional theory study. ChemSusChem 2013, 6(9):1688-1696.
176. Yang H., Yan R., et al. In-depth investigation of biomass pyrolysis based on three major components: hemicellulose, cellulose and lignin. Energy Fuels 2005, 20(1):388-393.
177. Zabaniotou a., Damartzis T. Modelling the intra-particle transport phenomena and chemical reactions of olive kernel fast pyrolysis. J. Anal. Appl. Pyrolysis 2007, 80(1):187-194.
178. Zakzeski J., Bruijnincx P.C.A., et al. The catalytic valorization of lignin for the production of renewable chemicals. Chem. Rev. 2010, 110(6):3552-3599.
179. Zhang M., Geng Z., et al. Density functional theory (DFT) study on the dehydration of cellulose. Energy Fuels 2011, 25(6):2664-2670.
180. Zhang X., Li J., et al. Formation mechanism of levoglucosan and formaldehyde during cellulose pyrolysis. Energy Fuels 2011, 25(8):3739-3746.
181. Zhang X., Yang W., et al. Levoglucosan formation mechanisms during cellulose pyrolysis. J. Anal. Appl. Pyrolysis 2013, 104:19-27.
182. Zhang Y., Liu C., et al. Mechanism studies on β-d-glucopyranose pyrolysis by density functional theory methods. J. Anal. Appl. Pyrolysis 2014, 105:23-34.
183. Zhang Y., Pidko E.A., et al. Molecular aspects of glucose dehydration by chromium chlorides in ionic liquids. Chem. - A Eur. J. 2011, 17(19):5281-5288.
184. Zhang Y., Wang A., et al. A new 3D mesoporous carbon replicated from commercial silica as a catalyst support for direct conversion of cellulose into ethylene glycol. Chem. Commun. 2010, 46(6):862-864.
185. Zheng M.-Y., Wang A.-Q., et al. Transition metal-tungsten bimetallic catalysts for the conversion of cellulose into ethylene glycol. ChemSusChem 2010, 3(1):63-66.
186. Zope B.N., Hibbitts D.D., et al. Reactivity of the gold/water interface during selective oxidation catalysis. Science 2010, 330(6000):74-78.