Acidolysis of α-O-4 Aryl-Ether Bonds in Lignin Model Compounds: A Modeling and Experimental Study

ACS Sustainable Chemistry and Engineering

Volumn 3, Issue 7, 2015, Pages 1339-1347

  Pelzer, Adam W ^c   Sturgeon, Matthew R ^a   Yanez, Abraham J ^c   Chupka, Gina ^a   O'Brien, Marykate H ^a   Katahira, Rui ^a   Cortright, Randy D ^b   Woods, Liz ^b   Beckham, Gregg T ^a   Broadbelt, Linda J ^c  

^a NATIONAL RENEWABLE ENERGY LABORATORY   (United States)

^b Virent Energy Systems Inc   (United States)

^c Northwestern University   (United States)

Author keywords

Density functional theory; Ether bond; Microkinetic modeling; O 4

Indexed keywords

ALKYLATION; CELLULOSE; ETHERS; FUNCTIONAL GROUPS; KINETICS; LIGNIN; METHYLATION; REACTION KINETICS; THERMODYNAMICS;

CELLULOSE AND HEMICELLULOSE; DILUTE ACID PRETREATMENT; DILUTE-ACID HYDROLYSIS; ETHER BOND; LIGNIN DEPOLYMERIZATION; LIGNOCELLULOSIC BIOMASS; MICROKINETIC MODELING; THERMODYNAMICS AND KINETICS;

DENSITY FUNCTIONAL THEORY;

EID: 84936792235     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/acssuschemeng.5b00070     Document Type: Article

References (63)

1. Chundawat, S. P.; Beckham, G. T.; Himmel, M. E.; Dale, B. E. Deconstruction of lignocellulosic biomass to fuels and chemicals Annu. Rev. Chem. Biomol. Eng. 2011, 2, 121-145
2. Davda, R. R.; Shabaker, J. W.; Huber, G. W.; Cortright, R. D.; Dumesic, J. A. A review of catalytic issues and process conditions for renewable hydrogen and alkanes by aqueous-phase reforming of oxygenated hydrocarbons over supported metal catalysts Appl. Catal., B 2005, 56, 171-186
3. Alonso, D. M.; Bond, J. Q.; Dumesic, J. A. Catalytic conversion of biomass to biofuels Green Chem. 2010, 12, 1493-1513
4. Atsumi, S.; Liao, J. C. Metabolic engineering for advanced biofuels production from Escherichia coli Curr. Opin. Biotechnol. 2008, 19, 414-419
5. Lee, S. Y.; Park, J. H.; Jang, S. H.; Nielsen, L. K.; Kim, J.; Jung, K. S. Fermentative butanol production by Clostridia Biotechnol. Bioeng. 2008, 101, 209-228
6. Peralta-Yahya, P. P.; Zhang, F.; del Cardayre, S. B.; Keasling, J. D. Microbial engineering for the production of advanced biofuels Nature 2012, 488, 320-328
7. Achyuthan, K. E.; Achyuthan, A. M.; Adams, P. D.; Dirk, S. M.; Harper, J. C.; Simmons, B. A.; Singh, A. K. Supramolecular self-assembled chaos: Polyphenolic lignin's barrier to cost-effective lignocellulosic biofuels Molecules 2010, 15, 8641-8688
8. Chapple, C.; Ladisch, M.; Meilan, R. Loosening lignin's grip on biofuel production Nat. Biotechnol. 2007, 25, 746-748
9. Ragauskas, A. J.; Beckham, G. T.; Biddy, M. J.; Chandra, R.; Chen, F.; Davis, M. F.; Davison, B. H.; Dixon, R. A.; Gilna, P.; Keller, M.,et al. Lignin valorization: Improving lignin processing in the biorefinery. Science 2014, 344.
10. Fu, C.; Mielenz, J. R.; Xiao, X.; Ge, Y.; Hamilton, C. Y.; Rodriguez, M.; Chen, F.; Foston, M.; Ragauskas, A.; Bouton, J.,et al. Genetic manipulation of lignin reduces recalcitrance and improves ethanol production from switchgrass Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 3803-3808
11. Bonawitz, N. D.; Kim, J. I.; Tobimatsu, Y.; Ciesielski, P. N.; Anderson, N. A.; Ximenes, E.; Maeda, J.; Ralph, J.; Donohoe, B. S.; Ladisch, M.,et al. Disruption of mediator rescues the stunted growth of a lignin-deficient Arabidopsis mutant Nature 2014, 509, 376-380
12. Chen, F.; Dixon, R. A. Lignin modification improves fermentable sugar yields for biofuel production Nat. Biotechnol. 2007, 25, 759-761
13. Lundquist, K. Acid degradation of lignin. Part 2: Separation and identification of low molecular weight phenols Acta Chem. Scand. 1970, 24, 889-907
14. Linger, J. G.; Vardon, D. R.; Guarnieri, M. T.; Karp, E. M.; Hunsinger, G. B.; Franden, M. A.; Johnson, C. W.; Chupka, G.; Strathmann, T. J.; Pienkos, P. T. Lignin valorization through integrated biological funneling and chemical catalysis Proc. Natl. Acad. Sci. U. S. A. 2014, 111, 12013-12018
15. Amen-Chen, C.; Pakdel, H.; Roy, C. Production of monomeric phenols by thermochemical conversion of biomass: A review Bioresour. Technol. 2001, 79, 277-299
16. Zakzeski, J.; Bruijnincx, P. C. A.; Jongerius, A. L.; Weckhuysen, B. M. Valorization of lignin for the production of renewable chemicals Chem. Rev. 2010, 110, 3552-3599
17. Lundquist, K.; Ericsson, L. Acid degradation of lignin. Part 3: Formation of formaldehyde Acta Chem. Scand. 1970, 24, 3681-3685
18. Lundquist, K.; Lundgren, R. Acid degradation of lignin. Part 7: Cleavage of ether bonds Acta Chem. Scand. 1972, 26, 2005-2023
19. Lundquist, K. Acid degradation of lignin. Part 8: Low molecualar weight phenols from acidolysis of birch lignin Acta Chem. Scand. 1973, 27, 2597-2606
20. Lundquist, K.; Hedlund, K. Acid degradation of lignin. Part 1: The formation of ketones of Hte guaiacylpropane series Acta Chem. Scand. 1967, 21, 1750-1754
21. Agbor, V. B.; Cicek, N.; Sparling, R.; Berlin, A.; Levin, D. B. Biomass pretreatment: Fundamentals toward application Biotechnol. Adv. 2011, 29, 675-685
22. Pepper, J. M.; Siddiqueullah, M. The effect of initial acid concentration on the lignin isolated by the acidolysis of aspen wood Can. J. Chem. 1961, 39, 1454-1461
23. Pu, Y.; Hu, F.; Huang, F.; Davison, B. H.; Ragauskas, A. J. Assessing the molecular structure basis for biomass recalcitrance during dilute acid and hydrothermal pretreatments Biotechnol. Biofuels 2013, 6, 15
24. Sarkanen, K. V.; Ludwig, C. H. Lignins: Occurrence, Formation, Structure and Reactions; Wiley-Interscience: New York, 1971.
25. Feldman, D.; LaCasse, M.; Beznaczuk Lignin-polymer systems and some applications Prog. Polym. Sci. 1987, 12, 271-299
26. Grabber, J. H. How do lignin composition, structure, and cross-linking affect degradability? A review of cell wall model studies Crop Sci. 2005, 45, 820-831
27. Heitner, C.; Dimmel, D.; Schmidt, J. A. Lignin and Lignans Advances in Chemistry; Taylor & Francis: Boca Raton, FL, 2010.
28. Boerjan, W.; Ralph, J.; Baucher, M. Lignin biosynthesis Annu. Rev. Plant Biol. 2003, 54, 519-546
29. Dolgonosov, B. M.; Gubernatorova, T. N. Modeling the biodegradation of multicomponent organic matter in an aquatic environment: 2. Analysis of the structural organization of lignin Water Resour. 2010, 37, 320-331
30. Roberts, V.; Fendt, S.; Lemonidou, A. A.; Lercher, J. A. Influence of alkali carbonates on benzyl phenyl ether cleavage pathways in superheated water Appl. Catal., B 2010, 95, 71-77
31. 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
32. Sturgeon, M. R.; Kim, S.; Lawrence, K.; Paton, R. S.; Chmely, S. C.; Nimlos, M.; Foust, T. D.; Beckham, G. T. A mechanistic investigation of acid-catalyzed cleavage of aryl-ether linkages: Implications for lignin depolymerization in acidic environments ACS Sustainable Chem. Eng. 2014, 2, 472-485
33. Grabow, L. C.; Gokhale, A. A.; Evans, S. T.; Dumesic, J. A.; Mavrikakis, M. Mechanism of the water gas shift reaction on Pt: First principles, experiments, and microkinetic modeling J. Phys. Chem. C 2008, 112, 4608-4617
34. Bera, T.; Thybaut, J. W.; Marin, G. B. Single-event microkinetics of aromatics hydrogenation on Pt/H-ZSM22 Ind. Eng. Chem. Res. 2011, 50, 12933-12945
35. Nikbin, N.; Caratzoulas, S.; Vlachos, D. G. A first principles-based microkinetic model for the conversion of fructose to 5-hydroxymethylfurfural ChemCatChem 2012, 4, 504-511
36. Craciun, I.; Reyniers, M.-F.; Marin, G. B. Liquid-phase alkylation of benzene with octenes over Y zeolites: Kinetic modeling including acidity descriptors J. Catal. 2012, 294, 136-150
37. Ma, R.; Schuette, G. F.; Broadbelt, L. J. Insights into the relationship of catalytic activity and structure: A comparison study of three carbonic anhydrase mimics Int. J. Chem. Kinet. 2014, 46, 683-700
38. Ma, R.; Schuette, G. F.; Broadbelt, L. J. Microkinetic modeling of CO2 hydrolysis over Zn-(1,4,7,10-tetraazacyclododecane) catalyst based on first principles: Revelation of rate-determining step J. Catal. 2014, 317, 176-184
39. 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, 9808-9826
40. Bjorkman, K. R.; Schoenfeldt, N. J.; Notestein, J. M.; Broadbelt, L. J. Microkinetic modeling of cis -cyclooctene oxidation on heterogeneous Mn-tmtacn complexes J. Catal. 2012, 291, 17-25
41. Mayes, H. B.; Broadbelt, L. J. Unraveling the reactions that unravel cellulose J. Phys. Chem. A 2012, 116, 7098-7106
42. Mayes, H. B.; Tian, J.; Nolte, M. W.; Shanks, B. H.; Beckham, G. T.; Gnanakaran, S.; Broadbelt, L. J. Sodium ion interactions with aqueous glucose: Insights from quantum mechanics, molecular dynamics, and experiment J. Phys. Chem. B 2013, 118, 1990-2000
43. Mayes, H. B.; Nolte, M. W.; Beckham, G. T.; Shanks, B. H.; Broadbelt, L. J. The alpha-bet(a) of glucose pyrolysis: Computational and experimental investigations of 5-hydroxymethylfurfural and levoglucosan formation reveal implications for cellulose pyrolysis ACS Sustainable Chem. Eng. 2014, 2, 1461-1473
44. Zhou, X.; Nolte, M. W.; Mayes, H. B.; Shanks, B. H.; Broadbelt, L. J. Experimental and mechanistic modeling of fast pyrolysis of neat glucose-based carbohydrates. 1. Experiments and development of a detailed mechanistic model Ind. Eng. Chem. Res. 2014, 53, 13274-13289
45. Zhou, X.; Nolte, M. W.; Shanks, B. H.; Broadbelt, L. J. Experimental and mechanistic modeling of fast pyrolysis of neat glucose-based carbohydrates. 2. Validation and evaluation of the mechanistic model Ind. Eng. Chem. Res. 2014, 53, 13290-13301
46. Wu, X. Y.; Lü, X. Y. Hydrolysis kinetics of benzyl phenyl ether in high temperature liquid water Chin. Chem. Lett. 2011, 22, 733-737
47. He, J.; Lu, L.; Zhao, C.; Mei, D.; Lercher, J. A. Mechanisms of catalytic cleavage of benzyl phenyl ether in aqueous and apolar phases J. Catal. 2014, 311, 41-51
48. Siskin, M.; Brons, G.; Vaughn, S. N. Aqueous organic chemistry. 3. Aquathermolysis: Reactivity of ethers and esters Energy Fuels 1990, 4, 488-492
49. Townsend, S. H.; Abraham, M. A.; Hupper, G. L.; Klein, M. T.; Paspek, S. C. Solvent effects during reactions in supercritical water Ind. Eng. Chem. Res. 1988, 27, 143-149
50. Koyama, M. Hydrocracking of lignin-related model dimers Bioresour. Technol. 1993, 44, 209-215
51. Mahdavi, B.; Lafrance, A.; Martel, A.; Lessard, J.; Menard, H. Electrocatalytic hydrogenolysis of lignin model dimers at Raney nickel electrodes J. Appl. Electrochem. 1997, 2, 605-611
52. Lajunen, M.; Laine, R.; Aaltonen, M. Acid-catalyzed hydrolysis of some primary alkyl phenyl ethers Acta Chem. Scand. 1997, 51, 1155-1161
53. Cox, R. A. Revised mechanism for the hydrolysis of ethers in aqueous acid1 Can. J. Chem. 2012, 90, 811-818
54. Cox, R. A.; Bunce, M. Three different mechanism for azo-ether hydrolyses in aqueous acid Can. J. Chem. 2012, 90, 791-797
55. Cox, R. A. A greatly under-appreciated fundamental principle of physical organic chemistry Int. J. Mol. Sci. 2011, 12, 8316-8332
56. 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., Jr.; Peralta, P. 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, N. J.; 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, Ö.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2009.
57. Pliego, J. R.; Riveros, J. M. The cluster-continuum model for the calculation of the solvation free energy of ionic species J. Phys. Chem. A 2001, 105, 7241-7247
58. Kelly, C. P.; Cramer, C. J.; Truhlar, D. G. Adding explicit solvent molecules to continuum solvent calculations for the calculation of aqueous acid dissociation constants J. Phys. Chem. A 2006, 110, 2493-2499
59. Yamabe, S.; Kawagishi, N. A computational study on the relationship between formation and electrolytic dissociation of carbonic acid Theor. Chem. Acc. 2011, 130, 909-918
60. Baker, J.; Pulay, P. Assessment of the Handy-Cohen optimized exchange density functional for organic reactions J. Chem. Phys. 2002, 117, 1441
61. Eyring, H. The activated complex in chemical reactions J. Chem. Phys. 1935, 3, 107
62. Calef, D. F.; Deutch, J. M. Diffusion-controlled reactions Annual Review Physical Chemistry 1983, 34, 493-524
63. Weinhold, F. Natural Bond Orbital analysis: A critical overview of relationships to alternative bonding perspectives J. Comput. Chem. 2012, 33, 2363-2379