Hydrolytic cleavage of C-O linkages in lignin model compounds catalyzed by water-tolerant Lewis acids

Industrial and Engineering Chemistry Research

Volumn 53, Issue 7, 2014, Pages 2633-2639

  Yang, Le ^a,b   Li, Yongdan ^a   Savage, Phillip E ^b  

^a TIANJIN UNIVERSITY   (China)

^b UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84894432285     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie403545n     Document Type: Article

References (35)

1. Wahyudiono; Kanetake, T.; Sasaki, M.; Goto, M. Decomposition of a Lignin Model Compound under Hydrothermal Conditions Chem. Eng. Technol. 2007, 30, 1113-1122
2. Sun, Y.; Cheng, J. Hydrolysis of lignocellulosic materials for ethanol production: A review Bioresour. Technol. 2002, 83, 1-11
3. Zakzeski, J.; Bruijnincx, P. C. A.; Jongerius, A. L.; Weckhuysen, B. M. The Catalytic Valorization of Lignin for the Production of Renewable Chemicals Chem. Rev. 2010, 110, 3552-3599
4. Pandey, M. P.; Kim, C. S. Lignin Depolymerization and Conversion: A Review of Thermochemical Methods Chem. Eng. Technol. 2011, 34, 29-41
5. Afifi, A. I.; Chornet, E.; Thring, R. W.; Overend, R. P. The aryl ether bond reactions with H-donor solvents: Guaiacol and tetralin in the presence of catalysts Fuel 1996, 75, 509-516
6. 2N catalysts supported on activated carbons Catal. Today 2011, 172, 232-239
7. Kunkes, E. L.; Simonetti, D. A.; West, R. M.; Serrano-Ruiz, J. C.; Gärtner, C. A.; Dumesic, J. A. Catalytic Conversion of Biomass to Monofunctional Hydrocarbons and Targeted Liquid-Fuel Classes Science 2008, 322, 417-421
8. Elliott, D. C.; Hart, T. R. Catalytic Hydroprocessing of Chemical Models for Bio-oil Energy Fuels 2008, 23, 631-637
9. Shimizu, K.; Miki, K.; Saitou, I. Acid-catalysed depolymerization of coal model compounds and subbituminous coal in a superacid-isopentane medium Fuel 1997, 76, 23-27
10. Yang, L.; Zhou, W.; Seshan, K.; Li, Y. Green and efficient synthesis route of catechol from guaiacol J. Mol. Catal. A: Chem. 2013, 368-369, 61-65
11. 3 as a catalyst in supercritical ethanol Catal. Commun. 2013, 30, 36-39
12. Wahyudiono; Sasaki, M.; Goto, M. Thermal decomposition of guaiacol in sub- and supercritical water and its kinetic analysis J. Mater. Cycles Waste Manage. 2011, 13, 68-79
13. Townsend, S. H.; Abraham, M. A.; Huppert, G. L.; Klein, M. T.; Paspek, S. C. Solvent Effects during Reactions in Supercritical Water Ind. Eng. Chem. Res. 1988, 27, 143-149
14. Penninger, J. M. L.; Kersten, R. J. A.; Baur, H. C. L. Reactions of diphenylether in supercritical water-Mechanism and kinetics J. Supercrit. Fluids 1999, 16, 119-132
15. Roberts, V.; Fendt, S.; Lemonidou, A. A.; Li, X.; Lercher, J. A. Influence of alkali carbonates on benzyl phenyl ether cleavage pathways in superheated water Appl. Catal. B: Environ. 2010, 95, 71-77
16. Kobayashi, S. Scandium Triflate in Organic Synthesis Eur. J. Org. Chem. 1999, 1999, 15-27
17. 3 as catalyst and dimethyl carbonate as a phosgene substitute Appl. Catal. B: Environ. 2006, 66, 72-80
18. Levine, R. B.; Bollas, A. A.; Durham, M. D.; Savage, P. E. Triflate-catalyzed (trans)esterification of lipids within carbonized algal biomass Bioresour. Technol. 2012, 111, 222-229
19. Rebacz, N. A.; Savage, P. E. Anisole hydrolysis in high temperature water Phys. Chem. Chem. Phys. 2013, 15, 3562-3569
20. Martino, C. J.; Savage, P. E. Thermal Decomposition of Substituted Phenols in Supercritical Water Ind. Eng. Chem. Res. 1997, 36, 1385-1390
21. Lawson, J. R.; Klein, M. T. Influence of water on guaiacol pyrolysis Ind. Eng. Chem. Fundam. 1985, 24, 203-208
22. Hurff, S. J.; Klein, M. T. Reaction pathway analysis of thermal and catalytic lignin fragmentation by use of model compounds Ind. Eng. Chem. Fundam. 1983, 22, 426-430
23. Yong, T. L.-K.; Yukihiko, M. Kinetic Analysis of Guaiacol Conversion in Sub- and Supercritical Water Ind. Eng. Chem. Res. 2013, 52, 9048-9059
24. Rebacz, N. A.; Savage, P. E. Hydration of 1-Phenyl-1-propyne in High-Temperature Water with Catalysis by Water-Tolerant Lewis Acids Ind. Eng. Chem. Res. 2009, 49, 535-540
25. Kobayashi, S.; Nagayama, S.; Busujima, T. Lewis Acid Catalysts Stable in Water. Correlation between Catalytic Activity in Water and Hydrolysis Constants and Exchange Rate Constants for Substitution of Inner-Sphere Water Ligands J. Am. Chem. Soc. 1998, 120, 8287-8288
26. Bartoli, G.; Dalpozzo, R.; De Nino, A.; Maiuolo, L.; Nardi, M.; Procopio, A.; Tagarelli, A. Cerium(III) Triflate versus Cerium(III) Chloride: Anion Dependence of Lewis Acid Behavior in the Deprotection of PMB Ethers Eur. J. Org. Chem. 2004, 2004, 2176-2180
27. Klein, M. T.; Mentha, Y. G.; Torry, L. A. Decoupling Substituent and Solvent Effects during Hydrolysis of Substituted Anisoles in Supercritical Water Ind. Eng. Chem. Res. 1992, 31, 182-187
28. Parkhurst, H. J., Jr.; Huibers, D. T. A.; Jones, M. W. Production of Phenol from Lignin, Preprints Am. Chem. Soc., Div. Pet. Chem. 1980, 25, 657-667
29. Dorrestijn, E.; Laarhoven, L. J. J.; Arends, I. W. C. E.; Mulder, P. The occurrence and reactivity of phenoxyl linkages in lignin and low rank coal J. Anal. Appl. Pyrolysis 2000, 54, 153-192
30. Katritzky, A. R.; Ignatchenko, E. S.; Allin, S. M.; Barcock, R. A.; Siskin, M.; Hudson, C. W. Aqueous High-Temperature Chemistry of Carbo- and Heterocycles. 29. Reactions of Aryl Hydrocarbons, Aryl N -Oxides, and Aryl Carbonyl Compounds in Supercritical Water at 460 C Energy Fuels 1997, 11, 160-173
31. Katritzky, A. R.; Barcock, R. A.; Balasubramanian, M.; Greenhill, J. V.; Siskin, M.; Olmstead, W. N. Aqueous High-Temperature Chemistry of Carbo- and Heterocycles. 20. Reactions of Some Benzenoid Hydrocarbons and Oxygen-Containing Derivatives in Supercritical Water at 460 C Energy Fuels 1994, 8, 487-497
32. Roberts, V. M.; Knapp, R. T.; Li, X.; Lercher, J. A. Selective Hydrolysis of Diphenyl Ether in Supercritical Water Catalyzed by Alkaline Carbonates ChemCatChem 2010, 2, 1407-1410
33. Varga, T. R.; Fazekas, Z.; Ikeda, Y.; Tomiyasu, H. Cleavage of diphenylether with boron trifluoride under supercritical conditions J. Supercrit. Fluids 2002, 23, 163-167
34. Penninger, J. M. L.; Kersten, R. J. A.; Baur, H. C. L. Hydrolysis of diphenylether in supercritical water: Effects of dissolved NaCl J. Supercrit. Fluids 2000, 17, 215-226
35. He, J.; Zhao, C.; Lercher, J. A. Ni-Catalyzed Cleavage of Aryl Ethers in the Aqueous Phase J. Am. Chem. Soc. 2012, 134, 20768-20775