Application of the Shvo catalyst in homogeneous hydrogenation of bio-oil obtained from pyrolysis of white poplar: New mild upgrading conditions

Fuel

Volumn 90, Issue 3, 2011, Pages 1197-1207

  Busetto, Luigi ^a   Fabbri, Daniele ^a   Mazzoni, Rita ^a   Salmi, Mauro ^a   Torri, Cristian ^a   Zanotti, Valerio ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Anhydrosugars; Homogenous hydrogenation; Hydroxyacetaldehyde; Pyrolysis bio oil upgrading; Shvo catalyst

Indexed keywords

ANHYDROSUGARS; BIO OIL; BIO-OILS; BIPHASIC MIXTURES; CATALYTIC SYSTEM; CHEMICAL NATURE; CINNAMALDEHYDE; DOUBLE BONDS; EFFICIENT CATALYSTS; FAST PYROLYSIS; GLYCOLALDEHYDES; HOMOGENEOUS CATALYST; HOMOGENOUS HYDROGENATION; HYDROXYACETALDEHYDE; MODEL COMPOUND; MODEL MIXTURES; MOLAR RATIO; PYROLYSIS OIL; REACTION CONDITIONS; SHVO CATALYST; SOLVENT FREE CONDITIONS; TEMPERATURE RANGE; WORK FOCUS;

ACETIC ACID; ALDEHYDES; CHEMICAL BONDS; CRACKING (CHEMICAL); HYDROGENATION; INTERNET PROTOCOLS; KETONES; OLIGOMERS; ORGANIC COMPOUNDS; RUTHENIUM; SUGARS;

CATALYST ACTIVITY;

EID: 79952001125     PISSN: 00162361     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.fuel.2010.10.036     Document Type: Article

References (48)

1. G.W. Huber, S. Iborra, and A. Corma Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering Chem Rev 106 2006 4044 4098 and references cited therein (Pubitemid 44560464)
2. G.W. Huber, and A. Corma Synergies between bio- and oil refineries for the production of fuels from biomass Angew Chem Int Ed 46 2007 7184 7201 (Pubitemid 47517907)
3. J.N. Chheda, G.W. Huber, and J.A. Dumesic Liquid-phase catalytic processing of biomass-derived oxygenated hydrocarbons to fuels and chemicals Angew Chem Int Ed 46 2007 7164 7183 (Pubitemid 47517906)
4. D. Mohan, C.U. Pittman Jr., and P.H. Steele Pyrolysis of wood/biomass for bio-oil: a critical review Energy Fuels 20 2006 848 889 (Pubitemid 43994825)
5. T. Bridgwater Biomass for energy J Sci Food Agric 86 2006 1755 1768 (Pubitemid 44385572)
6. S. Czernik, and A.V. Bridgwater Overview of applications of biomass fast pyrolysis oil Energy Fuels 18 2004 590 598
7. E. Furimsky Catalytic hydrodeoxygenation Appl Catal A 199 2000 147 190
8. D.C. Elliott, D. Beckman, A.V. Bridgwater, J.P. Diebold, S.B. Gevert, and Y. Solantausta Developments in direct thermochemical liquefaction of biomass: 1983-1990 Energy Fuels 5 1991 399 410 (Pubitemid 21714809)
9. L. Petrus, and M.A. Noordermeer Biomass to biofuels, a chemical perspective Green Chem 8 2006 861 867 (Pubitemid 44527087)
10. M. Schlaf, G. Prasenjit, P.J. Fagan, E. Hauptman, and R. Bullock Metal-catalyzed selective deoxygenation of diols to alcohols Angew Chem Int Ed 40 2001 3887 3890 (Pubitemid 33009587)
11. M. Schlaf Selective deoxygenation of sugar polyols to α,ω-diols and other oxygen content reduced materials - a new challenge to homogeneous ionic hydrogenation and hydrogenolysis catalysis Dalton Trans 39 2006 4645 4653 (Pubitemid 44522160)
12. 2 in acidic medium J Mol Catal A Chem 229 2005 151 158 (Pubitemid 40215338)
13. M. Schlaf, P. Ghosh, P.J. Fagan, E. Hauptman, and R. Morris Bullock Catalytic deoxygenation of 1,2-propanediol to give n-propanol Adv Synth Catal 351 2009 789 800
14. 6, N∩N = bipy, phen, 6,6′-diamino-bipy, 2,9-diamino-phen, n = 1,2: influence of the ortho-amine substituents on catalytic activity J Mol Catal A Chem 277 2007 233 251
15. D. Taher, M.E. Thibault, D. Di Mondo, M. Jennings, and M. Schlaf Acid-, water- and high-temperature-stable ruthenium complexes for the total catalytic deoxygenation of glycerol to propane Chem Eur J 15 2009 10132 10143
16. F.H. Mahfud, S. Bussemaker, B.J. Kooi, G.H. Ten Brink, and H.J. Heeres The application of water-soluble ruthenium catalysts for the hydrogenation of the dichloromethane soluble fraction of fast pyrolysis oil and related model compounds in a two phase aqueous-organic system J Mol Catal A Chem 277 2007 127 136 (Pubitemid 47589011)
17. F.H. Mahfud, F. Ghijsen, and H.J. Heeres Hydrogenation of fast pyrolysis oil and model compounds in a two-phase aqueous organic system using homogeneous ruthenium catalysts J Mol Catal A Chem 264 2007 227 236 (Pubitemid 46329586)
18. J. Wildschut, I. Melian-Cabrera, and H.J. Heeres Catalyst studies on the hydrotreatment of fast pyrolysis oil Appl Cat B: Env 99 2010 298 306
19. R.H. Venderbosch, A.R. Ardiyanti, J. Wildschut, A. Oasmaa, and H.J. Heeres Stabilization of biomass-derived pyrolysis oils J Chem Technol Biotechnol 85 2010 674 686
20. R.M. Bullock Catalytic ionic hydrogenations Chem Eur J 10 2004 2366 2374
21. 2-hydrogenation and transfer hydrogenation of polar bonds catalyzed by ruthenium hydride complexes Coord Chem Rev 248 2004 2201 2237
22. R. Karvembu, R. Prabhakaran, and N. Natarajan Shvo's diruthenium complex: a robust catalyst Coord Chem Rev 249 2005 911 918 (Pubitemid 40460939)
23. Y. Shvo, D. Czarkie, Y. Rahamim, and D.F. Chodosh A new group of ruthenium complexes: structure and catalysis J Am Chem Soc 108 1986 7400 7402
24. Y. Blum, D. Czarkie, Y. Rahamim, and Y. Shvo (Cyclopentadienone)ruthenium carbonyl complexes - a new class of homogeneous hydrogenation catalysts Organometallics 4 1985 1459 1461
25. B.L. Conley, M.K. Pennington-Boggio, E. Boz, and T.J. Williams Discovery, applications, and catalytic mechanisms of Shvo's catalyst Chem Rev 110 2010 2294 2312
26. N. Menashe, E. Salant, and Y. Shvo Efficient catalytic reduction of ketones with formic acid and ruthenium complexes J Organomet Chem 514 1996 97 102 (Pubitemid 126162984)
27. Y. Shvo, I. Goldberg, D. Czerkie, D. Reshef, and Z. Stein New ruthenium complexes in the catalytic hydrogenation of alkynes. Study of structure and mechanism Organometallics 16 1997 133 138 (Pubitemid 127586135)
28. J.S.M. Samec, A.H. Ell, J.B. Aberg, T. Privalov, L. Eriksson, and J.E. Backvall Mechanistic study of hydrogen transfer to imines from a hydroxycyclopentadienyl ruthenium hydride. Experimental support for a mechanism involving coordination of imine to ruthenium prior to hydrogen transfer J Am Chem Soc 128 2006 14293 14305 (Pubitemid 44707738)
29. A.H. Ell, J.B. Johnson, and J.E. Backvall Mechanism of ruthenium-catalyzed hydrogen transfer reactions. Evidence for a stepwise transfer of CH and NH hydrogens from an amine to a (cyclopentadienone)ruthenium complex Chem Comm 14 2003 1652 1653 (Pubitemid 36829580)
30. C.P. Casey, G.A. Bikzhanova, and I.A. Guzei Stereochemistry of imine reduction by a hydroxycyclopentadienyl ruthenium hydride J Am Chem Soc 128 2006 2286 2293
31. C.P. Casey, T.B. Clark, and I.A. Guzei Intramolecular trapping of an intermediate in the reduction of imines by a hydroxycyclopentadienyl ruthenium hydride: support for a concerted outer sphere mechanism J Am Chem Soc 129 2007 11821 11827 (Pubitemid 47479930)
32. C.P. Casey, S.E. Beetner, and J.B. Johnson Spectroscopic determination of hydrogenation rates and intermediates during carbonyl hydrogenation catalyzed by Shvo's hydroxycyclopentadienyl diruthenium hydride agrees with kinetic modeling based on independently measured rates of elementary reactions J Am Chem Soc 130 2008 2285 2295 (Pubitemid 351288006)
33. A. Comas-Vives, G. Ujaque, and A. Lledos Hydrogen transfer to ketones catalyzed by Shvo's ruthenium hydride complex: a mechanistic insight Organometallics 26 2007 4135 4144 (Pubitemid 47310043)
34. K.R.J. Thomas, M. Velusamy, J.T. Lin, C.H. Chuen, and Y.-T. Tao Hexaphenylphenylene dendronised pyrenylamines for efficient organic light-emitting diodes J Mater Chem 15 2005 4453 4459 (Pubitemid 41619215)
35. C.P. Casey, S.W. Singer, D.R. Powell, R.K. Hayashi, and M. Kavana Hydrogen transfer to carbonyls and imines from a hydroxycyclopentadienyl ruthenium hydride: evidence for concerted hydride and proton transfer J Am Chem Soc 123 2001 1090 1100 (Pubitemid 32149306)
36. D. Fabbri, C. Torri, and I. Mancini Pyrolysis of cellulose catalysed by nanopowder metal oxides: production and characterisation of a chiral hydroxylactone and its role as building block Green Chem 9 2007 1374 1379
37. Sigma Aldrich Database in .
38. Spectral Database for Organic Compounds (SDBS) organized by National Institute of Advanced Industrial Science and Technology (AIST), Japan in .
39. A. Oasmaa, E. Kuoppala, and Y. Solantausta Fast pyrolysis of forestry residue. 2. Physicochemical composition of product liquid Energy Fuels 17 2003 433 443
40. A. Oasmaa, and E. Kuoppala Solvent fractionation method with brix for rapid characterization of wood fast pyrolysis liquids Energy Fuels 22 2008 4245 4248
41. C. Torri, I.G. Lesci, and D. Fabbri Analytical study on the pyrolytic behaviour of cellulose in the presence of MCM-41 mesoporous materials J Anal Appl Pyrol 85 2009 192 196
42. D. Gardiner The dimeric forms of some α-hydroxycarbonyl compounds Carbohydr Res 2 1966 234 239
43. V.A. Yaylayan, S. Harty-Majors, and A.A. Ismail Investigation of the mechanism of dissociation of glycolaldehyde dimer (2,5-dihydroxy-1,4-dioxane) by FTIR spectroscopy Carbohydr Res 309 1998 31 38 (Pubitemid 28349922)
44. C. Luo, S. Wang, and H. Liu Cellulose conversion into polyols catalyzed by reversibly formed acids and supported ruthenium clusters in hot water Angew Chem Int Ed 46 2007 7636 7639 (Pubitemid 47557015)
45. 2 expanded liquid and hot water Green Chem 6 2004 382 386 (Pubitemid 39429334)
46. S.A. Nolen, C.L. Liotta, C.A. Eckert, and R. Glaser The catalytic opportunities of near-critical water: a benign medium for conventionally acid and base catalyzed condensations for organic synthesis Green Chem 5 2003 663 669 (Pubitemid 37443739)
47. J. Filley, and C. Roth Vanadium catalyzed guaiacol deoxygenation J Mol Catal A: Chem 139 1999 245 252
48. J. Zakzeski, P.C.A. Bruijnicx, A.L. Jongerius, and B.M. Weckhuysen The catalytic valorization of lignin for the production of renewable chemicals Chem Rev 110 2010 3552 3599