Single-pot formation of THFAL via catalytic hydrogenation of FFR over Pd/MFI catalyst

ACS Sustainable Chemistry and Engineering

Volumn 2, Issue 2, 2014, Pages 272-281

  Biradar, Narayan S ^a   Hengne, Amol M ^a   Birajdar, Shobha N ^a   Niphadkar, Prashant S ^a   Joshi, Praphulla N ^a   Rode, Chandrashekhar V ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Biomass conversion; Hydrogenation; Pd MFI; Recyclability; THFAL

Indexed keywords

BIOCONVERSION; CATALYSIS; CATALYST SELECTIVITY; HYDROGENATION; MOLECULAR SIEVES; PALLADIUM; SILICATES; X RAY DIFFRACTION;

BIOMASS CONVERSION; CATALYST SCREENING; CATALYTIC HYDROGENATION; REACTION CONDITIONS; RECYCLABILITY; SUPPORTED PD CATALYSTS; TETRAHYDROFURFURYL ALCOHOLS; THFAL;

CATALYST SUPPORTS;

EID: 84893228557     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc400302b     Document Type: Article

References (46)

1. Huber, G. W.; Iborra, S.; Corma, A. Synthesis of transportation fuels from biomass: Chemistry, catalysts, and engineering Chem. Rev. 2006, 106, 4044-4098
2. Corma, A.; Iborra, S.; Velty, A. Chemical routes for the transformation of biomass into chemicals Chem. Rev. 2007, 107, 2411-2502
3. Gallezot, P. Conversion of biomass to selected chemical products Chem. Soc. Rev. 2012, 41, 1538-1558
4. Bozell, J. J.; Petersen, G. R. Technology development for the production of biobased products from biorefinery carbohydrates-the U.S. Department of Energy's "Top 10" revisited Green Chem. 2010, 12, 539-554
5. Alonso, D. M.; Wettstein, S. G.; Dumesic, J. A. Bimetallic catalysts for upgrading of biomass to fuels and chemicals Chem. Soc. Rev. 2012, 41, 8075-8098
6. Egeblad, K.; Hansen, J. R.; Marsden, C. C.; Taarning, E.; Christensen, C. H. Heterogeneous catalysis for production of value-added chemicals from biomass Catalysis 2009, 21, 13-50
7. Tao, F.; Song, H.; Chou, L. Efficient conversion of cellulose into furans catalyzed by metal ions in ionic liquids J. Mol. Catal. A: Chemical 2012, 357, 11-18
8. Dutta, S.; De, S.; Saha, B.; Alam, Md.-I. Advances in conversion of hemicellulosic biomass to furfural and upgrading to biofuels Catal. Sci. Technol. 2012, 2, 2025-2036
9. Karinen, R.; Vilonenm, K.; Niemel, M. Biorefining: Heterogeneously catalyzed reactions of carbohydrates for the production of furfural and hydroxymethylfurfural ChemSusChem 2011, 4, 1002-1016
10. Daengprasert, W.; Boonnoun, P.; Laosiripojana, N.; Goto, M.; Shotipruk, A. Application of sulfonated carbon-based catalyst for solvothermal conversion of cassava waste to hydroxymethylfurfural and furfural Ind. Eng. Chem. Res. 2011, 50, 7903-7910
11. Weingarten, R.; Cho, J.; Conner, W. C.; Huber, G. W., Jr. Kinetics of furfural production by dehydration of xylose in a biphasic reactor with microwave heating Green Chem. 2010, 12, 1423-1429
12. Lam, E.; Majid, E.; Leung, A. C. W.; Chong, J. H.; Mahmoud, K. A.; Luong, J. H. T. Synthesis of furfural from xylose by heterogeneous and reusable nafion catalysts ChemSusChem 2011, 4, 535-541
13. Chheda, J. N.; Leshkov, Y. R.; Dumesic, J. A. Production of 5-hydroxymethylfurfural and furfural by dehydration of biomass-derived mono- and poly-saccharides Green Chem. 2007, 9, 342-350
14. Marcotullio, G.; Jong, W. D. Chloride ions enhance furfural formation from D-xylose in dilute aqueous acidic solutions Green Chem. 2010, 12, 1739-1746
15. 3 in acetic acid steam Green Chem. 2013, 15, 727-737
16. Vorotnikov, V.; Mpourmpakis, G.; Vlachos, D. G. DFT study of furfural conversion to furan, furfuryl alcohol, and 2-methylfuran on Pd(111) ACS Catal. 2012, 2, 2496-2504
17. Bechem, B.; Patman, R. L.; Hashmi, A. S. K.; Krische, M. J. Enantioselective carbonyl allylation, crotylation, and tert-prenylation of furan methanols and furfurals via iridium-catalyzed transfer hydrogenation J. Org. Chem. 2010, 75, 1795-1798
18. Baker, L. R.; Kennedy, G.; Spronsen, M. V.; Hervier, A.; Cai, X.; Chen, S.; Wang, L. W.; Omorjai, G. A. Furfuraldehyde hydrogenation on titanium oxide-supported platinum nanoparticles studied by sum frequency generation vibrational spectroscopy: Acid-base catalysis explains the molecular origin of strong metal-support interactions J. Am. Chem. Soc. 2012, 134, 14208-14216
19. Rodiansono, S. K.; Hara, T.; Ichikunia, N.; Shimazu, S. Highly efficient and selective hydrogenation of unsaturated carbonyl compounds using Ni-Sn alloy catalysts Catal. Sci. Technol. 2012, 2, 2139-2145
20. Nakagawa, Y.; Nakazawa, H.; Watanabe, H.; Tomishige, K. Total hydrogenation of furfural over a silica-supported nickel catalyst prepared by the reduction of a nickel nitrate precursor ChemCatChem 2012, 4, 1791-1797
21. Zheng, H. Y.; Zhua, Y. L.; Teng, B. T.; Bai, Z. Q.; Zhang, C. H.; Xiang, H. W.; Li, Y. W. Towards understanding the reaction pathway in vapour phase hydrogenation of furfural to 2-methylfuran J. Mol. Catal. A: Chem. 2006, 246, 18-23
22. Lessard, J.; Morin, J. F.; Wehrung, J. F.; Magnin, D. High yield conversion of residual pentoses into furfural via zeolite catalysis and catalytic hydrogenation of furfural to 2-methylfuran Top. Catal. 2010, 53, 1231-1234
23. Zheng, H. Y.; Zhu, Y. L.; Bai, Z. Q.; Huang, L.; Xianga, H. W.; Lia, Y. W. An environmentally benign process for the efficient synthesis of cyclohexanone and 2-methylfuran Green Chem. 2006, 8, 107-109
24. Yun, S.; Wei, L.; Minghui, Z.; Keyi, T. Hydrogenation of furfuryl alcohol to tetrahydrofurfuryl alcohol on NiB/SiO2 amorphous alloy catalyst. Front Chem. Eng. China 2007, 1 (2) 151-154
25. 2 catalyst Ind. Eng. Chem. Res. 2007, 46, 3275-3282
26. Sangeetha, P.; Nagaraja, B. M.; Shanthi, K.; Rama Rao, K. S.; Narayanan, S. Vapour phase hydrogenation of furfural over palladium supported catalysts Bull. Catal. Soc. India 2009, 8, 52-63
27. Pushkarev, V. V.; Musselwhite, N.; An, K.; Alayoglu, S.; Somorjai, G, A. High structure sensitivity of vapor-phase furfural decarbonylation/hydrogenation reaction network as a function of size and shape of Pt nanoparticles Nano Lett. 2012, 12, 5196-5201
28. Hronec, M.; Fulajtarova, K. Selective transformation of furfural to cyclopentanone Catal. Commun. 2012, 24, 100-104
29. 3 catalyst for simultaneous synthesis of furfuryl alcohol and cyclohexanone by a novel coupling route: Combination of furfural hydrogenation and cyclohexanol dehydrogenation J. Mol. Catal. A: Chem. 2007, 278, 29-37
30. Rama Rao, K. S.; Burri, D. R.; Sanakarasubbier, N.; Bhari, M. N.; Aytam, H. P.; Vasireddy, S.; Veldurthi, S.; Podila, S.; Reddy, S. S. Vapour Phase Catalytic Process for Simultaneous Furfural Hydrogenation and Cyclohexanol Dehydration. U.S. 7015359 B1, 2006.
31. 2 Angew. Chem., Int. Ed. 2010, 49, 8856-8859
32. Sitthisa, S.; Resasco, D. E. Hydrodeoxygenation of furfural over supported metal catalysts: A comparative study of Cu, Pd and Ni Catal. Lett. 2011, 141, 784-791
33. Gowda, A. S.; Parkin, S.; Ladipo, F. T. Hydrogenation and hydrogenolysis of furfural and furfuryl alcohol catalyzed by ruthenium(II) bis(diimine) complexes Appl. Organometal. Chem. 2012, 26, 86-93
34. Vetere, V.; Merlo, A. B.; Ruggera, J. F.; Casella, M. L. Transition metal-based bimetallic catalysts for the chemoselective hydrogenation of furfuraldehyde J. Braz. Chem. Soc. 2010, 21 (5) 914-920
35. Lee, S.-P.; Chen, Y. W. Selective hydrogenation of furfural on Ni-P, Ni-B, and Ni-P-B ultrafine materials Ind. Eng. Chem. Res. 1999, 38, 2548-2556
36. Adelmana, B. J.; Sachtler, W. M. H. The effect of zeolitic protons on NOx reduction over Pd/ZSM-5 catalysts App. Catal. B: Environ. 1997, 14, 1-11
37. Chen, H. Y.; Wang, X.; Sachtler, W. M. H. Reduction of NOx over zeolite MFI supported iron catalysts: Nature of active sites Phys. Chem. Chem. Phys. 2000, 2, 3083-3090
38. Jin, M. J.; Taher, A.; Kang, H. J.; Choi, M.; Ryoo, R. Palladium acetate immobilized in a hierarchical MFI zeolite-supported ionic liquid: A highly active and recyclable catalyst for Suzuki reaction in water Green Chem. 2009, 11, 309-313
39. Niphadkar, P. S.; Kotwal, M. S.; Deshpande, S. S.; Bokade, V. V.; Joshi, P. N. Tin-silicalite-1: Synthesis by dry gel conversion, characterization and catalytic performance in phenol hydroxylation reaction Mater. Chem. Phys. 2009, 114, 344-349
40. Treacy, M. M. J.; Higgins, J. B. Collection of Simulated XRD Powder Patterns for Zeolites, 4 th ed.; Elsevier: Amsterdam, 2001.
41. Jinka, K. M.; Bajaj, H. C.; Jasra, R. V.; Prasetyanto, E. A.; Park, S. E. Microwave synthesized mesoporous vanadium-mfi catalysts for epoxidation of styrene using molecular oxygen Top. Catal. 2010, 53, 238-246
42. Shetti, V. N.; Kim, J.; Srivastava, R.; Choi, M.; Ryoo, R. Assessment of the mesopore wall catalytic activities of MFI zeolite with mesoporous/ microporous hierarchical structures J. Catal. 2008, 254, 296-303
43. Philippaerts, A.; Paulussen, S.; Turner, S.; Lebedev, O. I.; Tendeloo, G. V.; Poelman, H.; Bulut, M.; Clippel, F. D.; Smeets, P.; Sels, B.; Jacobs, P. Selectivity in sorption and hydrogenation of methyl oleate and elaidate on MFI zeolites J. Catal. 2010, 270, 172-184
44. Khan, F. A.; Vallat, A.; Fink, G. S. Highly selective low-temperature hydrogenation of furfuryl alcohol to tetrahydrofurfuryl alcohol catalysed by hectorite-supported ruthenium nanoparticles Catal. Commun. 2011, 12, 1428-1431
45. Villaverde, M. M.; Bertero, N. M.; Garetto, T. F.; Marchi, A. J. Selective liquid-phase hydrogenation of furfural to furfuryl alcohol over Cu-based catalysts Catal. Today 2013, 213, 87-92
46. Nadgeri, J. M.; Telkar, M. M.; Rode, C. V. Hydrogenation activity and selectivity behavior of supported palladium nanoparticles Catal. Commun. 2008, 9, 441-446