Understanding the Performance and Stability of Supported Ni-Co-Based Catalysts in Phenol HDO

Catalysts

Volumn 6, Issue 11, 2016, Pages

  Huynh, Thuan M ^a   Armbruster, Udo ^b   Kreyenschulte, Carsten R ^b   Nguyen, Luong H ^a   Phan, Binh M Q ^a   Nguyen, Duc A ^a   Martin, Andreas ^b  

^a Vietnam Petroleum Institute   (Viet Nam)

^b LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

Aqueous phase hydrodeoxygenation; Batch experiments; Bimetallic catalyst; Continuous flow reactor; Ni Co alloy; Phenol

Indexed keywords

EID: 84995644729     PISSN: None     EISSN: 20734344     Source Type: Journal    
DOI: 10.3390/catal6110176     Document Type: Article

References (63)

1. BP Statistical Review of World Energy. June 2015. Available online: http://www.bp.com/en/global/ corporate/about-bp/energy-economics/statistical-review-of-world-energy.html (accessed on 24 May 2015).
2. Dincer, I. Renewable energy and sustainable development: A crucial review. Renew. Sustain. Energy Rev. 2000, 4, 157-175. [CrossRef]
3. Carpenter, D.; Westover, T.L.; Czernik, S.; Jablonski, W. Biomass feedstocks for renewable fuel production: A review of the impacts of feedstock and pretreatment on the yield and product distribution of fast pyrolysis bio-oils and vapors. Green Chem. 2014, 16, 384-406. [CrossRef]
4. Melero, J.A.; Iglesias, J.; Garcia, A. Biomass as renewable feedstock in standard refinery units. Feasibility, opportunities and challenges. Energy Environ. Sci. 2012, 5, 7393-7420. [CrossRef]
5. Furimsky, E. Catalytic hydrodeoxygenation. Appl. Catal. A 2000, 199, 147-190. [CrossRef]
6. Elliott, D.C. Historical Developments in Hydroprocessing Bio-oils. Energy Fuels 2007, 21, 1792-1815. [CrossRef]
7. Laurent, E.; Delmon, B. Influence of water in the deactivation of a sulfided catalyst during hydrodeoxygenation. J. Catal. 1994, 146, 281-291. [CrossRef]
8. Romero, Y.; Richard, F.; Brunet, S. Hydrodeoxygenation of 2-ethylphenol as a model compound of bio-crude over sulfided Mo-based catalysts: Promoting effect and reaction mechanism. Appl. Catal. B 2010, 98, 213-223. [CrossRef]
9. Wildschut, J.; Mahfud, F.H.; Venderbosch, R.H.; Heeres, H.J. Hydrotreatment of Fast Pyrolysis Oil Using Heterogeneous Noble-Metal Catalysts. Ind. Eng. Chem. Res. 2009, 48, 10324-10334. [CrossRef]
10. Hong, D.-Y.; Miller, S.J.; Agrawal, P.K.; Jones, C.W. Hydrodeoxygenation and coupling of aqueous phenolics over bifunctional zeolite-supported metal catalysts. Chem. Commun. 2010, 46, 1038-1040. [CrossRef] [PubMed]
11. Runnebaum, R.; Nimmanwudipong, T.; Block, D.; Gates, B. Catalytic Conversion of Anisole: Evidence of Oxygen Removalin Reactions with Hydrogen. Catal. Lett. 2011, 141, 817-820. [CrossRef]
12. 2 catalysts. J. Catal. 2011, 280, 17-27. [CrossRef]
13. Sitthisa, S.; Resasco, D. Hydrodeoxygenation of Furfural over Supported Metal Catalysts: A Comparative Study of Cu, Pd and Ni. Catal. Lett. 2011, 141, 784-791. [CrossRef]
14. Zhu, X.; Lobban, L.L.; Mallinson, R.G.; Resasco, D.E. Bifunctional transalkylation and hydrodeoxygenation of anisole over a Pt/HBeta catalyst. J. Catal. 2011, 281, 21-29. [CrossRef]
15. Ausavasukhi, A.; Huang, Y.; To, A.T.; Sooknoi, T.; Resasco, D.E. Hydrodeoxygenation of m-cresol over gallium-modified beta zeolite catalysts. J. Catal. 2012, 290, 90-100. [CrossRef]
16. Ohta, H.; Kobayashi, H.; Hara, K.; Fukuoka, A. Hydrodeoxygenation of phenols as lignin models under acid-free conditions with carbon-supported platinum catalysts. Chem. Commun. 2011, 47, 12209-12211. [CrossRef] [PubMed]
17. Li, N.; Huber, G.W. Aqueous-phase hydrodeoxygenation of sorbitol: Identification of the reaction pathway. J. Catal. 2010, 270, 48-59. [CrossRef]
18. Lee, C.R.; Yoon, J.S.; Suh, Y.-W.; Choi, J.-W.; Ha, J.-M.; Suh, D.J.; Park, Y.-K. Catalytic roles of metals and supports on hydrodeoxygenation of lignin monomer guaiacol. Catal. Commun. 2012, 17, 54-58. [CrossRef]
19. Zhao, C.; He, J.; Lemonidou, A.A.; Li, X.; Lercher, J.A. Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes. J. Catal. 2011, 280, 8-16. [CrossRef]
20. Zhao, C.; Kou, Y.; Lemonidou, A.A.; Li, X.; Lercher, J.A. Highly Selective Catalytic Conversion of Phenolic Bio-Oil to Alkanes. Angew. Chem. Int. Ed. 2009, 48, 3987-3990. [CrossRef] [PubMed]
21. Zhang, X.; Wang, T.; Ma, L.; Zhang, Q.; Jiang, T. Hydrotreatment of bio-oil over Ni-based catalyst. Bioresour. Technol. 2013, 127, 306-311. [CrossRef] [PubMed]
22. Mortensen, P.M.; Grunwaldt, J.-D.; Jensen, P.A.; Jensen, A.D. Screening of Catalysts for Hydrodeoxygenation of Phenol as a Model Compound for Bio-oil. ACS Catal. 2013, 3, 1774-1785. [CrossRef]
23. Zhao, C.; Kasakov, S.; He, J.; Lercher, J.A. Comparison of kinetics, activity and stability of Ni/HZSM-5 and Ni/Al2O3-HZSM-5 for phenol hydrodeoxygenation. J. Catal. 2012, 296, 12-23. [CrossRef]
24. 2 catalysts. J. Catal. 2011, 277, 1-13. [CrossRef]
25. 2 catalyst. Appl. Catal. B 2012, 115-116, 63-73. [CrossRef]
26. Deutsch, K.L.; Shanks, B.H. Hydrodeoxygenation of lignin model compounds over a copper chromite catalyst. Appl. Catal. A 2012, 447-448, 144-150. [CrossRef]
27. Alonso, D.M.; Wettstein, S.G.; Dumesic, J.A. Catalytic conversion of biomass to biofuels. Green Chem. 2010, 12, 1493-1513. [CrossRef]
28. 3 support. Appl. Catal. B 2012, 117-118, 105-117. [CrossRef]
29. 3 supported Pt-Ni and Pt-Co catalysts. Green Chem. 2012, 14, 1388-1397. [CrossRef]
30. Sun, J.; Karim, A.M.; Zhang, H.; Kovarik, L.; Li, X.S.; Hensley, A.J.; McEwen, J.-S.; Wang, Y. Carbon-supported bimetallic Pd-Fe catalysts for vapor-phase hydrodeoxygenation of guaiacol. J. Catal. 2013, 306, 47-57. [CrossRef]
31. Hong, Y.; Zhang, H.; Sun, J.; Ayman, K.M.; Hensley, A.J.R.; Gu, M.; Engelhard, M.H.; McEwen, J.-S.; Wang, Y. Synergistic Catalysis between Pd and Fe in Gas Phase Hydrodeoxygenation of m-Cresol. ACS Catal. 2014, 4, 3335-3345. [CrossRef]
32. 3: A universal catalyst for the hydrodeoxygenation of bio-oil and its model compounds. Catal. Commun. 2013, 41, 34-37. [CrossRef]
33. Nie, L.; de Souza, P.M.; Noronha, F.B.; An, W.; Sooknoi, T.; Resasco, D.E. Selective conversion of m-cresol to toluene over bimetallic Ni-Fe catalysts. J. Mol. Catal. A: Chem. 2014, 388-389, 47-55. [CrossRef]
34. Bykova, M.V.; Ermakov, D.Y.; Kaichev, V.V.; Bulavchenko, O.A.; Saraev, A.A.; Lebedev, M.Y.; Yakovlev, V.A. Ni-based sol-gel catalysts as promising systems for crude bio-oil upgrading: Guaiacol hydrodeoxygenation study. Appl. Catal. B 2012, 113-114, 296-307. [CrossRef]
35. Choudhary, T.V.; Phillips, C.B. Renewable fuels via catalytic hydrodeoxygenation. Appl. Catal. A 2011, 397, 1-12. [CrossRef]
36. Bu, Q.; Lei, H.; Zacher, A.H.; Wang, L.; Ren, S.; Liang, J.; Wei, Y.; Liu, Y.; Tang, J.; Zhang, Q., et al. A review of catalytic hydrodeoxygenation of lignin-derived phenols from biomass pyrolysis. Bioresour. Technol. 2012, 124, 470-477. [CrossRef] [PubMed]
37. Wang, H.; Male, J.; Wang, Y. Recent Advances in Hydrotreating of Pyrolysis Bio-Oil and Its Oxygen-Containing Model Compounds. ACS Catal. 2013, 3, 1047-1070. [CrossRef]
38. Saidi, M.; Samimi, F.; Karimipourfard, D.; Nimmanwudipong, T.; Gates, B.C.; Rahimpour, M.R. Upgrading of lignin-derived bio-oils by catalytic hydrodeoxygenation. Energy Environ. Sci. 2014, 7, 103-129. [CrossRef]
39. Massoth, F.E.; Politzer, P.; Concha, M.C.; Murray, J.S.; Jakowski, J.; Simons, J. Catalytic Hydrodeoxygenation of Methyl-Substituted Phenols: Correlations of Kinetic Parameters with Molecular Properties. J. Phys. Chem. B 2006, 110, 14283-14291. [CrossRef] [PubMed]
40. Newman, C.; Zhou, X.; Goundie, B.; Ghampson, I.T.; Pollock, R.A.; Ross, Z.; Wheeler, M.C.; Meulenberg, R.W.; Austin, R.N.; Frederick, B.G. Effects of support identity and metal dispersion in supported ruthenium hydrodeoxygenation catalysts. Appl. Catal. A 2014, 477, 64-74. [CrossRef]
41. Zhao, C.; Lercher, J.A. Selective Hydrodeoxygenation of Lignin-Derived Phenolic Monomers and Dimers to Cycloalkanes on Pd/C and HZSM-5 Catalysts. ChemCatChem 2012, 4, 64-68. [CrossRef]
42. De Souza, P.M.; Rabelo-Neto, R.C.; Borges, L.E.P.; Jacobs, G.; Davis, B.H.; Sooknoi, T.; Resasco, D.E.; Noronha, F.B. Role of Keto Intermediates in the Hydrodeoxygenation of Phenol over Pd on Oxophilic Supports. ACS Catal. 2015, 5, 1318-1329. [CrossRef]
43. Mortensen, P.M.; Gardini, D.; de Carvalho, H.W.P.; Damsgaard, C.D.; Grunwaldt, J.-D.; Jensen, P.A.; Wagner, J.B.; Jensen, A.D. Stability and resistance of nickel catalysts for hydrodeoxygenation: Carbon deposition and effects of sulfur, potassium, and chlorine in the feed. Catal. Sci. Technol. 2014, 4, 3672-3686. [CrossRef]
44. 3. An approach to O-removal from bio-oils. Fuel 2014, 117, 1061-1073. [CrossRef]
45. Le, T.A.; Ly, H.V.; Kim, J.; Kim, S.-S.; Choi, J.H.; Woo, H.-C.; Othman, M.R. Hydrodeoxygenation of 2-furyl methyl ketone as a model compound in bio-oil from pyrolysis of Saccharina Japonica Alga in fixed-bed reactor. Chem. Eng. J. 2014, 250, 157-163. [CrossRef]
46. Dickinson, J.G.; Savage, P.E. Development of NiCu Catalysts for Aqueous-Phase Hydrodeoxygenation. ACS Catal. 2014, 4, 2605-2615. [CrossRef]
47. Yoon, Y.; Rousseau, R.; Weber, R.S.; Mei, D.; Lercher, J.A. First-Principles Study of Phenol Hydrogenation on Pt and Ni Catalysts in Aqueous Phase. J. Am. Chem. Soc. 2014, 136, 10287-10298. [CrossRef] [PubMed]
48. Huynh, T.M.; Armbruster, U.; Pohl, M.-M.; Schneider, M.; Radnik, J.; Hoang, D.-L.; Phan, B.M. Q.; Nguyen, D.A.; Martin, A. Hydrodeoxygenation of Phenol as a Model Compound for Bio-oil on Non-noble Bimetallic Nickel-based Catalysts. ChemCatChem 2014, 6, 1940-1951. [CrossRef]
49. Huynh, T.M.; Armbruster, U.; Phan, B.M.Q.; Nguyen, D.A.; Martin, A. The influence of cobalt in bimetallic Ni-Co catalyst supported on H-Beta for phenol hydrodeoxygenation. Chim. Oggi 2014, 32, 40-44.
50. Huynh, T.M.; Armbruster, U.; Nguyen, L.H.; Nguyen, D.A.; Martin, A. Hydrodeoxygenation of Bio-Oil on Bimetallic Catalysts: From Model Compound to Real Feed. JSBS 2015, 5, 151-160. [CrossRef]
51. Huynh, T.M.; Armbruster, U.; Atia, H.; Bentrup, U.; Phan, B.M.Q.; Eckel, R.; Nguyen, L.H.; Nguyen, D.A.; Martin, A. Upgrading of bio-oil and subsequent co-processing under FCC conditions for fuel production. React. Chem. Eng. 2016, 1, 239-251. [CrossRef]
52. Emeis, C.A. Determination of Integrated Molar Extinction Coefficients for Infrared Absorption Bands of Pyridine Adsorbed on Solid Acid Catalysts. J. Catal. 1993, 141, 347-354. [CrossRef]
53. 2. Catal. Today 2016, 259, 277-284. [CrossRef]
54. Kruse, A.; Dinjus, E. Hot compressed water as reaction medium and reactant. Properties and synthesis reactions. J. Supercrit. Fluids 2007, 39, 362-380. [CrossRef]
55. Kruse, A.; Dinjus, E. Hot compressed water as reaction medium and reactant: 2. Degradation reactions. J. Supercrit. Fluids 2007, 41, 361-379. [CrossRef]
56. Ravenelle, R.M.; Schüler, F.; D’Amico, A.; Danilina, N.; van Bokhoven, J.A.; Lercher, J.A.; Jones, C.W.; Sievers, C. Stability of Zeolites in Hot LiquidWater. J. Phys. Chem. C 2010, 114, 19582-19595. [CrossRef]
57. Jentys, A.; Lercher, J.A. Techniques of zeolite characterization. In Studies in Surface Science and Catalysis; van Bekkum, H., Flanigen, E.M., Jacobs, P.A., Jansen, J.C., Eds.; Elsevier B.V.: Amsterdam, The Netherlands, 2001; Volume 137, pp. 345-386.
58. Gandarias, I.; Barrio, V.L.; Requies, J.; Arias, P.L.; Cambra, J.F.; Güemez, M.B. From biomass to fuels: Hydrotreating ofoxygenated compounds. Int. J. Hydrog. Energy 2008, 33, 3485-3488. [CrossRef]
59. Germain, J.E. Catalytic Conversion of Hydrocarbons; Academic Press: London, UK, 1969.
60. Van Donk, S.; Janssen, A.H.; Bitter, J.H.; de Jong, K.P. Generation, Characterization, and Impact of Mesopores in Zeolite Catalysts. Catal. Rev. 2003, 45, 297-319. [CrossRef]
61. Groen, J.C.; Peffer, L.A.A.; Moulijn, J.A.; Pérez-Ramírez, J. Mechanism of Hierarchical Porosity Development in MFI Zeolites by Desilication: The Role of Aluminium as a Pore-Directing Agent. Chem. Eur. J. 2005, 11, 4983-4994. [CrossRef] [PubMed]
62. Abelló, S.; Bonilla, A.; Pérez-Ramírez, J. Mesoporous ZSM-5 zeolite catalysts prepared by desilication with organic hydroxides and comparison with NaOH leaching. Appl. Catal. A 2009, 364, 191-198. [CrossRef]
63. Mortensen, P.M. Catalytic Conversion of Bio-oil to Fuel for Transportation. Ph.D. Thesis, Technical University of Denmark, Lyngby, Denmark, 2013.