Toward rational design of stable, supported metal catalysts for aqueous-phase processing: Insights from the hydrogenation of levulinic acid

Journal of Catalysis

Volumn 329, Issue , 2015, Pages 10-21

  Abdelrahman, Omar Ali ^a   Luo, Helen Y ^b   Heyden, Andreas ^c   Román Leshkov, Yuriy ^b   Bond, Jesse Q ^a  

^a Syracuse University   (United States)

^b Massachusetts Institute of Technology Cambridge   (United States)

^c The Department of Mechanical Engineering   (United States)

Author keywords

Aqueous phase stability; Ketone hydrogenation; Levulinic acid; Ruthenium; Sintering; Support effect; valerolactone

Indexed keywords

ACTIVATED ALUMINA; ACTIVATED CARBON; ALUMINUM OXIDE; AMORPHOUS CARBON; CATALYSTS; CHEMICAL BONDS; ELECTRONEGATIVITY; KETONES; ORGANIC ACIDS; PARTICLE SIZE; RUTHENIUM; SILICA; SINTERING; TITANIUM DIOXIDE;

AQUEOUS-PHASE PROCESSING; EXPERIMENTAL CONDITIONS; HYDROGENATION ACTIVITY; LEVULINIC ACID; PARTICLE SINTERING; SUPPORT EFFECTS; SUPPORTED-METAL CATALYSTS; TURNOVER FREQUENCY;

HYDROGENATION;

EID: 84938529985     PISSN: 00219517     EISSN: 10902694     Source Type: Journal    
DOI: 10.1016/j.jcat.2015.04.026     Document Type: Article

References (80)

1. Shabaker, J.W., Huber, G.W., Dumesic, J.A., Aqueous-phase reforming of oxygenated hydrocarbons over Sn-modified Ni catalysts. J. Catal. 222 (2004), 180–191.
2. Cortright, R.D., Davda, R.R., Dumesic, J.A., Hydrogen from catalytic reforming of biomass-derived hydrocarbons in liquid water. Nature 418 (2002), 964–967.
3. Lopez-Ruiz, J.A., Davis, R.J., Decarbonylation of heptanoic acid over carbon-supported platinum nanoparticles. Green Chem. 16 (2014), 683–694.
4. Bond, J.Q., Wang, D., Alonso, D.M., Dumesic, J.A., Interconversion between γ-valerolactone and pentenoic acid combined with decarboxylation to form butene over silica/alumina. J. Catal. 281 (2011), 290–299.
5. Kellicutt, A.B., Salary, R., Abdelrahman, O.A., Bond, J.Q., An examination of the intrinsic activity and stability of various solid acids during the catalytic decarboxylation of [gamma]-valerolactone. Catal. Sci. Technol. 4 (2014), 2267–2279.
6. Wang, D., Hakim, S.H., Martin Alonso, D., Dumesic, J.A., A highly selective route to linear alpha olefins from biomass-derived lactones and unsaturated acids. Chem. Commun. 49 (2013), 7040–7042.
7. Snåre, M., Kubičková, I., Mäki-Arvela, P., Eränen, K., Murzin, D.Y., Heterogeneous catalytic deoxygenation of stearic acid for production of biodiesel. Ind. Eng. Chem. Res. 45 (2006), 5708–5715.
8. Piskarev, I.M., Ushkanov, V.A., Aristova, N.A., Likhachev, P.P., Myslivets, T.S., Establishment of the redox potential of water saturated with hydrogen. Biophysics 55 (2010), 13–17.
9. West, R.M., Liu, Z.Y., Peter, M., Dumesic, J.A., Liquid alkanes with targeted molecular weights from biomass-derived carbohydrates. ChemSusChem 1 (2008), 417–424.
10. Moreno, B.M., Li, N., Lee, J., Huber, G.W., Klein, M.T., Modeling aqueous-phase hydrodeoxygenation of sorbitol over Pt/SiO2-Al2O3. RSC Adv. 3 (2013), 23769–23784.
11. Huber, G.W., Chheda, J.N., Barrett, C.J., Dumesic, J.A., Production of liquid alkanes by aqueous-phase processing of biomass-derived carbohydrates. Science 308 (2005), 1446–1450.
12. Huber, G.W., Shabaker, J.W., Evans, S.T., Dumesic, J.A., Aqueous-phase reforming of ethylene glycol over supported Pt and Pd bimetallic catalysts. Appl. Catal. B 62 (2006), 226–235.
13. Kunkes, E.L., Simonetti, D.A., Dumesic, J.A., Pyrz, W.D., Murillo, L.E., Chen, J.G., Buttrey, D.J., The role of rhenium in the conversion of glycerol to synthesis gas over carbon supported platinum–rhenium catalysts. J. Catal. 260 (2008), 164–177.
14. Shabaker, J.W., Davda, R.R., Huber, G.W., Cortright, R.D., Dumesic, J.A., Aqueous-phase reforming of methanol and ethylene glycol over alumina-supported platinum catalysts. J. Catal. 215 (2003), 344–352.
15. van Haasterecht, T., Ludding, C.C.I., de Jong, K.P., Bitter, J.H., Toward stable nickel catalysts for aqueous phase reforming of biomass-derived feedstock under reducing and alkaline conditions. J. Catal. 319 (2014), 27–35.
16. Luo, H.Y., Consoli, D.F., Gunther, W.R., Román-Leshkov, Y., Investigation of the reaction kinetics of isolated Lewis acid sites in Beta zeolites for the Meerwein–Ponndorf–Verley reduction of methyl levulinate to γ-valerolactone. J. Catal. 320 (2014), 198–207.
17. Chia, M., Dumesic, J.A., Liquid-phase catalytic transfer hydrogenation and cyclization of levulinic acid and its esters to [gamma]-valerolactone over metal oxide catalysts. Chem. Commun. 47 (2011), 12233–12235.
18. Jae, J., Mahmoud, E., Lobo, R.F., Vlachos, D.G., Cascade of liquid-phase catalytic transfer hydrogenation and etherification of 5-hydroxymethylfurfural to potential biodiesel components over lewis acid zeolites. ChemCatChem 6 (2014), 508–513.
19. Lewis, J.D., Van de Vyver, S., Crisci, A.J., Gunther, W.R., Michaelis, V.K., Griffin, R.G., Román-Leshkov, Y., A continuous flow strategy for the coupled transfer hydrogenation and etherification of 5-(hydroxymethyl)furfural using lewis acid zeolites. ChemSusChem 7 (2014), 2255–2265.
20. Bui, L., Luo, H., Gunther, W.R., Román-Leshkov, Y., Domino reaction catalyzed by zeolites with brønsted and lewis acid sites for the production of γ-valerolactone from furfural. Angew. Chem. Int. Ed. 52 (2013), 8022–8025.
21. Abdelrahman, O.A., Heyden, A., Bond, J.Q., Analysis of kinetics and reaction pathways in the aqueous-phase hydrogenation of levulinic acid to form γ-valerolactone over RU/C. ACS Catal. 4 (2014), 1171–1181.
22. Manzer, L.E., Catalytic synthesis of alpha-methylene-gamma-valerolactone: a biomass-derived acrylic monomer. Appl. Catal. A 272 (2004), 249–256.
23. Wu, Z.J., Ge, S.H., Ren, C.X., Zhang, M.H., Yip, A., Xu, C.M., Selective conversion of cellulose into bulk chemicals over Bronsted acid-promoted ruthenium catalyst: one-pot vs. sequential process. Green Chem. 14 (2012), 3336–3343.
24. Deng, L., Zhao, Y., Li, J.A., Fu, Y., Liao, B., Guo, Q.X., Conversion of levulinic acid and formic acid into gamma-valerolactone over heterogeneous catalysts. ChemSusChem 3 (2010), 1172–1175.
25. Luque, R., Clark, J.H., Water-tolerant Ru-Starbon (R) materials for the hydrogenation of organic acids in aqueous ethanol. Catal. Commun. 11 (2010), 928–931.
26. Maris, E.P., Ketchie, W.C., Vladimir, O., Davis, R.J., Metal particle growth during glucose hydrogenation over Ru/SiO2 evaluated by X-ray absorption spectroscopy and electron microscopy. J. Phys. Chem. B 110 (2006), 7869–7876.
27. Arena, B.J., Deactivation of ruthenium catalysts in continuous glucose hydrogenation. Appl. Catal. A 87 (1992), 219–229.
28. Yan, K., Liao, J., Wu, X., Xie, X., A noble-metal free Cu-catalyst derived from hydrotalcite for highly efficient hydrogenation of biomass-derived furfural and levulinic acid. RSC Adv. 3 (2013), 3853–3856.
29. Hengne, A.M., Rode, C.V., Cu–ZrO2 nanocomposite catalyst for selective hydrogenation of levulinic acid and its ester to [gamma]-valerolactone. Green Chem. 14 (2012), 1064–1072.
30. Wang, Y., Van de Vyver, S., Sharma, K.K., Roman-Leshkov, Y., Insights into the stability of gold nanoparticles supported on metal oxides for the base-free oxidation of glucose to gluconic acid. Green Chem. 16 (2014), 719–726.
31. Braden, D.J., Henao, C.A., Heltzel, J., Maravelias, C.C., Dumesic, J.A., Production of liquid hydrocarbon fuels by catalytic conversion of biomass-derived levulinic acid. Green Chem. 13 (2011), 1755–1765.
32. Bond, J.Q., Upadhye, A.A., Olcay, H., Tompsett, G.A., Jae, J., Xing, R., Alonso, D.M., Wang, D., Zhang, T., Kumar, R., Foster, A., Sen, S.M., Maravelias, C.T., Malina, R., Barrett, S.R.H., Lobo, R., Wyman, C.E., Dumesic, J.A., Huber, G.W., Production of renewable jet fuel range alkanes and commodity chemicals from integrated catalytic processing of biomass. Energy Environ. Sci. 7 (2014), 1500–1523.
33. Ide, M.S., Falcone, D.D., Davis, R.J., On the deactivation of supported platinum catalysts for selective oxidation of alcohols. J. Catal. 311 (2014), 295–305.
34. Cortright, R.D., Sanchez-Castillo, M., Dumesic, J.A., Conversion of biomass to 1,2-propanediol by selective catalytic hydrogenation of lactic acid over silica-supported copper. Appl. Catal. B 39 (2002), 353–359.
35. Zhang, Z., Jackson, J.E., Miller, D.J., Aqueous-phase hydrogenation of lactic acid to propylene glycol. Appl. Catal. A 219 (2001), 89–98.
36. Santiago, M.A.N., Sánchez-Castillo, M.A., Cortright, R.D., Dumesic, J.A., Catalytic reduction of acetic acid, methyl acetate, and ethyl acetate over silica-supported copper. J. Catal. 193 (2000), 16–28.
37. 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 322 (2008), 417–421.
38. Van Pelt, A.H., Simakova, O.A., Schimming, S.M., Ewbank, J.L., Foo, G.S., Pidko, E.A., Hensen, E.J.M., Sievers, C., Stability of functionalized activated carbon in hot liquid water. Carbon 77 (2014), 143–154.
39. Pham, H.N., Anderson, A.E., Johnson, R.L., Schmidt-Rohr, K., Datye, A.K., Improved hydrothermal stability of mesoporous oxides for reactions in the aqueous phase. Angew. Chem. Int. Ed. 51 (2012), 13163–13167.
40. Ketchie, W.C., Maris, E.P., Davis, R.J., In-situ X-ray absorption spectroscopy of supported Ru catalysts in the aqueous phase. Chem. Mater. 19 (2007), 3406–3411.
41. Xiong, H., Pham, H.N., Datye, A.K., Hydrothermally stable heterogeneous catalysts for conversion of biorenewables. Green Chem. 16 (2014), 4627–4643.
42. Xiong, H., Pham, H.N., Datye, A.K., A facile approach for the synthesis of niobia/carbon composites having improved hydrothermal stability for aqueous-phase reactions. J. Catal. 302 (2013), 93–100.
43. Luo, W., Sankar, M., Beale, A.M., He, Q., Kiely, C.J., Bruijnincx, P.C.A., Weckhuysen, B.M., High performing and stable supported nano-alloys for the catalytic hydrogenation of levulinic acid to γ-valerolactone. Nat. Commun., 6, 2015.
44. Wettstein, S.G., Bond, J.Q., Alonso, D.M., Pham, H.N., Datye, A.K., Dumesic, J.A., RuSn bimetallic catalysts for selective hydrogenation of levulinic acid to γ-valerolactone. Appl. Catal. B 117–118 (2012), 321–329.
45. Lowell, S., Characterization of Porous Solids and Powders: Surface Area, Pore Size and Density. 2004, Springer.
46. Vleeming, J.H., Kuster, B.F.M., Marin, G.B., Oudet, F., Courtine, P., Graphite-supported platinum catalysts: effects of gas and aqueous phase treatments. J. Catal. 166 (1997), 148–159.
47. Reyes, P., König, M.E., Pecchi, G., Concha, I., López Granados, M., Fierro, J.L.G., O-xylene hydrogenation on supported ruthenium catalysts. Catal. Lett. 46 (1997), 71–75.
48. Neri, G., Mercadante, L., Donato, A., Visco, A.M., Galvagno, S., Influence of Ru precursor, support and solvent in the hydrogenation of citral over ruthenium catalysts. Catal. Lett. 29 (1994), 379–386.
49. Basińska, A., Kępiński, L., Domka, F., The effect of support on WGSR activity of ruthenium catalysts. Appl. Catal. A 183 (1999), 143–153.
50. Pavlenko, N.V., Tripol'skii, A.I., Golodets, G.I., Vapor-phase hydrogenation of acetone on applied metals of the platinum group. Theor. Exp. Chem. 22 (1987), 667–675.
51. Sen, B., Vannice, M.A., Metal-support effects on acetone hydrogenation over platinum catalysts. J. Catal. 113 (1988), 52–71.
52. Rositani, F., Galvagno, S., Poltarzewski, Z., Staiti, P., Antonucci, P.L., Kinetics of acetone hydrogenation over Pt/Al2O3 catalysts. J. Chem. Technol. Biotechnol. 35 (1985), 234–240.
53. Wan, H., Vitter, A., Chaudhari, R.V., Subramaniam, B., Kinetic investigations of unusual solvent effects during Ru/C catalyzed hydrogenation of model oxygenates. J. Catal. 309 (2014), 174–184.
54. Manyar, H.G., Weber, D., Daly, H., Thompson, J.M., Rooney, D.W., Gladden, L.F., Hugh Stitt, E., Jose Delgado, J., Bernal, S., Hardacre, C., Deactivation and regeneration of ruthenium on silica in the liquid-phase hydrogenation of butan-2-one. J. Catal. 265 (2009), 80–88.
55. Madon, R.J., Boudart, M., Experimental criterion for the absence of artifacts in the measurement of rates of heterogeneous catalytic reactions. Ind. Eng. Chem. Fundam. 21 (1982), 438–447.
56. Koros, R.M., Nowak, E.J., A diagnostic test of the kinetic regime in a packed bed reactor. Chem. Eng. Sci., 22, 1967, 470.
57. Tauster, S.J., Strong metal-support interactions. Acc. Chem. Res. 20 (1987), 389–394.
58. Tauster, S.J., Fung, S.C., Garten, R.L., Strong metal-support interactions. Group 8 noble metals supported on titanium dioxide. JACS 100 (1978), 170–175.
59. Lefèvre, G., Duc, M., Lepeut, P., Caplain, R., Fédoroff, M., Hydration of γ-alumina in water and its effects on surface reactivity. Langmuir 18 (2002), 7530–7537.
60. Duan, J., Kim, Y.T., Lou, H., Huber, G.W., Hydrothermally stable regenerable catalytic supports for aqueous-phase conversion of biomass. Catal. Today 234 (2014), 66–74.
61. Luo, W., Deka, U., Beale, A.M., van Eck, E.R.H., Bruijnincx, P.C.A., Weckhuysen, B.M., Ruthenium-catalyzed hydrogenation of levulinic acid: influence of the support and solvent on catalyst selectivity and stability. J. Catal. 301 (2013), 175–186.
62. Bartholomew, C.H., Mechanisms of catalyst deactivation. Appl. Catal. A 212 (2001), 17–60.
63. Douidah, A., Marécot, P., Labruquère, S., Barbier, J., Stability of supported platinum catalysts in aqueous phase under hydrogen atmosphere. Appl. Catal. A 210 (2001), 111–120.
64. Douidah, A., Marécot, P., Barbier, J., Toward a better understanding of the stability of supported platinum catalysts in aqueous phase under hydrogen atmosphere at room temperature. Appl. Catal. A 225 (2002), 11–19.
65. Besson, M., Gallezot, P., Deactivation of metal catalysts in liquid phase organic reactions. Catal. Today 81 (2003), 547–559.
66. Nagai, Y., Hirabayashi, T., Dohmae, K., Takagi, N., Minami, T., Shinjoh, H., Matsumoto, S.I., Sintering inhibition mechanism of platinum supported on ceria-based oxide and Pt-oxide–support interaction. J. Catal. 242 (2006), 103–109.
67. Asakura, K., Iwasawa, Y., Surface structure and catalysis for CO hydrogenation of the supported Ru species derived from the Ru3(CO)12 inorganic oxides. J. Chem. Soc., Faraday Trans. 86 (1990), 2657–2662.
68. Butler, M.A., Ginley, D.S., Prediction of flatband potentials at semiconductor-electrolyte interfaces from atomic electronegativities. J. Electrochem. Soc. 125 (1978), 228–232.
69. Pearson, R.G., Hard and soft acids and bases, HSAB, part 1: fundamental principles. J. Chem. Educ., 45, 1968, 581.
70. Andersson, K., Gómez, A., Glover, C., Nordlund, D., Öström, H., Schiros, T., Takahashi, O., Ogasawara, H., Pettersson, L.G.M., Nilsson, A., Molecularly intact and dissociative adsorption of water on clean Cu(1 1 0): a comparison with the water/Ru(0 0 1) system. Surf. Sci. 585 (2005), L183–L189.
71. Andersson, K., Nikitin, A., Pettersson, L.G.M., Nilsson, A., Ogasawara, H., Water dissociation on Ru(0 0 1): an activated process. Phys. Rev. Lett., 93, 2004, 196101.
72. Cui, H., Park, J.-H., Park, J.-G., Effect of oxidizers on chemical mechanical planarization of ruthenium with colloidal silica based slurry. J. Solid State Sci. Technol. 2 (2013), P26–P30.
73. Kosmulski, M., The pH-dependent surface charging and the points of zero charge. J. Colloid Interface Sci. 253 (2002), 77–87.
74. Noh, J.S., Schwarz, J.A., Estimation of the point of zero charge of simple oxides by mass titration. J. Colloid Interface Sci. 130 (1989), 157–164.
75. Wachs, I.E., Molecular structures of surface metal oxide species: nature of catalytic active sites in mixed metal oxides. Fierro, J.L.G., (eds.) Metal Oxides: Chemistry and Applications, 2006, Taylor & Francis, 4.
76. Hao, X., Quach, L., Korah, J., Spieker, W.A., Regalbuto, J.R., The control of platinum impregnation by PZC alteration of oxides and carbon. J. Mol. Catal. A: Chem. 219 (2004), 97–107.
77. Samad, J.E., Hashim, S., Ma, S., Regalbuto, J.R., Determining surface composition of mixed oxides with pH. J. Colloid Interface Sci. 436 (2014), 204–210.
78. O'Neill, B.J., Jackson, D.H.K., Crisci, A.J., Farberow, C.A., Shi, F., Alba-Rubio, A.C., Lu, J., Dietrich, P.J., Gu, X., Marshall, C.L., Stair, P.C., Elam, J.W., Miller, J.T., Ribeiro, F.H., Voyles, P.M., Greeley, J., Mavrikakis, M., Scott, S.L., Kuech, T.F., Dumesic, J.A., Stabilization of copper catalysts for liquid-phase reactions by atomic layer deposition. Angew. Chem. 125 (2013), 14053–14057.
79. Alba-Rubio, A.C., O'Neill, B.J., Shi, F., Akatay, C., Canlas, C., Li, T., Winans, R., Elam, J.W., Stach, E.A., Voyles, P.M., Dumesic, J.A., Pore structure and bifunctional catalyst activity of overlayers applied by atomic layer deposition on copper nanoparticles. ACS Catal. 4 (2014), 1554–1557.
80. Lu, J., Elam, J.W., Stair, P.C., Synthesis and stabilization of supported metal catalysts by atomic layer deposition. Acc. Chem. Res. 46 (2013), 1806–1815.