High Activity Redox Catalysts Synthesised by Chemical Vapour Impregnation
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1 Supporting Online Information High Activity Redox Catalysts Synthesised by Chemical Vapour Impregnation Michael M. Forde, 1 Lokesh Kesavan, 1 Mohd Izham bin Saiman, 1 Qian He, 2 Nikolaos Dimitratos, 1 Jose Antonio Lopez-Sanchez, 1 Robert L. Jenkins, 1 Stuart H. Taylor, 1 Christopher J. Kiely, 2 and Graham J. Hutchings 1 1 Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building Park Place, Cardiff, CF10 3AT, United Kingdom. Tel.: ; Fax: Department of Materials Science and Engineering, Lehigh University, 5 East Packer Avenue, Bethlehem, PA , USA.
2 Directory of contents Table S1. Liquid phase oxidation of benzyl alcohol using Pd, Pt and Pd-Pt catalysts supported on TiO 2 prepared by the chemical vapour impregnation method. Table S2. Liquid phase oxidation of benzyl alcohol using Pd, Pt and Pd-Pt catalysts supported on TiO 2 and C prepared by the sol-immobilisation (SI) and impregnation (IW) methods. Table S3. Comparison of catalysts used in hydrogenation of levulinic acid to γ-valerolactone from recent literature Figure S1. Additional STEM-HAADF micrographs showing typical metal cluster morphologies for CVI prepared samples of (a) Pd/TiO 2 (b) Pt/TiO 2 and (c) Pd-Pt/TiO 2. Figure S2. STEM-HAADF and STEM-BF images of a 2.5wt%Pd/TiO 2 CVI catalyst that had been exposed to air for long periods. Figure S3. GC spectrum from the GC-MS analysis of the reaction mixture from the hydrogenation of levulinic acid using 1.25wt%Pd-1.25wt%Pt/TiO 2 catalyst. Figure S4. MS analysis of the reaction products (separated by GC) from the hydrogenation of levulinic acid using a 1.25wt/%Pd- 1.25wt%Pt/TiO 2 catalyst prepared by CVI.
3 Table S1. Liquid phase oxidation of benzyl alcohol using Pd, Pt and Pd-Pt catalysts supported on TiO 2 prepared by the chemical vapour impregnation method. a Selectivity (%) Catalyst Conv. Toluene Benzaldehyde Benzoic Benzyl TOF /h -1 b (%) acid benzoate 2.5% Pd/TiO % Pd-2.5% Pt/TiO %Pd-0.5%Pt/TiO %Pd-1.25%Pt/TiO % Pt/TiO a Reaction conditions: 40ml benzyl alcohol, 0.05g of catalyst, T = 120 ºC, po 2 = 150 psi, reaction time = 6h. b Calculation of TOF (h -1 ) was performed after 0.5 h of reaction. TOF numbers were calculated on the basis of total metal loading as measured by ICP except for the 2.5wt%Pd-2.5wt%Pt/TiO 2 catalyst where nominal metal loading was used.
4 Table S2. Liquid phase oxidation of benzyl alcohol using Pd, Pt and Pd-Pt catalysts supported on TiO 2 and C prepared by the sol-immobilisation (SI) and impregnation (IW) methods. a Catalyst Selectivity (%) TOF/ Toluene Benzaldehyde Benzoic acid Benzyl benzoate h -1 b 5% (2.5Pd+2.5Pt)/TiO 2 IW % (2.5Au+2.5Pd)/TiO 2 IW % (2.5Au+2.5Pd)/C IW wt%Pt/C SI wt%Pd/C SI wt% (0.5Pd+0.5Pt)/C SI wt% (0.5Au+0.5Pd)/C SI a Reaction conditions as given in Reference 1. b Calculation of TOF (h -1 ) was performed after 0.5 h of reaction.
5 Table S3. Comparison of catalysts used in the hydrogenation of levulinic acid to γ-valerolactone from recent literature. Catalyst Conditions Solvent 5% Ru/C mg 5% Ru/C Cu/ZrO 2 and Cu/Al 2 O 3 500mg 1%Pt/TiO 2 LA= levulinic acid GVL= γ-valerolactone 130 C 5% LA 12 bar H C, 50% LA 35 bar H C 5%LA 34.5bar H C 11% LA 40 bar H 2 Conversion % Selectivity to GVL % Ref. water water water water
6 a b c Figure S1. Additional STEM-HAADF micrographs showing typical metal cluster morphologies for CVI prepared samples of (a) Pd/TiO2 (b) Pt/TiO2 and (c) Pd-Pt/TiO2.
7 d e Figure S2. (a, b) STEM-HAADF and (c) STEM-BF images of a 2.5wt%Pd/TiO 2 CVI catalyst that had been exposed to air for long periods ( > 6months). The Pd nanoparticle interiors are metallic in nature, but the fuzzy outer surface appearance in (a) and (b) could indicate that a thin PdO x layer is coating the particle. Similar surface structures were also noted for the 6 month aged 1.25wt%Pd-1.25wt%Pt/TiO 2 CVI catalyst (d) and (e), but not for the 6 month aged 2.5wt%Pt/TiO 2 CVI catalyst.
8 Figure S3. GC spectrum from the GC-MS analysis of the reaction mixture from the hydrogenation of levulinic acid using 1.25wt%Pd-1.25wt%Pt/TiO 2 catalyst. A longer reaction time of 8h at 150 C was used to demonstrate the formation of other products for purposes of the analysis. 3.5 min-mthf; 7.2 min- pentan-1-ol; 14.5 min-pentanoic acid (valeric acid); 16.5 minγ-valerolactone; 17.3 min-1,4-pentanediol, 19.3 min- hydroxyvaleric acid. Pseudo-levulinic acid was not observed by GC or GC-MS techniques in any reaction.
9 Figure S4. MS analysis of the reaction products (separated by GC) from the hydrogenation of levulinic acid using a 1.25wt/%Pd wt%Pt/TiO 2 catalyst prepared by CVI. A longer reaction time of 8h at 150 C was used to demonstrate the formation of other products for purposes of the analysis.
10 References 1. He, Q.; Miedziak, P. J.; Kesavan, L.; Dimitratos, N.; Sankar, M.; Lopez-Sanchez, J. A.; Edwards, J. K.; Forde, M. M.; Knight, D. W.; Taylor, S., et al., Switching-Off Toluene Formation in the Solvent-Free Oxidation of Benzyl Alcohol Using Supported Trimetallic Au Pd Pt Nanoparticles. Faraday Disc. 2013, 162, Al-Shaal, M.; Wright, W. R. H.; Palkovits, R., Exploring the Ruthenium Catalyzed Synthesis of γ-valerolactone in Alcohols and Utilization of Mild Solvent-Free Reaction Conditions. Green Chem. 2012, 14, Serrano-Ruiz, J. C.; Wang, D.; Dumesic, J.A., Catalytic Upgrading of Levulinic Acid to 5-Nonanone. Green Chem. 2010, Hengne, A. M.; Rode, C. V., Cu-ZrO 2 Nanocomposite Catalyst for Selective Hydrogenation of Levulinic Acid and Its Ester to γ-valerolactone. Green Chem. 2012, 14, Lange, J.-P.; Price, R.; Ayoub, P. M.; Louis, J.; Petrus, L.; Clarke, L.; Gosselink, H., Valeric Biofuels: A Platform of Cellulosic Transportation Fuels. Angew. Chem. Int. Ed. 2010, 49,
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