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Research Article

Zero-oxidation state precursor assisted fabrication of highly dispersed and stable Pt catalyst for chemoselective hydrogenation of α,β-unsaturated aldehydes

Yu Liang1, Mark Douthwaite2, Xiaoyang Huang2, Binbin Zhao1, Qiong Tang1, Lei Liu1( ), Jinxiang Dong1
College of Chemical Engineering and Technology, Taiyuan University of Technology, Taiyuan 030024, China
Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK
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Graphical Abstract

Highly dispersed and stable Pt-based catalysts were developed by using Pt(0)-complex as the precursor through mild hydrogenation treatment. Pt/FeOx/SBA-15 exhibited markedly high catalytic performance and generality in the selective hydrogenation of α,β-unsaturated aldehydes.

Abstract

The chemoselective hydrogenation of α,β-unsaturated aldehydes is a key strategy for the synthesis of fine chemicals. Herein, we developed an efficient method of depositing Pt particles on FeOx/SBA-15. This strategy is dependent on using a platinum-divinyltetramethyldisiloxane complex (Pt0-DVTMS) as the precursor, which we demonstrate can be removed through a H2-treatment under mild conditions. This, in turn, allowed for the synthesis of catalysts with well dispersed Pt particles. The presence of FeOx species also aided Pt dispersion; when coated onto SBA-15, FeOx strongly interacted with dissociated Pt species, inhibiting both Pt aggregation and metal leaching. Using cinnamaldehyde as a model α,β-unsaturated aldehyde, it was demonstrated that this catalyst was highly selective towards the unsaturated alcohol and no obvious loss in activity was observed over five recycles. This catalyst was determined to be significantly more effective than an analogous catalyst prepared using chloroplatinic acid as a precursor, evidencing the importance of using the Pt0-DVTMS precursor. We corroborate the excellent catalytic performance to highly dispersed Pt-species, whereby Pt0 and Pt2+ play a critical role in activating H2 and the C=O bond. This research demonstrates that the Pt precursor can have a significant impact on the physicochemical properties and thus, the performance of the final catalyst. It also evidences how metal support interactions can dramatically influence selectivity in such hydrogenation reactions. This novel catalyst preparation protocol, using a DVTMS ligand for Pt impregnation, offers a facile approach to the design of multi-component heterogeneous catalysts.

Keywords

platinum catalystzero-oxidation statestabilitychemoselective hydrogenationα,β-unsaturated aldehydes

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References

[1]

Lan, X. C.; Wang, T. F. Highly selective catalysts for the hydrogenation of unsaturated aldehydes: A review. ACS Catal. 2020, 10, 2764–2790.
Crossref Google Scholar
[2]

Luo, X. X.; Jian, Y. M.; Li, H. Low-temperature reduction of bio-based cinnamaldehyde to α,β-(un)saturated alcohols enabled by a waste-derived catalyst. Catal. Commun. 2022, 162, 106391.
Crossref Google Scholar
[3]

Claus, P. Selective hydrogenation of ά, β-unsaturated aldehydes and other C=O and C=C bonds containing compounds. Top. Catal. 1998, 5, 51–62.
Crossref Google Scholar
[4]

Youngs, T. G. A.; Manyar, H.; Bowron, D. T.; Gladden, L. F.; Hardacre, C. Probing chemistry and kinetics of reactions in heterogeneous catalysts. Chem. Sci. 2013, 4, 3484–3489.
Crossref Google Scholar
[5]

Bachiller-Baeza, B.; Rodrı́guez-Ramos, I.; Guerrero-Ruiz, A. Influence of Mg and Ce addition to ruthenium based catalysts used in the selective hydrogenation of α,β-unsaturated aldehydes. Appl. Catal. A Gen. 2001, 205, 227–237.
Crossref Google Scholar
[6]

Wang, X. F.; Liang, X. H.; Geng, P.; Li, Q. B. Recent advances in selective hydrogenation of cinnamaldehyde over supported metal-based catalysts. ACS Catal. 2020, 10, 2395–2412.
Crossref Google Scholar
[7]

Dietrich, C.; Schild, D.; Wang, W.; Kübel, C.; Behrens, S. Bimetallic Pt/Sn-based nanoparticles in ionic liquids as nanocatalysts for the selective hydrogenation of cinnamaldehyde. Z. Anorg. Allg. Chem. 2017, 643, 120–129.
Crossref Google Scholar
[8]

Liu, Z.; Tan, X. L.; Li, J.; Lv, C. Easy synthesis of bimetal PtFe-containing ordered mesoporous carbons and their use as catalysts for selective cinnamaldehyde hydrogenation. New J. Chem. 2013, 37, 1350–1357.
Crossref Google Scholar
[9]

Zheng, Q.; Wang, D.; Yuan, F. L.; Han, Q.; Dong, Y. L.; Liu, Y. F.; Niu, X. Y.; Zhu, Y. J. An effective co-promoted platinum of Co-Pt/SBA-15 catalyst for selective hydrogenation of Cinnamaldehyde to Cinnamyl alcohol. Catal. Lett. 2016, 146, 1535–1543.
Crossref Google Scholar
[10]

Dai, Y. H.; Gao, X.; Chu, X. F.; Jiang, C. Y.; Yao, Y.; Guo, Z.; Zhou, C. M.; Wang, C.; Wang, H. M.; Yang, Y. H. On the role of water in selective hydrogenation of cinnamaldehyde to cinnamyl alcohol on PtFe catalysts. J. Catal. 2018, 364, 192–203.
Crossref Google Scholar
[11]

Vu, K. B.; Bukhryakov, K. V.; Anjum, D. H.; Rodionov, V. O. Surface-bound ligands modulate chemoselectivity and activity of a bimetallic nanoparticle catalyst. ACS Catal. 2015, 5, 2529–2533.
Crossref Google Scholar
[12]

Yuan, K.; Song, T. Q.; Wang, D. W.; Zhang, X. T.; Gao, X.; Zou, Y.; Dong, H. L.; Tang, Z. Y.; Hu, W. P. Effective and selective catalysts for cinnamaldehyde hydrogenation: Hydrophobic hybrids of metal-organic frameworks, metal nanoparticles, and micro- and mesoporous polymers. Angew. Chem., Int. Ed. 2018, 57, 5708–5713.
Crossref Google Scholar
[13]

Pan, H. Y.; Li, J. R.; Lu, J. Q.; Wang, G. M.; Xie, W. H.; Wu, P.; Li, X. H. Selective hydrogenation of cinnamaldehyde with PtFex/Al2O3@SBA-15 catalyst: Enhancement in activity and selectivity to unsaturated alcohol by Pt-FeOx and Pt-Al2O3@SBA-15 interaction. J. Catal. 2017, 354, 24–36.
Crossref Google Scholar
[14]

Wei, Z. J.; Zhu, X. M.; Liu, X. S.; Xu, H. Q.; Li, X. H.; Hou, Y. X.; Liu, Y. X. Pt-Re/rGO bimetallic catalyst for highly selective hydrogenation of cinnamaldehyde to cinnamylalcohol. Chin. J. Chem. Eng. 2019, 27, 369–378.
Crossref Google Scholar
[15]

Hu, Q. M.; Wang, S.; Gao, Z.; Li, Y. Q.; Zhang, Q.; Xiang, Q.; Qin, Y. The precise decoration of Pt nanoparticles with Fe oxide by atomic layer deposition for the selective hydrogenation of cinnamaldehyde. Appl. Catal. B Environ. 2017, 218, 591–599.
Crossref Google Scholar
[16]

He, S.; Xie, L. F.; Che, M. W.; Chan, H. C.; Yang, L. C.; Shi, Z. P.; Tang, Y.; Gao, Q. S. Chemoselective hydrogenation of α,β-unsaturated aldehydes on hydrogenated MoOx nanorods supported iridium nanoparticles. J. Mol. Catal. A Chem. 2016, 425, 248–254.
Crossref Google Scholar
[17]

Bhogeswararao, S.; Srinivas, D. Intramolecular selective hydrogenation of cinnamaldehyde over CeO2-ZrO2-supported Pt Catalysts. J. Catal. 2012, 285, 31–40.
Crossref Google Scholar
[18]

Tamura, M.; Tokonami, K.; Nakagawa, Y.; Tomishige, K. Effective NbOx-modified Ir/SiO2 catalyst for selective gas-phase hydrogenation of crotonaldehyde to crotyl alcohol. ACS Sustainable Chem. Eng. 2017, 5, 3685–3697.
Crossref Google Scholar
[19]

Wei, H. S.; Liu, X. Y.; Wang, A. Q.; Zhang, L. L.; Qiao, B. T.; Yang, X. F.; Huang, Y. Q.; Miao, S.; Liu, J. Y.; Zhang, T. FeOx-supported platinum single-atom and pseudo-single-atom catalysts for chemoselective hydrogenation of functionalized nitroarenes. Nat. Commun. 2014, 5, 5634.
Crossref Google Scholar
[20]

Zhao, F. Y.; Ikushima, Y.; Arai, M. Hydrogenation of nitrobenzene with supported platinum catalysts in supercritical carbon dioxide: Effects of pressure, solvent, and metal particle size. J. Catal. 2004, 224, 479–483.
Crossref Google Scholar
[21]

Bayram, E.; Lu, J.; Aydin, C.; Browning, N. D.; Özkar, S.; Finney, E.; Gates, B. C.; Finke, R. G. Agglomerative sintering of an atomically dispersed Ir1/zeolite Y catalyst: Compelling evidence against Ostwald ripening but for bimolecular and autocatalytic agglomeration catalyst sintering steps. ACS Catal. 2015, 5, 3514–3527.
Crossref Google Scholar
[22]

Jones, J.; Xiong, H. F.; DeLaRiva, A. T.; Peterson, E. J.; Pham, H.; Challa, S. R.; Qi, G.; Oh, S.; Wiebenga, M. H.; Hernández, X. I. P. et al. Thermally stable single-atom platinum-on-ceria catalysts via atom trapping. Science 2016, 353, 150–154.
Crossref Google Scholar
[23]

Qiao, B. T.; Wang, A. Q.; Yang, X. F.; Allard, L. F.; Jiang, Z.; Cui, Y. T.; Liu, J. Y.; Li, J.; Tao, Z. Single-atom catalysis of CO oxidation using Pt1/FeOx. Nat. Chem. 2011, 3, 634–641.
Crossref Google Scholar
[24]

Nguyen, L.; Zhang, S. R.; Wang, L.; Li, Y. Y.; Yoshida, H.; Patlolla, A.; Takeda, S.; Frenkel, A. I.; Tao, F. Reduction of nitric oxide with hydrogen on catalysts of singly dispersed bimetallic sites Pt1Com and Pd1Con. ACS Catal. 2016, 6, 840–850.
Crossref Google Scholar
[25]

Ida, S.; Kim, N.; Ertekin, E.; Takenaka, S.; Ishihara, T. Photocatalytic reaction centers in two-dimensional titanium oxide crystals. J. Am. Chem. Soc. 2015, 137, 239–244.
Crossref Google Scholar
[26]

Wang, J.; Zhao, X. C.; Lei, N.; Li, L.; Zhang, L. L.; Xu, S. T.; Miao, S.; Pan, X. L.; Wang, A. Q.; Zhang, T. Hydrogenolysis of glycerol to 1,3-propanediol under low hydrogen pressure over WOx-supported single/pseudo-single atom Pt catalyst. ChemSusChem 2016, 9, 784–790.
Crossref Google Scholar
[27]

Forde, M. M.; Kesavan, L.; Bin Saiman, M. I.; He, Q.; Dimitratos, N.; Lopez-Sanchez, J. A.; Jenkins, R. L.; Taylor, S. H.; Kiely, C. J., Hutchings, G. J. High activity redox catalysts synthesized by chemical vapor impregnation. ACS Nano 2014, 8, 957–969.
Crossref Google Scholar
[28]

Kyriakou, G.; Boucher, M. B.; Jewell, A. D.; Lewis, E. A.; Lawton, T. J.; Baber, A. E.; Tierney, H. L.; Flytzani-Stephanopoulos, M.; Sykes, E. C. H. Isolated metal atom geometries as a strategy for selective heterogeneous hydrogenations. Science 2012, 335, 1209–1212.
Crossref Google Scholar
[29]

Lang, R.; Du, X. R.; Huang, Y. K.; Jiang, X. Z.; Zhang, Q, Guo, Y. L.; Liu, K. P.; Qiao, B. T.; Wang, A. Q.; Zhang, T. Single-atom catalysts based on the metal-oxide interaction. Chem. Rev. 2020, 120, 11986–12043.
Crossref Google Scholar
[30]

Ketelson, H. A.; Brook, M. A.; Pelton, R.; Heng, Y. M. Hydridosilsesquioxane modified silica-supported platinum nanoparticles. Chem. Mater. 1996, 8, 2195–2199.
Crossref Google Scholar
[31]

Qin, R. X.; Liu, K. L.; Wu, Q. Y.; Zheng, N. F. Surface coordination chemistry of atomically dispersed metal catalysts. Chem. Rev. 2020, 120, 11810–11899.
Crossref Google Scholar
[32]

Maimaiti, Y.; Elliott, S. D. Kinetics and coverage dependent reaction mechanisms of the copper atomic layer deposition from copper dimethylamino-2-propoxide and diethylzinc. Chem. Mater. 2016, 28, 6282–6295.
Crossref Google Scholar
[33]

Sun, S. H.; Zhang, G. X.; Gauquelin, N.; Chen, N.; Zhou, J. G.; Yang, S. L.; Chen, W. F.; Meng, X. B.; Geng, D. S.; Banis, M. N. et al. Single-atom catalysis using Pt/graphene achieved through atomic layer deposition. Sci. Rep. 2013, 3, 1775.
Crossref Google Scholar
[34]

Huang, X. H.; Xia, Y. J.; Cao, Y. J.; Zheng, X. S.; Pan, H. B.; Zhu, J. F.; Ma, C.; Wang, H. W.; Li, J. J.; You, R. et al. Enhancing both selectivity and coking-resistance of a single-atom Pd1/C3N4 catalyst for acetylene hydrogenation. Nano Res. 2017, 10, 1302–1312.
Crossref Google Scholar
[35]

Gao, G. P.; Jiao, Y.; Waclawik, E. R.; Du, A. J. Single atom (Pd/Pt) supported on graphitic carbon nitride as an efficient photocatalyst for visible-light reduction of carbon dioxide. J. Am. Chem. Soc. 2016, 138, 6292–6297.
Crossref Google Scholar
[36]

Lin, L. H.; Chen, Z.; Chen, W. X. Single atom catalysts by atomic diffusion strategy. Nano Res. 2021, 14, 4398–4416.
Crossref Google Scholar
[37]

Lu, J.; Aydin, C.; Browning, N. D.; Gates, B. C. Imaging isolated gold atom catalytic sites in zeolite NaY. Angew. Chem. 2012, 124, 5944–5948.
Crossref Google Scholar
[38]

Hansen, T. W.; DeLaRiva, A. T.; Challa, S. R.; Datye, A. K. Sintering of catalytic nanoparticles: Particle migration or Ostwald ripening? Acc. Chem. Res. 2013, 46, 1720–1730.
Crossref Google Scholar
[39]

Yan, H.; Cheng, H.; Yi, H.; Lin, Y.; Yao, T.; Wang, C. L.; Li, J. J.; Wei, S. Q.; Lu, J. L. Single-atom Pd1/graphene catalyst achieved by atomic layer deposition: Remarkable performance in selective hydrogenation of 1, 3-butadiene. J. Am. Chem. Soc. 2015, 137, 10484–10487.
Crossref Google Scholar
[40]

Iimura, T.; Akasaka, N.; Kosai, T.; Iwamoto, T. A Pt(0) complex with cyclic (alkyl)(amino) silylene and 1,3-divinyl-1,1,3,3-tetramethyldisiloxane ligands: Synthesis, molecular structure, and catalytic hydrosilylation activity. Dalton Trans. 2017, 46, 8868–8874.
Crossref Google Scholar
[41]

Impéror-Clerc, M.; Davidson, P.; Davidson, A. Existence of a microporous corona around the mesopores of silica-based SBA-15 materials templated by triblock copolymers. J. Am. Chem. Soc. 2000, 122, 11925–11933.
Crossref Google Scholar
[42]

Wang, C.; Huang, Z. X. Controlled synthesis of α-Fe2O3 nanostructures for efficient photocatalysis. Mater. Lett. 2016, 164, 194–197.
Crossref Google Scholar
[43]

He, X. H.; Deng, Y. C.; Zhang, Y.; He, Q.; Xiao, D. Q.; Peng, M.; Zhao, Y.; Zhang, H.; Luo, R. C.; Gan, T. et al. Mechanochemical kilogram-scale synthesis of noble metal single-atom catalysts. Cell Rep. Phys. Sci. 2020, 1, 100004.
Crossref Google Scholar
[44]

Xue, Y. J.; Yao, R. H.; Li, J. R.; Wang, G. M.; Wu, P.; Li, X. H. Efficient Pt-FeOx/TiO2@SBA-15 catalysts for selective hydrogenation of cinnamaldehyde to cinnamyl alcohol. Catal. Sci. Technol. 2017, 7, 6112–6123.
Crossref Google Scholar
[45]

Lewis, L. N.; Colborn, R. E.; Grade, H.; Bryant, G. L.; Sumpter, C. A.; Scott, R. A. Mechanism of formation of platinum(0) complexes containing silicon-vinyl ligands. Organometallics 1995, 14, 2202–2213.
Crossref Google Scholar
[46]

Li, Y.; Zhu, P. F.; Zhou, R. X. Selective hydrogenation of cinnamaldehyde to cinnamyl alcohol with carbon nanotubes supported Pt-Co catalysts. Appl. Surf. Sci. 2008, 254, 2609–2614.
Crossref Google Scholar
[47]

Sermon, P. A.; Bond, G. C. Hydrogen spillover. Catal. Rev. 1974, 8, 211–239.
Crossref Google Scholar
[48]

Liu, T.; Zeng, X. R.; Lai, X. J.; Li, H. Q. Efficient organic-to-inorganic conversion of polysiloxane by novel platinum-thiol catalytic system. Polym. Degrad. Stab. 2020, 176, 109161.
Crossref Google Scholar
[49]

Iida, H.; Igarashi, A. Characterization of a Pt/TiO2 (rutile) catalyst for water gas shift reaction at low-temperature. Appl. Catal. A Gen. 2006, 298, 152–160.
Crossref Google Scholar
[50]

Thang, H. V.; Pacchioni, G.; DeRita, L.; Christopher, P. Nature of stable single atom Pt catalysts dispersed on anatase TiO2. J. Catal. 2018, 367, 104–114.
Crossref Google Scholar
[51]

Ding, K. L.; Gulec, A.; Johnson, A. M.; Schweitzer, N. M.; Stucky, G. D.; Marks, L. D.; Stair, P. C. Identification of active sites in CO oxidation and water-gas shift over supported Pt catalysts. Science 2015, 350, 189–192.
Crossref Google Scholar
[52]

Chen, Y. J.; Ji, S. F.; Chen, C.; Peng, Q.; Wang, D. S.; Li, Y. D. Single-atom catalysts: Synthetic strategies and electrochemical applications. Joule 2018, 2, 1242–1264.
Crossref Google Scholar
[53]

Tang, H. L.; Su, Y.; Zhang, B. S.; Lee, A. F.; Isaacs, M. A.; Wilson, K.; Li, L.; Ren, Y. G.; Huang, J. H.; Haruta, M. et al. Classical strong metal-support interactions between gold nanoparticles and titanium dioxide. Sci. Adv. 2017, 3, e1700231.
Crossref Google Scholar
[54]

Kim, M. J.; Lee, M. W.; Lee, K. Y. Improved catalytic wet peroxide oxidation of phenol over Pt-Fe2O3/SBA-15: Influence of platinum species and DFT calculations. Appl. Surf. Sci. 2021, 541, 148409.
Crossref Google Scholar
[55]

Navas-Cárdenas, C.; Benito, N.; Wolf, E. E.; Gracia, F. Tuning activity of Pt/FeOx/TiO2 catalysts synthesized through selective-electrostatic adsorption for hydrogen purification by prox reaction. Int. J. Hydrogen Energy 2022, 47, 20867–20880.
Crossref Google Scholar
[56]

Yuan, T.; Liu, D. R.; Pan, Y.; Pu, X. Q.; Xia, Y. D.; Wang, J. B.; Xiong, W. Magnetic anchored CoPt bimetallic nanoparticles as selective hydrogenation catalyst for cinnamaldehyde. Catal. Lett. 2019, 149, 851–859.
Crossref Google Scholar
[57]

Shi, Y. S.; Yuan, Z. F.; Wei, Q.; Sun, K. Q.; Xu, B. Q. Pt-FeOx/SiO2 catalysts prepared by galvanic displacement show high selectivity for cinnamyl alcohol production in the chemoselective hydrogenation of cinnamaldehyde. Catal. Sci. Technol. 2016, 6, 7033–7037.
Crossref Google Scholar
[58]

Xin, H. Y.; Zhang, W. B.; Xiao, X. X.; Chen, L.; Wu, P.; Li, X. H. Selective hydrogenation of cinnamaldehyde with NixFe1−xAl2O4+δ composite oxides supported Pt catalysts: C=O versus C=C selectivity switch by varying the Ni/Fe molar ratios. J. Catal. 2021, 393, 129–136.
Crossref Google Scholar
[59]

Shu, Y. J.; Chen, T.; Chan, H. C.; Xie, L. F.; Gao, Q. S. Chemoselective hydrogenation of cinnamaldehyde on iron-oxide modified Pt/MoO3−y Catalysts. Chem. Asian J. 2018, 13, 3737–3744.
Crossref Google Scholar
[60]

Yao, R. H.; Li, J. R.; Wu, P.; Li, X. H. The superior performance of a Pt catalyst supported on nanoporous SiC-C composites for liquid-phase selective hydrogenation of cinnamaldehyde. RSC Adv. 2016, 6, 81211–81218.
Crossref Google Scholar
[61]

Kuai, L.; Chen, Z.; Liu, S. J.; Kan, E. J.; Yu, N.; Ren, Y. M.; Fang, C. H.; Li, X. Y.; Li, Y. D.; Geng, B. Y. Titania supported synergistic palladium single atoms and nanoparticles for room temperature ketone and aldehydes hydrogenation. Nat. Commun. 2020, 11, 48.
Crossref Google Scholar
[62]

Li, L. C.; Wei, W.; Wang, W; Wang, X. L.; Zhang, L.; Tian, A. M. Selective hydrogenation of cinnamaldehyde catalyzed by Co-doped Pt clusters: A density functional theoretical study. RSC Adv. 2016, 6, 88277–88286.
Crossref Google Scholar
[63]

Pozdnyakova, O.; Teschner, D.; Wootsch, A.; Kröhnert, J.; Steinhauer, B.; Sauer, H.; Toth, L.; Jentoft, F. C.; Knop-Gericke, A.; Paál, Z. et al. Preferential CO oxidation in hydrogen (PROX) on ceria-supported catalysts, part I: Oxidation state and surface species on Pt/CeO2 under reaction conditions. J. Catal. 2006, 237, 1–16.
Crossref Google Scholar
Nano Research
Volume 16 Issue 5,
May 2023
Pages 6085-6093
DOI: 10.1007/s12274-022-4822-4
Cite this article:
Liang Y, Douthwaite M, Huang X, et al. Zero-oxidation state precursor assisted fabrication of highly dispersed and stable Pt catalyst for chemoselective hydrogenation of α,β-unsaturated aldehydes. Nano Research, 2023, 16(5): 6085-6093. https://doi.org/10.1007/s12274-022-4822-4
Topics:
Catalysts
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Key Nanomaterials for Industrial Chemical Process

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Received: 20 May 2022
Revised: 11 July 2022
Accepted: 26 July 2022
Published: 27 August 2022
© Tsinghua University Press 2022
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