Metal-organic framework supported single-site nickel catalysts for butene dimerization

Zheng, Jian; Löbbert, Laura; Chheda, Saumil; Khetrapal, Navneet; Schmid, Julian; Gaggioli, Carlo Alberto; Yeh, Benjamin; Bermejo-Deval, Ricardo; Motkuri, Radha Kishan; Balasubramanian, Mahalingam; Fulton, John L.; Gutiérrez, Oliver Y.; Siepmann, Joern Ilja; Neurock, Matthew; Gagliardi, Laura; Lercher, Johannes A.

doi:10.1016/j.jcat.2022.06.019

Metal-organic framework supported single-site nickel catalysts for butene dimerization

Journal Article · Tue Jun 14 00:00:00 EDT 2022 · Journal of Catalysis

DOI:https://doi.org/10.1016/j.jcat.2022.06.019· OSTI ID:2205218

Zheng, Jian ^[1]; Löbbert, Laura ^[2]; Chheda, Saumil ^[3]; Khetrapal, Navneet ^[3]; Schmid, Julian ^[1]; Gaggioli, Carlo Alberto ^[3]; Yeh, Benjamin ^[3]; Bermejo-Deval, Ricardo ^[2]; Motkuri, Radha Kishan ^[1]; Balasubramanian, Mahalingam ^[4]; Fulton, John L. ^[1]; Gutiérrez, Oliver Y. ^[1]; Siepmann, Joern Ilja ^[3]; Neurock, Matthew ^[3]; Gagliardi, Laura ^[5]; Lercher, Johannes A. ^[6]

Pacific Northwest National Laboratory (PNNL), Richland, WA (United States). Institute for Integrated Catalysis
Technische Univ. München, Garching (Germany)
Univ. of Minnesota, Minneapolis, MN (United States)
Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
Univ. of Chicago, IL (United States)
Pacific Northwest National Laboratory (PNNL), Richland, WA (United States). Institute for Integrated Catalysis; Technische Univ. München, Garching (Germany)

Homotopic sites in a well-controlled environment are not only ideal systems for mechanistic studies, but also allow optimal control of catalytic transformations. Sites having only a single metal cation and sites consisting of metal oxo complexes with few nickel (Ni) cations supported on the nodes of UiO-66 metal-organic framework (Ni-UiO-66) are studied for 1-butene dimerization. Monomeric Ni sites, which bind to the Zr₆ node via two Zr-OH(µ3) linkages, are active and selective for the dimerization of 1-butene to linear and mono-branched C₈ isomers. Ni oxo complexes with few Ni cations show lower activity and promote the oligomerization of transiently formed C₈ isomers. In conclusion, Kohn-Sham density function theory calculations combined with spectroscopic measurements and kinetic analyses indicate that dimerization follows a Cossee-Arlman reaction mechanism.

View Accepted Manuscript (DOE)

Research Organization:: Pacific Northwest National Laboratory (PNNL), Richland, WA (United States); Energy Frontier Research Centers (EFRC) (United States). Energy Frontier Research Center for Inorganometallic Catalyst Design (ICDC); Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS); SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States). Stanford Synchrotron Radiation Lightsource (SSRL)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division (CSGB)

Grant/Contract Number:: AC05-76RL01830; SC0012702; AC02-06CH11357

OSTI ID:: 2205218

Report Number(s):: PNNL-SA--174304

Journal Information:: Journal of Catalysis, Journal Name: Journal of Catalysis Vol. 413; ISSN 0021-9517

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (47)

Tailored Alkene Oligomerization with H-ZSM-57 Zeolite Martens, Johan A.; Ravishankar, Raman; Mishin, Igor E. Angewandte Chemie, Vol. 39, Issue 23 https://doi.org/10.1002/1521-3773(20001201)39:23<4376::AID-ANIE4376>3.0.CO;2-2	journal	December 2000
Sinter‐Resistant Platinum Catalyst Supported by Metal–Organic Framework Kim, In Soo; Li, Zhanyong; Zheng, Jian Angewandte Chemie, Vol. 130, Issue 4 https://doi.org/10.1002/ange.201708092	journal	January 2018
A Highly Selective Ethylene Tetramerization Catalyst Shaikh, Yacoob; Albahily, Khalid; Sutcliffe, Matthew Angewandte Chemie International Edition, Vol. 51, Issue 6 https://doi.org/10.1002/anie.201106517	journal	January 2012
Ziegler-Natta catalysis I. Mechanism of polymerization of $alpha;-olefins with Ziegler-Natta catalysts*1 Cossee, P. Journal of Catalysis, Vol. 3, Issue 1 https://doi.org/10.1016/0021-9517(64)90095-8	journal	February 1964
Ziegler-Natta catalysis II. Surface structure of layer-lattice transition metal chlorides Arlman, E. Journal of Catalysis, Vol. 3, Issue 1 https://doi.org/10.1016/0021-9517(64)90096-X	journal	February 1964
Catalytic cracking of hydrocarbons over modified ZSM-5 zeolites to produce light olefins: A review Rahimi, Nazi; Karimzadeh, Ramin Applied Catalysis A: General, Vol. 398, Issue 1-2 https://doi.org/10.1016/j.apcata.2011.03.009	journal	May 2011
Assessment of mass transfer limitations in oligomerization of butene at high pressure on H-beta Wulfers, Matthew J.; Lobo, Raul F. Applied Catalysis A: General, Vol. 505 https://doi.org/10.1016/j.apcata.2015.08.016	journal	September 2015
The role of different Ni sites in supported nickel catalysts for butene dimerization under industry-like conditions Brückner, A.; Bentrup, U.; Zanthoff, H. Journal of Catalysis, Vol. 266, Issue 1 https://doi.org/10.1016/j.jcat.2009.05.021	journal	August 2009
Propene oligomerization over Ni-exchanged Na-X zeolites Mlinar, Anton N.; Baur, Guillaume B.; Bong, Gerry G. Journal of Catalysis, Vol. 296 https://doi.org/10.1016/j.jcat.2012.09.010	journal	December 2012
Covalent organic frameworks as supports for a molecular Ni based ethylene oligomerization catalyst for the synthesis of long chain olefins Rozhko, Elena; Bavykina, Anastasiya; Osadchii, Dmitrii Journal of Catalysis, Vol. 345 https://doi.org/10.1016/j.jcat.2016.11.030	journal	January 2017
Nature of active sites on UiO-66 and beneficial influence of water in the catalysis of Fischer esterification Caratelli, Chiara; Hajek, Julianna; Cirujano, Francisco G. Journal of Catalysis, Vol. 352 https://doi.org/10.1016/j.jcat.2017.06.014	journal	August 2017
Stabilization of active, selective, and regenerable Ni-based dimerization catalysts by condensation of ethene withinordered mesopores Agirrezabal-Telleria, Iker; Iglesia, Enrique Journal of Catalysis, Vol. 352 https://doi.org/10.1016/j.jcat.2017.06.025	journal	August 2017
Olefin conversion on nitrogen-doped carbon-supported cobalt catalyst: Effect of feedstock Xu, Zhuoran; Zhao, Dongting; Chada, Joseph P. Journal of Catalysis, Vol. 354 https://doi.org/10.1016/j.jcat.2017.08.019	journal	October 2017
Mechanistic insights and consequences of intrapore liquids in ethene, propene, and butene dimerization on isolated Ni2+ sites grafted within aluminosilicate mesopores Agirrezabal-Telleria, Iker; Iglesia, Enrique Journal of Catalysis, Vol. 389 https://doi.org/10.1016/j.jcat.2020.06.038	journal	September 2020
Evolution of acid and basic sites in UiO-66 and UiO-66-NH2 metal-organic frameworks: FTIR study by probe molecules Chakarova, Kristina; Strauss, Ina; Mihaylov, Mihail Microporous and Mesoporous Materials, Vol. 281 https://doi.org/10.1016/j.micromeso.2019.03.006	journal	June 2019
On the role of co-cations in nickel exchanged LTA zeolite for butene dimerization Ehrmaier, Andreas; Peitz, Stephan; Sanchez-Sanchez, Maricruz Microporous and Mesoporous Materials, Vol. 284 https://doi.org/10.1016/j.micromeso.2019.03.047	journal	August 2019
Defect Engineering: Tuning the Porosity and Composition of the Metal–Organic Framework UiO-66 via Modulated Synthesis Shearer, Greig C.; Chavan, Sachin; Bordiga, Silvia Chemistry of Materials, Vol. 28, Issue 11 https://doi.org/10.1021/acs.chemmater.6b00602	journal	May 2016
Nickel Catalyzed Olefin Oligomerization and Dimerization Olivier-Bourbigou, H.; Breuil, P. A. R.; Magna, L. Chemical Reviews, Vol. 120, Issue 15 https://doi.org/10.1021/acs.chemrev.0c00076	journal	July 2020
Computationally Guided Discovery of a Catalytic Cobalt-Decorated Metal–Organic Framework for Ethylene Dimerization Bernales, Varinia; League, Aaron B.; Li, Zhanyong The Journal of Physical Chemistry C, Vol. 120, Issue 41 https://doi.org/10.1021/acs.jpcc.6b07362	journal	October 2016
Role of Surface Acidity in Formation and Performance of Active Ni Single Sites in Supported Catalysts for Butene Dimerization: A View inside by Operando EPR and In Situ FTIR Spectroscopy Vuong, T. Huyen; Rockstroh, N.; Bentrup, U. ACS Catalysis, Vol. 11, Issue 6 https://doi.org/10.1021/acscatal.0c04894	journal	March 2021
Gas-Phase Dimerization of Ethylene under Mild Conditions Catalyzed by MOF Materials Containing (bpy)Ni ^II Complexes Madrahimov, Sherzod T.; Gallagher, James R.; Zhang, Guanghui ACS Catalysis, Vol. 5, Issue 11 https://doi.org/10.1021/acscatal.5b01604	journal	October 2015
Ethene Oligomerization in Ni-Containing Zeolites: Theoretical Discrimination of Reaction Mechanisms Brogaard, Rasmus Y.; Olsbye, Unni ACS Catalysis, Vol. 6, Issue 2 https://doi.org/10.1021/acscatal.5b01957	journal	January 2016
Production of Linear Octenes from Oligomerization of 1-Butene over Carbon-Supported Cobalt Catalysts Xu, Zhuoran; Chada, Joseph P.; Zhao, Dongting ACS Catalysis, Vol. 6, Issue 6 https://doi.org/10.1021/acscatal.6b00655	journal	May 2016
Exploration of Homogeneous Ethylene Dimerization Mediated by Tungsten Mono(imido) Complexes Messinis, Antonis M.; Wright, William R. H.; Batsanov, Andrei S. ACS Catalysis, Vol. 8, Issue 12 https://doi.org/10.1021/acscatal.8b02201	journal	October 2018
Dimerization of Linear Butenes on Zeolite-Supported Ni ²⁺ Ehrmaier, Andreas; Liu, Yue; Peitz, Stephan ACS Catalysis, Vol. 9, Issue 1 https://doi.org/10.1021/acscatal.8b03095	journal	November 2018
Evidence for the Coordination–Insertion Mechanism of Ethene Dimerization at Nickel Cations Exchanged onto Beta Molecular Sieves Joshi, Ravi; Zhang, Guanghui; Miller, Jeffrey T. ACS Catalysis, Vol. 8, Issue 12 https://doi.org/10.1021/acscatal.8b03202	journal	October 2018
Ethene Dimerization on Zeolite-Hosted Ni Ions: Reversible Mobilization of the Active Site Brogaard, Rasmus Yding; Kømurcu, Mustafa; Dyballa, Michael Martin ACS Catalysis, Vol. 9, Issue 6 https://doi.org/10.1021/acscatal.9b00721	journal	May 2019
Olefin Oligomerization via Metallacycles: Dimerization, Trimerization, Tetramerization, and Beyond McGuinness, David S. Chemical Reviews, Vol. 111, Issue 3 https://doi.org/10.1021/cr100217q	journal	March 2011
Late-Metal Catalysts for Ethylene Homo- and Copolymerization Ittel, Steven D.; Johnson, Lynda K.; Brookhart, Maurice Chemical Reviews, Vol. 100, Issue 4 https://doi.org/10.1021/cr9804644	journal	April 2000
Selective Propene Oligomerization with Nickel(II)-Based Metal–Organic Frameworks Mlinar, Anton N.; Keitz, Benjamin K.; Gygi, David ACS Catalysis, Vol. 4, Issue 3 https://doi.org/10.1021/cs401189a	journal	January 2014
Nickel-Exchanged Zincosilicate Catalysts for the Oligomerization of Propylene Deimund, Mark A.; Labinger, Jay; Davis, Mark E. ACS Catalysis, Vol. 4, Issue 11 https://doi.org/10.1021/cs501313z	journal	October 2014
Selective Oligomerization of Isobutene on Lewis Acid Catalyst: Kinetic Modeling Sarkar, Amitava; Seth, Deepyaman; Ng, Flora T. T. Industrial & Engineering Chemistry Research, Vol. 53, Issue 49 https://doi.org/10.1021/ie501173z	journal	September 2014
Octahedral-Tetrahedral Coordination Equilibria of Nickel(II) and Copper(II) in Concentrated Aqueous Electrolyte Solutions¹ Angell, C. A.; Gruen, D. M. Journal of the American Chemical Society, Vol. 88, Issue 22 https://doi.org/10.1021/ja00974a029	journal	November 1966
MOF-Supported Selective Ethylene Dimerization Single-Site Catalysts through One-Pot Postsynthetic Modification Canivet, Jerome; Aguado, Sonia; Schuurman, Yves Journal of the American Chemical Society, Vol. 135, Issue 11 https://doi.org/10.1021/ja312120x	journal	March 2013
Site Densities, Rates, and Mechanism of Stable Ni/UiO-66 Ethylene Oligomerization Catalysts Yeh, Benjamin; Vicchio, Stephen P.; Chheda, Saumil Journal of the American Chemical Society, Vol. 143, Issue 48 https://doi.org/10.1021/jacs.1c09320	journal	November 2021
Metal–Organic Framework Nodes as Nearly Ideal Supports for Molecular Catalysts: NU-1000- and UiO-66-Supported Iridium Complexes Yang, Dong; Odoh, Samuel O.; Wang, Timothy C. Journal of the American Chemical Society, Vol. 137, Issue 23, p. 7391-7396 https://doi.org/10.1021/jacs.5b02956	journal	June 2015
Sintering-Resistant Single-Site Nickel Catalyst Supported by Metal–Organic Framework Li, Zhanyong; Schweitzer, Neil M.; League, Aaron B. Journal of the American Chemical Society, Vol. 138, Issue 6 https://doi.org/10.1021/jacs.5b12515	journal	February 2016
Methane Oxidation to Methanol Catalyzed by Cu-Oxo Clusters Stabilized in NU-1000 Metal–Organic Framework Ikuno, Takaaki; Zheng, Jian; Vjunov, Aleksei Journal of the American Chemical Society, Vol. 139, Issue 30 https://doi.org/10.1021/jacs.7b02936	journal	July 2017
Bridging Zirconia Nodes within a Metal–Organic Framework via Catalytic Ni-Hydroxo Clusters to Form Heterobimetallic Nanowires Platero-Prats, Ana E.; League, Aaron B.; Bernales, Varinia Journal of the American Chemical Society, Vol. 139, Issue 30 https://doi.org/10.1021/jacs.7b04997	journal	July 2017
Beyond the Active Site: Tuning the Activity and Selectivity of a Metal–Organic Framework-Supported Ni Catalyst for Ethylene Dimerization Liu, Jian; Ye, Jingyun; Li, Zhanyong Journal of the American Chemical Society, Vol. 140, Issue 36 https://doi.org/10.1021/jacs.8b06006	journal	August 2018
Well-Defined Rhodium–Gallium Catalytic Sites in a Metal–Organic Framework: Promoter-Controlled Selectivity in Alkyne Semihydrogenation to E -Alkenes Desai, Sai Puneet; Ye, Jingyun; Zheng, Jian Journal of the American Chemical Society, Vol. 140, Issue 45 https://doi.org/10.1021/jacs.8b08550	journal	October 2018
Highly Active and Stable Single-Atom Cu Catalysts Supported by a Metal–Organic Framework Abdel-Mageed, Ali M.; Rungtaweevoranit, Bunyarat; Parlinska-Wojtan, Magdalena Journal of the American Chemical Society, Vol. 141, Issue 13 https://doi.org/10.1021/jacs.8b11386	journal	March 2019
Oligomerization of Light Olefins Catalyzed by Brønsted-Acidic Metal–Organic Framework-808 Liu, Ping; Redekop, Evgeniy; Gao, Xiang Journal of the American Chemical Society, Vol. 141, Issue 29 https://doi.org/10.1021/jacs.9b03867	journal	June 2019
Raman and Infrared Spectroscopy of α and β Phases of Thin Nickel Hydroxide Films Electrochemically Formed on Nickel Hall, David S.; Lockwood, David J.; Poirier, Shawn The Journal of Physical Chemistry A, Vol. 116, Issue 25 https://doi.org/10.1021/jp303546r	journal	May 2012
Defining the Proton Topology of the Zr₆-Based Metal–Organic Framework NU-1000 Planas, Nora; Mondloch, Joseph E.; Tussupbayev, Samat The Journal of Physical Chemistry Letters, Vol. 5, Issue 21, p. 3716-3723 https://doi.org/10.1021/jz501899j	journal	October 2014
A facile synthesis of UiO-66, UiO-67 and their derivatives Katz, Michael J.; Brown, Zachary J.; Colón, Yamil J. Chemical Communications, Vol. 49, Issue 82 https://doi.org/10.1039/c3cc46105j	journal	January 2013
Proton transfers are key elementary steps in ethylene polymerization on isolated chromium(III) silicates Delley, M. F.; Nunez-Zarur, F.; Conley, M. P. Proceedings of the National Academy of Sciences, Vol. 111, Issue 32 https://doi.org/10.1073/pnas.1405314111	journal	July 2014

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
alkene dimerization
heterogeneous catalysis
metal-organic framework
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single site catalyst

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References (47)

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