Topological effects on separation of alkane isomers in metal–organic frameworks

Bobbitt, N. Scott; Rosen, Andrew S.; Snurr, Randall Q.

doi:10.1016/j.fluid.2020.112642

Topological effects on separation of alkane isomers in metal–organic frameworks

Journal Article · Mon May 11 00:00:00 EDT 2020 · Fluid Phase Equilibria

DOI:https://doi.org/10.1016/j.fluid.2020.112642· OSTI ID:1634804

Bobbitt, N. Scott ^[1]; Rosen, Andrew S. ^[2]; Snurr, Randall Q. ^[2]

Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)
Northwestern Univ., Evanston, IL (United States). Dept. of Chemical and Biological Engineering

Polymorphism in metal–organic frameworks (MOFs) means that the same chemical building blocks (nodes and linkers) can be used to construct isomeric MOFs with different topological networks. The choice of topology can substantially impact the pore network of the MOF, changing the sizes and shapes of the pores, which has implications for adsorption and separation applications. Here, we look at the influence of topology in 38 polymorphic MOFs on the separation of linear and branched C4–C6 alkane isomers, a separation of great importance to the petrochemical industry. We find that the MOF Cu₂(1,4-benzenedicarboxylate) in nbo topology (nbo-Cu₂BDC) has particularly high affinity for linear alkanes due to its small pore size, which excludes the branched isomers. Upon studying this MOF in further detail, we find that it can take either of two conformations: a cubic conformation, which is typical of nbo MOFs, and a unique star conformation that contains 1D triangular and hexagonal channels. The determination of which conformation the MOF will adopt depends on steric effects between the nodes and linkers.

View Accepted Manuscript (DOE)

Research Organization:: Sandia National Laboratories (SNL-NM), Albuquerque, NM (United States); US Air Force Office of Scientific Research (AFOSR); US Army Research Office (ARO)

Sponsoring Organization:: USDOE National Nuclear Security Administration (NNSA)

Grant/Contract Number:: AC04-94AL85000; NA0003525

OSTI ID:: 1634804

Report Number(s):: SAND--2020-5664J; 686444

Journal Information:: Fluid Phase Equilibria, Journal Name: Fluid Phase Equilibria Journal Issue: C Vol. 519; ISSN 0378-3812

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (53)

High H₂ Adsorption in a Microporous Metal-Organic Framework with Open Metal Sites Chen, Banglin; Ockwig, Nathan W.; Millward, Andrew R. Angewandte Chemie International Edition, Vol. 44, Issue 30, p. 4745-4749 https://doi.org/10.1002/anie.200462787	journal	July 2005
Computer-Assisted Screening of Ordered Crystalline Nanoporous Adsorbents for Separation of Alkane Isomers Dubbeldam, David; Krishna, Rajamani; Calero, Sofía Angewandte Chemie International Edition, Vol. 51, Issue 47 https://doi.org/10.1002/anie.201205040	journal	October 2012
Effect of the damping function in dispersion corrected density functional theory Grimme, Stefan; Ehrlich, Stephan; Goerigk, Lars Journal of Computational Chemistry, Vol. 32, Issue 7 https://doi.org/10.1002/jcc.21759	journal	March 2011
Identifying promising metal–organic frameworks for heterogeneous catalysis via high‐throughput periodic density functional theory Rosen, Andrew S.; Notestein, Justin M.; Snurr, Randall Q. Journal of Computational Chemistry, Vol. 40, Issue 12 https://doi.org/10.1002/jcc.25787	journal	February 2019
A survey of the mechanism in catalytic isomerization of alkanes Ono, Yoshio Catalysis Today, Vol. 81, Issue 1 https://doi.org/10.1016/S0920-5861(03)00097-X	journal	June 2003
Carbon nanotubes applications in separation science: A review Herrera-Herrera, Antonio V.; González-Curbelo, Miguel Ángel; Hernández-Borges, Javier Analytica Chimica Acta, Vol. 734 https://doi.org/10.1016/j.aca.2012.04.035	journal	July 2012
Potential of metal–organic frameworks for adsorptive separation of industrially and environmentally relevant liquid mixtures Mukherjee, Soumya; Desai, Aamod V.; Ghosh, Sujit K. Coordination Chemistry Reviews, Vol. 367 https://doi.org/10.1016/j.ccr.2018.04.001	journal	July 2018
Python Materials Genomics (pymatgen): A robust, open-source python library for materials analysis Ong, Shyue Ping; Richards, William Davidson; Jain, Anubhav Computational Materials Science, Vol. 68 https://doi.org/10.1016/j.commatsci.2012.10.028	journal	February 2013
Characterization and comparison of pore landscapes in crystalline porous materials Pinheiro, Marielle; Martin, Richard L.; Rycroft, Chris H. Journal of Molecular Graphics and Modelling, Vol. 44 https://doi.org/10.1016/j.jmgm.2013.05.007	journal	July 2013
Algorithms and tools for high-throughput geometry-based analysis of crystalline porous materials Willems, Thomas F.; Rycroft, Chris H.; Kazi, Michaeel Microporous and Mesoporous Materials, Vol. 149, Issue 1 https://doi.org/10.1016/j.micromeso.2011.08.020	journal	February 2012
Topologically Guided, Automated Construction of Metal–Organic Frameworks and Their Evaluation for Energy-Related Applications Colón, Yamil J.; Gómez-Gualdrón, Diego A.; Snurr, Randall Q. Crystal Growth & Design, Vol. 17, Issue 11 https://doi.org/10.1021/acs.cgd.7b00848	journal	September 2017
Control of Polymorphism of Metal–Organic Frameworks Using Mixed-Metal Approach Tanasaro, Thanadporn; Adpakpang, Kanyaporn; Ittisanronnachai, Somlak Crystal Growth & Design, Vol. 18, Issue 1 https://doi.org/10.1021/acs.cgd.7b01193	journal	December 2017
Identification Schemes for Metal–Organic Frameworks To Enable Rapid Search and Cheminformatics Analysis Bucior, Benjamin J.; Rosen, Andrew S.; Haranczyk, Maciej Crystal Growth & Design, Vol. 19, Issue 11 https://doi.org/10.1021/acs.cgd.9b01050	journal	September 2019
Computational Screening of Nanoporous Materials for Hexane and Heptane Isomer Separation Chung, Yongchul G.; Bai, Peng; Haranczyk, Maciej Chemistry of Materials, Vol. 29, Issue 15 https://doi.org/10.1021/acs.chemmater.7b01565	journal	July 2017
The Importance of Polymorphism in Metal–Organic Framework Studies Aulakh, Darpandeep; Varghese, Juby R.; Wriedt, Mario Inorganic Chemistry, Vol. 54, Issue 17 https://doi.org/10.1021/acs.inorgchem.5b01311	journal	August 2015
High-Throughput Screening of Metal–Organic Frameworks for Hydrogen Storage at Cryogenic Temperature Bobbitt, N. Scott; Chen, Jiayi; Snurr, Randall Q. The Journal of Physical Chemistry C, Vol. 120, Issue 48 https://doi.org/10.1021/acs.jpcc.6b08729	journal	November 2016
Functionalized MOFs for Enhanced CO ₂ Capture Torrisi, Antonio; Bell, Robert G.; Mellot-Draznieks, Caroline Crystal Growth & Design, Vol. 10, Issue 7 https://doi.org/10.1021/cg100646e	journal	July 2010
Consequences of Partial Flexibility in 1,3-Benzenedicarboxylate Linkers: Kagomé Lattice and NbO Supramolecular Isomers from Complexation of a Bulky 1,3-Benzenedicarboxylate to Cu(II) Paddlewheel Moieties Zhang, Zhenjie; Wojtas, Lukasz; Zaworotko, Michael J. Crystal Growth & Design, Vol. 11, Issue 5 https://doi.org/10.1021/cg200183x	journal	May 2011
Zr- and Hf-Based Metal–Organic Frameworks: Tracking Down the Polymorphism Bon, Volodymyr; Senkovska, Irena; Baburin, Igor A. Crystal Growth & Design, Vol. 13, Issue 3, p. 1231-1237 https://doi.org/10.1021/cg301691d	journal	February 2013
Two Metal–Organic Frameworks with a Tetratopic Linker: Solvent-Dependent Polymorphism and Postsynthetic Bromination Frahm, Daniela; Hoffmann, Frank; Fröba, Michael Crystal Growth & Design, Vol. 14, Issue 4 https://doi.org/10.1021/cg4018536	journal	March 2014
Hydrocarbon Separations in Metal–Organic Frameworks Herm, Zoey R.; Bloch, Eric D.; Long, Jeffrey R. Chemistry of Materials, Vol. 26, Issue 1 https://doi.org/10.1021/cm402897c	journal	September 2013
Topologies of Metal−Organic Frameworks Based on Pyrimidine-5-carboxylate and Unexpected Gas-Sorption Selectivity for CO ₂ Seo, Jinwoo; Jin, Narae; Chun, Hyungphil Inorganic Chemistry, Vol. 49, Issue 23 https://doi.org/10.1021/ic1012523	journal	December 2010
Separation of C ₆ Paraffins Using Zeolitic Imidazolate Frameworks: Comparison with Zeolite 5A Peralta, David; Chaplais, Gérald; Simon-Masseron, Angélique Industrial & Engineering Chemistry Research, Vol. 51, Issue 12 https://doi.org/10.1021/ie202995g	journal	March 2012
UFF, a full periodic table force field for molecular mechanics and molecular dynamics simulations Rappe, A. K.; Casewit, C. J.; Colwell, K. S. Journal of the American Chemical Society, Vol. 114, Issue 25, p. 10024-10035 https://doi.org/10.1021/ja00051a040	journal	December 1992
Origin of Long-Range Ferromagnetic Ordering in Metal–Organic Frameworks with Antiferromagnetic Dimeric-Cu(II) Building Units Shen, Lei; Yang, Shuo-Wang; Xiang, Shengchang Journal of the American Chemical Society, Vol. 134, Issue 41 https://doi.org/10.1021/ja3077654	journal	October 2012
Controlling the Polymorphism and Topology Transformation in Porphyrinic Zirconium Metal–Organic Frameworks via Mechanochemistry Karadeniz, Bahar; Žilić, Dijana; Huskić, Igor Journal of the American Chemical Society, Vol. 141, Issue 49 https://doi.org/10.1021/jacs.9b10251	journal	November 2019
The NIST Chemistry WebBook: A Chemical Data Resource on the Internet ^† Linstrom, Peter J.; Mallard, William G. Journal of Chemical & Engineering Data, Vol. 46, Issue 5 https://doi.org/10.1021/je000236i	journal	September 2001
First-Principles-Derived Force Field for Copper Paddle-Wheel-Based Metal−Organic Frameworks Tafipolsky, Maxim; Amirjalayer, Saeed; Schmid, Rochus The Journal of Physical Chemistry C, Vol. 114, Issue 34 https://doi.org/10.1021/jp104441d	journal	August 2010
Understanding Hydrocarbon Adsorption in the UiO-66 Metal–Organic Framework: Separation of (Un)saturated Linear, Branched, Cyclic Adsorbates, Including Stereoisomers Duerinck, T.; Bueno-Perez, R.; Vermoortele, F. The Journal of Physical Chemistry C, Vol. 117, Issue 24 https://doi.org/10.1021/jp402294h	journal	June 2013
Transferable Potentials for Phase Equilibria. 1. United-Atom Description of n-Alkanes Martin, Marcus G.; Siepmann, J. Ilja https://doi.org/10.1021/jp972543+		March 1998
Rapid and Accurate Machine Learning Recognition of High Performing Metal Organic Frameworks for CO ₂ Capture Fernandez, Michael; Boyd, Peter G.; Daff, Thomas D. The Journal of Physical Chemistry Letters, Vol. 5, Issue 17 https://doi.org/10.1021/jz501331m	journal	August 2014
Monte Carlo Simulation for the Adsorption and Separation of Linear and Branched Alkanes in IRMOF-1 Jiang, Jianwen; Sandler, Stanley I. Langmuir, Vol. 22, Issue 13 https://doi.org/10.1021/la060506g	journal	June 2006
Large-scale screening of hypothetical metal–organic frameworks Wilmer, Christopher E.; Leaf, Michael; Lee, Chang Yeon Nature Chemistry, Vol. 4, Issue 2, p. 83-89 https://doi.org/10.1038/nchem.1192	journal	November 2011
Polymorphism of metal–organic frameworks: direct comparison of structures and theoretical N ₂ -uptake of topological pto- and tbo-isomers Zhu, Nianyong; Lennox, Matthew J.; Düren, Tina Chem. Commun., Vol. 50, Issue 32 https://doi.org/10.1039/C3CC49829H	journal	January 2014
Ligand design for long-range magnetic order in metal–organic frameworks Tiana, Davide; Hendon, Christopher H.; Walsh, Aron Chem. Commun., Vol. 50, Issue 90 https://doi.org/10.1039/C4CC06433J	journal	January 2014
Role of entropic effects in controlling the polymorphism in formate ABX ₃ metal–organic frameworks Kieslich, Gregor; Kumagai, Shohei; Butler, Keith T. Chemical Communications, Vol. 51, Issue 85 https://doi.org/10.1039/C5CC06190C	journal	January 2015
Chemical principles underpinning the performance of the metal–organic framework HKUST-1 Hendon, Christopher H.; Walsh, Aron Chemical Science, Vol. 6, Issue 7 https://doi.org/10.1039/C5SC01489A	journal	January 2015
Benchmarking density functional theory predictions of framework structures and properties in a chemically diverse test set of metal–organic frameworks Nazarian, Dalar; Ganesh, P.; Sholl, David S. Journal of Materials Chemistry A, Vol. 3, Issue 44 https://doi.org/10.1039/C5TA03864B	journal	January 2015
Revisiting the structural homogeneity of NU-1000, a Zr-based metal–organic framework Islamoglu, Timur; Otake, Ken-ichi; Li, Peng CrystEngComm, Vol. 20, Issue 39 https://doi.org/10.1039/C8CE00455B	journal	January 2018
Entropy effects during sorption of alkanes in zeolites Krishna, Rajamani; Smit, Berend; Calero, Sofia Chemical Society Reviews, Vol. 31, Issue 3 https://doi.org/10.1039/b101267n	journal	April 2002
A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu Grimme, Stefan; Antony, Jens; Ehrlich, Stephan The Journal of Chemical Physics, Vol. 132, Issue 15 https://doi.org/10.1063/1.3382344	journal	April 2010
RASPA: molecular simulation software for adsorption and diffusion in flexible nanoporous materials Dubbeldam, David; Calero, Sofía; Ellis, Donald E. Molecular Simulation, Vol. 42, Issue 2 https://doi.org/10.1080/08927022.2015.1010082	journal	February 2015
Solution of Schrödinger’s equation for large systems Teter, Michael P.; Payne, Michael C.; Allan, Douglas C. Physical Review B, Vol. 40, Issue 18 https://doi.org/10.1103/PhysRevB.40.12255	journal	December 1989
Self-consistent calculations of the energy bands and bonding properties of B 12 C 3 Bylander, D. M.; Kleinman, Leonard; Lee, Seongbok Physical Review B, Vol. 42, Issue 2 https://doi.org/10.1103/PhysRevB.42.1394	journal	July 1990
Erratum: Self-consistent calculations of the energy bands and bonding properties of B 12 C 3 Bylander, D. M.; Kleinman, Leonard; Lee, Seongbok Physical Review B, Vol. 47, Issue 15 https://doi.org/10.1103/PhysRevB.47.10056	journal	April 1993
Projector augmented-wave method Blöchl, P. E. Physical Review B, Vol. 50, Issue 24, p. 17953-17979 https://doi.org/10.1103/PhysRevB.50.17953	journal	December 1994
Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set Kresse, G.; Furthmüller, J. Physical Review B, Vol. 54, Issue 16, p. 11169-11186 https://doi.org/10.1103/PhysRevB.54.11169	journal	October 1996
From ultrasoft pseudopotentials to the projector augmented-wave method Kresse, G.; Joubert, D. Physical Review B, Vol. 59, Issue 3, p. 1758-1775 https://doi.org/10.1103/PhysRevB.59.1758	journal	January 1999
Direct minimization technique for metals in density functional theory Freysoldt, Christoph; Boeck, Sixten; Neugebauer, Jörg Physical Review B, Vol. 79, Issue 24 https://doi.org/10.1103/PhysRevB.79.241103	journal	June 2009
Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/PhysRevLett.77.3865	journal	October 1996
Systematic Design of Pore Size and Functionality in Isoreticular MOFs and Their Application in Methane Storage Eddaoudi, Mohamed; Kim, Jaheon; Rosi, Nathaniel Science, Vol. 295, Issue 5554, p. 469-472 https://doi.org/10.1126/science.1067208	journal	January 2002
Separation of Hexane Isomers in a Metal-Organic Framework with Triangular Channels Herm, Z. R.; Wiers, B. M.; Mason, J. A. Science, Vol. 340, Issue 6135, p. 960-964 https://doi.org/10.1126/science.1234071	journal	May 2013
Review of Oxidation of Gasoline Surrogates and Its Components Piehl, J. A.; Zyada, A.; Bravo, L. Journal of Combustion, Vol. 2018 https://doi.org/10.1155/2018/8406754	journal	December 2018

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