Discrimination of xylene isomers in a stacked coordination polymer

Li, Liangying; Guo, Lidong; Olson, David H.; Xian, Shikai; Zhang, Zhiguo; Yang, Qiwei; Wu, Kaiyi; Yang, Yiwen; Bao, Zongbi; Ren, Qilong; Li, Jing

doi:10.1126/science.abj7659

Title: Discrimination of xylene isomers in a stacked coordination polymer

Journal Article · 15 July 2022 · Science

DOI:https://doi.org/10.1126/science.abj7659· OSTI ID:1980732

^[1];

^[2]; Olson, David H. ^[3]; Xian, Shikai ^[4];

^[5];

^[5]; Wu, Kaiyi ^[2];

^[5];

^[4]

Key Laboratory of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, P. R. China.; Department of Chemistry and Chemical Biology, Rutgers University, Piscataway, NJ 08854, USA.
Key Laboratory of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, P. R. China.
Department of Chemistry and Chemical Biology, Rutgers University, Piscataway, NJ 08854, USA.
Department of Chemistry and Chemical Biology, Rutgers University, Piscataway, NJ 08854, USA.; Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, P. R. China.
Key Laboratory of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, P. R. China.; Institute of Zhejiang University-Quzhou, Quzhou 324000, P. R. China.

The separation and purification of xylene isomers is an industrially important but challenging process. Developing highly efficient adsorbents is crucial for the implementation of simulated moving bed technology for industrial separation of these isomers. Herein, we report a stacked one-dimensional coordination polymer {[Mn(dhbq)(H₂O)₂], H₂dhbq = 2,5-dihydroxy-1,4-benzoquinone} that exhibits an ideal molecular recognition and sieving of xylene isomers. Its distinct temperature-adsorbate–dependent adsorption behavior enables full separation ofp-,m-, ando-xylene isomers in both vapor and liquid phases. The delicate stimuli-responsive swelling of the structure imparts this porous material with exceptionally high flexibility and stability, well-balanced adsorption capacity, high selectivity, and fast kinetics at conditions mimicking industrial settings. This study may offer an alternative approach for energy-efficient and adsorption-based industrial xylene separation and purification processes.

Cite

Export

Save

Research Organization:: Wake Forest Univ., Winston-Salem, NC (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0019902

OSTI ID:: 1980732

Journal Information:: Science, Vol. 377, Issue 6603; ISSN 0036-8075

Publisher:: AAAS

Country of Publication:: United States

Language:: English

References (57)

Understanding and revamping of industrial scale SMB units for p-xylene separation Minceva, Mirjana; Rodrigues, Alírio E. AIChE Journal, Vol. 53, Issue 1 https://doi.org/10.1002/aic.11062	journal	January 2006
Xylene isomer separations by intrinsically porous molecular materials Zhang, Gengwu; Ding, Yanjun; Hashem, Abdulmajeed Cell Reports Physical Science, Vol. 2, Issue 6 https://doi.org/10.1016/j.xcrp.2021.100470	journal	June 2021
Seven chemical separations to change the world Sholl, David S.; Lively, Ryan P. Nature, Vol. 532, Issue 7600 https://doi.org/10.1038/532435a	journal	April 2016
Separation of Xylene Isomers: A Review of Recent Advances in Materials Yang, Yuxi; Bai, Peng; Guo, Xianghai Industrial & Engineering Chemistry Research, Vol. 56, Issue 50 https://doi.org/10.1021/acs.iecr.7b03127	journal	December 2017
Adsorptive separation on metal–organic frameworks in the liquid phase Van de Voorde, Ben; Bueken, Bart; Denayer, Joeri Chem. Soc. Rev., Vol. 43, Issue 16 https://doi.org/10.1039/C4CS00006D	journal	January 2014
Separation of p-xylene from C8 aromatics on binder-free hydrophobic adsorbent of MFI zeolite. I. Studies on static equilibrium Guo, Guo-Qing; Chen, Hong; Long, Ying-Cai Microporous and Mesoporous Materials, Vol. 39, Issue 1-2 https://doi.org/10.1016/S1387-1811(00)00191-8	journal	September 2000
Near-Ideal Xylene Selectivity in Adaptive Molecular Pillar[ n ]arene Crystals Jie, Kecheng; Liu, Ming; Zhou, Yujuan Journal of the American Chemical Society, Vol. 140, Issue 22 https://doi.org/10.1021/jacs.8b02621	journal	May 2018
Benchmark selectivity p -xylene separation by a non-porous molecular solid through liquid or vapor extraction Sun, Na; Wang, Shi-Qiang; Zou, Ruqiang Chemical Science, Vol. 10, Issue 38 https://doi.org/10.1039/C9SC02621E	journal	January 2019
Shape-Induced Selective Separation of Ortho-substituted Benzene Isomers Enabled by Cucurbit[7]uril Host Macrocycles Zhang, Gengwu; Emwas, Abdul-Hamid; Shahul Hameed, Umar F. Chem, Vol. 6, Issue 5 https://doi.org/10.1016/j.chempr.2020.03.003	journal	May 2020
Solid-Vapor Sorption of Xylenes: Prioritized Selectivity as a Means of Separating All Three Isomers Using a Single Substrate Lusi, Matteo; Barbour, Leonard J. Angewandte Chemie International Edition, Vol. 51, Issue 16 https://doi.org/10.1002/anie.201109084	journal	March 2012
Record-Setting Selectivity for p -Xylene by an Intrinsically Porous Zero-Dimensional Metallocycle du Plessis, Marike; Nikolayenko, Varvara I.; Barbour, Leonard J. Journal of the American Chemical Society, Vol. 142, Issue 10 https://doi.org/10.1021/jacs.9b11314	journal	February 2020
A Polymorphic Azobenzene Cage for Energy‐Efficient and Highly Selective p ‐Xylene Separation Moosa, Basem; Alimi, Lukman O.; Shkurenko, Aleksander Angewandte Chemie International Edition, Vol. 59, Issue 48 https://doi.org/10.1002/anie.202007782	journal	October 2020
Separation of Xylene Isomers through Multiple Metal Site Interactions in Metal–Organic Frameworks Gonzalez, Miguel I.; Kapelewski, Matthew T.; Bloch, Eric D. Journal of the American Chemical Society, Vol. 140, Issue 9 https://doi.org/10.1021/jacs.7b13825	journal	February 2018
Pore-Filling-Dependent Selectivity Effects in the Vapor-Phase Separation of Xylene Isomers on the Metal−Organic Framework MIL-47 Finsy, Vincent; Verelst, Harry; Alaerts, Luc Journal of the American Chemical Society, Vol. 130, Issue 22 https://doi.org/10.1021/ja800686c	journal	June 2008
Separating Xylene Isomers by Commensurate Stacking of p -Xylene within Channels of MAF-X8 Torres-Knoop, Ariana; Krishna, Rajamani; Dubbeldam, David Angewandte Chemie International Edition, Vol. 53, Issue 30 https://doi.org/10.1002/anie.201402894	journal	June 2014
Refinement of pore size at sub-angstrom precision in robust metal–organic frameworks for separation of xylenes Li, Xiaolin; Wang, Juehua; Bai, Nannan Nature Communications, Vol. 11, Issue 1 https://doi.org/10.1038/s41467-020-17640-4	journal	August 2020
Carbohydrate-Mediated Purification of Petrochemicals Holcroft, James M.; Hartlieb, Karel J.; Moghadam, Peyman Z. Journal of the American Chemical Society, Vol. 137, Issue 17 https://doi.org/10.1021/ja511878b	journal	April 2015
Selective Adsorption and Separation of Xylene Isomers and Ethylbenzene with the Microporous Vanadium(IV) Terephthalate MIL-47 Alaerts, Luc; Kirschhock, Christine E. A.; Maes, Michael Angewandte Chemie International Edition, Vol. 46, Issue 23 https://doi.org/10.1002/anie.200700056	journal	June 2007
Efficient Separation of Xylene Isomers by a Pillar-Layer Metal–Organic Framework Yang, Liping; Liu, Hanbang; Yuan, Danhua ACS Applied Materials & Interfaces, Vol. 13, Issue 35 https://doi.org/10.1021/acsami.1c10462	journal	August 2021
Intermediate-sized molecular sieving of styrene from larger and smaller analogues Zhou, Dong-Dong; Chen, Pin; Wang, Chao Nature Materials, Vol. 18, Issue 9 https://doi.org/10.1038/s41563-019-0427-z	journal	July 2019
One-of-a-kind: a microporous metal–organic framework capable of adsorptive separation of linear, mono- and di-branched alkane isomers via temperature- and adsorbate-dependent molecular sieving Wang, Hao; Dong, Xinglong; Velasco, Ever Energy & Environmental Science, Vol. 11, Issue 5 https://doi.org/10.1039/C8EE00459E	journal	January 2018
Control of zeolite framework flexibility and pore topology for separation of ethane and ethylene Bereciartua, Pablo J.; Cantín, Ángel; Corma, Avelino Science, Vol. 358, Issue 6366 https://doi.org/10.1126/science.aao0092	journal	November 2017
Design and control of gas diffusion process in a nanoporous soft crystal Gu, Cheng; Hosono, Nobuhiko; Zheng, Jia-Jia Science, Vol. 363, Issue 6425 https://doi.org/10.1126/science.aar6833	journal	January 2019
Selective Adsorption and Separation of ortho -Substituted Alkylaromatics with the Microporous Aluminum Terephthalate MIL-53 Alaerts, Luc; Maes, Michael; Giebeler, Lars Journal of the American Chemical Society, Vol. 130, Issue 43 https://doi.org/10.1021/ja802761z	journal	October 2008
Highly Selective, High‐Capacity Separation of o ‐Xylene from C ₈ Aromatics by a Switching Adsorbent Layered Material Wang, Shi‐Qiang; Mukherjee, Soumya; Patyk‐Kaźmierczak, Ewa Angewandte Chemie International Edition, Vol. 58, Issue 20 https://doi.org/10.1002/anie.201901198	journal	May 2019
Framework-Flexibility Driven Selective Sorption of p-Xylene over Other Isomers by a Dynamic Metal-Organic Framework Mukherjee, Soumya; Joarder, Biplab; Manna, Biplab Scientific Reports, Vol. 4, Issue 1 https://doi.org/10.1038/srep05761	journal	July 2014
Efficient separation of xylene isomers by a guest-responsive metal–organic framework with rotational anionic sites Cui, Xili; Niu, Zheng; Shan, Chuan Nature Communications, Vol. 11, Issue 1 https://doi.org/10.1038/s41467-020-19209-7	journal	October 2020
Crystal Structure and Proton Conductivity of a One-dimensional Coordination Polymer, {Mn(DHBQ)(H ₂ O) ₂ } Morikawa, Shota; Yamada, Teppei; Kitagawa, Hiroshi Chemistry Letters, Vol. 38, Issue 7 https://doi.org/10.1246/cl.2009.654	journal	July 2009
Structures and Proton Conductivity of One-Dimensional M(dhbq)·nH₂O (M = Mg, Mn, Co, Ni, and Zn, H₂(dhbq) = 2,5-Dihydroxy-1,4-benzoquinone) Promoted by Connected Hydrogen-Bond Networks with Absorbed Water Yamada, Teppei; Morikawa, Shota; Kitagawa, Hiroshi Bulletin of the Chemical Society of Japan, Vol. 83, Issue 1 https://doi.org/10.1246/bcsj.20090216	journal	January 2010
Fine-Tuning Window Apertures in ZIF-8/67 Frameworks by Metal Ions and Temperature for High-Efficiency Molecular Sieving of Xylenes Polyukhov, Daniil M.; Poryvaev, Artem S.; Sukhikh, Aleksandr S. ACS Applied Materials & Interfaces, Vol. 13, Issue 34 https://doi.org/10.1021/acsami.1c12166	journal	August 2021
Adsorption of Xylenes on Faujasite-Type Zeolite Minceva, M.; Rodrigues, A. E. Chemical Engineering Research and Design, Vol. 82, Issue 5 https://doi.org/10.1205/026387604323142739	journal	May 2004
From molecules to solids with the DMol3 approach Delley, B. The Journal of Chemical Physics, Vol. 113, Issue 18 https://doi.org/10.1063/1.1316015	journal	November 2000
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
Self—Consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian—Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules Hehre, W. J.; Ditchfield, R.; Pople, J. A. The Journal of Chemical Physics, Vol. 56, Issue 5, p. 2257-2261 https://doi.org/10.1063/1.1677527	journal	March 1972
Selective gas adsorption and separation in metal–organic frameworks Li, Jian-Rong; Kuppler, Ryan J.; Zhou, Hong-Cai Chemical Society Reviews, Vol. 38, Issue 5, p. 1477-1504 https://doi.org/10.1039/b802426j	journal	January 2009
Molecular Dimensions for Adsorptives Webster, Charles Edwin; Drago, Russell S.; Zerner, Michael C. Journal of the American Chemical Society, Vol. 120, Issue 22 https://doi.org/10.1021/ja973906m	journal	June 1998
p -Xylene-Selective Metal–Organic Frameworks: A Case of Topology-Directed Selectivity Vermoortele, Frederik; Maes, Michael; Moghadam, Peyman Z. Journal of the American Chemical Society, Vol. 133, Issue 46 https://doi.org/10.1021/ja207287h	journal	November 2011
Computational Identification and Experimental Evaluation of Metal–Organic Frameworks for Xylene Enrichment Gee, Jason A.; Zhang, Ke; Bhattacharyya, Souryadeep The Journal of Physical Chemistry C, Vol. 120, Issue 22 https://doi.org/10.1021/acs.jpcc.6b03349	journal	May 2016
The separation of xylene isomers by ZIF-8: A demonstration of the extraordinary flexibility of the ZIF-8 framework Peralta, David; Chaplais, Gérald; Paillaud, Jean-Louis Microporous and Mesoporous Materials, Vol. 173 https://doi.org/10.1016/j.micromeso.2013.01.012	journal	June 2013
Structural, energetic and dynamic insights into the abnormal xylene separation behavior of hierarchical porous crystal Lin, Jiao-Min; He, Chun-Ting; Liao, Pei-Qin Scientific Reports, Vol. 5, Issue 1 https://doi.org/10.1038/srep11537	journal	June 2015
Shape Selectivity by Guest-Driven Restructuring of a Porous Material Warren, J. E.; Perkins, C. G.; Jelfs, K. E. Angewandte Chemie International Edition, Vol. 53, Issue 18 https://doi.org/10.1002/anie.201307656	journal	March 2014
Para-xylene adsorption separation process using nano-zeolite Ba-X Rasouli, Milad; Yaghobi, Nakisa; Allahgholipour, Fatemeh Chemical Engineering Research and Design, Vol. 92, Issue 6 https://doi.org/10.1016/j.cherd.2013.10.008	journal	June 2014
Influence of monovalent alkaline metal cations on binder-free nano-zeolite X in para-xylene separation Rasouli, Milad; Yaghobi, Nakisa; Movassaghi Gilani, Seyedeh Zahra Chinese Journal of Chemical Engineering, Vol. 23, Issue 1 https://doi.org/10.1016/j.cjche.2014.11.005	journal	January 2015
Influence of monovalent cations ion-exchange on zeolite ZSM-5 in separation of para-xylene from xylene mixture Rasouli, Milad; Yaghobi, Nakisa; Chitsazan, Sahar Microporous and Mesoporous Materials, Vol. 150 https://doi.org/10.1016/j.micromeso.2011.09.013	journal	March 2012
Adsorption and Separation of Xylene Isomers and Ethylbenzene on Two Zn−Terephthalate Metal−Organic Frameworks Gu, Zhi-Yuan; Jiang, Dong-Qing; Wang, He-Fang The Journal of Physical Chemistry C, Vol. 114, Issue 1 https://doi.org/10.1021/jp9063017	journal	November 2009
[Cu(4-phenylpyridine) ₄ (trifluoromethanesulfonate) ₂ ], a Werner complex that exhibits high selectivity for o -xylene Kałuża, Adrianna M.; Mukherjee, Soumya; Wang, Shi-Qiang Chemical Communications, Vol. 56, Issue 13 https://doi.org/10.1039/C9CC09525J	journal	January 2020
Metal-Organic Framework MIL-101 for High-Resolution Gas-Chromatographic Separation of Xylene Isomers and Ethylbenzene Gu, Zhi-Yuan; Yan, Xiu-Ping Angewandte Chemie International Edition, Vol. 49, Issue 8 https://doi.org/10.1002/anie.200906560	journal	January 2010
Adsorption and separation of xylene isomers vapors onto the chromium terephthalate-based porous material MIL-101(Cr): An experimental and computational study Trens, Philippe; Belarbi, Hichem; Shepherd, Céline Microporous and Mesoporous Materials, Vol. 183 https://doi.org/10.1016/j.micromeso.2013.08.040	journal	January 2014
Reverse shape selectivity in the adsorption of hexane and xylene isomers in MOF UiO-66 Bárcia, Patrick S.; Guimarães, Daniela; Mendes, Patrícia A. P. Microporous and Mesoporous Materials, Vol. 139, Issue 1-3 https://doi.org/10.1016/j.micromeso.2010.10.019	journal	March 2011
Reverse Shape Selectivity in the Liquid-Phase Adsorption of Xylene Isomers in Zirconium Terephthalate MOF UiO-66 Moreira, Mariana A.; Santos, João C.; Ferreira, Alexandre F. P. Langmuir, Vol. 28, Issue 13 https://doi.org/10.1021/la3004118	journal	March 2012
Adsorption and Separation of Xylene Isomers: CPO-27-Ni vs HKUST-1 vs NaY Peralta, David; Barthelet, Karin; Pérez-Pellitero, Javier The Journal of Physical Chemistry C, Vol. 116, Issue 41 https://doi.org/10.1021/jp306828x	journal	October 2012
Single- and Multicomponent Vapor-Phase Adsorption of Xylene Isomers and Ethylbenzene in a Microporous Metal−Organic Framework Nicolau, Marco P. M.; Bárcia, Patrick S.; Gallegos, Jose M. The Journal of Physical Chemistry C, Vol. 113, Issue 30 https://doi.org/10.1021/jp9006747	journal	July 2009
Molecular Simulation Study on the Separation of Xylene Isomers in MIL-47 Metal−Organic Frameworks Castillo, J. M.; Vlugt, T. J. H.; Calero, Sofia The Journal of Physical Chemistry C, Vol. 113, Issue 49 https://doi.org/10.1021/jp908247w	journal	October 2009
Liquid-Phase Multicomponent Adsorption and Separation of Xylene Mixtures by Flexible MIL-53 Adsorbents Agrawal, Mayank; Bhattacharyya, Souryadeep; Huang, Yi The Journal of Physical Chemistry C, Vol. 122, Issue 1 https://doi.org/10.1021/acs.jpcc.7b09105	journal	December 2017
Liquid-Phase Adsorption and Separation of Xylene Isomers by the Flexible Porous Metal–Organic Framework MIL-53(Fe) El Osta, Racha; Carlin-Sinclair, Abel; Guillou, Nathalie Chemistry of Materials, Vol. 24, Issue 14 https://doi.org/10.1021/cm301242d	journal	July 2012
Framework Breathing in the Vapour-Phase Adsorption and Separation of Xylene Isomers with the Metal-Organic Framework MIL-53 Finsy, Vincent; Kirschhock, Christine E. A.; Vedts, Gill Chemistry - A European Journal, Vol. 15, Issue 31 https://doi.org/10.1002/chem.200802672	journal	August 2009
Conformation-Controlled Sorption Properties and Breathing of the Aliphatic Al-MOF [Al(OH)(CDC)] Niekiel, Felicitas; Lannoeye, Jeroen; Reinsch, Helge Inorganic Chemistry, Vol. 53, Issue 9 https://doi.org/10.1021/ic500288w	journal	April 2014

Similar Records

Discrimination of xylene isomers in a stacked coordination polymer

Journal Article · 2022 · Science · OSTI ID:1980732

Li, Liangying; Guo, Lidong; Olson, David H.; +8 more

Sequential Separation of Linear, Mono–, and Di–Branched Hexane Isomers on a Robust Coordination Polymer with Nonbonding Flexibility

Journal Article · 2023 · Small · OSTI ID:1980732

Chen, Rundao; Li, Liangying; Olson, David H.; +8 more

Supramolecular Assembly of One-Dimensional Coordination Polymers for Efficient Separation of Xenon and Krypton

Journal Article · 2023 · ACS Applied Materials and Interfaces · OSTI ID:1980732

Li, Liangying; Chen, Lihang; Guo, Lidong; +8 more

Related Subjects

Science & Technology - Other Topics

Title: Discrimination of xylene isomers in a stacked coordination polymer

Citation Formats

References (57)

Similar Records

Related Subjects