A bifunctional zeolitic porous liquid with incompatible Lewis pairs for antagonistic cascade catalysis
Abstract
The emergence of porous liquids (PLs) opened opportunities to form unique antagonistic systems capable of fulfilling cascade reactions promoted by incompatible active sites in one pot, which is a long-term challenging subject in catalysis. Herein, unique bifunctional type III PL-based systems were facilely fabricated via assembly of zeolite nanosheets with ionic liquids. Rational structural design afforded PLs that feature high zeolite concentration, stable dispersion after 2 years, abundant cavity distribution, and involvement of antagonistic groups (acid and base sites) in separated and active form via steric hindrance control and electronic repulsion regulation. These unique properties worked cooperatively to fulfill the cascade deacetalization-Knoevenagel/Aldol condensation in one pot with superior catalytic efficiency outperforming the traditional systems. The key to success lies in the formation of bifunctional composites, transformation of zeolite from heterogeneous to homogeneous via surface modification, as well as rapid mass transfer ensured by the rigid porous architecture.
- Authors:
-
- Univ. of Tennessee, Knoxville, TN (United States); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
- Nanchang Univ. (China); Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
- Univ. of Tennessee, Knoxville, TN (United States)
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
- Nanchang Univ. (China)
- Jiangsu University, Zhenjiang (China)
- Tongji Unversity, Shanghai (China)
- Sinopec Shanghai Research Institute of Petrochemical Technology, Shanghai (China)
- Publication Date:
- Research Org.:
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1830136
- Alternate Identifier(s):
- OSTI ID: 1869352
- Grant/Contract Number:
- AC05-00OR22725
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Chem
- Additional Journal Information:
- Journal Volume: 7; Journal Issue: 12; Journal ID: ISSN 2451-9294
- Publisher:
- Cell Press, Elsevier
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; porous liquid; ionic liquid; zeolite; bifunctional; antagonistic cascade catalysis
Citation Formats
Chen, Hao, Yang, Zhenzhen, Peng, Honggen, Jie, Kecheng, Li, Peipei, Ding, Shunmin, Guo, Wei, Suo, Xian, Liu, Jixing, Yan, Ran, Liu, Wenming, Do-Thanh, Chi-Linh, Wang, Hongming, Wang, Zhendong, Han, Lu, Yang, Weimin, and Dai, Sheng. A bifunctional zeolitic porous liquid with incompatible Lewis pairs for antagonistic cascade catalysis. United States: N. p., 2021.
Web. doi:10.1016/j.chempr.2021.08.022.
Chen, Hao, Yang, Zhenzhen, Peng, Honggen, Jie, Kecheng, Li, Peipei, Ding, Shunmin, Guo, Wei, Suo, Xian, Liu, Jixing, Yan, Ran, Liu, Wenming, Do-Thanh, Chi-Linh, Wang, Hongming, Wang, Zhendong, Han, Lu, Yang, Weimin, & Dai, Sheng. A bifunctional zeolitic porous liquid with incompatible Lewis pairs for antagonistic cascade catalysis. United States. https://doi.org/10.1016/j.chempr.2021.08.022
Chen, Hao, Yang, Zhenzhen, Peng, Honggen, Jie, Kecheng, Li, Peipei, Ding, Shunmin, Guo, Wei, Suo, Xian, Liu, Jixing, Yan, Ran, Liu, Wenming, Do-Thanh, Chi-Linh, Wang, Hongming, Wang, Zhendong, Han, Lu, Yang, Weimin, and Dai, Sheng. Wed .
"A bifunctional zeolitic porous liquid with incompatible Lewis pairs for antagonistic cascade catalysis". United States. https://doi.org/10.1016/j.chempr.2021.08.022. https://www.osti.gov/servlets/purl/1830136.
@article{osti_1830136,
title = {A bifunctional zeolitic porous liquid with incompatible Lewis pairs for antagonistic cascade catalysis},
author = {Chen, Hao and Yang, Zhenzhen and Peng, Honggen and Jie, Kecheng and Li, Peipei and Ding, Shunmin and Guo, Wei and Suo, Xian and Liu, Jixing and Yan, Ran and Liu, Wenming and Do-Thanh, Chi-Linh and Wang, Hongming and Wang, Zhendong and Han, Lu and Yang, Weimin and Dai, Sheng},
abstractNote = {The emergence of porous liquids (PLs) opened opportunities to form unique antagonistic systems capable of fulfilling cascade reactions promoted by incompatible active sites in one pot, which is a long-term challenging subject in catalysis. Herein, unique bifunctional type III PL-based systems were facilely fabricated via assembly of zeolite nanosheets with ionic liquids. Rational structural design afforded PLs that feature high zeolite concentration, stable dispersion after 2 years, abundant cavity distribution, and involvement of antagonistic groups (acid and base sites) in separated and active form via steric hindrance control and electronic repulsion regulation. These unique properties worked cooperatively to fulfill the cascade deacetalization-Knoevenagel/Aldol condensation in one pot with superior catalytic efficiency outperforming the traditional systems. The key to success lies in the formation of bifunctional composites, transformation of zeolite from heterogeneous to homogeneous via surface modification, as well as rapid mass transfer ensured by the rigid porous architecture.},
doi = {10.1016/j.chempr.2021.08.022},
journal = {Chem},
number = 12,
volume = 7,
place = {United States},
year = {Wed Sep 22 00:00:00 EDT 2021},
month = {Wed Sep 22 00:00:00 EDT 2021}
}
Works referenced in this record:
Direct Phasing in Electron Crystallography: Ab Initio Determination of a New MCM-22 Zeolite Structure
journal, September 1995
- Nicolopoulos, S.; Gonzalez-Calbet, J. M.; Vallet-Regi, M.
- Journal of the American Chemical Society, Vol. 117, Issue 35
Acid–Base Bifunctional Shell Cross-Linked Micelle Nanoreactor for One-Pot Tandem Reaction
journal, January 2016
- Lee, Li-Chen; Lu, Jie; Weck, Marcus
- ACS Catalysis, Vol. 6, Issue 2
Multifunctional metal–organic framework catalysts: synergistic catalysis and tandem reactions
journal, January 2017
- Huang, Yuan-Biao; Liang, Jun; Wang, Xu-Sheng
- Chemical Society Reviews, Vol. 46, Issue 1
Porous Molecular Solids and Liquids
journal, May 2017
- Cooper, Andrew I.
- ACS Central Science, Vol. 3, Issue 6
Enhancing CO 2 Electroreduction to Methane with a Cobalt Phthalocyanine and Zinc–Nitrogen–Carbon Tandem Catalyst
journal, October 2020
- Lin, Long; Liu, Tianfu; Xiao, Jianping
- Angewandte Chemie International Edition, Vol. 59, Issue 50
Type 3 porous liquids based on non-ionic liquid phases – a broad and tailorable platform of selective, fluid gas sorbents
journal, January 2020
- Cahir, John; Tsang, Min Ying; Lai, Beibei
- Chemical Science, Vol. 11, Issue 8
The effect of acid–base pairing on catalysis: An efficient acid–base functionalized catalyst for aldol condensation
journal, April 2007
- Zeidan, R.; Davis, M.
- Journal of Catalysis, Vol. 247, Issue 2
Direct Dual-Template Synthesis of MWW Zeolite Monolayers
journal, September 2015
- Margarit, Vicente J.; Martínez-Armero, Marta E.; Navarro, M. Teresa
- Angewandte Chemie International Edition, Vol. 54, Issue 46
Controlling Gas Selectivity in Molecular Porous Liquids by Tuning the Cage Window Size
journal, March 2020
- Egleston, Benjamin D.; Luzyanin, Konstantin V.; Brand, Michael C.
- Angewandte Chemie International Edition, Vol. 59, Issue 19
Simultaneous oxidative and reductive reactions in one system by atomic design
journal, January 2021
- Zhao, Yafei; Zhou, Huang; Zhu, Xiaorong
- Nature Catalysis, Vol. 4, Issue 2
Porous Liquids: The Next Frontier
journal, December 2020
- Fulvio, Pasquale Fernando; Dai, Sheng
- Chem, Vol. 6, Issue 12
Control of four stereocentres in a triple cascade organocatalytic reaction
journal, June 2006
- Enders, Dieter; Hüttl, Matthias R. M.; Grondal, Christoph
- Nature, Vol. 441, Issue 7095
Electrostatic-Assisted Liquefaction of Porous Carbons
journal, October 2017
- Li, Peipei; Schott, Jennifer A.; Zhang, Jinshui
- Angewandte Chemie International Edition, Vol. 56, Issue 47
Mesoporus MCM-22 Zeolites Prepared through Organic Amine-Assisted Reversible Structural Change and Protective Desilication for Catalysis of Bulky Molecules
journal, July 2013
- Ji, Yong-Jun; Xu, Hao; Wang, Da-Rui
- ACS Catalysis, Vol. 3, Issue 8
Amphiphilic organosilane-directed synthesis of crystalline zeolite with tunable mesoporosity
journal, August 2006
- Choi, Minkee; Cho, Hae Sung; Srivastava, Rajendra
- Nature Materials, Vol. 5, Issue 9
Cascade Reactions Catalyzed by Metal Organic Frameworks
journal, July 2014
- Dhakshinamoorthy, Amarajothi; Garcia, Hermenegildo
- ChemSusChem, Vol. 7, Issue 9
A Core/Shell Catalyst Produces a Spatially Confined Effect and Shape Selectivity in a Consecutive Reaction
journal, January 2008
- Bao, Jun; He, Jingjiang; Zhang, Yi
- Angewandte Chemie, Vol. 120, Issue 2
Green Routes for Synthesis of Zeolites
journal, November 2013
- Meng, Xiangju; Xiao, Feng-Shou
- Chemical Reviews, Vol. 114, Issue 2
Amine-Functionalized GO as an Active and Reusable Acid–Base Bifunctional Catalyst for One-Pot Cascade Reactions
journal, December 2013
- Zhang, Fang; Jiang, Huangyong; Li, Xiaoyan
- ACS Catalysis, Vol. 4, Issue 2
Functional Acid and Base Hybrid Catalysts Organized by Associated (Organo)aluminosilicate Layers for C–C Bond Forming Reactions and Tandem Processes
journal, February 2017
- Gaona, Aidé; Díaz, Urbano; Corma, Avelino
- Chemistry of Materials, Vol. 29, Issue 4
Heterogeneous Catalysts for the One-Pot Synthesis of Chemicals and Fine Chemicals
journal, February 2011
- Climent, Maria J.; Corma, Avelino; Iborra, Sara
- Chemical Reviews, Vol. 111, Issue 2
Substrate channelling as an approach to cascade reactions
journal, March 2016
- Wheeldon, Ian; Minteer, Shelley D.; Banta, Scott
- Nature Chemistry, Vol. 8, Issue 4
Acid−Base Bifunctional and Dielectric Outer-Sphere Effects in Heterogeneous Catalysis: A Comparative Investigation of Model Primary Amine Catalysts
journal, March 2006
- Bass, John D.; Solovyov, Andrew; Pascall, Andrew J.
- Journal of the American Chemical Society, Vol. 128, Issue 11
Porous Liquids: A Promising Class of Media for Gas Separation
journal, November 2014
- Zhang, Jinshui; Chai, Song-Hai; Qiao, Zhen-An
- Angewandte Chemie International Edition, Vol. 54, Issue 3
C−C Bond Formation in Syngas Conversion over Zinc Sites Grafted on ZSM‐5 Zeolite
journal, February 2020
- Chen, Yuxiang; Gong, Ke; Jiao, Feng
- Angewandte Chemie International Edition, Vol. 59, Issue 16
Porous Ionic Liquids: Structure, Stability, and Gas Absorption Mechanisms
journal, March 2021
- Avila, Jocasta; Červinka, Ctirad; Dugas, Pierre‐Yves
- Advanced Materials Interfaces, Vol. 8, Issue 9
Coordination cages as permanently porous ionic liquids
journal, February 2020
- Ma, Lillian; Haynes, Cally J. E.; Grommet, Angela B.
- Nature Chemistry, Vol. 12, Issue 3
Optimized Cellulose Nanocrystal Organocatalysts Outperform Silica-Supported Analogues: Cooperativity, Selectivity, and Bifunctionality in Acid–Base Aldol Condensation Reactions
journal, March 2019
- Ellebracht, Nathan C.; Jones, Christopher W.
- ACS Catalysis, Vol. 9, Issue 4
Layered Materials with Coexisting Acidic and Basic Sites for Catalytic One-Pot Reaction Sequences
journal, June 2009
- Motokura, Ken; Tada, Mizuki; Iwasawa, Yasuhiro
- Journal of the American Chemical Society, Vol. 131, Issue 23
Heterogeneous Catalysis in Zeolites, Mesoporous Silica, and Metal-Organic Frameworks
journal, June 2017
- Liang, Jie; Liang, Zibin; Zou, Ruqiang
- Advanced Materials, Vol. 29, Issue 30
Porous Ionic Liquids or Liquid Metal-Organic Frameworks?
journal, August 2018
- Costa Gomes, Margarida; Pison, Laure; Červinka, Ctirad
- Angewandte Chemie International Edition, Vol. 57, Issue 37
Quantitative conversion of triglycerides to hydrocarbons over hierarchical ZSM-5 catalyst
journal, May 2015
- Chen, Hao; Wang, Qingfa; Zhang, Xiangwen
- Applied Catalysis B: Environmental, Vol. 166-167
Exploring Opportunities for Platinum Nanoparticles Encapsulated in Porous Liquids as Hydrogenation Catalysts
journal, March 2020
- Hemming, Ellen B.; Masters, Anthony F.; Maschmeyer, Thomas
- Chemistry – A European Journal, Vol. 26, Issue 31
Structure of synthetic zeolite ZSM-5
journal, March 1978
- Kokotailo, G. T.; Lawton, S. L.; Olson, D. H.
- Nature, Vol. 272, Issue 5652
On the nature of framework Brønsted and Lewis acid sites in ZSM-5
journal, October 1997
- Woolery, G. L.; Kuehl, G. H.; Timken, H. C.
- Zeolites, Vol. 19, Issue 4
Porous liquid zeolites: hydrogen bonding-stabilized H-ZSM-5 in branched ionic liquids
journal, January 2019
- Li, Peipei; Chen, Hao; Schott, Jennifer A.
- Nanoscale, Vol. 11, Issue 4
Bifunctionalized Mesoporous Materials with Site-Separated Brønsted Acids and Bases: Catalyst for a Two-Step Reaction Sequence
journal, December 2010
- Huang, Yulin; Xu, Shu; Lin, Victor S. -Y.
- Angewandte Chemie International Edition, Vol. 50, Issue 3
Acid Properties and Catalysis of MCM-22 with Different Al Concentrations
journal, February 2002
- Okumura, Kazu; Hashimoto, Masashi; Mimura, Takayuki
- Journal of Catalysis, Vol. 206, Issue 1
Heterogeneous Catalysis for Tandem Reactions
journal, January 2014
- Climent, Maria J.; Corma, Avelino; Iborra, Sara
- ACS Catalysis, Vol. 4, Issue 3
Expanding the Utility of One-Pot Multistep Reaction Networks through Compartmentation and Recovery of the Catalyst
journal, March 2006
- Phan, Nam T. S.; Gill, Christopher S.; Nguyen, Joseph V.
- Angewandte Chemie International Edition, Vol. 45, Issue 14
On the Controllable Soft-Templating Approach to Mesoporous Silicates
journal, July 2007
- Wan, Ying
- Chemical Reviews, Vol. 107, Issue 7
Generation of subnanometric platinum with high stability during transformation of a 2D zeolite into 3D
journal, September 2016
- Liu, Lichen; Díaz, Urbano; Arenal, Raul
- Nature Materials, Vol. 16, Issue 1
Cooperative Catalysis with Acid–Base Bifunctional Mesoporous Silica: Impact of Grafting and Co-condensation Synthesis Methods on Material Structure and Catalytic Properties
journal, June 2012
- Brunelli, Nicholas A.; Venkatasubbaiah, Krishnan; Jones, Christopher W.
- Chemistry of Materials, Vol. 24, Issue 13
Liquids with permanent porosity
journal, November 2015
- Giri, Nicola; Del Pópolo, Mario G.; Melaugh, Gavin
- Nature, Vol. 527, Issue 7577
Designing bifunctional acid–base mesoporous hybrid catalysts for cascade reactions
journal, January 2013
- Gianotti, Enrica; Diaz, Urbano; Velty, Alexandra
- Catalysis Science & Technology, Vol. 3, Issue 10
Chiral Brønsted Acid-Catalyzed Tandem Aza-Ene Type Reaction/Cyclization Cascade for a One-Pot Entry to Enantioenriched Piperidines
journal, August 2007
- Terada, Masahiro; Machioka, Kyoko; Sorimachi, Keiichi
- Journal of the American Chemical Society, Vol. 129, Issue 34
High-Pressure in Situ 129 Xe NMR Spectroscopy: Insights into Switching Mechanisms of Flexible Metal–Organic Frameworks Isoreticular to DUT-49
journal, June 2019
- Kolbe, Felicitas; Krause, Simon; Bon, Volodymyr
- Chemistry of Materials, Vol. 31, Issue 16
The Dam Bursts for Porous Liquids
journal, March 2016
- James, Stuart L.
- Advanced Materials, Vol. 28, Issue 27
Application of Ionic Liquids to Energy Storage and Conversion Materials and Devices
journal, January 2017
- Watanabe, Masayoshi; Thomas, Morgan L.; Zhang, Shiguo
- Chemical Reviews, Vol. 117, Issue 10
Hydroconversion of Jatropha Oil to Alternative Fuel over Hierarchical ZSM-5
journal, December 2014
- Chen, Hao; Wang, Qingfa; Zhang, Xiangwen
- Industrial & Engineering Chemistry Research, Vol. 53, Issue 51
Synthesis of reaction‐adapted zeolites as methanol-to-olefins catalysts with mimics of reaction intermediates as organic structure‐directing agents
journal, July 2018
- Li, Chengeng; Paris, Cecilia; Martínez-Triguero, Joaquín
- Nature Catalysis, Vol. 1, Issue 7
A Yolk-Shell Nanoreactor with a Basic Core and an Acidic Shell for Cascade Reactions
journal, August 2012
- Yang, Yan; Liu, Xiao; Li, Xiaobo
- Angewandte Chemie International Edition, Vol. 51, Issue 36
Expanding Applications of Metal−Organic Frameworks: Zeolite Imidazolate Framework ZIF-8 as an Efficient Heterogeneous Catalyst for the Knoevenagel Reaction
journal, January 2011
- Tran, Uyen P. N.; Le, Ky K. A.; Phan, Nam T. S.
- ACS Catalysis, Vol. 1, Issue 2
Controlled synthesis of hierarchical ZSM-5 for catalytic fast pyrolysis of cellulose to aromatics
journal, January 2018
- Chen, Hao; Shi, Xu; Liu, Jianfang
- Journal of Materials Chemistry A, Vol. 6, Issue 42
Fabrication and application of inorganic hollow spheres
journal, January 2011
- Hu, Jing; Chen, Min; Fang, Xiaosheng
- Chemical Society Reviews, Vol. 40, Issue 11
Hollow Hyper-Cross-Linked Nanospheres with Acid and Base Sites as Efficient and Water-Stable Catalysts for One-Pot Tandem Reactions
journal, April 2017
- Jia, Zhifang; Wang, Kewei; Tan, Bien
- ACS Catalysis, Vol. 7, Issue 5
A spatially orthogonal hierarchically porous acid–base catalyst for cascade and antagonistic reactions
journal, October 2020
- Isaacs, Mark A.; Parlett, Christopher M. A.; Robinson, Neil
- Nature Catalysis, Vol. 3, Issue 11
The Chemistry and Applications of Metal-Organic Frameworks
journal, August 2013
- Furukawa, H.; Cordova, K. E.; O'Keeffe, M.
- Science, Vol. 341, Issue 6149, p. 1230444-1230444
General Way To Construct Micro- and Mesoporous Metal–Organic Framework-Based Porous Liquids
journal, November 2019
- He, Sanfeng; Chen, Lihan; Cui, Jing
- Journal of the American Chemical Society, Vol. 141, Issue 50
Controllable direct-syntheses of delaminated MWW-type zeolites
journal, July 2020
- Wang, Zhendong; Cichocka, Magdalena O.; Luo, Yi
- Chinese Journal of Catalysis, Vol. 41, Issue 7
Transesterification Catalyzed by Ionic Liquids on Superhydrophobic Mesoporous Polymers: Heterogeneous Catalysts That Are Faster than Homogeneous Catalysts
journal, September 2012
- Liu, Fujian; Wang, Liang; Sun, Qi
- Journal of the American Chemical Society, Vol. 134, Issue 41
Towards a better understanding of Lewis acidic aluminium in zeolites
journal, September 2020
- Ravi, Manoj; Sushkevich, Vitaly L.; van Bokhoven, Jeroen A.
- Nature Materials, Vol. 19, Issue 10
Triblock Copolymer Syntheses of Mesoporous Silica with Periodic 50 to 300 Angstrom Pores
journal, January 1998
- Zhao, Dongyuan; Feng, Jianglin; Huo, Qisheng
- Science, Vol. 279, Issue 5350, p. 548-552
Bifunctional Tandem Catalysis on Multilamellar Organic–Inorganic Hybrid Zeolites
journal, August 2014
- Xu, Le; Li, Chen-geng; Zhang, Kun
- ACS Catalysis, Vol. 4, Issue 9
Transforming Porous Organic Cages into Porous Ionic Liquids via a Supramolecular Complexation Strategy
journal, February 2020
- Jie, Kecheng; Onishi, Nicole; Schott, Jennifer A.
- Angewandte Chemie International Edition, Vol. 59, Issue 6
New Class of Type III Porous Liquids: A Promising Platform for Rational Adjustment of Gas Sorption Behavior
journal, December 2017
- Shan, Weida; Fulvio, Pasquale F.; Kong, Liyun
- ACS Applied Materials & Interfaces, Vol. 10, Issue 1
Kinetic and Mechanistic Examination of Acid–Base Bifunctional Aminosilica Catalysts in Aldol and Nitroaldol Condensations
journal, December 2015
- Collier, Virginia E.; Ellebracht, Nathan C.; Lindy, George I.
- ACS Catalysis, Vol. 6, Issue 1
π–π interaction of aromatic groups in amphiphilic molecules directing for single-crystalline mesostructured zeolite nanosheets
journal, June 2014
- Xu, Dongdong; Ma, Yanhang; Jing, Zhifeng
- Nature Communications, Vol. 5, Issue 1