CO2 Chemisorption Behavior of Coordination-Derived Phenolate Sorbents

Suo, Xian; Yang, Zhenzhen; Fu, Yuqing; Do-Thanh, Chi-Linh; Chen, Hao; Luo, Huimin; Jiang, De-en; Mahurin, Shannon Mark; Xing, Huabin; Dai, Sheng

doi:10.1002/cssc.202100666

Title: CO₂ Chemisorption Behavior of Coordination-Derived Phenolate Sorbents

Journal Article · 22 July 2021 · ChemSusChem

DOI: https://doi.org/10.1002/cssc.202100666 · OSTI ID:1814295

^[1];

^[2]; Fu, Yuqing ^[3]; Do-Thanh, Chi-Linh ^[1]; Chen, Hao ^[1];

^[2]; Jiang, De-en ^[3];

^[2]; Xing, Huabin ^[4];

^[2]

Univ. of Tennessee, Knoxville, TN (United States)
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
Univ. of California, Riverside, CA (United States)
Zhejiang University (China)

CO₂ chemisorption via C-O bond formation is an efficient methodology in carbon capture especially using phenolate-based ionic liquids (ILs) as the sorbents to afford carbonate products. However, most of the current IL systems involve alkylphosphonium cations, leading to side reactions via the ylide intermediate pathway. It is important to figure out the CO₂ chemisorption behavior of phenolate-derived sorbents using inactive and easily accessible cation counterparts without active protons. Herein, phenolate-based systems were constructed via coordination between alkali metal cations with crown ethers to avoid the participation of active protons in CO₂ chemisorption. Reaction pathway study revealed that CO₂ uptake could be achieved by O-C bond formation to afford carbonate. CO₂ uptake capacity and reaction enthalpy were significantly influenced by the coordination effect, alkali metal types, and alkyl groups on the benzene ring.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1814295

Journal Information:: ChemSusChem, Journal Name: ChemSusChem Journal Issue: 14 Vol. 14; ISSN 1864-5631

Publisher:: ChemPubSoc EuropeCopyright Statement

Country of Publication:: United States

Language:: English

References (53)

Carbon Dioxide Capture by Superbase-Derived Protic Ionic Liquids Wang, Congmin; Luo, Huimin; Jiang, De-en Angewandte Chemie, Vol. 122, Issue 34 https://doi.org/10.1002/ange.201002641	journal	July 2010
Tuning the Basicity of Ionic Liquids for Equimolar CO2 Capture Wang, Congmin; Luo, Xiaoyan; Luo, Huimin Angewandte Chemie, Vol. 123, Issue 21 https://doi.org/10.1002/ange.201008151	journal	March 2011
Significant Improvements in CO ₂ Capture by Pyridine-Containing Anion-Functionalized Ionic Liquids through Multiple-Site Cooperative Interactions Luo, Xiaoyan; Guo, Yan; Ding, Fang Angewandte Chemie, Vol. 126, Issue 27 https://doi.org/10.1002/ange.201400957	journal	June 2014
Poly(Ionic Liquid)-Derived Carbon with Site-Specific N-Doping and Biphasic Heterojunction for Enhanced CO ₂ Capture and Sensing Gong, Jiang; Antonietti, Markus; Yuan, Jiayin Angewandte Chemie, Vol. 129, Issue 26 https://doi.org/10.1002/ange.201702453	journal	May 2017
Sorbenten zur direkten Gewinnung von CO ₂ aus der Umgebungsluft Shi, Xiaoyang; Xiao, Hang; Azarabadi, Habib Angewandte Chemie, Vol. 132, Issue 18 https://doi.org/10.1002/ange.201906756	journal	February 2020
Carbon Dioxide Capture by Superbase-Derived Protic Ionic Liquids Wang, Congmin; Luo, Huimin; Jiang, De-en Angewandte Chemie International Edition, Vol. 49, Issue 34 https://doi.org/10.1002/anie.201002641	journal	July 2010
Tuning the Basicity of Ionic Liquids for Equimolar CO2 Capture Wang, Congmin; Luo, Xiaoyan; Luo, Huimin Angewandte Chemie International Edition, Vol. 50, Issue 21 https://doi.org/10.1002/anie.201008151	journal	March 2011
Demonstration of Chemisorption of Carbon Dioxide in 1,3-Dialkylimidazolium Acetate Ionic Liquids Gurau, Gabriela; Rodríguez, Héctor; Kelley, Steven P. Angewandte Chemie International Edition, Vol. 50, Issue 50 https://doi.org/10.1002/anie.201105198	journal	October 2011
Significant Improvements in CO ₂ Capture by Pyridine-Containing Anion-Functionalized Ionic Liquids through Multiple-Site Cooperative Interactions Luo, Xiaoyan; Guo, Yan; Ding, Fang Angewandte Chemie International Edition, Vol. 53, Issue 27 https://doi.org/10.1002/anie.201400957	journal	June 2014
Poly(Ionic Liquid)-Derived Carbon with Site-Specific N-Doping and Biphasic Heterojunction for Enhanced CO ₂ Capture and Sensing Gong, Jiang; Antonietti, Markus; Yuan, Jiayin Angewandte Chemie International Edition, Vol. 56, Issue 26 https://doi.org/10.1002/anie.201702453	journal	May 2017
Sorbents for the Direct Capture of CO ₂ from Ambient Air Shi, Xiaoyang; Xiao, Hang; Azarabadi, Habib Angewandte Chemie International Edition, Vol. 59, Issue 18 https://doi.org/10.1002/anie.201906756	journal	February 2020
Tuning the Physicochemical Properties of Diverse Phenolic Ionic Liquids for Equimolar CO2 Capture by the Substituent on the Anion Wang, Congmin; Luo, Huimin; Li, Haoran Chemistry - A European Journal, Vol. 18, Issue 7 https://doi.org/10.1002/chem.201103092	journal	January 2012
Competing Reactions of CO ₂ with Cations and Anions in Azolide Ionic Liquids Gohndrone, Thomas R.; Bum Lee, Tae; DeSilva, M. Aruni ChemSusChem, Vol. 7, Issue 7 https://doi.org/10.1002/cssc.201400009	journal	May 2014
First- and second-sphere coordination chemistry of alkali metal crown ether complexes Steed, Jonathan W. Coordination Chemistry Reviews, Vol. 215, Issue 1 https://doi.org/10.1016/S0010-8545(01)00317-4	journal	May 2001
Selective oxidation of phenol and anisole derivatives to quinones with hydrogen peroxide and polymer-supported methylrhenium trioxide systems Saladino, Raffaele; Neri, Veronica; Mincione, Enrico Tetrahedron, Vol. 58, Issue 42 https://doi.org/10.1016/S0040-4020(02)01025-6	journal	October 2002
Low-viscous fluorine-substituted phenolic ionic liquids with high performance for capture of CO2 Zhang, Xiao-Min; Huang, Kuan; Xia, Shuang Chemical Engineering Journal, Vol. 274 https://doi.org/10.1016/j.cej.2015.03.052	journal	August 2015
Alkanolamine-based dual functional ionic liquids with multidentate cation coordination and pyrazolide anion for highly efficient CO 2 capture at relatively high temperature Qian, Weichuan; Xu, Yingjie; Xie, Bin International Journal of Greenhouse Gas Control, Vol. 56 https://doi.org/10.1016/j.ijggc.2016.11.032	journal	January 2017
Tuning the strength of cation coordination interactions of dual functional ionic liquids for improving CO2 capture performance Shu, Hegang; Xu, Yingjie International Journal of Greenhouse Gas Control, Vol. 94 https://doi.org/10.1016/j.ijggc.2019.102934	journal	March 2020
Amine–Oxide Hybrid Materials for CO ₂ Capture from Ambient Air Didas, Stephanie A.; Choi, Sunho; Chaikittisilp, Watcharop Accounts of Chemical Research, Vol. 48, Issue 10 https://doi.org/10.1021/acs.accounts.5b00284	journal	September 2015
Direct Capture of CO₂ from Ambient Air Sanz-Pérez, Eloy S.; Murdock, Christopher R.; Didas, Stephanie A. Chemical Reviews, Vol. 116, Issue 19, p. 11840-11876 https://doi.org/10.1021/acs.chemrev.6b00173	journal	August 2016
Ionic-Liquid-Based CO ₂ Capture Systems: Structure, Interaction and Process Zeng, Shaojuan; Zhang, Xiangping; Bai, Lu Chemical Reviews, Vol. 117, Issue 14 https://doi.org/10.1021/acs.chemrev.7b00072	journal	May 2017
CO ₂ Chemistry of Phenolate-Based Ionic Liquids Lee, Tae Bum; Oh, Seungmin; Gohndrone, Thomas R. The Journal of Physical Chemistry B, Vol. 120, Issue 8 https://doi.org/10.1021/acs.jpcb.5b06934	journal	November 2015
Crown Ethers: The Search for Selective Ion Ligating Agents Bradshaw, Jerald S.; Izatt, Reed M. Accounts of Chemical Research, Vol. 30, Issue 8 https://doi.org/10.1021/ar950211m	journal	August 1997
The Synthesis and Ion Bindings of Synthetic Multidentate Macrocyclic Compounds Christensen, James J.; Eatough, Delbert J.; Izatt, Reed M. Chemical Reviews, Vol. 74, Issue 3 https://doi.org/10.1021/cr60289a003	journal	June 1974
Review on the Use of Ionic Liquids (ILs) as Alternative Fluids for CO ₂ Capture and Natural Gas Sweetening Karadas, Ferdi; Atilhan, Mert; Aparicio, Santiago Energy & Fuels, Vol. 24, Issue 11 https://doi.org/10.1021/ef1011337	journal	November 2010
Carbon Dioxide Capture from Atmospheric Air Using Sodium Hydroxide Spray Stolaroff, Joshuah K.; Keith, David W.; Lowry, Gregory V. Environmental Science & Technology, Vol. 42, Issue 8 https://doi.org/10.1021/es702607w	journal	April 2008
Simulation of Enthalpy and Capacity of CO ₂ Absorption by Aqueous Amine Systems McCann, Nichola; Maeder, Marcel; Attalla, Moetaz Industrial & Engineering Chemistry Research, Vol. 47, Issue 6 https://doi.org/10.1021/ie070619a	journal	March 2008
Multinuclear NMR relaxation studies of crown ethers and alkali cation crown ether complexes Eliasson, Bertil; Larsson, Kerstin M.; Kowalewski, Jozef The Journal of Physical Chemistry, Vol. 89, Issue 2 https://doi.org/10.1021/j100248a016	journal	January 1985
CO₂ Capture by a Task-Specific Ionic Liquid Bates, Eleanor D.; Mayton, Rebecca D.; Ntai, Ioanna Journal of the American Chemical Society, Vol. 124, Issue 6, p. 926-927 https://doi.org/10.1021/ja017593d	journal	February 2002
Liquid Poly(ethylene glycol) and Supercritical Carbon Dioxide: A Benign Biphasic Solvent System for Use and Recycling of Homogeneous Catalysts Heldebrant, David J.; Jessop, Philip G. Journal of the American Chemical Society, Vol. 125, Issue 19 https://doi.org/10.1021/ja029131l	journal	May 2003
Structure and Properties of High Stability Geminal Dicationic Ionic Liquids Anderson, Jared L.; Ding, Rongfang; Ellern, Arkady Journal of the American Chemical Society, Vol. 127, Issue 2 https://doi.org/10.1021/ja046521u	journal	January 2005
Carbon Dioxide Capture from the Air Using a Polyamine Based Regenerable Solid Adsorbent Goeppert, Alain; Czaun, Miklos; May, Robert B. Journal of the American Chemical Society, Vol. 133, Issue 50, p. 20164-20167 https://doi.org/10.1021/ja2100005	journal	December 2011
Important Roles of Enthalpic and Entropic Contributions to CO ₂ Capture from Simulated Flue Gas and Ambient Air Using Mesoporous Silica Grafted Amines Alkhabbaz, Mustafa A.; Bollini, Praveen; Foo, Guo Shiou Journal of the American Chemical Society, Vol. 136, Issue 38 https://doi.org/10.1021/ja507655x	journal	September 2014
Low-Pressure Solubility of Carbon Dioxide in Room-Temperature Ionic Liquids Measured with a Quartz Crystal Microbalance Baltus, Ruth E.; Culbertson, Benjamin H.; Dai, Sheng The Journal of Physical Chemistry B, Vol. 108, Issue 2, p. 721-727 https://doi.org/10.1021/jp036051a	journal	January 2004
Carbene Formation in Ionic Liquids: Spontaneous, Induced, or Prohibited? Hollóczki, Oldamur; Firaha, Dzmitry S.; Friedrich, Joachim The Journal of Physical Chemistry B, Vol. 117, Issue 19 https://doi.org/10.1021/jp4004399	journal	May 2013
Global carbon dioxide levels near worrisome milestone Monastersky, Richard Nature, Vol. 497, Issue 7447 https://doi.org/10.1038/497013a	journal	April 2013
Cooperative insertion of CO2 in diamine-appended metal-organic frameworks McDonald, Thomas M.; Mason, Jarad A.; Kong, Xueqian Nature, Vol. 519, Issue 7543 https://doi.org/10.1038/nature14327	journal	March 2015
Direct air capture of CO2 via aqueous-phase absorption and crystalline-phase release using concentrated solar power Brethomé, Flavien M.; Williams, Neil J.; Seipp, Charles A. Nature Energy, Vol. 3, Issue 7 https://doi.org/10.1038/s41560-018-0150-z	journal	May 2018
Moisture-swing sorption for carbon dioxide capture from ambient air: a thermodynamic analysis Wang, Tao; Lackner, Klaus S.; Wright, Allen B. Phys. Chem. Chem. Phys., Vol. 15, Issue 2 https://doi.org/10.1039/C2CP43124F	journal	January 2013
Highly efficient CO ₂ capture by carbonyl-containing ionic liquids through Lewis acid–base and cooperative C–H⋯O hydrogen bonding interaction strengthened by the anion Ding, Fang; He, Xi; Luo, Xiaoyan Chem. Commun., Vol. 50, Issue 95 https://doi.org/10.1039/C4CC06944G	journal	January 2014
Active chemisorption sites in functionalized ionic liquids for carbon capture Cui, Guokai; Wang, Jianji; Zhang, Suojiang Chemical Society Reviews, Vol. 45, Issue 15 https://doi.org/10.1039/C5CS00462D	journal	January 2016
A novel phenolic ionic liquid for 1.5 molar CO ₂ capture: combined experimental and DFT studies Vafaeezadeh, Majid; Aboudi, Javad; Hashemi, Mohammad Mahmoodi RSC Advances, Vol. 5, Issue 71 https://doi.org/10.1039/C5RA09845A	journal	January 2015
Stability of amine-functionalized CO ₂ adsorbents: a multifaceted puzzle Jahandar Lashaki, Masoud; Khiavi, Soheil; Sayari, Abdelhamid Chemical Society Reviews, Vol. 48, Issue 12 https://doi.org/10.1039/C8CS00877A	journal	January 2019
Enhanced CO ₂ capture by reducing cation–anion interactions in hydroxyl-pyridine anion-based ionic liquids Luo, Xiao-Yan; Chen, Xiao-Yan; Qiu, Rong-Xing Dalton Transactions, Vol. 48, Issue 7 https://doi.org/10.1039/C8DT04680H	journal	January 2019
Cation-controlled catalysis with crown ether-containing transition metal complexes Yoo, Changho; Dodge, Henry M.; Miller, Alexander J. M. Chemical Communications, Vol. 55, Issue 35 https://doi.org/10.1039/C9CC00803A	journal	January 2019
Conversion of CO ₂ to value-added products mediated by ionic liquids Chen, Yu; Mu, Tiancheng Green Chemistry, Vol. 21, Issue 10 https://doi.org/10.1039/C9GC00827F	journal	January 2019
Synthesis of ammonia borane for hydrogen storage applications Heldebrant, David J.; Karkamkar, Abhi; Linehan, John C. Energy & Environmental Science, Vol. 1, Issue 1, p. 156-160 https://doi.org/10.1039/b808865a	journal	January 2008
Nanoporous molecular basket sorbent for NO2 and SO2 capture based on a polyethylene glycol-loaded mesoporous molecular sieve Wang, Xiaoxing; Ma, Xiaoliang; Zhao, Shuqi Energy & Environmental Science, Vol. 2, Issue 8 https://doi.org/10.1039/b906476a	journal	January 2009
Highly efficient CO2 capture by tunable alkanolamine-based ionic liquids with multidentate cation coordination Wang, Congmin; Guo, Yan; Zhu, Xiang Chemical Communications, Vol. 48, Issue 52 https://doi.org/10.1039/c2cc32365f	journal	January 2012
Carbon capture with ionic liquids: overview and progress Zhang, Xiangping; Zhang, Xiaochun; Dong, Haifeng Energy & Environmental Science, Vol. 5, Issue 5 https://doi.org/10.1039/c2ee21152a	journal	January 2012
Amine Scrubbing for CO2 Capture Rochelle, G. T. Science, Vol. 325, Issue 5948 https://doi.org/10.1126/science.1176731	journal	September 2009
CO2 capture from humid flue gases and humid atmosphere using a microporous coppersilicate Datta, S. J.; Khumnoon, C.; Lee, Z. H. Science, Vol. 350, Issue 6258 https://doi.org/10.1126/science.aab1680	journal	October 2015
Cooperative carbon capture and steam regeneration with tetraamine-appended metal–organic frameworks Kim, Eugene J.; Siegelman, Rebecca L.; Jiang, Henry Z. H. Science, Vol. 369, Issue 6502 https://doi.org/10.1126/science.abb3976	journal	July 2020

Similar Records

Surpassing the Performance of Phenolate-derived Ionic Liquids in CO₂ Chemisorption by Harnessing the Robust Nature of Pyrazolonates

Journal Article · 2023 · ChemSusChem · OSTI ID:2439829

Qiu, Liqi; Fu, Yuqing; Yang, Zhenzhen; +7 more

Supramolecular Complexation-Enhanced CO₂ Chemisorption in Amine-Derived Sorbents

Journal Article · 2024 · Chemistry - A European Journal · OSTI ID:2439831

Li, Errui; Li, Bo; Ganesan, Arvind; +7 more

New-Generation Carbon-Capture Ionic Liquids Regulated by Metal-Ion Coordination

Journal Article · 2021 · ChemSusChem · OSTI ID:1844853

Suo, Xian; Yang, Zhenzhen; Fu, Yuqing; +7 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
54 ENVIRONMENTAL SCIENCES

Title: CO2 Chemisorption Behavior of Coordination-Derived Phenolate Sorbents

Citation Formats

References (53)

Similar Records

Related Subjects

Title: CO₂ Chemisorption Behavior of Coordination-Derived Phenolate Sorbents