Incorporation of Amino Acid-Functionalized Ionic Liquids into Highly Porous MOF-177 to Improve the Post-Combustion CO2 Capture Capacity
Abstract
:1. Introduction
2. Results and Discussion
2.1. Characterization of the AAIL-Impregnated Sorbents
2.2. CO2 Adsorption Isotherms
2.3. Selectivity for CO2/N2
2.4. Equilibrium Isotherm Modeling
2.5. Isosteric Heat of Adsorption (Qst)
3. Materials and Methods
3.1. Materials
3.2. Preparation of the AAIL@MOF-177 Composites
3.3. Characterization
3.4. Adsorption Isotherms
3.5. Cyclic Adsorption–Desorption Test
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
- Sumida, K.; Rogow, D.L.; Mason, J.A.; McDonald, T.M.; Bloch, E.D.; Herm, Z.R.; Bae, T.-H.; Long, J.R. Carbon Dioxide Capture in Metal–Organic Frameworks. Chem. Rev. 2012, 112, 724–781. [Google Scholar] [CrossRef]
- Lin, Y.; Kong, C.; Zhang, Q.; Chen, L. Metal–Organic Frameworks for Carbon Dioxide Capture and Methane Storage. Adv. Energy Mater. 2017, 7, 1601296. [Google Scholar] [CrossRef]
- Amaro-Gahete, J.; Klee, R.; Esquivel, D.; Ruiz, J.R.; Jiménez-Sanchidrián, C.; Romero-Salguero, F.J. Fast Ultrasound-Assisted Synthesis of Highly Crystalline MIL-88A Particles and Their Application as Ethylene Adsorbents. Ultrason. Sonochem. 2019, 50, 59–66. [Google Scholar] [CrossRef]
- Li, H.; Wang, K.; Sun, Y.; Lollar, C.T.; Li, J.; Zhou, H.C. Recent Advances in Gas Storage and Separation Using Metal–Organic Frameworks. Mater. Today 2018, 21, 108–121. [Google Scholar] [CrossRef]
- Rojas-Luna, R.; Amaro-Gahete, J.; Gil-Gavilán, D.G.; Castillo-Rodríguez, M.; Jiménez-Sanchidrián, C.; Ruiz, J.R.; Esquivel, D.; Romero-Salguero, F.J. Visible-Light-Harvesting Basolite-A520 Metal Organic Framework for Photocatalytic Hydrogen Evolution. Microporous Mesoporous Mater. 2023, 355, 112565. [Google Scholar] [CrossRef]
- Zhao, Y.; Song, Z.; Li, X.; Sun, Q.; Cheng, N.; Lawes, S.; Sun, X. Metal Organic Frameworks for Energy Storage and Conversion. Energy Storage Mater. 2016, 2, 35–62. [Google Scholar] [CrossRef]
- Zhu, L.; Liu, X.Q.; Jiang, H.L.; Sun, L.B. Metal–Organic Frameworks for Heterogeneous Basic Catalysis. Chem. Rev. 2017, 117, 8129–8176. [Google Scholar] [CrossRef]
- Lawson, H.D.; Walton, S.P.; Chan, C. Metal–Organic Frameworks for Drug Delivery: A Design Perspective. ACS Appl. Mater. Interfaces 2021, 13, 7004–7020. [Google Scholar] [CrossRef]
- Hu, Z.; Wang, Y.; Shah, B.B.; Zhao, D. CO2 Capture in Metal–Organic Framework Adsorbents: An Engineering Perspective. Adv. Sustain. Syst. 2018, 3, 1800080. [Google Scholar] [CrossRef]
- Aghaie, M.; Rezaei, N.; Zendehboudi, S. A Systematic Review on CO2 Capture with Ionic Liquids: Current Status and Future Prospects. Renew. Sustain. Energy Rev. 2018, 96, 502–525. [Google Scholar] [CrossRef]
- Yu, J.; Xie, L.H.; Li, J.R.; Ma, Y.; Seminario, J.M.; Balbuena, P.B. CO2 Capture and Separations Using MOFs: Computational and Experimental Studies. Chem. Rev. 2017, 117, 9674–9754. [Google Scholar] [CrossRef] [PubMed]
- Belmabkhout, Y.; Guillerm, V.; Eddaoudi, M. Low Concentration CO2 Capture Using Physical Adsorbents: Are Metal–Organic Frameworks Becoming the New Benchmark Materials? Chem. Eng. J. 2016, 296, 386–397. [Google Scholar] [CrossRef]
- Adil, K.; Bhatt, P.M.; Belmabkhout, Y.; Abtab, S.M.T.; Jiang, H.; Assen, A.H.; Mallick, A.; Cadiau, A.; Aqil, J.; Eddaoudi, M. Valuing Metal–Organic Frameworks for Postcombustion Carbon Capture: A Benchmark Study for Evaluating Physical Adsorbents. Adv. Mater. 2017, 29, 1702953. [Google Scholar] [CrossRef] [PubMed]
- Yin, Z.; Wan, S.; Yang, J.; Kurmoo, M.; Zeng, M.H. Recent Advances in Post-Synthetic Modification of Metal–Organic Frameworks: New Types and Tandem Reactions. Coord. Chem. Rev. 2019, 378, 500–512. [Google Scholar] [CrossRef]
- Jasuja, H.; Walton, K.S. Experimental Study of CO2, CH4, and Water Vapor Adsorption on a Dimethyl-Functionalized UiO-66 Framework. J. Phys. Chem. C 2013, 117, 7062–7068. [Google Scholar] [CrossRef]
- Cmarik, G.E.; Kim, M.; Cohen, S.M.; Walton, K.S. Tuning the Adsorption Properties of Uio-66 via Ligand Functionalization. Langmuir 2012, 28, 15606–15613. [Google Scholar] [CrossRef]
- Shearer, G.C.; Vitillo, J.G.; Bordiga, S.; Svelle, S.; Olsbye, U.; Lillerud, K.P. Functionalizing the Defects: Postsynthetic Ligand Exchange in the Metal Organic Framework UiO-66. Chem. Mater. 2016, 28, 7190–7193. [Google Scholar] [CrossRef]
- Mutyala, S.; Yakout, S.M.; Ibrahim, S.S.; Jonnalagadda, M.; Mitta, H. Enhancement of CO2 Capture and Separation of CO2/N2 Using Post-Synthetic Modified MIL-100(Fe). N. J. Chem. 2019, 43, 9725–9731. [Google Scholar] [CrossRef]
- Su, X.; Bromberg, L.; Martis, V.; Simeon, F.; Huq, A.; Hatton, T.A. Postsynthetic Functionalization of Mg-MOF-74 with Tetraethylenepentamine: Structural Characterization and Enhanced CO2 Adsorption. ACS Appl. Mater. Interfaces 2017, 9, 11299–11306. [Google Scholar] [CrossRef]
- Lin, Y.; Yan, Q.; Kong, C.; Chen, L. Polyethyleneimine Incorporated Metal–Organic Frameworks Adsorbent for Highly Selective CO2 Capture. Sci. Rep. 2013, 3, 1859. [Google Scholar] [CrossRef]
- Choi, S.; Watanabe, T.; Bae, T.H.; Sholl, D.S.; Jones, C.W. Modification of the Mg/DOBDC MOF with Amines to Enhance CO2 Adsorption from Ultradilute Gases. J. Phys. Chem. Lett. 2012, 3, 1136–1141. [Google Scholar] [CrossRef] [PubMed]
- Fujie, K.; Kitagawa, H. Ionic Liquid Transported into Metal–Organic Frameworks. Coord. Chem. Rev. 2016, 307, 382–390. [Google Scholar] [CrossRef]
- Kulak, H.; Polat, H.M.; Kavak, S.; Keskin, S.; Uzun, A. Improving CO2 Separation Performance of MIL-53(Al) by Incorporating 1-n-Butyl-3-Methylimidazolium Methyl Sulfate. Energy Technol. 2019, 7, 1900157. [Google Scholar] [CrossRef]
- Kinik, F.P.; Altintas, C.; Balci, V.; Koyuturk, B.; Uzun, A.; Keskin, S. [BMIM][PF6] Incorporation Doubles CO2 Selectivity of ZIF-8: Elucidation of Interactions and Their Consequences on Performance. ACS Appl. Mater. Interfaces 2016, 8, 30992–31005. [Google Scholar] [CrossRef] [PubMed]
- Koyuturk, B.; Altintas, C.; Kinik, F.P.; Keskin, S.; Uzun, A. Improving Gas Separation Performance of ZIF-8 by [BMIM][BF4] Incorporation: Interactions and Their Consequences on Performance. J. Phys. Chem. C 2017, 121, 10370–10381. [Google Scholar] [CrossRef]
- Bates, E.D.; Mayton, R.D.; Ntai, I.; Davis, J.H. CO2 Capture by a Task-Specific Ionic Liquid. J. Am. Chem. Soc. 2002, 124, 926–927. [Google Scholar] [CrossRef]
- Fukumoto, K.; Yoshizawa, M.; Ohno, H. Room Temperature Ionic Liquids from 20 Natural Amino Acids. J. Am. Chem. Soc. 2005, 127, 2398–2399. [Google Scholar] [CrossRef]
- Sistla, Y.S.; Khanna, A. CO2 Absorption Studies in Amino Acid-Anion Based Ionic Liquids. Chem. Eng. J. 2015, 273, 268–276. [Google Scholar] [CrossRef]
- Muhammad, N.; Man, Z.B.; Bustam, M.A.; Mutalib, M.I.A.; Wilfred, C.D.; Rafiq, S. Synthesis and Thermophysical Properties of Low Viscosity Amino Acid-Based Ionic Liquids. J. Chem. Eng. Data 2011, 56, 3157–3162. [Google Scholar] [CrossRef]
- Zhang, J.; Zhang, S.; Dong, K.; Zhang, Y.; Shen, Y.; Lv, X. Supported Absorption of CO2 by Tetrabutylphosphonium Amino Acid Ionic Liquids. Chem.-A Eur. J. 2006, 12, 4021–4026. [Google Scholar] [CrossRef]
- Wang, X.; Akhmedov, N.G.; Duan, Y.; Luebke, D.; Hopkinson, D.; Li, B. Amino Acid-Functionalized Ionic Liquid Solid Sorbents for Post-Combustion Carbon Capture. ACS Appl. Mater. Interfaces 2013, 5, 8670–8677. [Google Scholar] [CrossRef] [PubMed]
- Uehara, Y.; Karami, D.; Mahinpey, N. CO2 Adsorption Using Amino Acid Ionic Liquid-Impregnated Mesoporous Silica Sorbents with Different Textural Properties. Microporous Mesoporous Mater. 2019, 278, 378–386. [Google Scholar] [CrossRef]
- Uehara, Y.; Karami, D.; Mahinpey, N. Amino Acid Ionic Liquid-Modified Mesoporous Silica Sorbents with Remaining Surfactant for CO2 Capture. Adsorption 2019, 1, 703–716. [Google Scholar] [CrossRef]
- Philip, F.A.; Henni, A. Enhancement of Post-Combustion CO2 Capture Capacity by Incorporation of Task-Specific Ionic Liquid into ZIF-8. Microporous Mesoporous Mater. 2021, 111580, 111580. [Google Scholar] [CrossRef]
- Furukawa, H.; Miller, M.A.; Yaghi, O.M. Independent Verification of the Saturation Hydrogen Uptake in MOF-177 and Establishment of a Benchmark for Hydrogen Adsorption in Metal–Organic Frameworks. J. Mater. Chem. 2007, 17, 3197–3204. [Google Scholar] [CrossRef]
- Mohamedali, M.; Henni, A.; Ibrahim, H. Investigation of CO2 Capture Using Acetate-Based Ionic Liquids Incorporated into Exceptionally Porous Metal–Organic Frameworks. Adsorption 2019, 25, 675–692. [Google Scholar] [CrossRef]
- Saha, D.; Deng, S. Structural Stability of Metal Organic Framework MOF-177. J. Phys. Chem. Lett. 2010, 1, 73–78. [Google Scholar] [CrossRef]
- Li, Y.; Yang, R.T. Gas Adsorption and Storage in Metal–Organic Framework MOF-177. Langmuir 2007, 23, 12937–12944. [Google Scholar] [CrossRef]
- Santos, K.M.C.; Santos, R.J.O.; De Araújo Alves, M.M.; De Conto, J.F.; Borges, G.R.; Dariva, C.; Egues, S.M.; Santana, C.C.; Franceschi, E. Effect of High Pressure CO2 Sorption on the Stability of Metalorganic Framework MOF-177 at Different Temperatures. J. Solid State Chem. 2019, 269, 320–327. [Google Scholar] [CrossRef]
- Zhu, J.; Wu, L.; Bu, Z.; Jie, S.; Li, B.G. Polyethyleneimine-Modified UiO-66-NH2 (Zr) Metal–Organic Frameworks: Preparation and Enhanced CO2 Selective Adsorption. ACS Omega 2019, 4, 3188–3197. [Google Scholar] [CrossRef]
- Gaikwad, S.; Kim, Y.; Gaikwad, R.; Han, S. Enhanced CO2 Capture Capacity of Amine-Functionalized MOF-177 Metal Organic Framework. J. Environ. Chem. Eng. 2021, 9, 105523. [Google Scholar] [CrossRef]
- Aarti; Bhadauria, S.; Nanoti, A.; Dasgupta, S.; Divekar, S.; Gupta, P.; Chauhan, R. [Cu3(BTC)2]-Polyethyleneimine: An Efficient MOF Composite for Effective CO2 Separation. RSC Adv. 2016, 6, 93003–93009. [Google Scholar] [CrossRef]
- Lin, Y.; Lin, H.; Wang, H.; Suo, Y.; Li, B.; Kong, C.; Chen, L. Enhanced Selective CO2 Adsorption on Polyamine/MIL-101(Cr) Composites. J. Mater. Chem. A 2014, 2, 14658–14665. [Google Scholar] [CrossRef]
- Thi Le, M.U.; Lee, S.Y.; Park, S.J. Preparation and Characterization of PEI-Loaded MCM-41 for CO2 Capture. Int. J. Hydrog. Energy 2014, 39, 12340–12346. [Google Scholar] [CrossRef]
- Saha, D.; Wei, Z.; Deng, S. Equilibrium, Kinetics and Enthalpy of Hydrogen Adsorption in MOF-177. Int. J. Hydrog. Energy 2008, 33, 7479–7488. [Google Scholar] [CrossRef]
- Ren, J.; Wu, L.; Li, B.G. Preparation and CO2 Sorption/Desorption of N-(3-Aminopropyl)Aminoethyl Tributylphosphonium Amino Acid Salt Ionic Liquids Supported into Porous Silica Particles. Ind. Eng. Chem. Res. 2012, 51, 7901–7909. [Google Scholar] [CrossRef]
- Gurkan, B.E.; De La Fuente, J.C.; Mindrup, E.M.; Ficke, L.E.; Goodrich, B.F.; Price, E.A.; Schneider, W.F.; Brennecke, J.F. Equimolar CO2 Absorption by Anion-Functionalized Ionic Liquids. J. Am. Chem. Soc. 2010, 132, 2116–2117. [Google Scholar] [CrossRef]
- Wang, X.; Akhmedov, N.G.; Duan, Y.; Luebke, D.; Li, B. Immobilization of Amino Acid Ionic Liquids into Nanoporous Microspheres as Robust Sorbents for CO2 Capture. J. Mater. Chem. A 2013, 1, 2978–2982. [Google Scholar] [CrossRef]
- Ferreira, T.J.; Ribeiro, R.P.P.L.; Mota, J.P.B.; Rebelo, L.P.N.; Esperança, J.M.S.S.; Esteves, I.A.A.C. Ionic Liquid-Impregnated Metal–Organic Frameworks for CO2/CH4 Separation. ACS Appl. Nano Mater. 2019, 2, 7933–7950. [Google Scholar] [CrossRef]
- Mohamedali, M.; Ibrahim, H.; Henni, A. Incorporation of Acetate-Based Ionic Liquids into a Zeolitic Imidazolate Framework (ZIF-8) as Efficient Sorbents for Carbon Dioxide Capture. Chem. Eng. J. 2018, 334, 817–828. [Google Scholar] [CrossRef]
Samples | SBET (m2·g−1) | SLangmuir (m2·g−1) | Pore Volume (cm3·g−1) |
---|---|---|---|
MOF-177 | 4172 | 4962 | 1.78 |
10-[Emim][Gly]@MOF-177 | 187 | 250 | 0.13 |
20-[Emim][Gly]@MOF-177 | 74 | 147 | 0.06 |
30-[Emim][Gly]@MOF-177 | 27 | 41 | 0.02 |
10-[Emim][Ala]@MOF-177 | 152 | 226 | 0.10 |
20-[Emim][Ala]@MOF-177 | 39 | 89 | 0.05 |
30-[Emim][Ala]@MOF-177 | 9.3 | 29 | 0.01 |
Composites | CO2 Uptake (mmol g−1) | CO2/N2 Selectivity a | Experimental Conditions | Ref. |
---|---|---|---|---|
20-[Emim][Gly]@MOF-177 | 0.45 | 13 | 0.2 bar/303 K | This work |
20-[Emim][Ala]@MOF-177 | 0.42 | 11 | 0.2 bar/303 K | This work |
10-[Emim][Ac]@MOF-1777 | 0.38 | - | 0.2 bar/303 K | [36] |
30-[Bmim][Ac]@ZIF-8 | 0.8 b | 12 | 0.2 bar/303 K | [50] |
30-[Emim][Ac]@ZIF-8 | 0.7 b | 4 | 0.2 bar/303 K | [50] |
30-[Emim][Gly]@ZIF-8 | 0.89 | 19 c | 0.2 bar/303 K | [34] |
30-[Emim][Ala]@ZIF-8 | 0.91 | 8 c | 0.2 bar/303 K | [34] |
2.5-PEI-CuBTC (HKUST) | 0.45 | 0.15 bar/313 K | [42] | |
30-[Bmim][PF6]@ZIF-8 | 0.18 b | 17 | 0.2 bar/298 K | [24] |
25-[Bmim][BF4]@ZIF-8 | 0.09 b | 13 | 0.2 bar/298 K | [25] |
Model Parameters | 10-[Emim][Gly]@ MOF-177 | 20-[Emim][Gly]@MOF-177 | 30-[Emim][Gly]@MOF-177 | ||||||
---|---|---|---|---|---|---|---|---|---|
30 °C | 40 °C | 50 °C | 30 °C | 40 °C | 50 °C | 30 °C | 40 °C | 50 °C | |
NA | 2.019 | 2.350 | 1.921 | 0.436 | 0.292 | 0.165 | 1.590 | 0.097 | 0.087 |
bA | 0.514 | 0.426 | 0.562 | 5.117 | 4.698 | 9.030 | 0.508 | 10.678 | 18.396 |
NB | 0.247 | 0.098 | 0.024 | 2.371 | 2.694 | 2.444 | 0.190 | 1.405 | 1.628 |
bB | 6.692 | 15.04 | 10,000 | 0.545 | 0.479 | 0.439 | 8.468 | 0.609 | 0.404 |
R2 | 1.000 | 1.000 | 1.000 | 1.000 | 1.000 | 1.000 | 1.000 | 1.000 | 1.000 |
Model Parameters | 10-[Emim][Ala]@ MOF-177 | 20-[Emim][Ala]@MOF-177 | 30-[Emim][Ala]@MOF-177 | ||||||
---|---|---|---|---|---|---|---|---|---|
30 °C | 40 °C | 50 °C | 30 °C | 40 °C | 50 °C | 30 °C | 40 °C | 50 °C | |
NA | 1.960 | 0.000 | 0.151 | 0.306 | 0.230 | 2.791 | 1.698 | 1.602 | 0.246 |
bA | 0.501 | 0.000 | 7.765 | 6.003 | 7.147 | 0.326 | 0.697 | 0.539 | 7.046 |
NB | 0.129 | 1.600 | 2.182 | 2.607 | 2.618 | 0.185 | 0.122 | 0.180 | 1.599 |
bB | 12.735 | 0.763 | 0.315 | 0.564 | 0.462 | 6.700 | 15.549 | 6.987 | 0.365 |
R2 | 1.000 | 0.999 | 1.000 | 1.000 | 1.000 | 1.000 | 1.000 | 1.000 | 1.000 |
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Philip, F.A.; Henni, A. Incorporation of Amino Acid-Functionalized Ionic Liquids into Highly Porous MOF-177 to Improve the Post-Combustion CO2 Capture Capacity. Molecules 2023, 28, 7185. https://doi.org/10.3390/molecules28207185
Philip FA, Henni A. Incorporation of Amino Acid-Functionalized Ionic Liquids into Highly Porous MOF-177 to Improve the Post-Combustion CO2 Capture Capacity. Molecules. 2023; 28(20):7185. https://doi.org/10.3390/molecules28207185
Chicago/Turabian StylePhilip, Firuz A., and Amr Henni. 2023. "Incorporation of Amino Acid-Functionalized Ionic Liquids into Highly Porous MOF-177 to Improve the Post-Combustion CO2 Capture Capacity" Molecules 28, no. 20: 7185. https://doi.org/10.3390/molecules28207185