Dissertation for the Degree of Doctor of Philosophy Design and Synthesis of Metal-Organic Frameworks for CO, CO2, and C7H8 Adsorption Le Van Nhieu Department of Chemical Engineering Graduate School Kyung Hee University Seoul, Korea June, 2021 Design and Synthesis of Metal-Organic Frameworks for CO, CO2, and C7H8 Adsorption Le Van Nhieu Department of Chemical Engineering Graduate School Kyung Hee University Seoul, Korea June, 2021 Design and Synthesis of Metal-Organic Frameworks for CO, CO2, and C7H8 Adsorption by Le Van Nhieu Advised by Prof. Jinsoo Kim Submitted to the Department of Chemical Engineering and the Faculty of the Gradual School of Kyung Hee University in partial fulfillment of the requirement for degree of Doctor of Philosophy Dissertation Committee Chairman Prof. Eun Yeol Lee Prof. Bum Jun Park Prof.
Chang Kyoo Yoo Prof. Kye Sang Yoo Prof. Jinsoo Kim ABSTRACT Design and Synthesis of Metal-Organic Frameworks for CO, CO2, and C7H8 Adsorption Le Van Nhieu Department of Chemical Engineering Graduate School of Kyung Hee University Seoul, Korea To date, gas adsorption has attracted attention in the context of more serious air pollution as a result of industrialization and the growing population. By the way, the gaseous contaminants are effectively managed to contribute to the improvement of air quality, simultaneously, supply several important chemicals (CO, CO2) used as raw materials for the industrial manufacturing process.
And, the derived-adsorbents from metal organic frameworks (MOFs) have gradually become a key contributor to the amelioration of gas adsorption performance. The separation of CO out of gas mixture, especially containing CO 2 is an important mission in the industrial production sector but encounter huge challenges due to the higher polarizability of CO2 than that of CO. Most of the investigation showed that after introducing Cu(I) into pore system of MOF-support, the resulting materials exhibited a higher adsorption capacity of CO than CO2 whereas a contrary result was observed on the original MOFs. This is due to -complexation formed between Cu(I) and CO species.
Among the reported MOFs, MIL-100(Fe) possesses high BET surface area, thermal stability ( ̴ 320 oC), and tunability of the oxidation state of iron ions (Fe(II) and Fe(III)) under high temperature (150 ̴ 250 oC). So, a simple route is employed to introduce Cu(I) on MIL-100(Fe), in which Cu(II) is directly transferred to Cu(I) thanks to Fe(II), but no requirement support from reducing agents. However, MIL-100(Fe) is typically synthesized in closed batch systems, which is i not favorable for large-scale production. Herein, we report a scalable MOF synthesis route based on a continuous flow tubular reactor equipped with microwave volumetric heating.
The system enabled continuous crystallization of MIL-100(Fe) with a high space-time yield of ~771.6 kg m-3 day-1 under relatively mild conditions in a range of temperature (100 ̴ 110 o C) and resident time of 50 min. The product quality is evaluated via porous property and crystallinity in comparison to the traditional method. Ultimately, the MIL-100(Fe) was used as a support to prepare Cu(I)-modified π complexation adsorbents. The adsorbents exhibited preferred CO adsorption over CO2, and the adsorption performance was confronted to, or even higher than most of the Cu(I)-modified π complexation adsorbents in previous reports.
Until now, the CO-selective adsorbents are kept developing towards the improvement of CO uptake capacity and CO/CO2 selectivity, but Cu(I)-incorporated MOFs are instability in the air. This is the main reason for reducing CO separation performance in the real gas environment being usually available a certain amount of oxygen and moisture. Recently, some reports have revealed a strategy to improve the stability of Cu(I)-incorporated MOFs, however, their CO adsorption capacity is modest. Therefore, The development of a CO- selective adsorbent with large CO adsorption capacity, high CO/CO 2 selectivity, and good stability is still a huge challenge.
In this dissertation, a novel Cu(I)-incorporated MIL-100(Fe) adsorbent for CO/CO2 separation is prepared using a host–guest redox strategy by combining the co-addition of Zn(II) and Cu(II) inside the MIL-100(Fe)’s pore system. The addition of Zn(II) resulted in a higher Cu(I) yield of the adsorbent due to the facilitated regeneration of Fe(II), which was utilized for the reduction of Cu(II). Therefore, both CO uptake amount and achieved CO/CO2 selectivity on Cu(I)Zn@MIL-100(Fe) with only 10 wt% of Zn loading were considerably higher than that of the benchmark Cu(I)-incorporated adsorbents. In addition, the presence of the Zn(II) in Cu(I)Zn@MIL-100(Fe)-10 improved the oxygen resistance.
This study opens a new perspective for developing efficient CO- selective π-complexation adsorbents with high CO/CO2 selectivity and superior oxygen resistance. Unlike CO adsorption, the MOF-adsorbent for capturing the target gas like CO2 or ii C7H8 is relatively diverse, in which the adsorbent perhaps possesses positive factors for gas adsorption like a superior surface area, a suitable pore structure, and a large amount of adsorption sites having an affinity toward adsorbates. Zirconium-based MOFs (UiO-66, UiO-67) are potential adsorbents for gas adsorption due to a quite large surface area, easily tunable pore structure as well as chemical surface, high chemical/thermal stability, and facilely large scale production thanks to using a microwave-assisted continuous tubular reactor. However, they exhibited a modest uptake capacity for both CO2 and C7H8 in comparison with the others.
So, gas adsorption capacity should be improved. For CO2 adsorption, an amino-defective UiO-66 was prepared by a one-step synthesis method using the mixed linkers of terephthalic acid and a cheap defect linker as 4- aminobenzoic acid. The presence of the 4-aminobenzoic acid in the reaction system, induced enhanced porosity owing to the missing-linker defects, simultaneously, created the amino (- NH2) groups in the framework. Both two factors contribute to the improvement of the CO2 capture capacity on modified UiO-66 as a result of the synergy effect.
Only with 10% in mole of used 4-amino benzoic acid in the mixed ligand, at 25 oC and 1 bar, the obtained CO2 uptake amount and ideal adsorbed solution theory-based CO2/N2 selectivity on the resulting material increased 47.8 higher times in comparison with the original UiO- 66 sample, respectively. These results exhibited an efficient approach (a cheap linker as 4- aminobenzoic acid and one-step synthesis) to prepare a defective UiO-66 adsorbent with amine functional groups, which not only improve CO2 separation performance but also reduce production cost. For C7H8 adsorption, some defective Zr-based biphenyl dicarboxylate (UiO-67) MOFs were prepared via fast modulated synthesis under microwave-assisted continuous tubular reactor by using formic, acetic, propionic, and benzoic acid as modulators. A surface- modified UiO-67(Zr) framework with high porosity and crystallinity could be rapidly produced in a few minutes due to the incomplete exchange between the bridging ligand and the modulator.
The defect concentration in the products was tuned by controlling both the modulator species and their concentrations. The adsorption ability toward toluene of the iii prepared UiO-67(Zr) MOFs was found to be related to their structural defects. The defective UiO-67(Zr) MOF synthesized with HCOOH as the modulator exhibited the highest toluene adsorption capacity (467 mg g –1), surpassing also most of the previously reported adsorbent materials, such as zeolites, activated carbon, UiO-66(Zr), H2N-UiO-66(Zr), ZIF-67, and CuBTC. Moreover, the experimental dynamic adsorption data were mathematically modeled to predict the adsorption behaviors of defective UiO-67(Zr) MOFs.
Additionally, zirconium-based MOFs has still had limitations in fixed-bed adsorption system owing to its tiny sub-micron crystallite size leading to inconvenience in transportation, difficult recovery and serious pressure loss in fixed-bed adsorption system. Thus, an approach to construct mm-scale granules using UiO-66(Zr) powder is required. In this work, UiO-66(Zr) particles were prepared by the solvothermal method under microwave irradiation for only 20 min, then fabricated into spherical granules of UiO-66/PVA by freeze granulation technique. PVA was added as a binder to connect UiO-66 particles together to spherical beads with high mechanical strength, not affecting the crystalline and micropore structures of UiO-66.
The regular octahedron of the UiO-66 individual particles remained intact and the pore size did not change with increasing PVA concentration. However, PVA bound the particles together to form compact and cohesive network clusters that reduced the BET surface area and total pore volume. This consequently lowered the toluene adsorption efficacy slightly due to the premature breakthrough that limited the toluene molecules exposure into the micropores of the individual UiO-66 particles. iv Table of Contents ABSTRACT.
i List of Tables. ix List of Figures. xi CHAPTER 1 - Introduction. 12 CHAPTER 2 – Literature Review.
Isosteric heat of adsorption. Ideal adsorption solution theory (IAST) selectivity. Metal organic frameworks. Iron-based metal organic framework (MIL-100Fe) .2 Zirconium-based metal organic framework (UiO-66 & UiO-67).
Application of MOFs for gas adsorption. Mechanism of gas adsorption. Metal organic frameworks for CO adsorption. Metal organic framework for CO2 adsorption.
Metal organic framework for toluene adsorption. 37 CHAPTER 3 - Microwave-assisted continuous flow synthesis of MIL-100 (Fe) and its application to Cu(I)-loaded adsorbent for CO/CO2 separation. Materials and methods. Results and discussion.
Synthesis of MIL-100(Fe) in a microwave-assisted flow reactor. 61 CHAPTER 4 - A novel approach to prepare Cu(I)Zn@MIL-100(Fe) adsorbent with high CO adsorption capacity, CO/CO2 selectivity and stability. Synthesis of MIL-100(Fe). Synthesis of Cu(I)@MIL-100(Fe) and Cu(I)Zn@MIL-100(Fe) adsorbents.
CO and CO2 adsorption test. Results and discussion. Characterizations of MIL-100(Fe) and Cu(I)Zn@MIL-100(Fe). CO and CO2 adsorption on Cu(I)Zn@MIL-100(Fe) adsorbents.
Regeneration and stability test. 88 CHAPTER 5 - Facile one-step synthesis of amino-defective UiO-66 using 4-amino benzoic acid for enhanced CO2 adsorption performance. Synthesis of MOF materials. CO2 and N2 adsorption.
Results and Discussions. CO2 and N2 adsorption. Isosteric heat of CO2 adsorption and the regeneration of the adsorbent. Adsorption selectivity of CO2/N2 on UiO-66 and UiO-66#10-NH2.
119 CHAPTER 6 - Defect engineering of UiO-67(Zr) under continuous-flow microwave synthesis condition and application for toluene adsorption. Toluene recovery test. Results and discussion. Microwave-assisted continuous-flow synthesis of UiO-67(Zr).
Adsorption and desorption of toluene. Dynamic adsorption of toluene. 148 CHAPTER 7 - Facile synthesis of UiO-66/PVA spherical granules and their application for toluene adsorption. Synthesis of UiO-66(Zr) assisted by microwave and UiO-66/PVA beads.
Toluene adsorption/desorption. Results and discussion. Characterizations of UiO-66 and UiO-66/PVA granules. Toluene adsorption/desorption test.
174 CHAPTER 8 - Summary and further works. 181 viii List of Tables Table 3.1 Texture properties of MIL-100(Fe) synthesized in a microwave assisted continuous flow tubular reactor (MW-MIL-100(Fe)), synthesized in a conventional batch reactor (CB-MIL-100(Fe)), and the corresponding data previously reported in the literature. *: Brunauer–Emmett–Teller (BET) surface area, #: specific pore volume, $: microwave- assisted flow tubular reactor, and $$: conventional batch reactor.2 Comparison of MIL-100(Fe) yields synthesized in a microwave-assisted continuous flow tubular reactor (MW-MIL-100(Fe)), synthesized in a conventional batch reactor (CB-MIL-100(Fe)), and the corresponding data previously reported in the literature.3 Texture properties of MIL-100(Fe) synthesized in a microwave assisted continuous flow tubular reactor (MW-MIL-100(Fe)) as a function of CuCl loading.4 Fitted dual-site Langmuir–Freundlich (DSLF) parameters for CO and CO2 isotherms experimentally obtained for MW-MIL-100(Fe) and xCuCl@MIL-100(Fe) at 298 K .5 Comparison of equilibrium CO adsorption performances of xCuCl@MIL-100(Fe) with reported Cu(I)-modified π complexation adsorbents. Equilibrium selectivity was calculated by taking ratio between CO and CO2 adsorption capacity at 100 kPa and 298 K.1 Textural properties of MIL-100(Fe), Cu(I)@MIL-100(Fe), and Cu(I)Zn@MIL- 100(Fe)-x samples.2 Comparison of CO working capacity and CO/CO2 separation factor with those of other benchmark Cu(I)-incorporated adsorbents .1 Textural properties of the UiO-66 and modified UiO-66 samples depending on ix PABA concentration.2 Components of oxygen calculated from O 1s spectra .3 Comparison of CO2 uptake capacity on different adsorbents at 1bar.4 The obtained parameters and correlation coefficients from fitting the Langmuir– Freundlich model .1 Microwave –assisted continuous flow synthesis of UiO-67(Zr).2 Number of linkers per Zr6 formular unit and linker deficiency derived from TGA analyses .3 Equilibrium toluene adsorption capacity of various adsorbent materials .4 Adsorption parameters of the Yan and Thomas models .1 Effect of PVA content on compressive strength .2 BET surface area and pore volume of UiO-66 and UiO-66/PVA samples .3 Toluene uptake capacity of various MOF-adsorbents .4 The model fitting parameters .