Hyper-Crosslinked Porous Organic Frameworks with Ultra-micropores

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Hyper-Crosslinked Porous Organic Frameworks with Ultra-micropores for Selective Xenon Capture Debanjan Chakraborty, Shyamapada Nandi, Michael Sinnwell, Jian Liu, Rinku Kushwaha, Praveen K. Thallapally, and Ramanathan Vaidhyanathan ACS Appl. Mater. Interfaces, Just Accepted Manuscript • DOI: 10.1021/acsami.9b01619 • Publication Date (Web): 19 Mar 2019 Downloaded from http://pubs.acs.org on March 20, 2019

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ACS Applied Materials & Interfaces

Hyper-Crosslinked Porous Organic Frameworks with Ultra-micropores for Selective Xenon Capture Debanjan Chakraborty,a Shyamapada Nandi,a Michael A. Sinnwell,c Jian Liu,c Rinku Kushwaha,a Praveen K. Thallapally,c* and Ramanathan Vaidhyanathanab* aDepartment

and

of Chemistry, bCentre for Energy Science, Indian Institute of Science Education

Research,

Dr

Homi

Bhabha

Rd.

Pashan,

Pune,

411008,

India.

E-mail:

[email protected] cPacific

Northwest National Laboratory, Richland, Washington 99354, United States. E-mail:

[email protected] KEYWORDS Porous organic framework, Xenon capture, Xenon separation, Nuclear fuel, Ultramicroporous.

ABSTRACT Exceptionally stable ultra-microporous C-C bonded porous organic framework (IISERP-POF6, 7, 8) have been prepared using simple Friedel-Crafts reaction. These polymers exhibit permanent porosity with a BET surface area of 645-800 m2/g. Xe/Kr adsorptive separation has been carried out with these polymers and they display selective Xe

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capture (s(Xe/Kr)) = 6.7, 6.3, 6.3) at 298K and 1 bar pressure. Interestingly, these polymers also show remarkable Xe/N2 (s(Xe/N2)) = 200, 180, 160 at 298K and 1 bar) and Xe/CO2 selectivity (s(Xe/CO2)) = 5.6, 7.4, 5.6) for a 1:99 composition of Xe:N2/Xe:CO2. Selective removal of Xe at such low concentrations is extremely challenging; the observed selectivities are higher compared to those observed in porous carbons and MOFs. Breakthrough studies were performed using the composition relevant to nuclear off-gas mixture with the polymers and we find that the polymers hold Xe for a longer time in the column which illustrates the Xe/Kr separation performance under dynamic condition.

Introduction Pressing global energy demand opens up the need for seeking alternate clean energy sources. They provide opportunities for socio-economic development and can advance national safety and security. Nuclear energy is considered to be one of the most efficient alternate sources because of its high energy density and it poses significantly lower greenhouse gas threats. However, in the associated nuclear fission process, many radioactive wastes primarily (Xe, Kr) are being released from the power plant.1 Of this, the nonradioactive Xe isotope is of value in other applications in the optical lighting and medical sector.2-4 Therefore, selective capture of Xe from its analogous noble gas Kr and other gases found in the nuclear off-gas stream (1300 ppm Xe, 130 ppm Kr, 78% N2, 21% O2, 0.9% Ar, 0.03% CO2) is imperative.2,5


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Currently, cryogenic separation is the industrially opted process for separating Xe/Kr from Used Nuclear Fuel (UNF) by utilizing the difference in their boiling points (Xe = 108.1°C and Kr = -153.2°C). This is energy demanding as well as an explosive hazardous process. Adsorptive separation is a potential alternate where Xe is adsorbed selectively at ambient temperature and pressure. Energy economy of such adsorptive separations to a large extent rely on the efficiency (capacity + selectivity) of the solid sorbent.2 Solid sorbents like porous carbon,5 zeolites,6 metal organic frameworks,2 porous membranes (particularly zeolite, MOF and aluminophosphate based membranes),6-10 and organic cages11 are being investigated for selective Xe capture. But the number of investigations on Xe separation is scant compared to other gas separations. The Xe/Kr mixtures escape from the coolant system into the moist air, and Xe needs to be captured under relatively wet conditions. This compels the adsorbents to possess moisture and chemical stability. Porous polymers12,13 are one of the most important classes of materials for different applications such as gas separation, storage.14-18 During the last decade, a range of porous polymers has been synthesized employing Schiff chemistry,19 azo bond formation,20,21 Bakelite chemistry,16,17 Friedel Craft reactions,22-25 click chemistry26 and been investigated for several gas separation applications. However, to the best of our knowledge, report on Xe/Kr separation using organic polymers is absent. If such porous polymers can be constructed using non-hydrolyzable covalent bonds, it is of immense value. Here, we have investigated the selective Xe capture possibilities of CC bonded porous polymers made through Friedel-Crafts reaction using AlCl3 as the catalyst.


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The advantages with these C-C linked porous polymers are their remarkable chemical and thermal stability, soft synthetic routes, gram scale preparation and good recyclability. Results and Discussions The

polymers

were

prepared

by

reacting

1,3,5-tris(bromomethyl)-2,4,6-

trimethylbenzene with corresponding aromatic molecules (Naphthalene, Pyrene and Triphenyl methane) under mild conditions (Figure 1A). In a typical synthesis, the components were dissolved in dry dichloromethane (DCM), followed by addition of anhydrous AlCl3. Then, the mixture was warmed from 25°C to 40°C under N2 atmosphere and maintained at 40°C for 24 hours. The crude solid was filtered and dispersed in 3M HCl to remove the excess AlCl3. Pure polymers


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Figure 1. (A) Synthesis scheme. (B) Solid state 13C MASNMR spectra of the polymers. The * marked peaks correspond to side bands. (C) IR spectra of the polymers. (D) FESEM images of IISERP-POF6 exhibiting spherical morphology, with the spheres ranging from ~8 nm to a micron in diameter. (E) HRTEM image of IISERP-POF6.

were isolated as a brown powder by washing with water, organic solvents and finally via hot soxhlet extraction. Rigorous EDAX analysis was done to confirm the absence of any unreacted brominated sites (see supporting information). All the polymers are amorphous as confirmed by PXRD (Figure S1A). They exhibit exceptional thermal (Figure S1B) as well as chemical stability which makes these polymers special for any industrial applications. The cross condensation has been confirmed by solidstate

13C

Magic Angle Spinning Nuclear Magnetic Resonance (MASNMR) spectroscopy

(Figure 1B) and Infra-Red (IR) spectra (Figures 1C). The peak at around δ=130–135 ppm in the solid-state NMR corresponds to aromatic carbons of the polymers. Meanwhile, the cocondensation of the building blocks has been corroborated by the two broad peaks obtained at around δ=40 and δ=20 ppm, corresponding to the methylene and methyl carbons. There is a little shift in the δ value of the NMR spectra of the respective three polymers because of the different aromatic ring current of the three different aromatic units (naphthalene, pyrene and triphenyl methane). IR spectra of the respective polymers showing the characteristics vibrations present in the polymeric network. Peak at 2920 cm-1, 2850 cm-1 represent aromatic C-H and asymmetric CH2 stretching frequencies. The frequencies correspond to ~1440 cm-1, 12050 cm-1 and 1620 cm-1 relates to the CH2 scissoring, CH2 rocking and aromatic C=C bond vibrations. IISERP-POF8 has its unique sp3 C-H vibration at 3040 cm-1


5


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(Figure 1C, S2). The morphology of all the polymers was visualized from the Field Emission Scanning Electron Microscopy (FESEM) (Figures 1D, S3-S6). They display a spherical morphology that has been predominant in other Bakelite type polymers and melamineformaldehyde resins.16,17,27 This is further corroborated by High Resolution Transmission Electron Microscopic (HRTEM) images. The polymers appear as aggregated spheres with an individual sphere dimension of 80 to 120 nm (Figure 1E, S7). The permanent porosity of all three polymers was established from the N2 adsorption isotherms at 77K. They display combination of type-I and type-IV isotherms with a prominent hysteresis (Figure 2A).28 Being hyper-crosslinked, the polymers possess hierarchical pores which are responsible for the mesoporosity and hysteresis (Figure 2B).


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Figure 2. (A) N2 adsorption isotherms for the polymers at 77K. (B) Pore size distribution obtained from NLDFT fitting. Stability of IISERP-POF6 evaluated from (C) 77K N2 isotherms and (D) IR spectra.

Brunauer-Emmett-Teller (BET) surface areas were estimated to be 890, 630 and 813 m2/g for IISERP-POF6, IISERP-POF7 and IISERP-POF8 respectively (Figure S8). A Non-local Density Functional Theory (NLDFT) was fit to the adsorption branch of 77K N2 isotherms the polymers reveals the presence of hierarchical pores with the major pore dimension of 6 Å (Figure 2B). Pore size distribution obtained from the CO2 273K is comparable to that from the N2 77K data (Figure S9). Notably, there are significant amounts of ultra-micropores, which could be key to realizing high selectivities. The exceptional chemical stability of these polymers towards acid and base was confirmed from BET surface area analysis recorded after treating samples with 9N HCl and 9N NaOH, which showed no drop in surface area or isotherm shape. Obtaining these amorphous polymers in gram scales with porosity matching the mg scale synthesized samples can be tricky, and proposing these as sorbents for largescale separations demand that such scale-up be demonstrated. For this, we synthesized multiple batches of the polymers in gram scale (~5 g) using the same mild methods (40°C for 36 hrs). These samples showed N2 uptakes at 77K, which matched well with the uptakes found for the samples from mg scale synthesis (Figures 2C, 2D and S10-S12). The Xe/Kr isotherms were recorded at three different temperatures (278K, 288K, and 298K) up to 1 bar pressure. All of these polymers show selective uptake of Xe over Kr at these temperatures. Figure 3 shows the Xe uptakes of 37.7, 34.6 and 38.5 cc/g (P/P0 = 1) for


7


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IISERP-POF6, IISERP-POF7 and IISERP-POF8, respectively (Figures 3). These uptakes are comparable with some of the well-investigated Xe adsorbing porous materials like IRMOF_1 (44.3 cc/g),29 Noria (34.7),30 SBMOF1 (31 cc/g),31 CROFOUR_1_Ni and CROFOUR_2_Ni (40.3 cc/g and 36 cc/g) (P/P0 = 1).32 Although, there are MOFs, organic cages known to have very high Xe capacity at 1 bar, 298K (Ag @ Ni_MOF74, 108 cc/g; Activated carbon, 94.1 cc/g; MOF-Cu-H , 71.5 cc/g; SBMOF2, 63.4 cc/g; CC3, 53.8 cc/g) (P/P0 = 1)5,11,33-35 (Table 1), these metal-free or all-organic nature of these polymers can bring advantages particularly when needed to work under harsh conditions as well as when desired as membranes.

Figure 3. (A, B, C) Xe and Kr adsorption isotherms for IISERP-POF6, IISERP-POF7 and IISERPPOF8 at different temperatures. (D) Heat of Adsorption for Xe calculated from Virial method. (E) Heat of Adsorption for Kr calculated from Virial model. (F) Xe/Kr selectivity at 298 K calculated from IAST model employing a nominal composition of 20Xe:80Kr. (G) Xe/N2 selectivity at 298 K calculated using IAST method with a nominal composition of 1Xe:99N2. (H) Xe/CO2 selectivity at 298 K calculated from IAST model using a nominal composition of 1Xe:99CO2.


8

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The Heat of Adsorption (HOA) was calculated using the Virial method employing the Xe and Kr isotherms collected at 278, 288 and 298 K. The zero loading HOA value for Xe was calculated to be 26 kJ/mol (Figure 3C and Figures S13-S15), which is slightly higher than that for Kr (~22 kJ/mol) (Figure 3D and S16). This suggests that Xe interacts strongly with the polymeric frameworks compared to Kr. This observation concurs with the Xe/Kr selectivity. Ideal Adsorption Solution Theory (IAST) was employed to determine the Xe/Kr selectivity with a composition of 20/80 (Xe/Kr). The Xe/Kr selectivity values were 6.7, 6.3 and 6.3 for IISERP-POF6, IISERP-POF7 and IISERP-POF8, respectively (Figure 3F and S17). These Xe/Kr selectivities are lower than only a few of the top-performing MOFs and cages11,31-33 and is higher than the selectivities shown by Zeolites (s(Xe/Kr) = 4-6),6 Porous Carbon (~3)5 and is comparable to some of the well-known MOFs (Ni-MOF-74: 5-6; IRMOF-1: 3; UTSA49: 9.2; Ag@NiMOF-74: 6.8), organic cages (12.5) (Table 1).5,11,29,33,36 Importantly, it is quite substantial for a first-time report using a porous polymer, and we believe, there is significant room for improvement. Xenon recovery from nuclear off-gas stream involves their separation from a mixture of Xe and N2/CO2. This is made difficult by the fact that the Xe is present in exceptionally small partial pressures compare to N2. Surprisingly, these polymers exhibit very high Xe selectivity over nitrogen (IAST selectivity: s(Xe/N2): 200, 180, 160 for IISERP-POF6, 7and 8 at 298 K, 1 bar, employing a nominal composition of 1Xe:99N2 (Figures 3G and S18). These values are much higher than those reported with other porous materials (Carbon-ZX: 120; Carbon-Z:


9


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80; HKUST: 80; PCN-14: 26; ZIF-8: 18.3; IRMOF-1: 5.2)37,38 (Table S1). Also, these polymers show promising Xe/CO2 separation ability. The Xe/CO2 selectivities from IAST were found to be 5.6, 7.4 and 5.6 for IISERP-POF6, 7 and 8, respectively, for a composition of 1Xe:99CO2 (Figure 3H). These selectivities are higher than ZIF-8 and porous carbon.37 Notably, the energy input (based on temperature and pressure) in the synthesis of these polymers are substantially smaller compared to these MOF and porous carbons. The observed preferential Xe adsorption over Kr, N2 and CO2 is related to the higher dipole moment of Xe as compared to the other gases. This would promote a stronger interaction of Xe with the porous polymer, and therefore the higher Xe uptakes. To demonstrate the separation performance of the polymers under dynamic condition we performed breakthrough separation for each of the polymers where a mixture of Xe/Kr (1300 ppm Xe/ 130 ppm Kr, UNF) was passed through a column packed with the polymers (~200300 mg). As can be seen from Figure 4, the Xe shows noticeably better retention compared to the


10

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Figure 4. Breakthrough curves for different polymers. The polymers illustrate dynamic separation of Xe under nuclear processing condition.

other gases (Kr, CO2, O2 and Ar) for all the three polymers. IISERP-POF7 has the highest retention time for Xe (8.5 min) compared Kr (3.8 min) which is also reflected in the selectivity value (2.3) obtained from breakthrough. Similar to IISERP-POF7, IISERP-POF6 and IISERP-POF8 also exhibit selective retention of Xe with selectivities of 1.7 and 1.5 (Table 2). This illustrates the Xe/Kr separation performance of the polymers under dynamic condition with significant Xe/Kr selectivities. Conclusion In summary, we have developed three new exceptionally stable C-C bonded hypercrosslinked porous organic polymers, using very mild synthesis methods, whose ultramicroporous character enables good Xe/Kr, Xe/N2 and Xe/CO2 separation. These advantages combine with their easy scalability makes them potential candidates for large-scale


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separation of Used Nuclear Fuel (UNF) off-gas stream mixtures; however, further work needs to be done to improve their capacity and Xe/Kr selectivity.

Table 1: Comparison of the Xe/Kr selectivities of the polymers with some of the highperforming porous materials. S.No.

Material

Xe Uptake (cc/g) at 1bar and 298K (P/P0 =1)

S(Xe/Kr) at 1 bar, 298K for (20Xe:80Kr)

1

CROFOUR-1-Ni

40.3

22a

2

MOF-Cu-H

71.5

16.7a, 15.8b

3

SBMOF-1

31

16b

4

CROFOUR-2-Ni

36

15.5a

5

CC3

53.7

12.5a

6

Ag@MOF-74Ni

103

11.5a

7

Co3(HCOO)6

44.8

11a

8

SBMOF-2

63.4

10a

9

HKUST-1

~120

6.90b

10

IISERP_POF6

37.7

6.7a

11

IISERP_POF7

34.6

6.3a

12

IISERP_POF8

38.5

6.3a

13

PCN-14

~160

6.5c

14

NOTT series

~100-150

5.5-7c

15

MOF-74-Mg

125.4

6c

16

MOF-74-Ni

94.1

4c


12

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17

IRMOF-series

-

2.8-4.2b

18

Activated Carbon

94

3c

calculated using IAST modeling. bSelectivity calculated from Henry’s constant. cSelectivity calculated from break through experiment.

aSelectivity

Table 2: Summarized parameters of the Xe/Kr breakthrough experiments performed using POFs at room temperature.

Adsorbent IISERP-POF6 IISERP-POF6 IISERP-POF7 IISERP-POF7 IISERP-POF8 IISERP-POF8

Gas Xe Kr Xe Kr Xe Kr

Time (min) 7.5133 4.3083 8.5678 3.803 5.8587 3.8361

Conc. (ppm) 1282 132 1282 132 1282 132

Xe/Kr selectivity 1.7 2.3 1.5

ASSOCIATED CONTENT Supporting Information includes all the materials methods and characterization data. “This material is available free of charge via the Internet at http://pubs.acs.org.” AUTHOR INFORMATION Corresponding Author *[email protected]; [email protected] Author Contributions The manuscript was written through contributions of all authors. All authors have given approval to the final version of the manuscript.


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Notes The authors declare no competing financial interest. ACKNOWLEDGMENT We acknowledge IISER-Pune, DST-MES program and SERB. DC thanks DST-Inspire for financial support. SN thanks DST and IISER Pune for the fellowship. REFERENCES (1)

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For Table of Contents Only Hyper-Crosslinked Porous Organic Frameworks with Ultra-micropores for Selective Xenon Capture. Debanjan Chakraborty, Shyamapada Nandi, Michael A. Sinnwell, Jian Liu, Rinku Kushwaha, Praveen K. Thallapally* and Ramanathan Vaidhyanathan*


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Hyper-Crosslinked Porous Organic Frameworks with Ultra-micropores

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