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Enhancing ethane/ethylene separation performance through the amino-functionalization of ethane-selective MOF
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Yao-Yu Ma, Wen-Juan Shi*, Gang-Ding Wang, Xin Liu, Lei Hou*, Yao-Yu Wang
Chinese Chemical Letters | 2025, 36(3) : 109729
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Chinese Chemical Letters | 2025, 36(3): 109729
• Communication •
Enhancing ethane/ethylene separation performance through the amino-functionalization of ethane-selective MOF
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Yao-Yu Ma, Wen-Juan Shi*, Gang-Ding Wang, Xin Liu, Lei Hou*, Yao-Yu Wang
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  • Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, Shaanxi Key Laboratory of Physico-Inorganic Chemistry, College of Chemistry & Materials Science, Northwest University, Xi'an 710069, China
Published: 2025-03-15 doi: 10.1016/j.cclet.2024.109729
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The utilization of ethane-selective materials for adsorption-based separation technology presents an energy-efficient alternative to cryogenic distillation for ethylene (C2H4) purification from ethane (C2H6). To study the relations between separation performance and pore environments, we carried out the isoreticular chemistry rule to introduce the -NH2 groups into a C2H6-selective MOF [Cu1.5(BTC)(DPU)1.5(H2O)1.5], and successfully improved the adsorption capacity and selectivity for C2H6 over C2H4. The NH2-functionalized MOF [Cu1.5(NH2-BTC)(DPU)1.5(H2O)1.5] with a relatively narrow pore not only forms appropriate pore restriction but also provides additional binding sites to enhance the adsorption capacity of C2H6 relative to C2H4. Both gas adsorption and dynamic breakthrough results indicated that the -NH2 functionalization significantly enhanced the separation performance of materials for C2H6/C2H4 mixtures, allowing the production of C2H4 with a purity of over 99.99% and a productivity of up to 30.02 L/kg in one step. Theoretical calculations revealed that the synergistic effect of appropriate pore confinement and NH2-modified functional surfaces imposed stronger interactions on C2H6 than C2H4.

Metal-organic framework  /  Amino-functionalization  /  Gas adsorption  /  Adsorption selectivity  /  Separation
Yao-Yu Ma, Wen-Juan Shi, Gang-Ding Wang, Xin Liu, Lei Hou, Yao-Yu Wang. Enhancing ethane/ethylene separation performance through the amino-functionalization of ethane-selective MOF[J]. Chinese Chemical Letters, 2025 , 36 (3) : 109729 - . DOI: 10.1016/j.cclet.2024.109729
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Ethylene (C2H4), as one of the world's largest chemical products, is the core of the petrochemical industry. Currently, a majority of the world's C2H4 is produced by thermal cracking of ethane (C2H6) or steam cracking, and C2H6 is inevitably existed as a major byproduct [1]. The separation of C2H6 from C2H4 is thereby a critical process to yield polymer-grade C2H4 (> 99.9%) for polymer production [2]. The industrial separation of C2H4 from C2H6 typically relies on high-pressure cryogenic distillation at temperatures as low as −160 ℃ because of the similar sizes and volatilities between them, representing one of the most energy-intensive processes [3]. Hence, the energy-efficient separation technology for the production of polymer grade C2H4 is highly desired and challenging [4].
Separation by means of adsorption using porous materials is recognized as a promising alternative because of low energy consumption and high efficiency [5-11]. Metal-organic frameworks (MOFs) are porous crystalline materials formed by self-assembly of inorganic metal centers with organic ligands. In comparison to traditional porous materials, MOFs are regarded as excellent C2H6/C2H4 separation and purification platforms owing to their ability to accurately adjust the framework structures and functionalize the pore surfaces. MOFs for C2H6/C2H4 separation were divided into C2H4-selective MOFs and C2H6-selective MOFs [12-17]. In general, the design of C2H4-selective MOFs is easier to implement through taking advantage of stronger interactions between unsaturated C2H4 molecules and high polar binding centers, such as open metal sites. However, to get C2H4 product, the next desorption process is necessary, which is still difficult to produce highly pure C2H4 due to co-adsorption of C2H6 in materials, so it needs the multiple adsorption-desorption cycles and is also energetically costly [18-23]. On the contrary, C2H6-selective MOFs can preferentially capture C2H6 impurity to directly produce C2H4 at the separation column outlet [24-28], which is more facile and economical process, and can also greatly reduce energy consumption [29]. But C2H6-selective MOFs usually exhibit relatively low loading or selectivity due to lacking strong binding sites. So it is imperative to develop new C2H6-selective MOFs for efficient C2H4 purity [30-35].
The challenge of separating C2H6 and C2H4 stems from their very close molecular sizes and boiling points (Table S1 in Supporting information) [36]. Compared to C2H4, C2H6 has a smaller quadrupole moment (0.65 × 10−26 esu cm2 vs. 1.50 × 10−26 esu cm2) and a larger polarizability (44.7 × 10−25 cm3 vs. 42.52 × 10−25 cm3), indicating that dispersion and induction interactions would make major contributions in C2H6-selective adsorbents [37]. C2H6-selective MOFs can be obtained by designing inert pore surfaces or implanting C2H6 affinity sites which will preferentially adsorb C2H6 over C2H4 [17,24,38-42]. For example, Chen et al. reported a microporous MOF, Fe2(O2)(dobdc), with iron (Fe)-peroxo sites for preferential binding of C2H6 over C2H4, showing a separation selectivity of up to 4.4 for C2H6/C2H4 [24]. By virtue of pore engineering, Li et al. successfully designed an inert ultramicroporous material (Cu(Qc)2) with optimized pore structure, realizing excellent C2H6-selective adsorption behavior [39]. Although some C2H6-selective MOFs have been reported, there are still some deficiencies such as typical "trade-off" effect between selectivity and capacity, balancing these issues remains a constant challenge [43].
The adsorption amounts and selectivity for gases in MOFs are crucial for separation, which are closely dependent on the pore environments of MOFs. Therefore, the regulation of pore walls through using functionalized ligands would provide an important approach to enhance the separation performance of MOFs for C2H6/C2H4 mixtures (Scheme 1). To target MOFs with the preferential binding of C2H6 over C2H4, we initially designed a C2H6-selective MOF [Cu1.5(BTC)(DPU)1.5(H2O)1.5] (Cu-MOF) from 1, 3, 5-benzenetricarboxylic acid (H3BTC) and 1, 3-di(pyridin-4-yl)urea (DPU) linkers, which possesses abundant urea groups in pores and will provide stronger multiple interactions with C2H6 over C2H4. Then according to the isoreticular principle, the -NH2 groups that could be the potential adsorption sites through hydrogen bonds with gas molecules were embedded into the pores through replacing H3BTC with NH2H3BTC ligands, generating the isomorphic framework Cu-MOF(NH2), [Cu1.5(NH2-BTC)(DPU)1.5(H2O)1.5], with more accessible sites in pores to study the control of pore chemistry for advancing C2H6/C2H4 separation. It was found that due to the electronegative N/O sites and the coordination between water and metal centers hindering the open metal sites (OMSs), both MOFs exhibited C2H6-selective adsorption behaviors. In particular, the introduction of -NH2 groups in pores provides additional binding sites to more enhance the binding affinity for C2H6, leading to increased C2H6 and C2H4 uptakes and C2H6/C2H4 selectivity (from 1.4 to 1.8) in Cu-MOF(NH2) compared to Cu-MOF. The breakthrough experiments also showed that Cu-MOF(NH2) can obtain highly pure C2H4 (≥99.99%) in one step with longer breakthrough interval times and higher C2H4 productivity.
The synthesis details of Cu-MOF and Cu-MOF(NH2) were given in Supporting information. Single-crystal X-ray diffraction analysis determined that two MOFs exhibited isomorphic network and crystallized in the same trigonal crystal system (Tables S2 and S3 in Supporting information). The crystal structure of NH2-functionalized Cu-MOF(NH2) was described representatively. The asymmetric unit contains half a Cu2+ ion, half a DPU ligand, two-thirds of deprotonated NH2-BTC ligand, and half a H2O coordinated molecule. The Cu2+ ion has a distorted square pyramidal geometry constituted by two carboxylate O atoms from two NH2-BTC and two pyridine N atoms from two DPU on the base plane and one water O atom on the vertex (Fig. 1a). Six Cu2+ ions and six NH2-BTC are alternately connected to form a 48-membered planar ring, which extends outward to form a layer with hexagonal windows (Fig. 1b). Furthermore, the linkages of adjacent layers with DPU as pillars to afford a (3, 4)-connected three-dimensional network, which with large windows is threaded by the other network to afford a two-folded interpenetrated framework. The upper and lower BTC—Cu coordinated motifs in an independent network are supported by three DPU pillars to form a triangular prism-like cage (cage Ⅰ), and which passes through one ring in the layer of the other network to form a cavity with six windows (Fig. 1c). Along the c axis, the other cage (cage Ⅱ) (Fig. 1d) is also formed between two independent networks on both sides of cage Ⅰ. These cavities are connected to form channels with abundant accessible N/O sites (Fig. 1e), in particular the modification of -NH2 groups in Cu-MOF(NH2) provides more potential sites in channels compared to Cu-MOF, which may play a positive role in enhancing the separation performance for C2H6/C2H4 mixtures.
Sample purity was verified by matched powder X-ray diffraction (PXRD) between the measured results of as-synthesized samples and the simulated patterns from single crystal structures (Figs. S1 and S2 in Supporting information). Thermogravimetric analysis (TGA) indicated the initial weight loss of lattice solvent molecules in two MOFs before 110 ℃. After a thermal stable platform, the skeleton began to decompose at 250 ℃ (Figs. S3 and S4 in Supporting information). Fourier transform infrared spectrum (FT-IR) peaks of Cu-MOF(NH2) at 3306 and 3400 cm−1 are the characteristic peaks of N—H vibration from -NH2 groups, however, Cu-MOF only possessed one peak at 3307 cm−1 (Figs. S5 and S6 in Supporting information). Meanwhile, Cu-MOF(NH2) also showed the peak at 1379 cm−1, resulted from the C—N bond between the benzene ring and the amino group (Fig. S6 in Supporting information) [44]. The frameworks of two MOFs were activated by heating at 110 ℃ under vacuum for 3 h for the acetone-exchanged (72 h) samples. It can be found that the coordinated water molecules which correspond to the initial weight loss in activated samples were held (Figs. S3 and S4 in Supporting information). The coordination water molecules exclude the exposed metal ions which are not favorable for C2H6 selectivity over C2H4.
The identical frameworks but different potential adsorption sites between two MOFs provide good platforms for studying the influence of pore environments on gas separation. Two MOFs revealed type-I N2 adsorption isotherms with the close loadings of about 280 cm3/g at 77 K and 100 kPa as well as the pore sizes of 6.5–8.5 Å (Figs. S7 and S8 in Supporting information). To evaluate the adjustment on C2H6/C2H4 separation by -NH2 modification, single-component adsorption isotherms were measured. As shown in Figs. 2a and b, the uptakes of Cu-MOF for C2H4 and C2H6 at 100 kPa are 110.8 and 109.3 cm3/g at 273 K and 91.6 and 91.5 cm3/g at 298 K, respectively, however, those valves in Cu-MOF(NH2) are increased to 119.6 and 117.6 cm3/g at 273 K and 98.8 and 101.3 cm3/g at 298 K, respectively. At the same time, the adsorption isotherms of Cu-MOF(NH2) are moderately steeper than Cu-MOF, indicating that the pore modification by -NH2 groups makes an increase in adsorption for two gases. Further, the isosteric heat of adsorption (Qst) was calculated by fitting adsorption isotherms to virial equation, which revealed the affinity of MOFs toward adsorbates (Figs. S9-S12 in Supporting information). As shown in Figs. 2c and d, the initial Qst values for C2H6 of 30.6 kJ/mol in Cu-MOF(NH2) and 27.6 kJ/mol in Cu-MOF are higher than the corresponding values for C2H4 of 26.1 and 23.0 kJ/mol, indicating stronger interactions of two MOFs for C2H6. Meanwhile, the slopes of C2H6 isotherms are also significantly larger than those of C2H4. These results illustrated a stronger affinity of the framework for C2H6 than C2H4, supporting the C2H6-selective behavior in two MOFs. In addition, the adsorption cyclic tests of Cu-MOF(NH2) showed repeated results with no decrease in adsorption capacity (Fig. S13 in Supporting information).
After surveying the improvement of C2H6-selective adsorption and higher C2H6-binding affinity in Cu-MOF(NH2), ideal adsorbed solution theory (IAST) was utilized to calculate the adsorption selectivity of Cu-MOF(NH2) for 1/1, 1/9, and 1/15 of C2H6/C2H4 mixtures and compared to those of Cu-MOF (Figs. S14-S17 in Supporting information). As shown in Fig. 3a, Cu-MOF(NH2) exhibits the C2H6/C2H4 selectivity of about 1.8 for equimolar mixtures at 298 K and 100 kPa, which is significantly higher than that of Cu-MOF (1.4), and is equivalent to some top-performing C2H6-selective materials, such as CPM-733 (1.75) [45], ZIF-8 (1.7) [46], PCN-250 (1.9) [47], and Zn-atz-ipa (1.7) [40], but greatly surpasses some excellent MOFs, including TJT-100(1.2) [30], Azole-Th-1 (1.46) [25], UPC-612 (1.4) [26], and Ni(bdc)(ted)0.5 (1.6) [48]. We used the separation potential (∆q) as a further evaluation and screening metric of MOFs [49]. As shown in Fig. 3b, Figs. S18 and S19 (Supporting information), the pure amounts of C2H4 recovered from Cu-MOF are 0.66, 1.40, and 1.49 mmol/g for the 1/1, 1/9, and 1/15 mixtures, respectively, however which are greatly increased to 1.24, 2.95, and 3.17 mmol/g for Cu-MOF(NH2). In addition, taking the 1/15 mixtures as an example, the ∆q of Cu-MOF(NH2) are higher than many benchmark C2H6-selective materials, including MUF-15 (2.97 mmolg) [31], UiO-67-(NH2)2 (2.51 mmol/g) [50], and Cu(Qc)2 (1.73 mmol/g) [39], thus outperforming many reported adsorbents [17,42,47].
Adsorption amount is as equally important as the selectivity, however, due to frequently existed "trade-off" effect between selectivity and adsorption amount for separation in MOFs, it is challenging to simultaneously achieve both high C2H6/C2H4 selectivity and high C2H6 loading in one MOF. Although the C2H6 uptake of Cu-MOF(NH2) (101.3 cm3/g) is not as good as several prominent MOFs, such as CPM-733 (159.6 cm3/g) [45], Ni-MOF 2 (133 cm3/g) [35], PCN-250 (116.7 cm3/g) [47], and ZJU-120a (110 cm3/g) [33], based on different pore environments and framework topologies, but is greatly higher than most reported MOFs, such as MAF-49 (38.8 cm3/g) [38], Cu(Qc)2 (41.5 cm3/g) [39], ZIF-8 (56 cm3/g) [46], Fe2(O2)(dobdc) (74.3 cm3/g) [24], and UPC-612 (80.1 cm3/g) (Fig. 3c) [26]. Taken together, Cu-MOF(NH2) not only exhibits good C2H6/C2H4 selectivity but also excellent C2H6 uptake, signifying the potential as an efficient material for one-step purity of C2H4 from C2H6/C2H4 mixtures (Fig. 3d).
To further evaluate the effect of -NH2 groups on C2H6/C2H4 separation performance, dynamic breakthrough experiments were conducted in a packed column filled with activated MOFs for C2H6/C2H4/Ar (5/5/90, 1/9/90, and 1/15/84, v/v/v, flow rate = 7.0 mL/min, Ar as carrier gas) mixtures at 298 K and 100 kPa, respectively. As shown in Fig. 4, two MOFs can separate C2H6/C2H4 mixtures, whereby Cu-MOF(NH2) presents a considerably superior performance compared to Cu-MOF, aligning with the predicted results based on gas adsorption amount and IAST selectivity. As shown in Fig. 4a, C2H6 can be effectively separated from C2H6/C2H4 (50/50) mixtures in Cu-MOF, in which a high-purity C2H4 (≥99.9%) of 3.77 L/kg productivity is obtained at the outlet. However, Cu-MOF is failed to efficiently eliminate C2H6 from 1/9 and 1/15 C2H6/C2H4 mixtures because of low selectivity for C2H6 over C2H4, which leads to negligible C2H4 productivity and short separation time (Figs. 4b and c). By contrast, for Cu-MOF(NH2), the ≥99.99% purity of C2H4 with 5.81, 8.33, and 30.02 L/kg productivity can be directly recovered from the 1/1, 1/9, and 1/15 C2H6/C2H4 mixtures in one cycle, respectively. The higher C2H4 productivity and longer breakthrough interval times determined by breakthrough experiments indicated that the immobilization of -NH2 groups in MOF successfully optimized pore confinement, which associated with additional binding sites significantly improved the separation of material for C2H6/C2H4 mixtures (Fig. 4d). Considering better separation performance of Cu-MOF(NH2), the breakthrough measurements at different flow rates of C2H6/C2H4 mixtures (1/15, v/v) were further conducted at 298 K in Cu-MOF(NH2), it also indicated the complete separation of C2H6/C2H4 mixtures (Fig. 5a). Notably, as shown in Fig. 5b, Cu-MOF(NH2) can also be easily regenerated by purging with Ar at 323 K, in which the adsorbed C2H4 due to weaker binding affinity is desorbed more quickly than C2H6. The breakthrough experiment cycles were performed on equimolar C2H6/C2H4 mixtures to investigate the reproducibility and recyclability of Cu-MOF(NH2), which showed no decrease in separation performance (Fig. 5c). In addition, the PXRD measurements revealed that the framework treated with different environments retained structural integrity with no phase change and loss of crystallinity observed (Fig. 5d).
To in-depth elucidate the origin of C2H6-selective behavior enhanced by -NH2 functionalization, grand canonical Monte Carlo (GCMC) simulations were done to investigate the interactions between the frameworks and gas molecules. As shown in Figs. 6a and b, in Cu-MOF the preferential adsorption sites for C2H4 and C2H6 are located in cages Ⅰ and Ⅱ, respectively. The C2H4 molecule interacts with one pyridine ring and one urea N atom from DPU, and one carboxylate O atom from BTC, through C—H···π and C—H···N/O interactions. By contrast, the C2H6 molecule is resided between two BTC linkers and involved in more hydrogen bonds and C—H···π interactions with the phenyl rings. For Cu-MOF(NH2), the preferential adsorption sites for C2H6 and C2H4 are both located in cage Ⅱ (Figs. 6c and d). The C2H4 molecule forms two C—H···N hydrogen bonds and two C—H···π interactions with the -NH2 groups and phenyl rings in the upper and lower NH2-BTC ligands, while the C2H6 molecule interacts with two phenyl rings from two NH2-BTC through forming four C—H···C and one C—H···π interactions with the distances of 2.915–3.041 Å, as well as two stronger C—H···N (H···N = 2.939 and 2.999 Å) interactions compared to C2H4 (H···N = 2.996 and 3.187 Å). Therefore, the introduction of -NH2 groups not only changes the position of preferential adsorption sites, but also makes C2H4 and C2H6 molecules more closely contact with the pore walls. In particular, there obviously exist more supramolecular contacts between C2H6 molecule and pore walls in Cu-MOF(NH2). Meanwhile, the calculated binding energies for C2H6 and C2H4 in Cu-MOF(NH2) (42.5 kJ/mol vs. 32.3 kJ/mol) also showed the higher values compared to Cu-MOF (37.5 kJ/mol vs. 29.4 kJ/mol). These findings are consistent with the better C2H6-selectivity for Cu-MOF(NH2) than Cu-MOF, as found in experimental results.
Furthermore, the more different binding sites were further explored by GCMC simulations at 298 K and 100 kPa to evaluate the binding of C2H4 and C2H6 molecules in Cu-MOF (Fig. 7) and Cu-MOF(NH2) (Fig. 8). The detailed data on these interactions was listed in Table S4. The results revealed that the adsorption sites are mainly located in cavities for two MOFs through forming C—H···C/N/O/π interactions. Comparing the interactions between the framework and gas molecules: C2H4 in Figs. 7a and b vs. C2H6 in Figs. 7c and d for Cu-MOF; C2H4 in Figs. 8a and b vs. C2H6 in Figs. 8c and d for Cu-MOF(NH2), it clearly revealed that the interactions between the framework and C2H6 are more and stronger than C2H4 in two MOFs. In particular, the -NH2 groups in Cu-MOF(NH2) make both C2H6 and C2H4 molecules have closer contacts with the framework, leading to increased C—H···N interactions as a result, and which is more evident for C2H6 in pores, agreeing well with the experimental findings of more C2H6 capture and higher C2H6/C2H4 selectivity in Cu-MOF(NH2) relative to Cu-MOF.
In summary, based on pore decoration strategy, we have effectively tuned the pore environment through installing -NH2 functionalized groups and obtained an isomorphic Cu-MOF(NH2) for targeting highly efficient one-step C2H4 purification from C2H6/C2H4 mixtures. The -NH2 groups enhanced the interactions of the framework with C2H6 molecules, which preferentially adsorbed more C2H6 from C2H6/C2H4 mixtures. Cu-MOF(NH2) with high C2H6 uptakes and significant C2H6/C2H4 selectivity effectively reduced "trade-off" effect in comparison to Cu-MOF. As a result, Cu-MOF(NH2) produced polymer-grade C2H4 (≥99.99%) in one-step separation with a high productivity of 30.02 L/kg, which was 3.3 times higher than that of C2H4 produced by Cu-MOF, and a significantly higher purity than Cu-MOF. The utilization of this pore engineering approach will aid in the development and utilization of MOF materials for the challenging separation of critical chemicals.
Declaration of competing interest
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The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Acknowledgments
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This work is supported by National Natural Science Foundation of China (Nos. 22371226 and 22371225) and Natural Science Basic Research Program of Shaanxi (No. 2024JC-JCQN-18).
Supplementary materials
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Supplementary material associated with this article can be found, in the online version, at doi:10.1016/j.cclet.2024.109729.
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doi: 10.1016/j.cclet.2024.109729
  • Receive Date：2023-12-26
  • Online Date：2025-11-07
  • Published：2025-03-15
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  • Received：2023-12-26
  • Revised：2024-01-29
  • Accepted：2024-02-23
Affiliations
    Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, Shaanxi Key Laboratory of Physico-Inorganic Chemistry, College of Chemistry & Materials Science, Northwest University, Xi'an 710069, China
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表12种不同金属材料的力学参数
科
Family		 属数
Number of
genus		 种数
Number of
species		 占总种数比例
Percentage of
total species (%)		 属
Genus		 种数
Number of
species		 占总种数比例
Percentage of total
species (%)
鹅膏菌科Amanitaceae 2 11 5.26 鹅膏菌属 Amanita 10 4.78
小菇科 Mycenaceae 2 12 5.74 丝盖伞属 Inocybe 5 2.39
多孔菌科 Polyporaceae 8 14 6.70 蜡蘑属 Laccaria 5 2.39
红菇科 Russulaceae 3 23 11.00 小皮伞属 Marasmius 6 2.87
小菇属 Mycena 11 5.26
光柄菇属 Pluteus 5 2.39
红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
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