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Ncomms9697.Pdf ARTICLE Received 20 Jul 2015 | Accepted 16 Sep 2015 | Published 29 Oct 2015 DOI: 10.1038/ncomms9697 OPEN Efficient purification of ethene by an ethane-trapping metal-organic framework Pei-Qin Liao1, Wei-Xiong Zhang1, Jie-Peng Zhang1 & Xiao-Ming Chen1 Separating ethene (C2H4) from ethane (C2H6) is of paramount importance and difficulty. Here we show that C2H4 can be efficiently purified by trapping the inert C2H6 in a judiciously designed metal-organic framework. Under ambient conditions, passing a typical cracked gas mixture (15:1 C2H4/C2H6) through 1 litre of this C2H6 selective adsorbent directly produces 56 litres of C2H4 with 99.95% þ purity (required by the C2H4 polymerization reactor) at the outlet, with a single breakthrough operation, while other C2H6 selective materials can only produce ca. p1 litre, and conventional C2H4 selective adsorbents require at least four adsorption–desorption cycles to achieve the same C2H4 purity. Single-crystal X-ray diffraction and computational simulation studies showed that the exceptional C2H6 selectivity arises from the proper positioning of multiple electronegative and electropositive functional groups on the ultramicroporous pore surface, which form multiple C–H ÁÁÁN hydrogen bonds with C2H6 instead of the more polar competitor C2H4. 1 MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, P.R. China. Correspondence and requests for materials should be addressed to J.-P.Z. (email: [email protected]). NATURE COMMUNICATIONS | 6:8697 | DOI: 10.1038/ncomms9697 | www.nature.com/naturecommunications 1 & 2015 Macmillan Publishers Limited. All rights reserved. ARTICLE NATURE COMMUNICATIONS | DOI: 10.1038/ncomms9697 s the most important chemical product, ethene (C2H4)is well as short bridging lengths for construction of an ultra- generally obtained through steam cracking and thermal microporous framework. Reaction of H2batz and Zn(OH)2 in Adecomposition of naphtha or ethane (C2H6) (ref. 1). dilute aqueous ammonia produced a porous metal-azolate Besides being obtained as a byproduct of petroleum refining, framework [Zn(batz)] Á 0.5H2O (MAF-49 Á H2O). Single-crystal C2H6 is also isolated on an industrial scale from natural gas (CH4 X-ray diffraction (SCXRD) analysis of MAF-49 Á H2O B B B 70 96%, C2H6 1 14% and CO2 0 8%) (ref. 2). As a result of (Supplementary Table 2 and Supplementary Data 1) showed that their similar physical properties, it is difficult to separate C2H6, each Zn(II) is tetrahedrally coordinated by four triazolate nitro- 2– C2H4 and CO2 (refs 3–5). In industry, C2H6 and C2H4 are gen atoms from three batz ligands (Supplementary Fig. 1), and separated by cryogenic high-pressure distillation, typically at each batz2– ligand coordinates to three Zn(II) ions in a bisimi- 7–28 bar and 183–258 K using very high towers consisting of over dazolate mode, giving a three-dimensional (3D) coordination 150 trays, which is very energy consuming (7 GJ t À 1) and framework with narrow 1D zigzag channels (Fig. 1a). Since only constitutes a notable portion of the ethylene cost6,7. To save four of the eight nitrogen donors of batz2– are utilized according energy, separation methods effective at the ambient temperature to the coordination requirement of Zn(II), the pore surface of and pressure are highly demanded8–11. Passing the gas mixture MAF-49 is rich with electronegative nitrogen atoms, although through a fixed-bed adsorber can be a very simple and promising some of them form intra-framework N–H ÁÁÁN hydrogen bonds approach to afford low energy consumption and high product to reduce their abilities as hydrogen-bonding acceptors. Notably, purity. the narrowest section of the 1D channel (3.3 Â 3.0 Å2)is Because unsaturated hydrocarbons like to coordinate with approximately a folded four-membered ring defined by a pair of metal ions, C2H4 can be selectively bound and separated from its free amino groups (with their lone electron pairs) and a pair of saturated counterpart C2H6 (refs 12–16). Compared with other methylene groups with a cis-configuration, which is occupied by a types of porous materials, porous metal-organic frameworks guest H2O molecule with two O–H ÁÁÁN and two C–H ÁÁÁO (MOFs) are unique for their diversified/designable framework hydrogen bonds (Fig. 1b). structures and pore surfaces, including the ease of introducing Thermogravimetry and powder XRD showed that MAF- open metal sites (OMSs), which have shown great potentials 49 Á H2O can be readily activated and is stable to 450 °Cin 17–22 for C2H4/C2H6 separation . In the fix-bed separation process, nitrogen (Supplementary Fig. 2), in boiling water for at least the un-adsorbed C2H6 first breakthrough, and C2H4 enriched in 1 month and in aqueous acid/base (4rpHr12) at room the stationary phase is later obtained by heating and/or inert-gas temperature for at least 1 week (Supplementary Fig. 3), which blowing. Because the un-adsorbed C2H6 residing in the is extraordinary among MOFs and can be partly explained by 38 mobile phase contaminates the desired product C2H4 during the strong metal-azolate coordination bonds . SCXRD showed the desorption stage, the highest C2H4 purity produced by a that complete dehydration leads to a slight framework expansion full adsorption–desorption cycle can just reach 99% þ (0.17% in volume, Supplementary Table 2 and Supplementary (refs 13,17,23,24), and at least four such cycles are necessary to Data 2). achieve 99.95% þ (ref. 25), the lower limit required by the C2H4 26–28 polymerization reactor . Obviously, this problem can be Gas adsorption property and mechanism. Single-component solved by using a C H selective adsorbent, which not only 2 6 adsorption isotherms for CH4,C2H6,C2H4 and CO2 were improves the C2H4 purity but also reduces energy consumption. measured for guest-free MAF-49 at 298 K, 307 K and 316 K The simple separation operation and device (just one adsorption (Fig. 2a and Supplementary Fig. 4). According to their different process in a single breakthrough operation) are also necessary for isotherm shapes, it can be judged that the host–guest binding onsite supply of purified C H . However, such an unusual 2 4 follows C2H64C2H44CO24CH4. The gas adsorption enthalpies adsorption behaviour has been only reported for a few low- 29–36 were calculated quantitatively by Virial analyses (Fig. 2b and polarity or hydrophobic MOFs , and their C2H4/C2H6 Supplementary Fig. 5), which are 60 kJ mol À 1, 48 kJ mol À 1, separation performances (that is, C H /C H selectivities) are À 1 À 1 2 6 2 4 30 kJ mol and 25 kJ mol for C2H6,C2H4,CO2, and CH4, poor, because the polarities of C2H4 and C2H6 are very similar respectively, at zero-coverage. The mixed gas adsorption iso- and can be hardly distinguished by hydrophobic adsorbents. therms for equimolar C2H6/C2H4,C2H6/CO2 and C2H6/CH4 As C2H6 possesses the lowest polarity (quadrupole moment) mixtures were simulated by the ideal adsorbed solution theory39, compared with similar molecules such as C2H4 and CO2 37 in which the single-component adsorption isotherms were fitted (Supplementary Table 1) ; polar adsorbents are generally by the Langmuir À Freundlich model (Supplementary Fig. 6). selective for the latter gases. However, considering that the At total pressure of 100 kPa and a temperature of 316 K, the electropositive and electronegative portions locate quite C2H6/C2H4,C2H6/CO2 and C2H6/CH4 selectivities of these differently among these gas molecules, we speculated that by mixtures were calculated as ca. 9, 40 and 170, respectively rational utilization of polar functional groups, it is still possible to design a MOF with optimized pore size/shape and surface electrostatic distribution that can bind C2H6 much stronger than ab for C2H4. Herein, we report the design, structure and gas adsorption/separation properties of such a C2H6-trapping MOF, which is useful for not only direct producing highly pure C2H4 from C2H4/C2H6 mixtures, but also efficient separation of four-component CH4/C2H4/C2H6/CO2 mixtures and extraction of C2H6 from natural gas. Results Synthesis, structure and stability. Bis(5-amino-1H-1,2,4-triazol- Figure 1 | X-ray crystal structure of MAF-49 . H2O. (a) Framework 3-yl)methane (H2batz) with two 3-amino-1,2,4-triazole rings (Zn purple, C dark grey, H light grey, N blue) and pore surface (yellow/grey bridged by a methylene group was designed as a new ligand curved surface) structures. Guest molecules are omitted for clarity. combining multiple nitrogen atoms as hydrogen-bonding (b) Local environment and hydrogen-bonding interactions of the narrowest acceptors and methylene groups as dipole repulsion groups, as channel neck (highlighted by green dashed lines). 2 NATURE COMMUNICATIONS | 6:8697 | DOI: 10.1038/ncomms9697 | www.nature.com/naturecommunications & 2015 Macmillan Publishers Limited. All rights reserved. NATURE COMMUNICATIONS | DOI: 10.1038/ncomms9697 ARTICLE ab40 C2H6 60 C2H4 C H ) 2 6 –1 30 50 g 3 CO ) C2H4 2 –1 40 20 CO2 30 CH2 (kJ mol CH4 st 20 10 Q Gas uptake (cm 10 0 0 1E-5 1E-4 1E-3 0.01 0.1 1 0.0 0.2 0.4 0.6 0.8 1.0 1.2 Pressure (bar) Adsorption amount (mmol g–1) cd 70 63 IRMOF-8 MAF-49 ) 60 54 –1 g 3 50 ) 45 –1 40 36 MAF-3 MAF-3 IRMOF-8 30 27 MAF-49 (kJ mol st 20 Q 18 MAF-4 Gas uptake (cm 10 9 MAF-4 0 0 1E-4 1E-3 0.01 0.1 1 0.0 0.5 1.0 1.5 2.0 2.5 3.0 Pressure (bar) Adsorption amount (mmol g–1) Figure 2 | Single-component gas adsorption properties.
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