A pyrazine based metal-organic framework for selective removal of copper from strongly acidic solutions

Highlights

● pz-UiO-66 was synthesized facilely by a solvothermal method.

● Efficient capture of copper from highly acidic solution was achieved by pz-UiO-66.

● pz-UiO-66 exhibited excellent selectivity and capacity for copper capture.

● Pyrazine-N in pz-UiO-66 was shown to be the dominant adsorption site.

Abstract

The selective capture of copper from strongly acidic solutions is of vital importance from the perspective of sustainable development and environmental protection. Metal organic frameworks (MOFs) have attracted the interest of many scholars for adsorption due to their fascinating physicochemical characteristics, including adjustable structure, strong stability and porosity. Herein, pz-UiO-66 containing a pyrazine structure is successfully synthesized for the efficient separation of copper from strongly acidic conditions. Selective copper removal at low pH values is accomplished by using this material that is not available in previously reported metal–organic frameworks. Furthermore, the material exhibits excellent adsorption capacity, with a theoretical maximum copper uptake of 247 mg/g. As proven by XPS and FT-IR analysis, the coordination of pyrazine nitrogen atoms with copper ions is the dominant adsorption mechanism of copper by pz-UiO-66. This work provides an opportunity for efficient and selective copper removal under strongly acidic conditions, and promises extensive application prospects for the removal of copper in the treatment for acid metallurgical wastewater.

Graphical abstract

Keywords

Pyrazine / Metal-organic frameworks / Copper removal / Strong acidity / High selectivity

References

[1] Ai K, Ruan C, Shen M, Lu L. (2016). MoS₂ nanosheets with widened interlayer spacing for high-efficiency removal of mercury in aquatic systems. Advanced Functional Materials, 26(30): 5542–5549

[2] Awual M R. (2019). Novel ligand functionalized composite material for efficient copper (II) capturing from wastewater sample. Composites Part B: Engineering, 172: 387–396

[3] Brady D C, Crowe M S, Turski M L, Hobbs G A, Yao X, Chaikuad A, Knapp S, Xiao K, Campbell S L, Thiele D J, Counter C M. (2014). Copper is required for oncogenic BRAF signalling and tumorigenesis. Nature, 509(7501): 492–496

[4] Bui N T, Kang H, Teat S J, Su G M, Pao C W, Liu Y S, Zaia E W, Guo J, Chen J L, Meihaus K R, Dun C, Mattox T M, Long J R, Fiske P, Kostecki R, Urban J J. (2020). A nature-inspired hydrogen-bonded supramolecular complex for selective copper ion removal from water. Nature Communications, 11(1): 1–12

[5] Cao Y, Xiao W, Shen G, Ji G, Zhang Y, Gao C, Han L. (2019). Carbonization and ball milling on the enhancement of Pb(II) adsorption by wheat straw: competitive effects of ion exchange and precipitation. Bioresource Technology, 273: 70–76

[6] Cavka J H, Jakobsen S, Olsbye U, Guillou N, Lamberti C, Bordiga S, Lillerud K P. (2008). A new zirconium inorganic building brick forming metal organic frameworks with exceptional stability. Journal of the American Chemical Society, 130(42): 13850–13851

[7] Chen T, Liu F, Ling C, Gao J, Xu C, Li L, Li A. (2013a). Insight into highly efficient coremoval of copper and p-nitrophenol by a newly synthesized polyamine chelating resin from aqueous media: competition and enhancement effect upon site recognition. Environmental Science & Technology, 47(23): 13652–13660

[8] Chen X, Chen A, Zhao Z, Liu X, Shi Y, Wang D. (2013b). Removal of Cu from the nickel electrolysis anolyte using nickel thiocarbonate. Hydrometallurgy, 133: 106–110

[9] Chen Y, Pan B, Li H, Zhang W, Lv L, Wu J. (2010). Selective removal of Cu(II) ions by using cation-exchange resin-supported polyethyleneimine (PEI) nanoclusters. Environmental Science & Technology, 44(9): 3508–3513

[10] Choudhary M, Kumar R, Neogi S. (2020). Activated biochar derived from Opuntia ficus-indica for the efficient adsorption of malachite green dye, Cu²⁺ and Ni²⁺ from water. Journal of Hazardous Materials, 392: 122441

[11] Daliran S, Ghazagh-Miri M, Oveisi A R, Khajeh M, Navalón S, Âlvaro M, Ghaffari-Moghaddam M, Samareh Delarami H, García H. (2020). A pyridyltriazol functionalized zirconium metal-organic framework for selective and highly efficient adsorption of palladium. ACS Applied Materials & Interfaces, 12(22): 25221–25232

[12] Demiral H, Güngör C. (2016). Adsorption of copper(II) from aqueous solutions on activated carbon prepared from grape bagasse. Journal of Cleaner Production, 124: 103–113

[13] Feng H, Li Y, Luo D, Tan G, Jiang J, Yuan H, Peng S, Qian D. (2016). Novel visible-light-responding InVO₄-Cu₂O-TiO₂ ternary nanoheterostructure: preparation and photocatalytic characteristics. Chinese Journal of Catalysis, 37(6): 855–862

[14] FitzgeraldD J (1998). Safety guidelines for copper in water. The American journal of clinical nutrition, 67(5 Suppl): 1098S–1102S

[15] Hosseinpournajjar E, Kianfar A H, Dinari M. (2022). Synthesizing and characterization of Cu(II) polymer complex: application for removing heavy metals from aqueous solutions. Journal of the Iranian Chemical Society, 19(5): 1963–1977

[16] Irving H, Williams R J P. (1953). The stability of transition-metal complexes. Journal of the Chemical Society (Resumed), 3192–3210

[17] Jiang C, Wang X, Wang G, Hao C, Li X, Li T. (2019). Adsorption performance of a polysaccharide composite hydrogel based on crosslinked glucan/chitosan for heavy metal ions. Composites Part B: Engineering, 169: 45–54

[18] Kuz’min V I, Kuz’min D V. (2014). Sorption of nickel and copper from leach pulps of low-grade sulfide ores using Purolite S930 chelating resin. Hydrometallurgy, 141: 76–81

[19] Lee S, Barin G, Ackerman C M, Muchenditsi A, Xu J, Reimer J A, Lutsenko S, Long J R, Chang C J. (2016). Copper capture in a thioether-functionalized porous polymer applied to the detection of Wilson’s disease. Journal of the American Chemical Society, 138(24): 7603–7609

[20] LinS, Kumar Reddy D H, BediakoJ K, SongM H, WeiW, KimJ A, Yun Y S (2017). Effective adsorption of Pd(Ⅱ), Pt(Ⅳ) and Au(Ⅲ) by Zr(Ⅳ)-based metal-organic frameworks from strongly acidic solutions. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 5(26): 13557–13564

[21] Ma Y, Lu W, Han X, Chen Y, da Silva I, Lee D, Sheveleva A M, Wang Z, Li J, Li W, Fan M, Xu S, Tuna F, McInnes E J L, Cheng Y, Rudić S, Manuel P, Frogley M D, Ramirez-Cuesta A J, Schröder M, Yang S. (2022). Direct observation of ammonia storage in UiO-66 incorporating Cu(II) binding sites. Journal of the American Chemical Society, 144(19): 8624–8632

[22] Marcus Y. (1988). Ionic radii in aqueous solutions. Chemical Reviews, 88(8): 1475–1498

[23] Miniyar P B, Murumkar P R, Patil P S, Barmade M A, Bothara K G. (2013). Unequivocal role of pyrazine ring in medicinally important compounds: a review. Mini reviews in medicinal chemistry, 13(11): 1607–1625

[24] Park I, Tabelin C B, Jeon S, Li X, Seno K, Ito M, Hiroyoshi N. (2019). A review of recent strategies for acid mine drainage prevention and mine tailings recycling. Chemosphere, 219: 588–606

[25] Peng Y, Huang H, Zhang Y, Kang C, Chen S, Song L, Liu D, Zhong C. (2018). A versatile MOF-based trap for heavy metal ion capture and dispersion. Nature Communications, 9(1): 1–9

[26] Shao P, Liang D, Yang L, Shi H, Xiong Z, Ding L, Yin X, Zhang K, Luo X. (2020). Evaluating the adsorptivity of organo-functionalized silica nanoparticles towards heavy metals: quantitative comparison and mechanistic insight. Journal of Hazardous Materials, 387: 121676

[27] Wang D B, Chen B H, Zhang B, Ma Y X. (1997). XPS study of aroylhydrazones containing triazole and their chelates. Polyhedron, 16(15): 2625–2629

[28] Wang L, Shi Y, Yao D, Pan H, Hou H, Chen J, Crittenden J C. (2019). Cd complexation with mercapto-functionalized attapulgite (MATP): adsorption and DFT study. Chemical Engineering Journal, 366: 569–576

[29] Wang N, Feng J, Yan W, Zhang L, Liu Y, Mu R. (2022). Dual-functional sites for synergistic adsorption of Cr(VI) and Sb(V) by polyaniline-TiO₂ hydrate: adsorption behaviors, sites and mechanisms. Frontiers of Environmental Science & Engineering, 16(8): 1–14

[30] Xie L, Yu Z, Islam S M, Shi K, Cheng Y, Yuan M, Zhao J, Sun G, Li H, Ma S, Kanatzidis M G. (2018). Remarkable acid stability of polypyrrole-MoS₄: a highly selective and efficient scavenger of heavy metals over a wide pH range. Advanced Functional Materials, 28(20): 1800502

[31] Xu M, Meng S S, Liang H, Gu Z Y. (2020). A metal-organic framework with tunable exposed facets as a high-affinity artificial receptor for enzyme inhibition. Inorganic Chemistry Frontiers, 7(19): 3687–3694

[32] Yao Z, Shao P, Fang D, Shao J, Li D, Liu L, Huang Y, Yu Z, Yang L, Yu K, Luo X. (2022). Thiol-rich, porous carbon for the efficient capture of silver: understanding the relationship between the surface groups and transformation pathways of silver. Chemical Engineering Journal, 427: 131470

[33] Yu H, Shao P, Fang L, Pei J, Ding L, Pavlostathis S G, Luo X. (2019). Palladium ion-imprinted polymers with PHEMA polymer brushes: role of grafting polymerization degree in anti-interference. Chemical Engineering Journal, 359: 176–185

[34] Zhang X, Tong S, Huang D, Liu Z, Shao B, Liang Q, Wu T, Pan Y, Huang J, Liu Y, Cheng M, Chen M. (2021). Recent advances of Zr based metal organic frameworks photocatalysis: energy production and environmental remediation. Coordination Chemistry Reviews, 448: 214177

[35] Zhang Y, Xie Z, Wang Z, Feng X, Wang Y, Wu A. (2016). Unveiling the adsorption mechanism of zeolitic imidazolate framework-8 with high efficiency for removal of copper ions from aqueous solutions. Dalton Transactions, 45(32): 12653–12660

Acknowledgements

This study was financially supported by the National Natural Science Foundation of China (Nos. 52125002 and 51908270), the Natural Science Foundation of Jiangxi Province (No. 20212ACB213006), and the National Key Research and Development Program of China (No. 2019YFC1907900).

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://doi.org/10.1007/s11783-023-1633-0 and is accessible for authorized users.

RIGHTS & PERMISSIONS

2023 Higher Education Press