Exceptional removal capacity of clenbuterol from aqueous solution by mechano-synthesized [Cu (INA)2]-MOF via ball-mill |
Marinah Mohd, Ariffin
(Faculty of Science and Marine Environment, Universiti Malaysia Terengganu)
Usman, Armaya'u (Faculty of Science and Marine Environment, Universiti Malaysia Terengganu) Saw Hong, Loh (Faculty of Science and Marine Environment, Universiti Malaysia Terengganu) Wan Mohd Afiq Wan Mohd, Khalik (Faculty of Science and Marine Environment, Universiti Malaysia Terengganu) Hanis Mohd, Yusoff (Faculty of Science and Marine Environment, Universiti Malaysia Terengganu) |
1 | Petrovic, M., Skrbic, B., Zivancev, J., Ferrando-Climent, L. and Barcelo, D. (2014), "Determination of 81 pharmaceutical drugs by high performance liquid chromatography coupled to mass spectrometry with hybrid triple quadrupole-linear ion trap in different types of water in Serbia", Sci. Total Environ., 415-428. https://doi.org/10.1016/j.scitotenv.2013.08.079 DOI |
2 | Pichon, A., Lazuen-Garay, A. and James, S.L. (2006), "Solventfree synthesis of a microporous metal-organic framework", CrystEngComm, 8(3), 211-214. https://doi.org/10.1039/b513750k DOI |
3 | Policicchio, A., Filosa, R., Abate, S., Desiderio, G. and Colavita, E. (2017), "Activated carbon and metal organic framework as adsorbent for low-pressure methane storage applications: An overview", J. Porous Mater., 24(4), 905-922. https://doi.org/10.1007/s10934-016-0330-9 DOI |
4 | Quintana, J.B., Rodil, R. and Cela, R. (2012), "Reaction of β-blockers and β-agonist pharmaceuticals with aqueous chlorine: Investigation of kinetics and by-products by liquid chromatography quadrupole time-of-flight mass spectrometry", Anal. Bioanal. Chem., 403(8), 2385-2395. https://doi.org/10.1007/s00216-011-5707-7 DOI |
5 | Rodil, R., Quintana, J.B., Concha-Grana, E., Lopez-Mahia, P., Muniategui-Lorenzo, S. and Prada-Rodriguez, D. (2012), "Emerging pollutants in sewage, surface and drinking water in Galicia (NW Spain)", Chemosphere, 86(10), 1040-1049. https://doi.org/10.1016/j.chemosphere.2011.11.053 DOI |
6 | Sakai, N., Mohd Yusof, R., Sapar, M., Yoneda, M. and Ali Mohd, M. (2016), "Spatial analysis and source profiling of betaagonists and sulfonamides in Langat River basin, Malaysia", Sci. Total Environ., 43-50. https://doi.org/10.1016/j.scitotenv.2016.01.040 DOI |
7 | Sakai, N., Sakai, M., Mohamad Haron, D.E., Yoneda, M. and Ali Mohd, M. (2016), "Beta-agonist residues in cattle, chicken and swine livers at the wet market and the environmental impacts of wastewater from livestock farms in Selangor State, Malaysia", Chemosphere, 165, 183-190. https://doi.org/10.1016/j.chemosphere.2016.09.022 DOI |
8 | Salem, A.A., Wasfi, I.A. and Al-Nassibi, S.S. (2012), "Trace determination of β-blockers and β2-agonists in distilled and waste-waters using liquid chromatography-tandem mass spectrometry and solid-phase extraction", J. Chromatogr. B, 908, 27-38. https://doi.org/10.1016/j.jchromb.2012.09.026 DOI |
9 | Saruchi, and Kumar, V. (2019), "Adsorption kinetics and isotherms for the removal of rhodamine B dye and Pb +2 ions from aqueous solutions by a hybrid ion-exchanger", Arab. J. Chem., 12(3), 316-329. https://doi.org/10.1016/j.arabjc.2016.11.009 DOI |
10 | Schneemann, A., Bon, V., Schwedler, I., Senkovska, I., Kaskel, S. and Fischer, R.A. (2014), "Flexible metal-organic frameworks", Chem. Soc. Rev., 43(16), 6062-6096. https://doi.org/10.1039/c4cs00101j DOI |
11 | Selkala, T., Suopajarvi, T., Sirvio, J.A., Luukkonen, T., Lorite, G.S., Kalliola, S., Sillanpaa, M. and Liimatainen, H. (2018), "Rapid uptake of pharmaceutical salbutamol from aqueous solutions with anionic cellulose nanofibrils: The importance of pH and colloidal stability in the interaction with ionizable pollutants", Chem. Eng. J., 350, 378-385. https://doi.org/10.1016/j.cej.2018.05.163 DOI |
12 | Slotkin, T.A. and Seidler, F.J. (2013), "Terbutaline impairs the development of peripheral noradrenergic projections: Potential implications for autism spectrum disorders and pharmacotherapy of preterm labor", Neurotoxicol. Teratol., 36, 91-96. https://doi.org/10.1016/j.ntt.2012.07.003 DOI |
13 | Stock, N. and Biswas, S. (2012), "Synthesis of metal-organi frameworks (MOFs): Routes to various MOF topologies morphologies, and composites", Chem. Rev., 112(2), 933-969. https://doi.org/10.1021/cr200304e DOI |
14 | Soc, C., James, S.L., Adams, C.J., Bolm, C., Braga, D., Collier, P., Jones, W., Krebs, A., Mack, J., Maini, L., Orpen, A.G., Parkin, I.P., Shearouse, W.C., Steed, W., Waddell, D.C., James, S., Bolm, C., Braga, D., Collier, P., … Steed, J. (2012), "Mechanochemistry : Opportunities for new and cleaner synthesis", Chem. Soc. Rev., 41(1), 413-447. https://doi.org/10.1039/c1cs15171a DOI |
15 | Song, J.Y. and Jhung, S.H. (2017), "Adsorption of pharmaceuticals and personal care products over metal-organic frameworks functionalized with hydroxyl groups: Quantitative analyses of H-bonding in adsorption", Chem. Eng. J., 322, 366-374. https://doi.org/10.1016/j.cej.2017.04.036 DOI |
16 | Spisso, B.F., Lopes, C.C., Marques, M.A.S. and Neto, F.R.A. (2000), "Determination of beta-agonists in bovine urine : Comparison of two extraction / clean-up procedures for highresolution gas chromatography- mass spectrometry analysis", J. Anal. Toxicol., 24. |
17 | Tang, Y., Gao, Z., Wang, S., Gao, X., Gao, J., Ma, Y., Liu, X. and Li, J. (2015), "Upconversion particles coated with molecularly imprinted polymers as fluorescence probe for detection of clenbuterol", Biosens. Bioelectron., 71, 44-50. https://doi.org/10.1016/j.bios.2015.04.005 DOI |
18 | Tang, Y., Lan, J., Gao, X., Liu, X., Zhang, D., Wei, L., Gao, Z. and Li, J. (2016), "Determination of clenbuterol in pork and potable water samples by molecularly imprinted polymer through the use of covalent imprinting method", Food Chem., 190, 952-959. https://doi.org/10.1016/j.foodchem.2015.06.067 DOI |
19 | Tella, A., Nwosu, F. and Adimula, V. (2016), "Removal of Anthracene from solution using [Cu(INA)2 ] metal- organic frameworks synthesized by a solvent free method", Nigerian J. Mater. Sci. Eng., 7, 26. |
20 | Tella, A.C., Owalude, S.O., Ojekanmi, C.A. and Oluwafemi, O.S. (2014), "Synthesis of copper-isonicotinate metal-organic frameworks simply by mixing solid reactants and investigation of their adsorptive properties for the removal of the fluorescein dye", New J. Chem., 38(9), 4494-4500. https://doi.org/10.1039/c4nj00411f DOI |
21 | Ternes, T.A. (1998), "Occurrence of drugs in German sewage treatment plants and rivers", Water Res., 32(11), 3245-3260. https://doi.org/10.1016/S0043-1354(98)00099-2 DOI |
22 | Valcarcel, Y., Gonzalez Alonso, S., Rodriguez-Gil, J.L., Gil, A. and Catala, M. (2011), "Detection of pharmaceutically active compounds in the rivers and tap water of the Madrid Region (Spain) and potential ecotoxicological risk", Chemosphere, 84(10), 1336-1348. https://doi.org/10.1016/j.chemosphere.2011.05.014 DOI |
23 | Ternes, T. and Joss, A. (2015), "Human pharmaceuticals, hormones and fragrances - The challenge of micropollutants in urban water management", Water Intell. Online, 5, 479. https://doi.org/10.2166/9781780402468 DOI |
24 | Toma, M., Sanchez, A., Casas, J., Sordo, J., Garcia-Tasende, M., Castellano, E., Ellena, J. and Berdan, I. (2006), "New thallium(III) chloride complexes with pyridine carboxylic acids: From molecular compounds to supramolecular associations", Open Chem., 1(4), 441-464. https://doi.org/10.2478/bf02475227 DOI |
25 | Truong, T., Nguyen, C.V., Truong, N.T. and Phan, N.T.S. (2015), "Ligand-free N-arylation of heterocycles using metal-organic framework [Cu(INA) 2 ] as an efficient heterogeneous catalyst", RSC Adv., 5(130), 107547-107556. https://doi.org/10.1039/c5ra24165k DOI |
26 | Xing, G., Li, D., Woo, A.Y., Zhi, Z., Ji, L., Xing, R., Lv, H., He, B., An, H., Zhao, H., Lin, B., Pan, L. and Cheng, M. (2021), "Discovery of a highly selective β 2 ‑ adrenoceptor agonist with a 2 ‑ Amino-2-phenylethanol scaffold as an oral antiasthmatic agent", J. Med. Chem., 65(7), 5514-5527. https://doi.org/10.1021/acs.jmedchem.1c02006 DOI |
27 | Yu, Y. and Wu, L. (2011), "Comparison of four extraction methods for the analysis of pharmaceuticals in wastewater", J. Chromatogr. A, 1218(18), 2483-2489. https://doi.org/10.1016/j.chroma.2011.02.050 DOI |
28 | Yan, K., Zhang, H., Hui, W., Zhu, H., Li, X., Zhong, F., Tong, X. and Chen, C. (2016), "Rapid screening of toxic salbutamol, ractopamine, and clenbuterol in pork sample by highperformance liquid chromatography-UV method", J. Food Drug Anal., 24(2), 277-283. https://doi.org/10.1016/j.jfda.2015.12.002 DOI |
29 | Yan, S., Yao, B., Lian, L., Lu, X., Snyder, S.A., Li, R. and Song, W. (2017), "Development of fluorescence surrogates to predict the photochemical transformation of pharmaceuticals in wastewater effluents", Environ. Sci. Technol., 51(5), 2738-2747. https://doi.org/10.1021/acs.est.6b05251 DOI |
30 | Yang, H., Wang, B., Cheng, J., Wang, R., Zhang, S., Dong, S., Wei, S., Wang, P. and Li, J.R. (2019), "Determination and removal of clenbuterol with a stable fluorescent zirconium (IV)-based metal organic framework", Microchim. Acta, 186(7), 454. https://doi.org/10.1007/s00604-019-3586-3 DOI |
31 | Zango, Z.U., Abu Bakar, N.H.H., Sambudi, N.S., Jumbri, K., Abdullah, N.A.F., Kadir, E.A. and Saad, B. (2020), "Adsorption of chrysene in aqueous solution onto MIL-88(Fe) and NH2-MIL-88(Fe) metal-organic frameworks: Kinetics, isotherms, thermodynamics and docking simulation studies", J. Environ. Chem. Eng., 8(2), 103544. https://doi.org/10.1016/j.jece.2019.103544 DOI |
32 | Zango, Z.U., Jumbri, K., Sambudi, N.S., Ramli, A., Abu Bakar, N.H.H., Saad, B., Rozaini, M.N.H., Isiyaka, H.A., Jagaba, A.H., Aldaghri, O. and Sulieman, A. (2020), "A critical review on metal-organic frameworks and their composites as advanced materials for adsorption and photocatalytic degradation of emerging organic pollutants from wastewater", Polymers, 12(11), 2648. https://doi.org/10.3390/polym12112648 DOI |
33 | Almasi, M., Vargova, Z., Gyepes, R., Varga, R. and Zelenak, V. (2014), "An unprecedented coordination mode of isonicotinate ligand in novel copper(II) polymeric complex: Synthesis, spectral, thermal and magnetic properties and their comparison with known molecular analog", Inorg. Chem. Commun., 46, 118-121. https://doi.org/10.1016/j.inoche.2014.05.026 DOI |
34 | Zhang, W., Wang, P. and Su, X. (2016), "Current advancement in analysis of β-agonists", TrAC Trends Anal. Chem., 85, 1-16. https://doi.org/10.1016/j.trac.2016.08.011 DOI |
35 | Zhou, Y.Y., Zhang, C.Y., Yan, Z.G., Li, K.J., Wang, L., Xie, Y.B., Li, F.S., Liu, Z. and Yang, J. (2012), "The use of copper(II) isonicotinate-based micro-solid-phase extraction for the analysis of polybrominated diphenyl ethers in soils", Anal. Chim. Acta, 747(8), 36-41. https://doi.org/10.1016/j.aca.2012.08.023 DOI |
36 | Aboul-Enein, H.Y. and Serignese, V. (1999), "Quantitative determination of clenbuterol enantiomers in human plasma by high-performance liquid chromatography using the macrocyclic antibiotic chiral stationary phase teicoplanin1", Biomed. Chromatogr., 13(8), 520-524. https://doi.org/10.1002/(SICI)1099-0801(199912)13:8<520::AID-BMC919>3.0.CO;2-7 DOI |
37 | Alves, T.C., Cabrera-Codony, A., Barcelo, D., Rodriguez-Mozaz, S., Pinheiro, A. and Gonzalez-Olmos, R. (2018), "Influencing factors on the removal of pharmaceuticals from water with micro-grain activated carbon", Water Res., 144, 402-412. https://doi.org/10.1016/j.watres.2018.07.037 DOI |
38 | Armaya'u, U., Ariffin, M.M., Loh, S.H., Mohd Khalik, W.M.A.W. and Yusoff, H.M. (2022), "β-Agonist in the environmental waters: a review on threats and determination methods", Green Chem. Lett. Rev., 15(1), 232-251. https://doi.org/10.1080/17518253.2022.2032843 DOI |
39 | Benhafsa, F.M., Bouchama, A., Chadli, A., Tadjer, B. and Addad, D. (2022), "Comparative study of Pb (II) adsorption from water on used cardboard and powdered activated carbon", Membr. Water Treat., 13(2), 73-83. https://doi.org/10.12989/mwt.2022.13.2.073 DOI |
40 | Aryee, A.A., Dovi, E., Guo, Q., Liu, M., Han, R., Li, Z. and Qu, L. (2021), "Selective removal of anionic dyes in single and binary system using Zirconium and iminodiacetic acid modified magnetic peanut husk", Environ. Sci. Pollut. Res., 100. https://doi.org/10.1007/s11356-021-13030-5 DOI |
41 | Daughton, C.G. and Ternes, T.A. (1999), "Pharmaceuticals and personal care products in the environment: Agents of subtle change?", Environ. Health Perspect., 107(6), 907-938. https://doi.org/10.1289/ehp.99107s6907 DOI |
42 | David, N. and Dixon, E. (2015), "Synthesis, morphology and lead ion adsorption properties of metal organic frameworks of copper and cobalt", Chem. Sci. J., 6(4). https://doi.org/10.4172/2150-3494.1000113 DOI |
43 | de Ridder, D.J., Verliefde, A.R.D., Heijman, S.G.J., Verberk, J.Q.J.C., Rietveld, L.C., van der Aa, L.T.J., Amy, G.L. and van Dijk, J.C. (2011), "Influence of natural organic matter on equilibrium adsorption of neutral and charged pharmaceuticals onto activated carbon", Water Sci. Technol., 63(3), 416-423. https://doi.org/10.2166/wst.2011.237 DOI |
44 | Dhaka, S., Kumar, R., Deep, A., Kurade, M.B., Ji, S.W. and Jeon, B.H. (2019), "Metal-organic frameworks (MOFs) for the removal of emerging contaminants from aquatic environments", Coord. Chem. Rev., 380, 330-352. https://doi.org/10.1016/j.ccr.2018.10.003 DOI |
45 | Dotto, G.L., Costa, J.A.V. and Pinto, L.A.A. (2013),"Kinetic tudies on the biosorption of phenol by nanoparticles from Spirulina sp. LEB 18", J. Environ. Chem. Eng., 1(4), 1137-1143. https://doi.org/10.1016/j.jece.2013.08.029 DOI |
46 | Hong, S.H., Lee, C.G., Jeong, S. and Park, S.J. (2019), "Synthesis of polysulfone beads impregnated with Ca-sepiolite for phosphate removal", Membr. Water Treat., 11(1), 69-77. https://doi.org/10.12989/mwt.2020.11.1.069 DOI |
47 | Hasan, Z. and Jhung, S. H. (2015), "Removal of hazardous organics from water using metal-organic frameworks (MOFs): Plausible mechanisms for selective adsorptions", J. Hazard. Mater., 283, 329-339. https://doi.org/10.1016/j.jhazmat.2014.09.046 DOI |
48 | Hemmati, M., Rajabi, M. and Asghari, A. (2017), "Ultrasound-promoted dispersive micro solid-phase extraction of trace anti-hypertensive drugs from biological matrices using a sonochemically synthesized conductive polymer nanocomposite", Ultrason. Sonochem., 39, 12-24. https://doi.org/10.1016/j.ultsonch.2017.03.024 DOI |
49 | Hignite, C. and Azarnoff, D. L. (1977), "Drugs and drug metabolites as environmental contaminants: Chlorophenoxyisobutyrate and salicylic acid in sewage water effluent", Life Sci., 20(2), 337-341. https://doi.org/10.1016/0024-3205(77)90329-0 DOI |
50 | Hu, M.L., Masoomi, M.Y. and Morsali, A. (2019), "Template strategies with MOFs", Coord. Chem. Rev., 387, 415-435. https://doi.org/10.1016/j.ccr.2019.02.021 DOI |
51 | Isiyaka, H.A., Jumbri, K., Sambudi, N.S., Zango, Z.U., Fathihah Abdullah, N.A., Saad, B. and Mustapha, A. (2020), "Adsorption of dicamba and MCPA onto MIL-53(Al) metal- organic framework: Response surface methodology and artificial neural network model studies", RSC Adv., 10(70), 43213-43224. https://doi.org/10.1039/D0RA07969C DOI |
52 | Kuppler, R.J., Timmons, D.J., Fang, Q.R., Li, J.R., Makal, T.A., Young, M.D., Yuan, D., Zhao, D., Zhuang, W. and Zhou, H.C. (2009), "Potential applications of metal-organic frameworks", Coord. Chem. Rev., 253(23-24), 3042-3066. https://doi.org/10.1016/j.ccr.2009.05.019 DOI |
53 | Li, P., Cheng, F.F., Xiong, W.W. and Zhang, Q. (2018), "New synthetic strategies to prepare metal-organic frameworks", Inorg. Chem. Front., 5(11), 2693-2708. https://doi.org/10.1039/c8qi00543e DOI |
54 | Kyzas, G.Z., Koltsakidou, A., Nanaki, S.G., Bikiaris, D.N. and Lambropoulou, D.A. (2015), "Removal of beta-blockers from aqueous media by adsorption onto graphene oxide", Sci. Total Environ., 537, 411-420. https://doi.org/10.1016/j.scitotenv.2015.07.144 DOI |
55 | Lan, Y., Coetsier, C., Causserand, C. and Groenen Serrano, K. (2018), "An experimental and modelling study of the electrochemical oxidation of pharmaceuticals using a boron-doped diamond anode", Chem. Eng. J., 333(2017), 486-494. https://doi.org/10.1016/j.cej.2017.09.164 DOI |
56 | Li, C., Wu, Y.L., Yang, T., Zhang, Y. and Huang-Fu, W.G. (2010), "Simultaneous determination of clenbuterol, salbutamol and ractopamine in milk by reversed-phase liquid chromatography tandem mass spectrometry with isotope dilution", J. Chromatogr. A, 1217(50), 7873-7877. https://doi.org/10.1016/j.chroma.2010.10.055 DOI |
57 | Liu, Y.H., Lu, Y.L., Tsai, H.L., Wang, J.C. and Lu, K.L. (2001), "Hydrothermal synthesis, crystal structure, and magnetic property of copper(II) coordination networks with chessboard tunnels", J. Solid State Chem., 158(2), 315-319. https://doi.org/10.1006/jssc.2001.9118 DOI |
58 | Liu, Z., Zhang, B., Sun, J., Yi, Y., Li, M., Du, D., Zhu, F. and Luan, J. (2018), "Highly efficient detection of salbutamol in environmental water samples by an enzyme immunoassay", Sci. Total Environ., 861-865. https://doi.org/10.1016/j.scitotenv.2017.08.324 DOI |
59 | Lu, J.Y. and Babb, A.M. (2002), "An extremely stable openframework metal-organic polymer with expandable structure and selective adsorption capability", Chem. Commun., 2(13), 1340-1341. https://doi.org/10.1039/b200213b DOI |
60 | Lv, J., Chen, Q., Liu, J.H., Yang, H.S., Wang, P., Yu, J., Xie, Y., Wu, Y.F. and Li, J.R. (2021), "Effective removal of clenbuterol and ractopamine from water with a stable Al(III)-based metal-organic framework", Inorg. Chem., 60(3), 1814-1822. https://doi.org/10.1021/acs.inorgchem.0c03296 DOI |
61 | Manousi, N. and Zachariadis, G.A. (2020), "Recent advances in the extraction of polycyclic aromatic hydrocarbons from environmental samples", Molecules, 25(9), 2182. https://doi.org/10.3390/molecules25092182 DOI |
62 | Mansano Willig, J.C., Granetto, G., Reginato, D., Dutra, F.R., Poruczinski, E.F., de Oliveira, I.M., Stefani, H.A., de Campos, S.D., de Campos, E.A., Manarin, F. and Botteselle, G.V. (2020), "A comparative study between Cu(INA) 2 -MOF and [Cu(INA) 2 (H 2 O) 4 ] complex for a click reaction and the Biginelli reaction under solvent-free conditions", RSC Adv., 10(6), 3407-3415. https://doi.org/10.1039/C9RA10171C DOI |
63 | Nakamoto, K. (2006), "Infrared and Raman Spectra of Inorganic and Coordination Compounds", Handbook of Vibrational Spectroscopy, 1872-1892. https://doi.org/10.1002/9780470027325.s4104 DOI |
64 | Nguyen, T.V., Ong, T.D., Lam, A.H.M., Pham, V.T., Phan, N.T.S. and Truong, T. (2017), "Nucleophilic trifluormethylation of aryl boronic acid under heterogeneous Cu(INA)2 catalysis at room temperature: The catalytic copper-based protocol", Mol. Catal., 436, 60-66. https://doi.org/10.1016/j.mcat.2017.04.010 DOI |
65 | Perrotti, T.C., Freitas, N.S., Alzamora, M., Sanchez, D.R. and Carvalho, N.M.F. (2019), "Green iron nanoparticles supported on amino-functionalized silica for removal of the dye methyl orange", J. Environ. Chem. Eng., 7(4), 103237. https://doi.org/10.1016/j.jece.2019.103237 DOI |