Синтезованийкополімернийпохіднийполі(стирен-альт-малеїновий ангидрид) як нова хелативна смола для видалення йонів важких металів з водного розчину

1
Marand Faculty of Technical and Engineering, University of Tabriz
2
Department of Chemistry, Miyaneh Branch, Islamic Azad University

Хелатовусмолуякновийкополімердлявидаленняйонівметалівготували з використанням 3- (4-гідроксифеніл)циклопропан-1,1,2,2-тетракарбонової кислоти, 1,2-діаміноетану таполі(стирен-альт-малеїновогоангідриду). Параметрисорбційноїповедінкидосліджувались в різнихумовах. Дослідженнякінетикипоказали, щопроцесадсорбціїпідтвердивкінетикупсевдодругогопорядку, і даніадсорбціїдобревідповідалиізотерміЛенгмюра.

[1] Isobe, N.; Chen, X.; Kim,U.-J.;Kimura, S.;Wada, M.;Saito, T.;Isogai, A.TEMPO-Oxidized Cellulose Hydrogel as a High-Capacity and Reusable Heavy Metal Ion Adsorbent.J. Hazard. Mater.2013, 260,195-201.https://doi.org/10.1016/j.jhazmat.2013.05.024
[2] Chibuike, G.U.;Obiora, S.C.Heavy Metal Polluted Soils: Effect on Plants and Bioremediation Methods.Appl. Environ. Soil. Sci. 2014,2014, 1. https://doi.org/10.1155/2014/752708
[3] Sharma, S.; Sharma, S.;Upreti,N.; Sharma, K.P.Monitoring Toxicity of an Azo Dye Methyl Red and a Heavy Metal Cu, Using Plant and Animal Bioassays.Toxicol. Environ. Chem.2009, 91, 109-120.https://doi.org/10.1080/02772240802010987
[4] Brieger, G.; Wells, J.R.; Hunter, R.D. Plant and Animal Species Composition and Heavy Metal Content in Fly Ash Ecosystems.Water Air Soil Poll. 1992, 63, 87-103. https://doi.org/10.1007/BF00475624
[5] Oehmen, A.; Vergel, D.; Fradinho, J.;Reis, M.A.M.;Crespo, J.G.;Velizarov, S.Mercury Removal from Water Streams Through the Ion Exchange Membrane Bioreactor Concept.J. Hazard. Mater.2014, 264, 65-70.https://doi.org/10.1016/j.jhazmat.2013.10.067
[6] Zou, W.;Filatov, M.; Atwood, D.; Cremer, D.Removal of Mercury from the Environment: A Quantum-Chemical Study with the Normalized Elimination of the Small Component Method.Inorg. Chem.2013, 52, 2497-2504.https://doi.org/10.1021/ic302444b
[7] Fu, F.;Wang, Q.RemovalofHeavy MetalIons fromWastewaters: A review.J. Environ. Manage. 2011, 92,407-418.https://doi.org/10.1016/j.jenvman.2010.11.011
[8] Kurniawan, T.A.; Chan, G.Y.S.; Lo, W.-H.; Babel, S.Physico–Chemical Treatment TechniquesforWastewater Laden with Heavy Metals.Chem. Eng. J.2006, 118, 83-98. https://doi.org/10.1016/j.cej.2006.01.015
[9] Luo, S.; Xu, X.; Zhou, G.; Liu, C.; Tang, Y.; Liu, Y. Amino Siloxane Oligomer-Linked Graphene Oxide as an Efficient Adsorbent for Removal of Pb(II) from Wastewater.J. Hazard. Mater. 2014, 274, 145-155.https://doi.org/10.1016/j.jhazmat.2014.03.062
[10] Zhao, F.;Tang, W.Z.; Zhao, D.; Meng, Y.; Yin, D.;Sillanpää, M.Adsorption Kinetics, Isotherms and Mechanisms of Cd(II), Pb(II), Co(II) and Ni(II) by a Modified Magnetic Polyacrylamide MicrocompositeAdsorbent.J. Water. Process. Eng.2014, 4, 47-57.https://doi.org/10.1016/j.jwpe.2014.09.003
[11] Tripathi, K.M.; Tyagi, A.; Ashfaq, M.; Gupta, R.K. Temperature Dependent, Shape Variant Synthesis of Photoluminescent and Biocompatible Carbon Nanostructures from Almond Husk for Applications in Dye Removal.RSC Adv.2016, 6,29545-29553. https://doi.org/10.1039/C5RA27432J
[12] Zhao, D.; Zhang Q.; Xuan H.;Chen, Y.; Zhang, K.; Feng, S.; Alsaedi, A.; Hayat, T.; Chen, C. EDTA Functionalized Fe3O4/Graphene Oxide for Efficient Removal of U(VI) from Aqueous Solutions.J. Colloid. Interface Sci. 2017,506, 300-307. https://doi.org/10.1016/j.jcis.2017.07.057
[13] Zeng, W.; Liu, Y.-G.; Hu, X.-J.; Liu, S.-B.; Zeng, G.-M.; Zheng, B.-H.; Jiang, L.-H.; Guo, F.-Y.; Ding, Y.; Xu, Y. Decontamination of Methylene Blue from Aqueous Solution by Magnetic Chitosan Lignosulfonate Grafted with Graphene Oxide: Effects of Environmental Conditions and Surfactant.RSC Adv. 2016, 6, 19298-19307. https://doi.org/10.1039/C5RA27657H
[14] Deng, S.; Wang, P.;Zhang, G.;Dou, Y.Polyacrylonitrile-Based Fiber ModifiedwithThiosemicarbazidebyMicrowave Irradiation and its Adsorption BehaviorforCd(II) and Pb(II).J. Hazard. Mater.2016,307, 64-72.https://doi.org/10.1016/j.jhazmat.2016.01.002
[15] Zhou, P.; Yuan, H.;Ou, L.;Zhiyuan, P.RemovalofCd(II) and Cu(II) Ions fromAqueous Solutions Using Tannin-Phenolic Polymer Immobilized on Cellulose.J. Macromol. Sci. A2019, 56,717-722.https://doi.org/10.1080/10601325.2019.1601496
[16] Rivas, B.L.; Morales, D.V.;Kabay, N.;Bryjak, M.Cr(III) Removal from Aqueous Solution Byion Exchange Resins Containing Carboxylic Acid and Sulphonic Acid Groups.J. Chil. Chem. Soc.2018, 63, 4012-4018. https://doi.org/10.4067/s0717-97072018000204012
[17] Wang, Y.-P.; Zhou, P.; Luo, S.Z.; Liao, X.-P.;Wang, B.; Shao, Q.; Guo, X.; Guo, Z. Controllable Synthesis of Monolayer Poly(acrylic acid) on the Channel Surface of Mesoporous Alumina for Pb(II) Adsorption.Langmuir2018,34, 7859-7868. https://doi.org/10.1021/acs.langmuir.8b00789
[18] Muhanna, F.J.; Dari, K.A.; Mubarak, M.S. Chelation Properties of Chitosan Functionalized with 1-Hydroxy-2-pyridinethione-4-carboxylic Acid Toward Some Heavy Metal Ions in Aqueous Solutions.J. Macromol. Sci. A2012,49,15-29. https://doi.org/10.1080/10601325.2012.630930
[19] Samadi, N.; Ansari, R.;Khodavirdilo, B.Removal of Copper Ions from Aqueous Solutions Using Polymer Derivations of Poly (Styrene-Alt-Maleic Anhydride).Egypt. J. Petrol. 2017, 26, 375-389. https://doi.org/10.1016/j.ejpe.2016.05.010
[20] Cui, L.; Wang, Y.; Gao, L.; Hu, L.; Yan, L.; Wei, Q.; Du, B. EDTA Functionalized Magnetic Graphene Oxide for Removal of Pb(II), Hg(II) and Cu(II) in Water Treatment: Adsorption Mechanism and Separation Property.Chem. Eng. J.2015, 281, 1-10.https://doi.org/10.1016/j.cej.2015.06.043
[21] Hasanzadeh, R.; Moghadam, P.N.;Samadi, N.Synthesis and Application of Modified Poly (Styrene-alt-maleic anhydride) Networks as a Nano Chelating Resin for Uptake of Heavy Metal Ions.Polym. Adv. Technol. 2013, 24, 34-41.https://doi.org/10.1002/pat.3046
[22] Masoumi, A.;Ghaemy, M.Adsorption of Heavy Metal Ions and Azo Dyes by CrosslinkedNanochelating Resins Based onPoly(methylmethacrylate-co-maleic anhydride).Express. Polym. Lett.2014, 8, 187-196.https://doi.org/10.3144/expresspolymlett.2014.22
[23] Liu, Z.S.;Rempel, G.L.Removal of Transition Metals from Dilute Aqueous Solution by CarboxylicAcid Group Containing Absorbent Polymers.Hydrol. Curr. Res.2011,2,1.https://doi.org/10.4172/2157-7587.1000107
[24] Moghadam, P.N.;Hasanzadeh, R.;Khalafy,J.Preparation of SMA Functionalized Sulfanilic Acid Hydrogels and Investigation of their Metal Ions Adsorption Behavior.Iran. Polym. J.2013, 22, 133-142. https://doi.org/10.1007/s13726-012-0111-5
[25] Hosseinzadeh, M.Removalof Heavy Metal Ions fromAqueous Solutions UsingModifiedPoly(styrene-alt-maleicanhydride) Copolymer as a ChelatingResin.Russ. J. Appl. Chem. 2018,91, 1984-1993. https://doi.org/10.1134/S1070427218120108
[26] Hartman, W.W.; Dreger, E.E.A Publicationof Reliable MethodsforthePreparationofOrganic Compounds.Org. Synth. 1931, 11, 30. https://doi.org/10.15227/orgsyn.011.0030
[27] Hosseinzadeh, M.;Pesyan, N.N.;Moghadam, P.N. Synthesis and Characterization of PolymerMetal Chelates Derived from Poly(2,2,3,3-tetramethyleneaminecyclopropyl)phenyl Acrylate.Adv. Polym. Technol. 2018, 37, 461. https://doi.org/10.1002/adv.21685
[28] Kashani, E.; Pesyan, N.N.; Rashidnejad, H.;Marjani, A.;Asl, H.Y.Synthesis and Characterization of Novel Polymeric Organic–Inorganic Complex Framework Based on Sodium 2,4‑Dioxo‑6‑aryl‑3‑oxa‑bicyclo[3.1.0]hexane‑1,5‑dicarboxylate (SDAOBDC) with Three‑Dimensional Hybrid Networks.J. Iran.Chem. Soc.2017, 14,2143-2156.https://doi.org/10.1007/s13738-017-1151-8
[29] Henry, S.M.; El-Sayed, M.E.H.; Pirie, C.M.;Hoffman, A.S.; Stayton, P.S. pH-Responsive Poly(styrene-alt-maleic anhydride) Alkylamide Copolymers for Intracellular Drug Delivery.Biomacromolecules2006,7, 2407-2414.https://doi.org/10.1021/bm060143z
[30] Wang, C.-C.; Chang, C.-Y.; Chen, C.-Y.Study on Metal Ion Adsorption of Bifunctional Chelating/Ion-Exchange Resins.Macromol. Chem. Phys. 2001,202, 882-890. https://doi.org/10.1002/1521-3935(20010301)202:6%3C882::AID-MACP882%3E3.0.CO;2-K
[31]Chen, C.L.; Wang, X.K.;Nagatsu, M.Europium Adsorption on Multiwall Carbon Nanotube/Iron Oxide Magnetic Composite in the Presence ofPolyacrylic Acid.Environ. Sci. Technol.2009, 43, 2362-2367. https://doi.org/10.1021/es803018a
[32] Chen, C.; Hu, J.; Shao; Li, J.; Wang, X. Adsorption Behavior of Multiwall Carbon Nanotube/Iron Oxide Magnetic Composites for Ni(II) and Sr(II).J. Hazard. Mater.2009, 164, 923-928. https://doi.org/10.1016/j.jhazmat.2008.08.089
[33] Gomes, E.C.C.; de Sousa, A.; Vasconcelos, P.H.M.;Melo, D.Q.;Diógenes, I.C.N.;deSousa, E.H.S.;do Nascimento, R.F.;San Gil, R.A.S.;Longhinotti, E.Synthesis of Bifunctional Mesoporous Silica Spheres as Potential Adsorbent for Ions in Solution.Chem. Eng. J.2013, 214, 27-33. https://doi.org/10.1016/j.cej.2012.10.053
[34] Zhao, G.; Li, J.; Ren, X.;Chen, C.;Wang, X. Few-Layered Graphene Oxide Nanosheets As Superior Sorbents for Heavy Metal Ion Pollution Management. Environ. Sci. Technol. 2011, 45, 10454-10462. https://doi.org/10.1021/es203439v
[35] Huang, Y.; Keller, A.A.EDTA Functionalized Magnetic Nanoparticle Sorbents for Cadmium and Lead Contaminated Water Treatment. Water. Res.2015, 80, 159-168. https://doi.org/10.1016/j.watres.2015.05.011