Design of amino-functionalized chelated macroporous copolymer [poly(GMA-co-EGDMA)] for the sorption of Cu (II) ions

Ljiljana Suručić, Aleksandra B. Nestorović, Antonije E. Onjia, Goran Vilotija Janjić, Aleksandra Acika Rakić

Abstract


Polymer-based, highly porous nanocomposites with functionalized ligands attached to the core structure are extremely efficient in detection, removal and recovery of metals through the process of sorption. Quantum-chemical models can be helpful for sorption process analyses. The sorption of Cu(II) ion to amino-functionalized chelated macroporous copolymer [poly(GMA-co-EGDMA)-amine] and sorption selectivity of the subject copolymers: ethylenediamine (en), diethylenetriamine (deta) and triethyl­enetetramine (teta); were successfully modelled by quantum chemical calculations. Considering the crystal structures from CSD and experimental conditions during the formation of metal complexes, the most frequent mononuclear complexes are those with tetradentate teta ligand, while binuclear complexes are formed when the metal ion is in large excess. Although the en-copolymer was the most effective functionalized one, higher maximum sorption capacities (Qmax) were observed for deta- and teta-copolymers, due to their abilities to form binuclear complexes. The enthalpy term has the greatest contribution to the total Gibbs free energy of reaction for the formation of mononuclear Cu(II) complexes (ΔGaq), while solvation energy of the reaction has the greatest contribution in the formation of binuclear complexes. The results of the study indicate that small amines with the ability to form binuclear complex are the best choice for functionalization of the considered copolymer.


Keywords


sorption of metal ions; amino-functionalized copolymer; DFT modelling; coordination isomers; CSD

Full Text:

PDF (1,282 kB)

References


Z. L. He, X. E. Yang, P. J. Stoffella, J. Trace Elem. Med. Biol.19 (2005) 125 (https://doi.org/10.1016/j.jtemb.2005.02.010)

Q. Zhuang, G.Li, Z. Liu, Catena 170 (2018) 386 (https://doi.org/10.1016/j.catena.2018.06.037)

S. Deniz, N. Taşci, E. Yetimoğlu, M. Kahraman, J. Serb. Chem. Soc.82 (2017) 83(https://doi.org/10.2298/JSC180606085T)

A. S. Mohammed, A. Kapri, R. Goel, Heavy Metal Pollution: Source, Impact, and Remedies, Biomanagement of Metal-Contaminated Soils, Springer, Dordrecht, Netherlands, (2011) 1 (https://doi.org/10.1007/978-94-007-1914-9_1)

J. P. Kaware S. R. Dhokpande, IJESIT 2 (2013) 304

A. Azimi, A. Azari, M. Rezakazemi, M. Ansarpour, ChemBioEng Reviews 4 (2017) 37 (https://doi.org/10.1002/cben.201600010)

C. Santhosh,V.Velmurugan, G. Jacob, S. K. Jeong, A. N. Grace, A. Bhatnagar, Chem Eng J 306 (2016) 1116 (https://doi.org/10.1016/j.cej.2016.08.053)

D. T. Sun,L. Peng,W. S. Reeder, S. M. Moosavi, D. Tiana, D. K. Britt, E. Oveisi,W. L. Queen, ACS Cent Sci 4 (2018) 349 (https://doi.org/10.1021/acscentsci.7b00605)

G. Lofrano ,M. Carotenuto, G. Libralato, R. F. Domingos, A. Markus, L. Dini,R. K. Gautam, D. Baldantoni, M. Rossi,S. K. Sharma, M. C. Chattopadhyaya, M. Giugni,S. Meric, Water Res 92 (2016) 22 (https://doi.org/10.1016/j.watres.2016.01.033)

E. E. El Sayed, WSJ32 (2018) 32 (https://doi.org/10.1016/j.wsj.2018.02.001)

M. R. Awual, S. Suzuki,T. Taguchi, H. Shiwaku,Y. Okamoto,T. Yaita, Chem Eng J 242 (2014) 127 (https://doi.org/10.1016/j.cej.2013.12.072)

A. Shahat, M. R.Awual, M. Naushad, Chem Eng J 271 (2015) 155 (https://doi.org/10.1016/j.cej.2015.02.097)

M. R. Awual, M. M. Hasan, M. A. Khaleque, M. C. Sheikh, Chem Eng J 288 (2016) (https://doi.org/10.1016/j.cej.2015.11.108)

M. R. Awual, Chem Eng J 289 (2016) 65 (https://doi.org/10.1016/j.cej.2015.12.078)

M. R. Awual,Y. Miyazaki,T. Taguchi,H. Shiwaku,T. Yaita, Chem Eng J 291 (2016) 128 (https://doi.org/10.1016/j.cej.2016.01.109)

M. R. Awual, Chem Eng J 300 (2016) 264 (http://dx.doi.org/10.1016/j.cej.2016.04.071)

M. R. Awual, Chem Eng J 303 (2016) 539 (http://dx.doi.org/10.1016/j.cej.2016.06.040)

M. R. Awual, Chem Eng J 307 (2017) (http://dx.doi.org/10.1016/j.cej.2016.08.108)

M. R. Awual,T. Yaita,T. Taguchi, H. Shiwaku, S. Suzuki,Y. Okamoto, J Hazard Mater 278 (2014) 227 (http://dx.doi.org/10.1016/j.jhazmat.2014.06.011)

M. R. Awual, J Ind Eng Chem 20 (2014) 3493(http://dx.doi.org/10.1016/j.jiec.2013.12.040)

X. F. Tan,Y. G. Liu,Y. L. Gu,Y. Xu,G. M. Zeng,X. J. Hu,S. B. Liu,X. Wang,S. M. Liu,J. Li, Bioresour Technol 212 (2016) 318 (http://dx.doi.org/10.1016/j.biortech.2016.04.093)

S. H. Ho, S. Zhu,J. S. Chang, Bioresour Technol 246 (2017) 123 (http://dx.doi.org/10.1016/j.biortech.2017.08.061)

H. Li,X. Dong, E. B. da Silva, L. M. de Oliveira,Y. Chen,L. Q. Ma, Chemosphere 178 (2017) 466 (http://dx.doi.org/10.1016/j.chemosphere.2017.03.072)

D. Wei,B. Li,H. Huang, L. Luo, J. Zhang,Y. Yang, J. Guo, L. Tang, G. Zeng,Y. Zhou, Chemosphere 197 (2018) 165 (http://dx.doi.org/10.1016/j.chemosphere.2017.12.193)

R. Seth,S. Yang,S. Choi,M. Sabean,E. A. Roberts, Toxicol In Vitro 18 (2004) 501 (http://dx.doi.org/10.1016/j.tiv.2004.01.006)

C. G. Fraga, Mol.Aspects of Med. 26 (2005) 235 (http://dx.doi.org/10.1016/j.mam.2005.07.013)

R. Seth, S. Yang, S. Choi, M. Sabean, E. A. Roberts, Toxicology in vitro 18 (2004) 501 (https://doi.org/10.1016/j.tiv.2004.01.006)

J. Y. Uriu-Adams, C. L. Keen, Mol. Aspects Med.26 (2005) 268 (https://doi.org/10.1016/j.mam.2005.07.015)

S. A. Al-Saydeh, M. H. El-Naas, S. J. Zaidi, J. Ind.and Eng. Chem.56 (2017) 35 (https://doi.org/10.1016/j.jiec.2017.07.026)

M. R. Awual,T. Yaita,S. A. El-Safty,H. Shiwaku,S. Suzuki,Y. Okamoto, Chem Eng J 221 (2013) 322 (http://dx.doi.org/10.1016/j.cej.2013.02.016)

M. R. Awual, M. Ismael,T. Yaita,S. A. El-Safty,H. Shiwaku,Y. Okamoto, S. Suzuki, Chem Eng J 222 (2013) 67 (http://dx.doi.org/10.1016/j.cej.2013.02.042)

M. R. Awual, I. M. M. Rahman,T. Yaita, M. A. Khaleque, M. Ferdows, Chem Eng J 236 (2014) 100 (http://dx.doi.org/10.1016/j.cej.2013.09.083)

M. R. Awual, Chem Eng J 266 (2015) 368 (http://dx.doi.org/10.1016/j.cej.2014.12.094)

M. R. Awual, G. E. Eldesoky,T. Yaita, M. Naushad, H. Shiwaku, Z. A. Al Othman, S.Suzuki, Chem Eng J 279 (2015) 639 (http://dx.doi.org/10.1016/j.cej.2015.05.049)

M. R. Awual, Chem Eng J 307 (2017) 85 (http://dx.doi.org/10.1016/j.cej.2016.07.110)

M. R. Awual, M. Ismael, M.A. Khaleque,T. Yaita, J Ind Eng Chem 20 (2014) 2332 (http://dx.doi.org/10.1016/j.jiec.2013.10.009)

S. A. El-Safty, M. A. Shenashen, M. Ismael, M. Khairy, M. R. Awual, Microporous Mesoporous Mater 166 (2013) 195 (http://dx.doi.org/10.1016/j.micromeso.2012.03.021)

M. R. Awual,T.Yaita,Y. Okamoto, Sens Actuators B Chem 203 (2014) 71 (http://dx.doi.org/10.1016/j.snb.2014.06.088)

M. R. Awual, M. M. Hasan, Sens Actuators B Chem 206 (2015) 692 (http://dx.doi.org/10.1016/j.snb.2014.09.086)

A. S. Mohammed, A. Kapri, R. Goel, Heavy Metal Pollution: Source, Impact, and Remedies, Biomanagement of Metal-Contaminated Soils, Springer, Dordrecht, Netherlands, 2011 (https://doi.org/10.1007/978-94-007-1914-9_1)

C. Chen, C. Chiang, C. Chen,Sep. Purif. Technol.54 (2007) 396 (https://doi.org/10.1016/j.seppur.2006.10.020)

L. Malović, A. Nastasović, Z. Sandić, J. Marković, D. Đorđević,Z. Vuković, J. Mater. Sci.42 (2007) 3326 (https://doi.org/10.1007/s10853-006-0958-y)

Z. P. Sandić, A. B. Nastasović, Hem. Ind.63 (2009) 269 (https://doi.org/10.2298/HEMIND0903269S)

M. T. Gokmen, F. E. Du Prez, Prog. Polym. Sci.37 (2012) 365 (https://doi.org/10.1016/j.progpolymsci.2011.07.006)

B. M. Marković, Z. M. Vuković, V. V. Spasojević, V. B. Kusigerski, V. B. Pavlović, A. E. Onjia, A. B. Nastasović, J. Alloys Compd.705 (2017) 38 (https://doi.org/10.1016/j.jallcom.2017.02.108)

A. Nastasović, S. Jovanović, D. Đorđević, A. Onjia, D. Jakovljević,T. Novaković, Reac. Funct. Polym.58 (2004) 139 (https://doi.org/10.1016/j.reactfunctpolym.2003.11.015)

A. Nastasović, Z. Sandić, L. Suručić, D. Maksin, D. Jakovljević, A. Onjia, J. Hazard. Mater.171 (2009) 153 (https://doi.org/10.1016/j.jhazmat.2009.05.116)

A. Borowiak-Resterna, R. Cierpiszewski, K. Prochaska, J. Hazard. Mater.179 (2010) 828 (https://doi.org/10.1016/j.jhazmat.2010.03.078)

P. M. van Berkel, M. Punt, G. J. A. A. Koolhaas, W. L. Driessen, J. Reedijk, D. C. Sherrington, React. Funct. Polym.32 (1997) 139 (https://doi.org/10.1016/S1381-5148(96)00077-6)

D. D. Maksin, A. B. Nastasović, A. D. Milutinović-Nikolić, L. T. Suručić, Z. P. Sandić, R. V. Hercigonja, A. E. Onjia, J. Hazard. Mater.209-210 (2012) 99 (https://doi.org/10.1016/j.jhazmat.2011.12.079)

F. H. Allen, ActaCrystallogr. Sect. B Struct. Sci.58 (2002) 380 (https://doi.org/10.1107/S0108768102003890)

M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09 (Gaussian, Inc., Wallingford CT, 2009)

V. M. Nurchi, G. Crisponi, M. Crespo-Alonso, J. I. Lachowicz, Z. Szewczuk, G. J. Cooper, Dalton T. 42(2013) 6161 (https://doi.org/10.1039/C2DT32252H)




DOI: https://doi.org/10.2298/JSC190125031S

Copyright (c) 2019 J. Serb. Chem. Soc.

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

IMPACT FACTOR 0.828 (140 of 172 journals)
5 Year Impact Factor 0.917 (140 of 172 journals)