Synthesis and Characterization of Terpolymer Adsorbents Using Photopolymerization: Investigation of Heavy Metal Adsorption Capacity

Öz

In this study, poly(allylphenol-co-methylmethacrylate-co-vinyl imidazole) (PAMV) terpolymer adsorbents were synthesized using the photopolymerization method with 1-vinyl imidazole, methyl methacrylate, and 2-allylphenol monomers. Structural and surface analyzes of PAMV polymers obtained using different mole ratios 1H-Nuclear Magnetic Resonance, Fourier-Transform Infrared Spectroscopy, X-Ray Photoelectron Spectroscopy, Scanning Electron Microscopy-Energy Dispersive X-Ray and thermal characterization were performed using Thermogravimetry methods. Inductively Coupled Plasma Mass Spectrometry was used for adsorption studies. Optimization studies were carried out at different pH values. According to the results obtained, the pH range in which adsorbents operate at maximum efficiency is between 6-10. Although many different metals have been studied, the holding capacity of the obtained polymeric adsorbent on cadmium, chromium and mercury metal ions is quite remarkable.

Anahtar Kelimeler

• terpolymers
• adsorption
• photopolymerization
• characterization

Destekleyen Kurum

Manisa Celal Bayar Üniversitesi

Proje Numarası

2021-110

Teşekkür

This work was supported by the Research Council of Manisa Celal Bayar University with the project number of 2021-110.

Kaynakça

1. Ahmed, S., Akhtar, N., Rahman, A., Mondal, N.C., Khurshid, S., Sarah, S., Khan, M.A.K., Kamboj, V. (2022) Evaluating groundwater pollution with emphasizing heavy metal hotspots in an urbanized alluvium watershed of Yamuna River, northern India. Environmental Nanotechnology, Monitoring and Management, 18, 100744.
2. Kumar, S., Prasad, S., Yadav, K.K., Shrivastava, M., Gupta, N., Nagar, S., Bach, Q., Kamyab, H., Khan, S., Yadav, S., Malav, L. (2019) Hazardous heavy metals contamination of vegetables and food chain: Role of sustainable remediation approaches-A review. Environmental Research, 179, 108792.
3. Islam, M.S., Ismail, Z., Jamal, M.H., Ibrahim, Z., Jumain, M., Islam, T. (2022) Heavy metals from different land use soil in the capital of ancient Pundranagar, Bangladesh: a preliminary study for ecological risk assessment. Chemistry and Ecology, 38 (8), 720-743.
4. Du, J., Zhang, B., Li, J., Lai, B. (2020) Decontamination of heavy metal complexes by advanced oxidation processes: A review. Chinese Chemical Letters, 31, 2575–2582.
5. Zheng, M., Sun, Z., Han, H., Zhang, Z., Ma, W. Xu, C. (2021) Enhanced coagulation coupled with heavy metal capturing for heavy metals removal from coal gasification brine and a novel mathematical model. Journal of Water Process Engineering, 40, 101954.
6. Gunarathne, V., Rajapaksha, A.U., Vithanage, M., Alessi, D.S., Selvasembian, R. Naushad, M., You, S., Oleszczuk, P., Ok, Y.S. (2022) Hydrometallurgical processes for heavy metals recovery from industrial sludges. Critical Reviews in Environmental Science and Technology, 52 (6), 1022-1062.
7. Zhang, Y., Duan, X. (2020) Chemical precipitation of heavy metals from wastewater by using the synthetical magnesium hydroxy carbonate. Water Science and Technology, 81 (6), 1130-1136.
8. Jia, L., Liu, H., Kong, Q., Li, M., Wu, S., Wu, H. (2020) Interactions of high-rate nitrate reduction and heavy metal mitigation in iron-carbon-based constructed wetlands for purifying contaminated groundwater. Water Research, 169, 115285.

9. Bashir, A., Malik, L.A., Ahad, S., Manzoor, T., Bhat, M.A., Dar, G.N., Pandith, A.N. (2019) Removal of heavy metal ions from aqueous system by ion exchange and biosorption methods. Environmental Chemistry Letters, 17, 729–754.
10. Saltan, F., Murat Saltan, G. (2022) Synthesis of a new adsorbent poly(allylisothiocyanate-co-hydroxyethylmethacrylate-co-vinylimidazole) via photopolymerization: Characterization and investigation of heavy metal adsorption capacity. Journal of Applied Polymer Science, 139, e52639.
11. Qiu, B., Tao, X., Wang, H., Li, W., Ding, X. Chu, H. (2021) Biochar as a low-cost adsorbent for aqueous heavy metal removal: A review. Journal of Analytical and Applied Pyrolysis, 155, 105081.
12. Sheth, Y., Dharaskar, S., Khalid, M., Sonawane, S. (2021) An environment friendly approach for heavy metal removal from industrial wastewater using chitosan based biosorbent: A review. Sustainable Energy Technologies and Assessments, 43, 100951.
13. Bhatt, R.R., Shah, B.A. (2015) Sorption studies of heavy metal ions by salicylic acid–formaldehyde–catechol terpolymeric resin: Isotherm, kinetic and thermodynamics. Arabian Journal of Chemistry, 8, 414–426.
14. Sidharaj, N., Rajarajan, G., Senthil, M., Velmurugan, G. (2022) Synthesis, characterization and applications: Novel terpolymer and its composite. Materials Today: Proceedings, 59, 309–315.
15. Velmurugan, G., Ahamed, K.R., Azarudeen, R.S. (2015) A novel comparative study: synthesis, characterization and thermal degradation kinetics of a terpolymer and its composite for the removal of heavy metals. Iranian Polymer Journal, 24, 229–242.
16. Azarudeen, R.S., Subha, R., Jeyakumar, D., Burkanudeen, A.R. (2013) Batch separation studies for the removal of heavy metal ions using a chelating terpolymer: Synthesis, characterization and isotherm models. Separation and Purification Technology, 116, 366–377.
17. Saltan, F. (2021) Preparation of poly(eugenol co methyl methacrylate)/polypropylene blend by creative route approach: structural and thermal characterization. Iranian Polymer Journal, 30, 1227–1236.
18. Soykan, U., Öztoprak, B. (2020) A Yield Study on Self-Initiated Photopolymerization of Acrylate Monomers Bearing Benzophenone Pendant Unit. Journal of New Results in Science, 9, 1-8.
19. Temel, G., Karaca, N., Arsu, N. (2010) Synthesis of Main Chain Polymeric Benzophenone Photoinitiator via Thiol-ene Click Chemistry and Its Use in Free Radical Polymerization. Journal of Polymer Science Part A-Polymer Chemistry, 48, 5306-5312.
20. Arasaretnam, S., Dilshani Jayarathna, U.P. (2020) Synthesis, Characterization, and Metal Adsorption Properties of Formaldehyde-Based Terpolymeric Resins Derived from Anthranilic Acid, Salicylic Acid, and Catechol. Journal of Chemistry, 2020, 8843162.
21. Pekel, N., Güven, O. (1999) Investigation of complex formation between poly(N-vinyl imidazole) and various metal ions using the molar ratio method. Colloid and Polymer Science, 277, 570-573.
22. Fujisawa, S., Atsumi, T., Kadoma, Y., Sakagami, H. (2002) Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity. Toxicology, 177 (1), 39-54.
23. Nenadis, N., Papapostolou, M., Tsimidou, M.Z. (2021) Suggestions on the Contribution of Methyl Eugenol and Eugenol to Bay Laurel (Laurus nobilis L.) Essential Oil Preservative Activity through Radical Scavenging. Molecules, 26, 2342.
24. Poljanšek, I., Krajnc, M. (2005) Characterization of Phenol-Formaldehyde Prepolymer Resins by In Line FT-IR Spectroscopy. Acta Chimica Slovenica, 52 (3), 238–244
25. Murugan, E., Jebaranjitham, J.N. (2012) Synthesis and characterization of silver nanoparticles supported on surface-modified poly(N-vinylimidazale) as catalysts for the reduction of 4-nitrophenol. Journal of Molecular Catalysis A: Chemical, 365, 128–135.
26. Wu, K.H., Tsai, C.W., Huang, W.C., Hung, W.C. (2021) Structural design and characterization of tricycloalkyl-containing methacrylate with methyl methacrylate copolymers. Materials Science and Engineering B, 267, 115088.
27. Farrokhi, M., Abdollahi, M. (2020) Enhancing medium/high temperature proton conductivity of poly (benzimidazole)-based proton exchange membrane via blending with poly (vinyl imidazole-co-vinyl phosphonic acid) copolymer: Proton conductivitycopolymer microstructure relationship. European Polymer Journal, 131, 109691.
28. Navarchian, A.H., Najafipoor, N., Ahangaran, F. (2019) Surface-modified poly(methyl methacrylate) microcapsules containing linseed oil for application in self-healing epoxy-based coatings. Progress in Organic Coatings, 132, 288-297.
29. Sanchez-Paniagua Lo´pez, M., Lo´pez-Cabarcos, E., Lo´pez Ruiz, B. (2009) Biosensors Based on Poly(vinylimidazole) Microparticles. Electroanalysis, 21 (3-5), 512–520.
30. Gonçalves, G., Paula Marques, A.A.P., Barros-Timmons, A., Bdkin, I., Singh, M.K., Emami, N., Gracio, J. (2010) Graphene oxide modified with PMMA via ATRP as a reinforcement filler. Journal of Materials Chemistry, 20, 9927-9934.
31. Camacho-Cruz, L.A., Velazco-Medel, M.A., Parra-Delgado, H., Bucio, E. (2021) Functionalization of cotton gauzes with poly(N-vinylimidazole) and quaternized poly(N-vinylimidazole) with gamma radiation to produce medical devices with pH-buffering and antimicrobial properties. Cellulose, 28, 3279–3294.
32. Acevedo, B., Martınez, F., Olea, F. (2013) Synthesıs, Thermal Behavıor, and Aggregatıon in Aqueous Solutıon of Poly(Methyl Methacrylate)-b-Poly(2-Hydroxyethyl Methacrylate). Journal of the Chilean Chemical Society, 58 (4), 2038-2042.
33. Liu, J., Li, R., Guo, M., Tao, H., Sun, D. Zong, C., Liu, C., Fu, F. (2017) Study of the thermal degradation of benzene-containing glycerol carbonate derivatives by a combined TG–FTIR and theoretical calculation. Thermochimica Acta, 654, 179-185.
34. Zhao, M., Cao, Y., Liu, X., Deng, J., Li, D. Gu, H. (2014) Effect of nitrogen atomic percentage on N+-bombarded MWCNTs in cytocompatibility and hemocompatibility. Nanoscale Research Letters, 9, 142.
35. Ranganathan, K., Morais, A., Nongwe, I., Longo, C., Nogueira, A.F. Coville, N.J. (2016) Study of photoelectrochemical water splitting using composite films based on TiO2 nanoparticles and nitrogen or boron doped hollow carbon spheres as photoanodes. Journal of Molecular Catalysis A: Chemical, 422, 165-174.
36. Gavrielides, A., Duguet, T., Esvan, J., Lacaze-Dufaure, C., Bagus, P.S. (2016) A poly-epoxy surface explored by Hartree-Fock #SCF simulations of C1s XPS spectra. The Journal of Chemical Physics, 145, 074703.
37. Culbertson, B.M., Post, L.K., Aulabaugh, A.E. (1983) Polymers derved from ally lephenol or substıtuted allylphenol and malec anhydrıde. United States Patent, 4, 388-451.
38. Mu, S., Liu, W., Zhao, L., Long, Y., Gu, H. (2019) Antimicrobial AgNPs composites of gelatin hydrogels crosslinked by ferrocene-containing tetrablock terpolymer. Polymer, 169, 80-94.
39. Cardenas-Peña, A.M., Ibanez, J.G., Vasquez-Medrano, R. (2012) Determination of the Point of Zero Charge for Electrocoagulation Precipitates from an Iron Anode. International Journal of Electrochemical Science, 7, 6142-6153.