Abstract
Polyethersulphone (PES) membranes modified with urethane functional groups were prepared through an interfacial reaction using electron beam irradiation. The removal of eight endocrine disrupting chemicals (EDCs) was studied using both pristine and functionalized PES membranes. The prepared membranes underwent characterization using several techniques, including attenuated total reflectance-Fourier transform infrared (ATR-FTIR) spectroscopy, scanning electron microscopy, contact angle analysis, and measurements of pure water flux. Furthermore, dynamic adsorption experiments were conducted to evaluate the adsorption mechanism of the prepared membrane toward the eight EDCs. The urethane functionalized membranes were hydrophilic (52° contact angle) and maintained a high permeate flux (26000 L/h m2 bar) throughout the filtration process. Dynamic adsorption results demonstrated that the introduction of urethane functional groups on the membranes significantly enhanced the removal efficiency of 17β-estradiol, estriol, bisphenol A, estrone, ethinylestradiol, and equilin. The adsorption loading of 17β-estradiol on the functionalized PES membrane was 6.7 ± 0.7 mg/m2, exhibiting a 5-fold increase compared to the unmodified PES membrane. The membranes were successfully regenerated and reused for three adsorption cycles without experiencing any loss of adsorption capacity.
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References
Akindoyo J O, Beg M D H, Ghazali S, Islam M R, Jeyaratnam N, Yuvaraj A R (2016). Polyurethane types, synthesis and applications: a review. RSC Advances, 6(115): 114453–114482
Ameri E, Sadeghi M, Zarei N, Pournaghshband A (2015). Enhancement of the gas separation properties of polyurethane membranes by alumina nanoparticles. Journal of Membrane Science, 479: 11–19
Azizi D, Arif A, Blair D, Dionne J, Filion Y, Ouarda Y, Pazmino A G, Pulicharla R, Rilstone V, Tiwari B, et al. (2022). A comprehensive review on current technologies for removal of endocrine disrupting chemicals from wastewaters. Environmental Research, 207: 112196
Bandyopadhyay P, Park W B, Layek R K, Uddin M E, Kim N H, Kim H G, Lee J H (2016). Hexylamine functionalized reduced graphene oxide/polyurethane nanocomposite-coated nylon for enhanced hydrogen gas barrier film. Journal of Membrane Science, 500: 106–114
Belgiorno V, Rizzo L, Fatta D, Della Rocca C, Lofrano G, Nikolaou A, Naddeo V, Meric S (2007). Review on endocrine disrupting-emerging compounds in urban wastewater: occurrence and removal by photocatalysis and ultrasonic irradiation for wastewater reuse. Desalination, 215(1–3): 166–176
Breite D, Went M, Prager A, Kühnert M, Schulze A (2020). Reduction of biofouling of a microfiltration membrane using amide functionalities-hydrophilization without changes in morphology. Polymers, 12(6): 1379
Cecen F, Aktaş Ö (2011). Activated Carbon for Water and Wastewater Treatment: Integration of Adsorption and Biological Treatment. Washington, DC: Wiley-VCH Verlag GmbH & Co. KGaA
Comerton A M, Andrews R C, Bagley D M, Yang P (2007). Membrane adsorption of endocrine disrupting compounds and pharmaceutically active compounds. Journal of Membrane Science, 303(1–2): 267–277
Das R, Kuehnert M, Sadat Kazemi A, Abdi Y, Schulze A (2019). Water softening using a light-responsive, spiropyran-modified nanofiltration membrane. Polymers, 11(2): 344
Dolar D, Drašinac N, Košutić K, Škorić I, Ašperger D (2017). Adsorption of hydrophilic and hydrophobic pharmaceuticals on RO/NF membranes: identification of interactions using FTIR. Journal of Applied Polymer Science, 134(5): 44426
Han J, Meng S, Dong Y, Hu J, Gao W (2013). Capturing hormones and bisphenol A from water via sustained hydrogen bond driven sorption in polyamide microfiltration membranes. Water Research, 47(1): 197–208
Hao S, Jia Z, Wen J, Li S, Peng W, Huang R, Xu X (2021). Progress in adsorptive membranes for separation: a review. Separation and Purification Technology, 255: 117772
Jin X, Hu J, Ong S L (2007). Influence of dissolved organic matter on estrone removal by NF membranes and the role of their structures. Water Research, 41(14): 3077–3088
Khoo Y S, Goh P S, Lau W J, Ismail A F, Abdullah M S, Mohd Ghazali N H, Yahaya N K E M, Hashim N, Othman A R, Mohammed A, et al. (2022). Removal of emerging organic micropollutants via modified-reverse osmosis/nanofiltration membranes: a review. Chemosphere, 305: 135151
Kim I, Yu Z, Xiao B, Huang W (2007). Sorption of male hormones by soils and sediments. Environmental Toxicology and Chemistry, 26(2): 264–270
Kim S, Chu K H, Al-Hamadani Y A J, Park C M, Jang M, Kim D H, Yu M, Heo J, Yoon Y (2018). Removal of contaminants of emerging concern by membranes in water and wastewater: a review. Chemical Engineering Journal, 335: 896–914
Koloti L E, Gule N P, Arotiba O A, Malinga S P (2018). Laccase-immobilized dendritic nanofibrous membranes as a novel approach towards the removal of bisphenol A. Environmental Technology, 39(3): 392–404
Król P, Król B (2020). Structures, properties and applications of the polyurethane ionomers. Journal of Materials Science, 55(1): 73–87
Lin D, Xing B (2008). Adsorption of phenolic compounds by carbon nanotubes: role of aromaticity and substitution of hydroxyl groups. Environmental Science & Technology, 42(19): 7254–7259
Liu Y L, Wang X M, Yang H W, Xie Y F (2018). Adsorption of pharmaceuticals onto isolated polyamide active layer of NF/RO membranes. Chemosphere, 200: 36–47
Mahdavi H, Razmi F, Shahalizade T (2016). Polyurethane TFC nanofiltration membranes based on interfacial polymerization of poly(bis-MPA) and MDI on the polyethersulfone support. Separation and Purification Technology, 162: 37–44
Mansor N A, Tay K S (2020). Potential toxic effects of chlorination and UV/chlorination in the treatment of hydrochlorothiazide in the water. Science of the Total Environment, 714: 136745
McCallum E A, Hyung H, Do T A, Huang C H, Kim J H (2008). Adsorption, desorption, and steady-state removal of 17β-estradiol by nanofiltration membranes. Journal of Membrane Science, 319(1–2): 38–43
Miller D J, Dreyer D R, Bielawski C W, Paul D R, Freeman B D (2017). Surface modification of water purification membranes. Angewandte Chemie International Edition, 56(17): 4662–4711
Muhamad M S, Salim M R, Lau W J, Hadibarata T, Yusop Z (2016). Removal of bisphenol A by adsorption mechanism using PES-SiO2 composite membranes. Environmental Technology, 37(15): 1959–1969
Nghiem L D, Schäfer A I (2002). Adsorption and transport of trace contaminant estrone in NF/RO membranes. Environmental Engineering Science, 19(6): 441–451
Nguyen M N, Hérvas-Martínez R, Schäfer A I (2021). Organic matter interference with steroid hormone removal by single-walled carbon nanotubes-ultrafiltration composite membrane. Water Research, 199:117148
Niavarani Z, Breite D, Prager A, Abel B, Schulze A (2021). Estradiol removal by adsorptive coating of a microfiltration membrane. Membranes, 11(2): 99
Niedergall K, Bach M, Hirth T, Tovar G E M, Schiestel T (2014). Removal of micropollutants from water by nanocomposite membrane adsorbers. Separation and Purification Technology, 131: 60–68
Pironti C, Ricciardi M, Proto A, Bianco P M, Montano L, Motta O (2021). Endocrine-disrupting compounds: an overview on their occurrence in the aquatic environment and human exposure. Water, 13(10): 1347
Rana D, Narbaitz R M, Garand-Sheridan A M, Westgate A, Matsuura T, Tabe S, Jasim S Y (2014). Development of novel charged surface modifying macromolecule blended PES membranes to remove EDCs and PPCPs from drinking water sources. Journal of Materials Chemistry. A, Materials for Energy and Sustainability, 2(26): 10059–10072
Rao A, Kumar A, Dhodapkar R, Pal S (2021). Adsorption of five emerging contaminants on activated carbon from aqueous medium: kinetic characteristics and computational modeling for plausible mechanism. Environmental Science and Pollution Research International, 28(17): 21347–21358
Elakkiya S, Arthanareeswaran G, Das D B (2021). Embedding low–cost 1D and 2D iron pillared nanoclay to enhance the stability of polyethersulfone membranes for the removal of bisphenol A from water. Separation and Purification Technology, 266: 118560
Schäfer A I, Akanyeti I, Semião A J (2011). Micropollutant sorption to membrane polymers: a review of mechanisms for estrogens. Advances in Colloid and Interface Science, 164(1–2): 100–117
Schmidt M, Zahn S, Gehlhaar F, Prager A, Griebel J, Kahnt A, Knolle W, Konieczny R, Gläser R, Schulze A (2021). Radiation-induced graft immobilization (RIGI): covalent binding of non-vinyl compounds on polymer membranes. Polymers, 13(11): 1849
Schmitt A, Mendret J, Roustan M, Brosillon S (2020). Ozonation using hollow fiber contactor technology and its perspectives for micropollutants removal in water: a review. Science of the Total Environment, 729: 138664
Schulze A, Breite D, Kim Y, Schmidt M, Thomas I, Went M, Fischer K, Prager A (2017). Bio-inspired polymer membrane surface cleaning. Polymers, 9(3): 97
Shin M G, Choi W, Park S J, Jeon S, Hong S, Lee J H (2022). Critical review and comprehensive analysis of trace organic compound (TOrC) removal with polyamide RO/NF membranes: mechanisms and materials. Chemical Engineering Journal, 427: 130957
Star A, Han T R, Gabriel J C P, Bradley K, Grüner G (2003). Interaction of aromatic compounds with carbon nanotubes: correlation to the hammett parameter of the substituent and measured carbon nanotube FET response. Nano Letters, 3(10): 1421–1423
Tirouni I, Sadeghi M, Pakizeh M (2015). Separation of C3H8 and C2H6 from CH4 in polyurethane–zeolite 4Å and ZSM-5 mixed matrix membranes. Separation and Purification Technology, 141: 394–402
Trellu C, Oturan N, Keita F K, Fourdrin C, Pechaud Y, Oturan M A (2018). Regeneration of activated carbon fiber by the electro-fenton process. Environmental Science & Technology, 52(13): 7450–7457
Wang P, Wong Y S, Tam N F Y (2017). Green microalgae in removal and biotransformation of estradiol and ethinylestradiol. Journal of Applied Phycology, 29(1): 263–273
Wu Y, Chen M, Lee H J, Ganzoury M A, Zhang N, de Lannoy C F (2022). Nanocomposite polymeric membranes for organic micropollutant removal: a critical review. ACS ES&T Engineering, 2(9): 1574–1598
Yasir M, Asabuwa Ngwabebhoh F, Šopík T, Ali H, Sedlařík V (2022). Electrospun polyurethane nanofibers coated with polyaniline/poly-vinyl alcohol as ultrafiltration membranes for the removal of ethinylestradiol hormone micropollutant from aqueous phase. Journal of Environmental Chemical Engineering, 10(3): 107811
Yilmaz B, Terekeci H, Sandal S, Kelestimur F (2020). Endocrine disrupting chemicals: exposure, effects on human health, mechanism of action, models for testing and strategies for prevention. Reviews in Endocrine & Metabolic Disorders, 21(1): 127–147
Yoon Y, Westerhoff P, Snyder S A, Wert E C (2006). Nanofiltration and ultrafiltration of endocrine disrupting compounds, pharmaceuticals and personal care products. Journal of Membrane Science, 270(1–2): 88–100
Yoon Y, Westerhoff P, Snyder S A, Wert E C, Yoon J (2007). Removal of endocrine disrupting compounds and pharmaceuticals by nanofiltration and ultrafiltration membranes. Desalination, 202(1–3): 16–23
Zhang D, Liu W, Wang S, Zhao J, Xu S, Yao H, Wang H, Bai L, Wang Y, Gu H, et al. (2022). Risk assessments of emerging contaminants in various waters and changes of microbial diversity in sediments from Yangtze River chemical contiguous zone, Eastern China. Science of the Total Environment, 803: 149982
Zia K M, Anjum S, Zuber M, Mujahid M, Jamil T (2014). Synthesis and molecular characterization of chitosan based polyurethane elastomers using aromatic diisocyanate. International Journal of Biological Macromolecules, 66: 26–32
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Highlights
• Urethane functionalities created on PES membranes via electron beam irradiation.
• Water contact angle decreased from 58° to 52°, higher hydrophilicity.
• 13% increase in water permeability via functionalization.
• 17β-estradiol adsorption enhanced by five times.
• Functionalized membranes reused for three cycles without a loss of adsorption capacity.
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Removal of endocrine disrupting chemicals from water through urethane functionalization of microfiltration membranes via electron beam irradiation
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Niavarani, Z., Breite, D., Yasir, M. et al. Removal of endocrine disrupting chemicals from water through urethane functionalization of microfiltration membranes via electron beam irradiation. Front. Environ. Sci. Eng. 18, 45 (2024). https://doi.org/10.1007/s11783-024-1805-6
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DOI: https://doi.org/10.1007/s11783-024-1805-6