Abstract
The solubilization laws of pollutants in micelles and their separation efficiency are very important in the successfully efficient application of micellar enhanced ultrafiltration (MEUF). The solubilization behavior of o-toluidine (OT) and tricyclazole (TC) into sodium dodecyl sulfate (SDS) micelles in MEUF was studied using nonlinear equation sets for concentration analysis, which resolved the issue on the overlap of absorption spectra of multicomponent compounds restricting the application of conventional ultraviolet (UV) spectroscopic method. The solubilization isotherms for both pollutants could be best explained by the Langmuir-Freudlich model (R2>0.99) followed by the modes of Langmuir and Freudlich, inferring the complexity of solubilization mechanism and solubilization advantage of monolayer over multilayer. The calculated thermodynamic parameters (ΔG0, ΔH0 and ΔS0) indicated that this process was endothermic and spontaneous. The solubilization of OT and TC well followed the pseudo second-order and pseudo first-order kinetics, respectively. The separation and recovery of SDS solubilizing these two pollutants were also investigated through lowering solution temperature to 2 °C followed by centrifugation. The best recovery rate of about 66% for SDS was achieved containing 10 and 5% of each initial amount of OT and TC, respectively, at near-neutral solution pH value. The recovery of SDS could decrease to some extent under alkaline and acidic conditions.
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References
Acero JL, Benitez FJ, Real FJ, Teva F (2017) Removal of emerging contaminants from secondary effluents by micellar-enhanced ultrafiltration. Sep Pur Technol 181:123–131
Aichour A, Zaghouane-Boudiaf H (2020) Single and competitive adsorption studies of two cationic dyes from aqueous mediums onto cellulose-based modified citrus peels/calcium alginate composite. Int J Biol Macromol 154:1227–1236
Arkhangelsky E, Kuzmenko D, Gitis V (2007) Impact of chemical cleaning on properties and functioning of polyethersulfone membranes. J Membrane Sci 305:176–184
Azarkan S, Peña A, Draoui K, Sainz-Díaz CI (2016) Adsorption of two fungicides on natural clays of morocco. Appl Clay Sci 23:37–46
Bahmani P, Maleki A, Rezaee R, Khamforoush M, Yetilmezsoy K, Athar SD, Gharibi F (2019a) Simultaneous removal of arsenate and nitrate from aqueous solutions using micellar-enhanced ultrafiltration process. J Water Process Eng 27:24–31
Bahmani P, Maleki A, Rezaee R, Mahvi AH, Khamforoush M, Athar SD, Daraei H, Gharibi F, McKay G (2019b) Arsenate removal from aqueous solutions using micellar-enhanced ultrafiltration. J Environ Health Sci Eng 17:115–127
Chen M, Shafer-Peltier K, Randtke SJ, Peltier E (2018) Modeling arsenic (V) removal from water by micellar enhanced ultrafiltration in the presence of competing anions. Chemosphere 213:285–294
Chen M, Jafvert CT, Wu Y, Cao X, Hankins NP (2020) Inorganic anion removal using micellar enhanced ultrafiltration (MEUF), modeling anion distribution and suggested improvements of MEUF: A review. Chem Eng J. https://doi.org/10.1016/j.cej.2020.125413
Childress AE, Elimelech M (2000) Relating nanofiltration membrane performance to membrane charge (electrokinetic) characteristics. Environ Sci Technol 34:3710–3716
Das C, Dasgupta S, De S (2008a) Simultaneous Separation of Mixture of Metal Ions and Aromatic Alcohol using Cross Flow Micellar-Enhanced Ultrafiltration and Recovery of Surfactant. Sep Sci Technol 43(1):71–92
Das C, Maity P, Dasgupta S, De S (2008b) Separation of cation–anion mixture using micellar-enhanced ultrafiltration in a mixed micellar system. Chem Eng J 144:35–41
Exall K, Balakrishnan VK, Toito J, McFadyen R (2013) Impact of selected wastewater constituents on the removal of sulfonamide antibiotics via ultrafiltration and micellar enhanced ultrafiltration. Sci Total Environ 461:371–376
Febrianto J, Kosasih AN, Sunarso J (2009) Equilibrium and kinetic studies in adsorption of heavy metals using biosorbent: A summary of recent studies. J Hazard Mater 162:616–645
Ghaedi M, Mazaheri H, Khodadoust S, Hajati S, Purkait MK (2015) Application of central composite design for simultaneous removal of methylene blue and Pb2+ ions by walnut wood activated carbon. Spectrochim Acta A 135:479–490
Gosetti F, Chiuminatto U, Mazzucco E, Mastroianni R, Bolfi B, Marengo E (2015) Ultra-high performance liquid chromatography tandem high-resolution mass spectrometry study of tricyclazole photodegradation products in water. Environ Sci Pollut Res 22:8288–8295
Huang JH, Zeng GM, Zhou CF, Li X, Shi LJ, He SB (2010) Adsorption of surfactant micelles and Cd2+/Zn2+ in micellar-enhanced ultrafiltration. J Hazard Mater 183:287–293
Huang J, Qi F, Zeng G, Shi L, Li X, Gu Y, Shi Y (2017) Repeating recovery and reuse of SDS micelles from MEUF retentate containing Cd2+ by acidification UF. Colloid Surface A 520:361–368
Huang J, Shi L, Zeng G, Li H, Huang H, Gu Y, Shi Y, Yi K, Li X (2019a) Removal of Cd(II) by micellar enhanced ultrafiltration: Role of SDS behaviors on membrane with low concentration. J Clean Prod 209:53–61
Huang J, Zhu L, Zeng G, Shi L, Shi Y, Yi K, Li X (2019b) Recovery of Cd(II) and surfactant in permeate from MEUF by foam fractionation with anionic-nonionic surfactant mixtures. Colloid Surface A 570:81–88
Innocenzi V, Tortora F, Prisciandaro M, Michelis ID, Vegliò F, Celso GMD (2018) Purification of residual leach liquors from hydrometallurgical process of NiMH spent batteries through micellar enhanced ultra filtration. J Environ Manag 215:377–384
Kim H, Baek K, Lee J, Iqbal J, Yang JW (2006) Comparison of separation methods of heavy metal from surfactant micellar solutions for the recovery of surfactant. Desalination 191:186–192
Kiso Y, Sugiura Y, Kitao T, Nishimura K (2001) Effects of hydrophobicity and molecular size on rejection of aromatic pesticides with nanofiltration membranes. J Membrane Sci 192:1–10
Lee SH, Shrestha S (2014) Application of micellar enhanced ultrafiltration (MEUF) process for zinc (II) removal in synthetic wastewater: Kinetics and two-parameter isotherm models. Int Biodeter Biodegr 95:241–250
Lin W, Zhang B, Ye X, Hawboldt K (2021) Sulfate removal using colloid-enhanced ultrafiltration: performance evaluation and adsorption studies. Environ Sci Pollut Res 28:5609–5624
Masomboon N, Chen CW, Jin A, Lu MC (2010) A statistical experimental design to determine o-toluidine degradation by the photo-Fenton process. Chem Eng J 159:116–122
Miller JN (1991) Basic statistical methods for Analytical Chemistry. Part 2. Calibration and regression methods. A review. Analyst 116:3–14
Ni YN (1988) Simultaneously spectrophotometric analysis of multicomponent systems-nonlinear equation set method. Chem J Chinese U 9:404–406 (In Chinese)
Padovani L, Capri E, Padovani C, Puglisi E, Trevisan M (2006) Monitoring tricyclazole residues in rice paddy watersheds. Chemosphere 62:303–314
Pargoletti E, Mostoni S, Rassu G, Pifferi V, Meroni D (2017) Zn-vs Bi-based oxides for o-toluidine photocatalytic treatment under solar light. Environ Sci Pollut Res 24:8287–8296
Phong TK, Dang TTN, Motobayashi T, Dang QT, Watanabe H (2009) Fate and transport of nursery-box-applied tricyclazole and imidacloprid in paddy fields. Water Air Soil Poll 202:3–12
Pinto HB, de Souza BM, Dezotti M (2018) Treatment of a pesticide industry wastewater mixture in a moving bed biofilm reactor followed by conventional and membrane processes for water reuse. J Clean Prod 201:1061–1070
Purkait MK, DasGupta S, De S (2005) Separation of aromatic alcohols using micellar-enhanced ultrafiltration and recovery of surfactant. J Membrane Sci 250:47–59
Qamruzzaman, Nasar A (2014) Degradation of tricyclazole by colloidal manganese dioxide in the absence and presence of surfactants. J Ind Eng Chem 20:897–902
Rodrigues RP, Licínio M, Gando-Ferreira QMJ (2020) Micellar enhanced ultrafiltration for the valorization of phenolic compounds and polysaccharides from winery wastewaters. J Water Process Eng. https://doi.org/10.1016/j.jwpe.2020.101565
Samal K, Das C, Mohanty K (2017) Application of saponin biosurfactant and its recovery in the MEUF process for removal of methyl violet from wastewater. J Environ Manage 203:8–16
Schwarze M, Chiappisi L, Prévost S, Gradzielski M (2014) Oleylethoxycarboxylate-An efficient surfactant for copper extraction and surfactant recycling via micellar enhanced ultrafiltration. J Colloid Interf Sci 421:184–190
Schwarze M, Schaefer L, Chiappisi L, Gradzielski M (2018) Micellar enhanced ultrafiltration (MEUF) of methylene blue with carboxylate surfactants. Sep Purif Technol 199:20–26
Verma SP, Sarkar B (2018) Simultaneous removal of Cd(II) and p-cresol from wastewater by micellar-enhanced ultrafiltration using rhamnolipid: flux decline, adsorption kinetics and isotherm studies. J Environ Manage 213:217–235
Verma SP, Sarkar B (2019) Use of rhamnolipid in micellar-enhanced ultrafiltration for simultaneous removal of Cd+2 and crystal violet from aqueous solution. Asia-Pac J Chem Eng. https://doi.org/10.1002/apj.2315
Víctor-Ortega MD, Martins RC, Gando-Ferreira LM, Quinta-Ferreira RM (2017) Recovery of phenolic compounds from wastewaters through micellar enhanced ultrafiltration. Colloid Surface A 531:18–24
Wu H, Shen J, Jiang X, Liu X, Sun X, Li J, Han W, Mu Y, Wang L (2018) Bioaugmentation potential of a newly isolated strain Sphingomonas sp. NJUST37 for the treatment of wastewater containing highly toxic and recalcitrant tricyclazole. Bioresource Technol 264:98–105
Wu P, Liu Y, Fu Y, Wang S, Wang H, Zhou J (2019) Separation and concentration of o–toluidine and tricyclazole from water with micellar enhanced ultrafiltration based on sodium dodecyl sulfate surfactant. Environ Technol. https://doi.org/10.1080/09593330.2019.1673826
Yi XS, Shi WX, Yu SL, Wang Y (2011) Isotherm and kinetic behavior of adsorption of anion polyacrylamide (APAM) from aqueous solution using two kinds of PVDF UF membranes. J Hazard Mater 189:495–501
Yue QY, Li Q, Gao BY, Wang Y (2007) Kinetics of adsorption of disperse dyes by polyepicholorohydrin-dimethylamine cationic polymer/bentonite. Sep Pur Technol 54:279–290
Zhang W, Tsang DCW, Lo IMC (2007) Removal of Pb and MDF from contaminated soils by EDTA- and SDS-enhanced washing. Chemosphere 66:2025–2034
Zhang W, Huang G, Wei J, Li H, Zheng R, Zhou Y (2012) Removal of phenol from synthetic waste water using Gemini micellar-enhanced ultrafiltration (GMEUF). J Hazard Mater 235-236:128–137
Funding
This work was financially supported by the grants from Science & Technology Department of Sichuan Province of China for the key research project (No. 2017SZ0175) and key special project (No. 2018SZDZX0026). Yiqing Liu acknowledgments the financial support from the Fundamental Research Funds for the Central Universities (No. 2682018CX32). The authors are also thankful to anonymous reviewers for their helpful suggestions.
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PW carried out the experiments, summarized the results and wrote the manuscript under the supervision of Dr. YL and Prof. YF. GZ and JD participated in preparing the experimental materials and finishing partly concentration tests of water quality. All authors read and approved the presented manuscript to be published.
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Wu, P., Liu, Y., Fu, Y. et al. Solubilization and separation of o-toluidine and tricyclazole in sodium dodecyl sulfate micelles in micellar enhanced ultrafiltration. Environ Sci Pollut Res 28, 42694–42705 (2021). https://doi.org/10.1007/s11356-021-13646-7
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DOI: https://doi.org/10.1007/s11356-021-13646-7