Skip to main content
Log in

Solubilization and separation of o-toluidine and tricyclazole in sodium dodecyl sulfate micelles in micellar enhanced ultrafiltration

  • Research Article
  • Published:
Environmental Science and Pollution Research Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

Data availability

All data generated or analyzed during this study are included in the presented article and its supplementary information files.

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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • Arkhangelsky E, Kuzmenko D, Gitis V (2007) Impact of chemical cleaning on properties and functioning of polyethersulfone membranes. J Membrane Sci 305:176–184

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • Miller JN (1991) Basic statistical methods for Analytical Chemistry. Part 2. Calibration and regression methods. A review. Analyst 116:3–14

    Article  CAS  Google Scholar 

  • Ni YN (1988) Simultaneously spectrophotometric analysis of multicomponent systems-nonlinear equation set method. Chem J Chinese U 9:404–406 (In Chinese)

    CAS  Google Scholar 

  • Padovani L, Capri E, Padovani C, Puglisi E, Trevisan M (2006) Monitoring tricyclazole residues in rice paddy watersheds. Chemosphere 62:303–314

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

Download references

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.

Author information

Authors and Affiliations

Authors

Contributions

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.

Corresponding authors

Correspondence to Yiqing Liu or Yongsheng Fu.

Ethics declarations

Ethics approval and consent to participate

Ethical approval

Not applicable

Consent to participate

Not applicable

Consent for publication

Not applicable

Competing interests

The authors declare that they have no competing interests.

Additional information

Responsible Editor: Tito Roberto Cadaval Jr

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

ESM 1

(DOCX 144 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

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

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11356-021-13646-7

Keywords

Navigation