Abstract
Alkylphenols and alkylphenol polyethoxylates are emerging hazardous contaminants due in particular to their endocrine-disrupting properties. These compounds originate from consumer products such as paints and latex paints, adhesives, inks, formulation of pesticides, paper industry, textile and leather industry, petroleum recovery chemicals, metal working fluids, personal care products, washing agents, cleaners, and detergents. Since classical wastewater treatments have not been designed to remove alkylphenols, these compounds end up polluting ecosystems. Here we review three advanced methods to remove alkylphenols and derivatives. First, innovative polymers, such as cyclodextrin polymers and molecularly imprinted polymers, allow to remove alkylphenols from effluents by adsorption. Second, biotechnologies such as microalgae, biodegradation in constructed wetlands and sequential anaerobic–aerobic digestion treatments. Third, advanced oxidation processes to degrade recalcitrant alkylphenols, e.g., ozone-carbon coupling, electrochemical degradation, photocatalysis, zero-valent iron-activated persulfate coupling, and catalytic ozonation.
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References
Abdel-Raouf N, Al-Homaidan AA, Ibraheem IBM (2012) Microalgae and wastewater treatment. Saudi J Biol Sci 19:257–275. https://doi.org/10.1016/j.sjbs.2012.04.005
Adams CD, Spitzer S, Cowan RM (1996) Biodegradation of nonionic surfactants and effects of oxidative pretreatment. J Environ Eng 122:477–483. https://doi.org/10.1061/(ASCE)0733-9372(1996)122:6(477)
Ahmadpanah K, Soltani M, Islami HR, Shamsaie M (2019) Effects of nonylphenol on hematological parameters and immune responses in immature rainbow trout (Oncorhynchus mykiss). Mar Freshw Behav Physiol 52:151–165. https://doi.org/10.1080/10236244.2019.1661779
Alexander C, Andersson HS, Andersson LI, Ansell RJ, Kirsch N, Nicholls IA, O’Mahony J, Whitcombe MJ (2006) Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003. J Mol Recognit 19:106–180
Alvarez PM, Garcia-Araya JF, Beltran FJ, Giraldes I, Jaramillo J, Gomez-Serrano V (2006) The influence of various factors on aqueous ozone decomposition by granular activated carbons and the development of a mechanistic approach. Carbon 44:3102–3112. https://doi.org/10.1016/j.carbon.2006.03.016
Alvarez-Lorenzo C, Concheiro A (2013) Handbook of molecularly imprinted polymers. Smithers Rapra Technology Ltd., Shawburry
Alvarino T, Komesli O, Suarez S, Lema JM, Omil F (2016) The potential of the innovative SeMPAC process for enhancing the removal of recalcitrant organic micropollutants. J Hazard Mater 308:29–36. https://doi.org/10.1016/j.jhazmat.2016.01.040
Ameta R, Benjamin S, Ameta A, Ameta SC (2012) Photocatalytic degradation of organic pollutants: a review. Mater Sci Forum. https://doi.org/10.4028/www.scientific.net/MSF.734.247
Anandan S, Lee G, Yang C, Ashokkumar M, Wu JJ (2012) Sonochemical synthesis of Bi2CuO4 nanoparticles for catalytic degradation of nonylphenol ethoxylate. Chem Eng J 183:46–52. https://doi.org/10.1016/j.cej.2011.12.018
Armijos-Alcocer KG, Espinoza-Montero PJ, Frontana-Uribe BA, Barrera-Diaz CE, Nevarez-Martinez MC, Fierro-Naranjo GC (2017) Electrochemical degradation of nonylphenol ethoxylate-7 (NP7EO) Using a diaclean (R) cell equipped with boron-doped diamond electrodes (BDD). Water Air Soil Pollut 228:289. https://doi.org/10.1007/s11270-017-3471-9
Arslan-Alaton I, Teksoy S (2007) Acid dyebath effluent pretreatment using Fenton’s reagent: process optimization, reaction kinetics and effects on acute toxicity. Dyes Pigments 73:31–39. https://doi.org/10.1016/j.dyepig.2005.09.027
Bagheri AR, Aramesh N, Khan AA, Gul I, Ghotekar S, Bilal M (2021) Molecularly imprinted polymers-based adsorption and photocatalytic approaches for mitigation of environmentally-hazardous pollutants - A review. J Environ Chem Eng 9:104879. https://doi.org/10.1016/j.jece.2020.104879
Baig S, Hansmann G, Paolini B (2008) Ozone oxidation of oestrogenic active substances in wastewater and drinking water. Water Sci Technol 58:451–458. https://doi.org/10.2166/wst.2008.665
Balarama Krishna MV, Chandrasekaran K, Karunasagar D, Arunachalam J (2001) A combined treatment approach using Fenton’s reagent and zero valent iron for the removal of arsenic from drinking water. J Hazard Mater 84:229–240. https://doi.org/10.1016/S0304-3894(01)00205-9
Barbosa PFP, Cumba LR, Andrade RDA, do Carmo DR, (2019) Chemical modifications of cyclodextrin and chitosan for biological and environmental applications: metals and organic pollutants adsorption and removal. J Polymers Environ 27:1352–1366. https://doi.org/10.1007/s10924-019-01434-x
Barrera-Díaz CE, Frontana-Uribe BA, Rodríguez-Peña M, Gomez-Palma JC, Bilyeu B (2018) Integrated advanced oxidation process, ozonation-electrodegradation treatments, for nonylphenol removal in batch and continuous reactor. Catal Today 305:108–116. https://doi.org/10.1016/j.cattod.2017.09.003
Barrera H, Roa-Morales G, Balderas-Hernandez P, Barrera-Díaz CE, Frontana-Uribe BA (2019) Catalytic effect of hydrogen peroxide in electrochemical treatment of phenolic pollutants using BDD anode. Chem Electro Chem. https://doi.org/10.1002/celc.201900174
Barrera H, Ureña-Nuñez F, Barrios JA, Becerril E, Frontana-Uribe BA, Barrera-Díaz CE (2021) Degradation of nonylphenol ethoxylate 10 (NP10EO) in a synthetic aqueous solution using a combined treatment: electrooxidation-gamma irradiation. Fuel 283:118929. https://doi.org/10.1016/j.fuel.2020.118929
Barrios JA, Becerril E, De León C, Barrera-Díaz C, Jiménez B (2015) Electrooxidation treatment for removal of emerging pollutants in wastewater sludge. Fuel 149:26–33. https://doi.org/10.1016/j.fuel.2014.10.055
Barrios JA, Cano A, Becerril JE, Jiménez B (2016) Influence of solids on the removal of emerging pollutants in electrooxidation of municipal sludge with boron-doped diamond electrodes. J Electroanal Chem 776:148–151. https://doi.org/10.1016/j.jelechem.2016.07.018
Basile T, Petrella A, Petrella M, Boghetich G, Petruzzelli V, Colasuonno S, Petruzzelli D (2011) Review of endocrine-disrupting-compound removal technologies in water and wastewater treatment plants: an EU perspective. Ind Eng Chem Res 50:8389–8401. https://doi.org/10.1021/ie101919v
BelBruno JJ (2019) Molecularly imprinted polymers. Chem Rev 119:94–119. https://doi.org/10.1021/acs.chemrev.8b00171
Bergendahl JA, Thies TP (2004) Fenton’s oxidation of MTBE with zero-valent iron. Water Res 38:327–334. https://doi.org/10.1016/j.watres.2003.10.003
Bertanza G, Pedrazzani R, Papa M, Mazzoleni G, Steimberg N, Caimi L, Montani C, Dilorenzo D (2010) Removal of BPA and NPnEOs from secondary effluents of municipal WWTPs by means of ozonation. Ozone Sci Eng 32:204–208. https://doi.org/10.1080/01919511003795303
Biris-Dorhoi ES, Tofana M, Mihaiescu T, Mihaiescu R, Odagiu A (2016) Applications of microalgae in wastewater treatments: a review. Pro Environment 9:459–463
Bodzek M (2019) Membrane separation techniques removal of inorganic and organic admixtures and impurities from water environment review. Arch Environ Protection 45:4–19. https://doi.org/10.24425/aep.2019.130237
Böhler M, Fleiner J, McArdell CS, Teichler R, Siegrist H, Kiene C, Langer M, Wunderlin P (2017) Projekt ReTreat. Untersuchungen zu verfahren für die biologische nachbehandlung nach ozonung. Aqua Gas 5:54–63
Bokare AD, Choi W (2014) Review of iron-free Fenton-like systems for activating H2O2 in advanced oxidation processes. J Hazard Mater 275:121–135. https://doi.org/10.1016/j.jhazmat.2014.04.054
Bonenfant D, Niquette P, Mimeault M, Furtos-Matei A, Hausler R (2009) UV-Vis and FTIR spectroscopic analyses of inclusion complexes of nonylphenol and nonylphenol ethoxylate with β-cyclodextrin. Water Res 43:3575–3581. https://doi.org/10.1016/j.watres.2009.05.010
Bonenfant D, Niquette P, Mimeault M, Hausler R (2010) Adsorption and recovery of nonylphenol ethoxylate on a crosslinked β-cyclodextrin-carboxymethylcellulose polymer. Water Sci Technol 61:2293–2301. https://doi.org/10.2166/wst.2010.152
Bonenfant D, Niquette P, Mimeault M, Hausler R (2012) Adsorption study of a commonly used antidepressant drug, fluoxetine hydrochloride, onto a crosslinked β-cyclodextrin-carboxymethylcellulose polymer. Water Sci Technol 66:224–220. https://doi.org/10.2166/wst.2012.112
Bourgin M, Beck B, Boehler M, Borowska E, Fleiner J, Salhi E, Teichler R, von Gunten U, Siegrist H, McArdell CS (2018) Evaluation of a full-scale wastewater treatment plant upgraded with ozonation and biological post-treatments: abatement of micropollutants, formation of transformation products and oxidation by-products. Water Res 129:486–498. https://doi.org/10.1016/j.watres.2017.10.036
Bozyiğit GD, Ayyıldız MF, Chormey DS, Turan NB, Kapukıran F, Engin GO, Bakırdere S (2022) Removal of selected pesticides, alkylphenols, hormones and bisphenol A from domestic wastewater by electrooxidation process. Water Sci Technol 85:220. https://doi.org/10.2166/wst.2021.63
Braguglia CM, Coors A, Gallipoli A, Gianico A, Guillon E, Kunkel U, Mascolo G, Richter E, Ternes TA, Tomei MC, Mininni G (2015) Quality assessment of digested sludges produced by advanced stabilization processes. Environ Sci Pollut Res 22:7216–7235. https://doi.org/10.1007/s11356-014-3090-6
Bremner DH, Burgess AE, Houllemare D, Namkung KC (2006) Phenol degradation by using hydroxyl radicals generated from zero-valence iron and hydrogen peroxide. Appl Catal B 63:15–19. https://doi.org/10.1016/j.apcatb.2005.09.005
Brinker CJ, Scherer GW (1990) Sol-gel science: the physics and chemistry of sol-gel processing. New York: Academic Press, Doi: https://doi.org/10.1016/C2009-0-22386-5
Cantarella M, Carroccio S, Dattilo S, Avolio R, Castaldo R, Puglisi C, Privitera V (2019) Molecularly imprinted polymer for selective adsorption of diclofenac from contaminated water. Chem Eng J 367:180–188. https://doi.org/10.1016/j.cej.2019.02.146
Cantarella M, Impellizzeri G, Privitera V (2017) Functional nanomaterials for water purification. Rivista Nuovo Cimento 40:595–632
Cases V, Alonso V, Argandoña V, Rodriguez M, Prats D (2011) Endocrine disrupting compounds: a comparison of removal between conventional activated sludge and membrane bioreactors. Des 272:240–245. https://doi.org/10.1016/j.desal.2011.01.026
Castro J, Paz S, Mena N, Urresta J, Machuca-Martinez F (2019) Evaluation of heterogeneous catalytic ozonation process for diclofenac degradation in solutions synthetically prepared. Environ Sci Pollut Res 26:4488–4497. https://doi.org/10.1007/s11356-018-2582-1
Celebioglu A, Topuz F, Uyar T (2019) Water-insoluble hydrophilic electrospun fibrous mat of cyclodextrin-epichlorohydrin polymer as highly effective sorbent. Appl Polym Mater 1:54–62. https://doi.org/10.1021/acsapm.8b00034
Charles J, Crini G, Morin-Crini N, Badot PM, Trunfio G, Sancey B, de Carvalho M, Avramescu BC, S, Winterton P, Gavoille S, Torri G, (2014) Advanced oxidation (UV-ozone) and cyclodextrin sorption: effects of individual and combined action on the chemical abatement of organic pollutants in industrial effluents. J Taiwan Institute Chem Eng 45:603–608. https://doi.org/10.1016/j.jtice.2013.06.023
Charles J, Bradu C, Morin-Crini M, Sancey B, Winterton P, Torri G, Badot PM, Crini G (2016) Pollutant removal from industrial discharge water using individual and combined effects of adsorption and ion-exchange processes: chemical abatement. J Saudi Chem Soc 20:185–194. https://doi.org/10.1016/j.jscs.2013.03.007
Chen D, Zhang H, Hu S, Li J (2008) Preparation and enhanced photoelectrochemical performance of coupled bicomponent ZnO-TiO2 nanocomposites. J Phys Chem C 112:117–122. https://doi.org/10.1021/jp077236a
Chen W, Xue M, Xue F, Mu X, Xu Z, Meng Z, Zhu G, Shea KJ (2015) Molecularly imprinted hollow spheres for the solid phase extraction of estrogens. Talanta 140:68–72
Chen L, Wang X, Lu W, Wu X, Li J (2016) Molecular imprinting: perspectives and applications. Chem Soc Rev 45:2137
Chowdhury SD, Surampalli RY, Bhunia P (2022) Potential of the constructed wetlands and the earthworm-based treatment technologies to remove the emerging contaminants: A Review. J Hazard Toxic Radioactive Waste 26:04021066
Cook MM, Symonds EM, Gerber B, Hoare A, Van Vleet ES, Breitbart M (2016) Removal of six estrogenic endocrine-disrupting compounds (EDCs) from municipal wastewater using aluminum electrocoagulation. Water 8:128. https://doi.org/10.3390/w8040128
Cova TFGG, Murthino D, Pais AACC, Valente AJM (2018) Cyclodextrin-based materials for removing micropollutants from wastewater. Current Org Chem 22:2146–2177. https://doi.org/10.2174/138527822666181019125315
Crane RA, Scott TB (2012) Nanoscale zero-valent iron: future prospects for an emerging water treatment technology. J Hazard Mater 211–212:112–125. https://doi.org/10.1016/j.jhazmat.2011.11.073
Crini, (2005) Recent developments in polysaccharide-based materials used as adsorbents in wastewater treatment. Prog Polym Sci 30:38–70. https://doi.org/10.1016/j.progpolymsci.2004.11.002
Crini, (2014) Review: a history of cyclodextrin. Chem Rev 114:10940–10975. https://doi.org/10.1021/cr500081p
Crini G, Morcellet M (2002) Synthesis and applications of adsorbents containing cyclodextrins. J Sep Sci 25:789–813. https://doi.org/10.1002/1615-9314(20020901)25:13%3c789:aid-jssc789%3e3.0.co;2-j
Crini G, Fourmentin S, Fenyvesi É, Torri G, Fourmentin M, Morin-Crini N (2018) Cyclodextrins, from molecules to applications. Environ Chem Lett 16:1361–1375. https://doi.org/10.1007/s10311-018-0763-2
Crini G, Lichtfouse E, Wilson LD, Morin-Crini N (2019) Conventional and non-conventional adsorbents for wastewater treatment. Environ Chem Lett 17:145–155. https://doi.org/10.1007/s10311-018-0785-9
Crini G, Cosentino C, Bradu C, Fourmentin M, Torri G, Ruzimuradov O, Alaton IA, Tomei MC, Derco J, Barhoumi M, Prosen H, Malinović BN, Vrabeľ M, Huq MM, Soltan J, Lichtfouse E, Morin-Crini N (2021a) Advanced treatments for the removal of alkylphenols and alkylphenol polyethoxylates from wastewater. In: Emerging Contaminants: Remediation. G. Crini and E. Lichtfouse, eds. Springer Nature, Environmental Chemistry for a Sustainable World, volume 2, chapter 4, pp. 305–398
Crini G, Bradu C, Fourmentin M, Cosentino C, Ribeiro ARL, Morin-Crini N (2021b) Sorption of 4-n-nonylphenol, 4-n-octylphenol, and 4-tert-octylphenol on cyclodextrin polymers. Environ Sci Pollut Res. https://doi.org/10.1007/s11356-021-14435-y
Cserhati T, Fenyvesi E, Szejtli J (1992) Interaction of nonylphenol and tributylphenyl ethylene-oxide ionic surfactants with highly soluble cyclodextrin derivatives. J Incl Phenom Mol Recognition Chem 14:181–188. https://doi.org/10.1007/BF01029666
Cyclopure (2020) www. cyclopure.com
da Silva SW, Bordignon GL, Viegas C, Rodrigues MAS, Arenzon A, Bernardes AM (2015a) Treatment of solutions containing nonylphenol ethoxylate by photoelectrooxidation. Chemosphere 119:S101–S108. https://doi.org/10.1016/j.chemosphere.2014.03.134
da Silva SW, Klauck CR, Siqueira MA, Bernardes AM (2015b) Degradation of the commercial surfactant nonylphenol ethoxylate by advanced oxidation processes. J Hazard Mater 282:241–248. https://doi.org/10.1016/j.jhazmat.2014.08.014
Dan A, Zhang NC, Qiu RL, Li C, Wang SZ, Ni ZB (2020) Accelerated biodegradation of p-tert-butylphenol in the Phragmites australis rhizosphere by phenolic root exudates. Environ Exp Botany 169:103891. https://doi.org/10.1016/j.envexpbot.2019.103891
Dai YD, Yuan C, Huang CP, Chiang PC (2017) Regeneration of spent carbon nanotubes by electrochemical oxidation over RuO2/Ti electrode. Sep Purif Technol 178:207–214. https://doi.org/10.1016/j.seppur.2017.01.021
de Leon-Condes C, Barrera-Diaz C, Barrios J, Becerril E, Reyes-Perez H (2017) A coupled ozonation-electrooxidation treatment for removal of bisphenol A, nonylphenol and triclosan from wastewater sludge. Int J Environ Sci Technol 14:707–716. https://doi.org/10.1007/s13762-016-1178-x
De la Fuente L, Acosta T, Babay P, Curutchet G, Candal R, Litter MI (2010) Degradation of nonylphenol ethoxylate-9 (NPE-9) by photochemical advanced oxidation technologies. Ind Eng Chem Res 49:6909–6915
De la Noüe J, De Pauw N (1988) The potential of microalgal biotechnology. A review of production and uses of microalgae. Biotechnol Adv 6:725–770
de la Paz A, Matamoros SN (2019) Unravelling the role of vegetation in the attenuation of contaminants of emerging concern from wetland systems: preliminary results from column studies. Water Res 166:115031. https://doi.org/10.1016/j.watres.2019.115031
Delrue F, Álvarez-Díaz PD, Fon-Sing S, Fleury G, Sassi JF (2016) The environmental biorefinery: using microalgae to remediate wastewater, a win-win paradigm. Energies 9:132. https://doi.org/10.3390/en9030132
Diao M, Yao M (2009) Use of zero-valent iron nanoparticles in inactivating microbes. Water Res 43:5243–5251
Do CVT, Pham MHT, Pham TYT, Dinh CT, Bui TUT, Tran TD, Nguyen VT (2022) Microalgae and bioremediation of domestic wastewater. Current Opinion Green Sustainable Chem 34:100595
Dong S, Feng J, Fan M, Pi Y, Hu L, Han X, Liu M, Sun J, Sun J (2015) Recent developments in heterogeneous photocatalytic water treatment using visible light-responsive photocatalysts: a review. RSC Adv 5:14610–14630. https://doi.org/10.1039/C4RA13734E
Eggen RIL, Hollender J, Joss A, Scharer M, Stamm C (2014) Reducing the discharge of micropollutants in the aquatic environment: the benefits of upgrading wastewater treatment plants. Environ Sci Technol 48:7683–7689. https://doi.org/10.1021/es500907n
EU (2000) European Union working document on sludge, 3rd Draft. ENV.E.3/LM. Brussels, 27 April 2000. [http://www.ewa-online.eu/comments.html?file=tl_files/_media/content/documents_pdf/European%20Water%20Policy/Comments/Sewage%20Sludge/EWA_WD_sludge_en.pdf].
EU (2010) European Union working document on sludge and biowaste. DG ENV C2/BZ/tb. Brussels, 21 September 2010. [http://www.ewa-online.eu/comments.html?file=tl_files/_media/content/documents_pdf/European%20Water%20Policy/Comments/Biowaste/EWA_WD_on_sludge_and_biowaste
Fan Z, Shi H, Zhao H, Cai J, Zhao G (2018) Application of carbon aerogel electrosorption for enhanced Bi2WO6 photoelectrocatalysis and elimination of trace nonylphenol. Carbon 126:279–288. https://doi.org/10.1016/j.carbon.2017.10.009
Fan Z, Wei T, Shi H, Tang B, Zhao G (2019) Adsorption driven preferential degradation of alkyl phenols on hydrophobic perfluoroalkyl modified-TiO2. Chem Eng J 357:689–697. https://doi.org/10.1016/j.cej.2018.09.198
Farrell J, Wang J, O’Day P, Conklin M (2001) Electrochemical and spectroscopic study of arsenate removal from water using zero-valent iron media. Environ Sci Technol 35:2026–2032. https://doi.org/10.1021/es0016710
Fenyvesi É, Puskás I, Szente L (2019) Applications of steroid drugs entrapped in cyclodextrins. Environ Chem Lett 17:375–391. https://doi.org/10.1007/s10311-018-0807-7
Fenyvesi É, Barkács K, Gruiz K, Varga E, Kenyeres I, Záray G, Szente L (2020) Removal of hazardous micropollutants from treated wastewater using cyclodextrin bead polymer - A pilot demonstration case. J Hazard Mat 383:121181. https://doi.org/10.1016/j.jhazmat.2019.121181
Fernández MA, Fernando Silva O, Vivo RV, de Rossi RH (2019) Complex systems that incorporate cyclodextrins to get materials for some specific applications. Carbohydr Res 480:12–34. https://doi.org/10.1016/j.carres.2019.05.006
Fourmentin S, Crini G, Lichtfouse É (Eds.) (2018) Cyclodextrin applications in medicine, food, environment and liquid crystals. Springer: environmental chemistry for a sustainable world https://doi.org/10.1007/978-3-319-76162-6
Fu F, Dionysiou DD, Liu H (2014) The use of zero-valent iron for groundwater remediation and wastewater treatment: a review. J Hazard Mater 267:194–205. https://doi.org/10.1016/j.jhazmat.2013.12.062
Gao XF, Sun WT, Hu ZD, Ai G, Zhang YL, Feng S, Li F, Peng LM (2009) An efficient method to form heterojunction CdS/TiO2 photoelectrodes using highly ordered TiO2 nanotube array films. J Phys Chem C 113:20481–20485. https://doi.org/10.1021/jp904320d
Gao QT, Wong YS, Tam NFY (2011) Removal and biodegradation of nonylphenol by different Chlorella species. Marine Pollut Bull 63:445–451
Garcia-Rodríguez A, Matamoros V, Salvadó FC (2014) The ability of biologically based wastewater treatment systems to remove emerging organic contaminants - a review. Environ Sci Pollut Res 21:2014. https://doi.org/10.1007/s11356-013-2448-5
García-Zubiri IX, González-Gaitano G, Isasi JR (2006) Thermal stability of solid dispersions of naphthalene derivatives with β-cyclodextrin and β-cyclodextrin polymers. Thermochim Acta 444:57–64. https://doi.org/10.1016/j.tca.2006.02.024
Gautam GJ, Chaube R (2021) Toxic impact of alkylphenols on the fish reproduction and endocrine disruption. Proceedings Zoological Soc 74:648–659. https://doi.org/10.1007/s12595-021-00416-z
González-Carcía CM, Denoyel R, González-Martín ML, Gómez-Serrano V (2001) Influence of porosity on the adsorption enthalpies of a non-ionic surfactant onto carbonaceous materials. Thermochim Acta 375:177–185. https://doi.org/10.1016/S0040-6031(01)00526-3
Gorito AM, Ribeiro AR, Almeida CMR, Silva AMT (2017) A review on the application of constructed wetlands for the removal of priority substances and contaminants of emerging concern listed in recently launched EU legislation. Environ Pollut 227:428–443. https://doi.org/10.1016/j.envpol.2017.04.060
Gorito AM, Lado Ribeiro AR, Pereira MFR, Almeida CMR, Silva AMT (2022) Advanced oxidation technologies and constructed wetlands in aquaculture farms: What do we know so far about micropollutant removal? Environ Res 204:111
Grandclement C, Seyssiecq I, Piram A, Wong-Wah-Chung P, Vanot G (2017) From the conventional biological wastewater treatment to hybrid processes, the evaluation of organic micropollutant removal: a review. Water Res 111:297–317. https://doi.org/10.1016/j.watres.2017.01.005
Greenlee L, Torrey JD, Amaro RL, Shaw JM (2012) Kinetics of zero valent iron nanoparticle oxidation in oxygenated water. Environ Sci Technol 46:12913–12920. https://doi.org/10.1021/es303037k
Grieger KD, Fjordbøge A, Hartmann NB, Eriksson E, Bjerg PL, Baun A (2010) Environmental benefits and risks of zero-valent iron nanoparticles (n-ZVI) for in-situ remediation: risk mitigation or trade-off? J Contam Hydrol 118:165–183. https://doi.org/10.1016/j.jconhyd.2010.07.011
Gryshchenko A, Bottaro CS (2014) Development of molecularly imprinted polymer in porous film format for binding of phenol and alkylphenols from water. Int J Mol Sci 15:1338–1357. https://doi.org/10.3390/ijms15011338
Guedes P, Mateus EP, Couto N, Rodríguez Y, Ribeiro AB (2014) Electrokinetic remediation of six emerging organic contaminants from soil. Chemosphere 117:124–131. https://doi.org/10.1016/j.chemosphere.2014.06.017
Gupta SK, Bux F (2019) Application of microalgae in wastewater. Springer Nature Switzerland AG, Domestic and industrial wastewater treatment. https://doi.org/10.1007/978-3-030-13913-1
Han W, Fu F, Cheng Z, Tang B, Wu S (2016) Studies on the optimum conditions using acid-washed zero-valent iron/aluminum mixtures in permeable reactive barriers for the removal of different heavy metal ions from wastewater. J Hazard Mater 302:437–446. https://doi.org/10.1016/j.jhazmat.2015.09.041
Hassan I, Chowdhury SR, Prihartato PK, Razzak SA (2021) Wastewater treatment using constructed wetland: Current trends and future potential. Processes 9:1917
Hasegawa G, Sato T, Kanamori K, Nakano K, Yajima T, Kobayashi Y, Kageyama H, Abe T, Nakanishi K (2013) Hierarchically porous monoliths based on N-doped reduced titanium oxides and their electric and electrochemical properties. Chem Mater 25:3504–3512. https://doi.org/10.1021/cm401933a
He N, Sun X, Zhong Y, Sun K, Liu W, Duan S (2016) Removal and biodegradation of nonylphenol by four freshwater microalgae. Int J Environ Res Public Health 13:1239. https://doi.org/10.3390/ijerph13121239
He N, Liu ZW, Sun X, Wang SG, Liu WJ, Sun D, Duan SS (2020) Phytotoxicity, bioaccumulation, and degradation of nonylphenol in different microalgal species without bacterial influences. Int J Mol Sci 21:1338. https://doi.org/10.3390/ijms21041338
Henriques DM, Kümmerer K, Mayer FM, Vasconcelos TG, Martins AF (2012) Nonylphenol polyethoxylate in hospital wastewater: A study of the subproducts of electrocoagulation. J Environ Sci Health Part A 47:497–505. https://doi.org/10.1080/10934529.2012.640249
Herrera-Melian J, Guedes-Alonso R, Borreguero-Fabelo A, Santana-Rodriguez J, Sosa-Ferrera Z (2018) Study on the removal of hormones from domestic wastewaters with lab-scale constructed wetlands with different substrates and flow directions. Environ Sci Pollut Res 25:20374–20384. https://doi.org/10.1007/s11356-017-9307-8
Hidaka H, Yamada S, Suenaga S, Zhao J, Serpone N, Pelizzetti E (1990) Photodegradation of surfactants: Part VI. Complete photocatalytic degradation of anionic cationic and nonionic surfactants in aqueous semiconductor dispersions. J Mol Catal 59:279–290. https://doi.org/10.1016/0304-5102(90)85101-M
Hoang H, Yu N, Toyama T, Inoue D, Sei K, Ike M (2010) Accelerated degradation of a variety of aromatic compounds by Spirodela polyrrhiza-bacterial associations and contribution of root exudates released from S. polyrrhiza. J Environ Sci 22:494–499. https://doi.org/10.1016/S1001-0742(09)60135-2
Hoigne J, Bader H (1983) Rate constants of reactions of ozone with organic and inorganic compounds in water. I: non-dissociating organic compounds. Water Res 17:173–183. https://doi.org/10.1016/0043-1354(83)90098-2
Hojamberdiev M, Prasad RM, Morita K, Zhu Y, Schiavon MA, Gurlo A, Riedel R (2012) Template-free synthesis of polymer-derived mesophorous SiOC/TiO2 and SiOc/N-doped TiO2 ceramic composites for application in the removal of organic dyes from contaminated water. Appl Catal B 115–116:303–313. https://doi.org/10.1016/j.apcatb.2011.12.036
Hollender J, Saskia G, Zimmermann SG, Koepke S, Krauss M, McArdell CHS, Ort Ch, Singer H, von Gunten U, Siegrist H (2009) Elimination of organic micropollutants in a municipal wastewater treatment plant upgraded with a full-scale post-ozonation followed by sand filtration. Environ Sci Technol 43:7862–7869. https://doi.org/10.1021/es9014629
Huber MM, Anke Göbel A, Joss A, Hermann N, Dirk Löffler D, McArdell ChS, Ried A, Siegrist H, Thomas A, Ternes TA, von Gunten U (2005) Oxidation of pharmaceuticals during ozonation of municipal wastewater effluents: a pilot study. Environ Sci Technol 39:4290–4299. https://doi.org/10.1021/es048396s
Huang DL, Wang RZ, Liu YG, Zeng GM, Lai C, Xu P, Lu BA, Xu JJ, Wang C, Huang C (2015) Application of molecularly imprinted polymers in wastewater treatment: a review. Environ Sci Pollut Res 22:963–977
Hung KC, Nguyen NT, Sun YL, Huang SL (2019) Bio-Fenton reaction involved in the cleavage of the ethoxylate chain of nonionic surfactants by dihydrolipoamide dehydrogenase from Pseudomonas nitroreducens TX1. Sci Rep 9:6827. https://doi.org/10.1038/s41598-019-43266-8
Hwang JH, Church J, Lee SJ, Park J, Lee WH (2016) Use of microalgae for advanced wastewater treatment and sustainable bioenergy generation. Environ Eng Sci. https://doi.org/10.1089/ees.2016.0132
Ibáňez M, Gracia-Lor E, Bijlsma L, Morales E, Pastor L, Hernandez F (2013) Removal of emerging contaminants in sewage water subjected to advanced oxidation with ozone. J Hazard Mater 260:389–398. https://doi.org/10.1016/j.jhazmat.2013.05.023
Ibhadon AO, Fitzpatrick P (2013) Heterogeneous photocatalysis: recent advances and applications. Catalysts 3:189–218. https://doi.org/10.3390/catal3010189
Ike M, Asano M, Belkada FD, Tsunoi S, Tanaka M, Fujita M (2002) Degradation of biotansformation products of nonylphenol ethoxylates by ozonation and UV/TiO2 treatment. Water Sci Technol 46:127–132
Inglezakis VJ, Zorpas AA, Karagiannidis A, Samaras P, Voukkali I, Sklari S (2014) European Union legislation on sewage sludge management. Fresenius Environ Bull 23:635–639
Janousek RM, Muller J, Knepper TP (2020) Combined study of source, environmental monitoring and fate of branched alkylphenols: the chain length matters. Chemosphere 241:124950. https://doi.org/10.1016/j.chemosphere.2019.124950
Jans U, Hoigne J (1998) Activated carbon and carbon black catalyzed transformation of aqueous ozone into OH-radicals. Ozone Sci Eng 20:67–90. https://doi.org/10.1080/01919519808547291
Ji Y, Niu J, Fang Y, Nou AT, Warsinger DM (2022) Micelles inhibit electro-oxidation degradation of nonylphenol ethoxylates. Chem Eng J 430:133167. https://doi.org/10.1016/j.cej.2021.133167
Johnson AC, Aerni HR, Gerritsen A, Gibert M, Giger W, Hylland K, Jurgens M, Nakarni T, Pickering A, Suter MJF, Svenson A, Wettstein FE (2005) Comparing steroid estrogen and nonylphenol content across a range of European sewage plants with different treatment and management practices. Water Res 39:47–58. https://doi.org/10.1016/j.watres.2004.07.025
Jones OAH, Green PG, Voulvoulis N, Lester JN (2007) Questioning the excessive use of advanced treatment to remove organic micropollutants from wastewater. Environ Sci Technol 41:5085–5089. https://doi.org/10.1021/es0628248
Kaur R, Talan A, Tiwari B, Pilli S, Sellamuthu B, Tyagi RD (2020) Constructed wetlands for the removal of organic micro-pollutants. In: current developments in biotechnology and bioengineering. Emerging organic micro-pollutants. Varjani S, Pandey A, Tyagi RD, Ngo HH and Larroche C (Eds.). Amsterdam: Elsevier. Chapter 5, pp. 87–140
Kharisov BI, Dias HVR, Kharissova OV, Jiménez-Pérez VM, Pérez BO, Flores BM (2012) Iron-containing nanomaterials: synthesis, properties, and environmental applications. RSC Adv 2:9325–9358. https://doi.org/10.1039/C2RA20812A
Khosravanipour Mostafazadeh A, Benguit AT, Carabin A, Drogui P, Brien E (2019) Development of combined membrane filtration, electrochemical technologies, and adsorption processes for treatment and reuse of laundry wastewater and removal of nonylphenol ethoxylates as surfactants. J Water Process Eng 28:277–292. https://doi.org/10.1016/j.jwpe.2019.02.014
Kim JY, Davis AP, Kim KW (2003) Stabilization of available arsenic in highly contaminated mine tailings using iron. Environ Sci Technol 37:189–195. https://doi.org/10.1021/es020799+
Kim H, Borse P, Choi W, Lee J (2005a) Photocatalytic nanodiodes for visible-light photocatalysis. Angew Chem Int Ed 44:4585–4589. https://doi.org/10.1002/anie.200500064
Kim J, Korshin GV, Velichenkio AB (2005b) Comparative study of electrochemical degradation and ozonation of nonylphenol. Water Res 39:2527–2534. https://doi.org/10.1016/j.watres.2005.04.070
Kumar N, Novak JT, Murthy S (2006) Effect of secondary aerobic digestion on properties of anaerobic digested biosolids. In: water environmental federation, 79th Annual Technical Exhibition and Conference, Dallas, pp. 6806–6829
Kusic H, Peternel I, Koprivanac N, Loncaric Bozic A (2011) Iron-activated persulfate oxidation of an azo dye in model wastewater: influence of iron activator type on process optimization. J Environ Eng 137:454–463
Lackovic JA, Nikolaidis NP, Dobbs GM (2000) Inorganic arsenic removal by zero-valent iron. Environ Eng Sci 17:29–39
Li L, Zhu W, Zhang P, Zhang Z, Wu H, Han W (2006) Comparison of AC/O3eBAC and O3eBAC processes for removing organic pollutants in secondary effluent. Chemosphere 62:1514–1522. https://doi.org/10.1016/j.chemosphere.2005.06.043
Li H, Wan J, Ma Y, Huang M, Wang Y, Chen Y (2014a) New insights into the role of zero-valent iron surface oxidation layers in persulfate oxidation of dibutyl phthalate solutions. Chem Eng J 250:137–147
Li X, Chen S, Li L, Quan X, Zhao H (2014b) Electrochemically enhanced adsorption of nonylphenol on carbon nanotubes: kinetics and isotherms study. J Colloid Int Sci 415:159–164. https://doi.org/10.1016/j.jcis.2013.10.021
Li S, Show PL, Ngo HH, Ho SH (2022) Algae-mediated antibiotic wastewater treatment: A critical review. Environ Sci Ecotechnol 9:100145
Liang H, Tai X, Du Z (2020) Photocatalytic degradation of nonylphenol ethoxylate and its degradation mechanism. J Mol Liq 302:112567. https://doi.org/10.1016/j.molliq.2020.112567
Lien H, Wilkin RT (2005) High-level arsenate removal from groundwater by zero-valent iron. Chemosphere 59:377–386. https://doi.org/10.1016/j.chemosphere.2004.10.055
López-Sánchez A, Silva-Gálvez AL, Aguilar-Juárez Ó, Senés-Guerrero C, Orozco-Nunnelly DA, Carrillo-Nieves D, Gradilla-Hernández MS (2022) Microalgae-based livestock wastewater treatment (MbWT) as a circular bioeconomy approach: Enhancement of biomass productivity, pollutant removal and high-value compound production. J Environ Manage 308:114612
Loureiro JM, Kartel MT (2006) Combined and hybrid adsorbents. Fundamentals and Applications Springer, Netherlands,. https://doi.org/10.1007/1-4020-5172-7
Lu Z (2014) Analysis, toxicity, occurrence and biodegradation of nonylphenol isomers: a review. Environ Int 73:334–345. https://doi.org/10.1016/j.envint.2014.08.017
Luo Y, Guo W, Ngo HH, Nghiem LD, Hai FI, Zhang J, Liang S, Wang XC (2014) A review on the occurrence of micropollutants in the aquatic environment and their fate and removal during wastewater treatment. Sci Total Environ 473–474:619–641. https://doi.org/10.1016/j.scitotenv.2013.12.065
Madikizela LM, Tavengwa NT, Chimuka L (2018) Applications of molecularly imprinted polymers for solid-phase extraction of non-steroidal anti-inflammatory drugs and analgesics from environmental waters and biological samples. J Pharm Biomed Anal 147:624–633
Mailler R, Gasperi J, Patureau D, Vulliet E, Delgenes N, Danel A, Deshayes S, Eudes V, Guerin S, Moilleron R, Chebbo G, Rocher V (2017) Fate of emerging and priority micropollutants during the sewage sludge treatment: case study of Paris conurbation. Part 1: contamination of the different types of sewage sludge. Waste Manage 59:379–393. https://doi.org/10.1016/j.wasman.2016.11.010
Manning BA, Hunt M, Amrhein C, Yarmoff JA (2002) Arsenic(III) and arsenic(V) reactions with zero valent iron corrosion products. Environ Sci Technol 36:5455–5461
Mao QM, Zhou YY, Yang YA, Zhang JC, Liang LF, Wang HL, Luo S, Luo L, Jeyakumar P, Ok YS (2019) Experimental and theoretical aspects of biochar-supported nanoscale zero-valent iron activating H2O2 for ciprofloxacin removal from aqueous solution. J Hazard Mater 380:120848. https://doi.org/10.1016/j.jhazmat.2019.120848
Mao Y, Schoeneich C, Asmus KD (1993) TiO2 photocatalytic purification and treatment of water and air. In: Ollis DF, Al-Ekabi H (eds) photocatalytic purification and treatment of water and air. Elsevier, New York, pp 49–66
Mara DD, Pearson H (1986) Artificial freshwater environment: waste stabilization ponds. In: biotechnology. Rehm HJ and Reed G (Eds.), Weinheim: VCH Verlagsgesellschaft. 8: 177–206
Matějíček D, Grycová A, Vlček J (2013) The use of molecularly imprinted polymers for the multicomponent determination of endocrine-disrupting compounds in water and sediment. J Sep Sci 36:1097–1103. https://doi.org/10.1002/jssc.201200992
Maza-Márquez P, González-Martínez, Juárez-Jiménez B, Rodelas B, González-López J (2018) Microalgae-bacteria consortia for the removal of phenolic compounds from industrial wastewaters. In: approaches in bioremediation. Prasad R and Aranda E (Eds.). Springer Nature Switzerland AG. Chapter 8, pp. 135–184. https://doi.org/10.1007/978-3-030-02369-8
McKay G (1996) Use of adsorbents for the removal of pollutants from wastewaters. CRC Press Inc, Boca Raton
Metwally MG, Benhawy AH, Khalifa RM, El Nashar RM, Trojanowicz M (2021) Application of molecularly imprinted polymers in the analysis of waters and wastewaters. Molecules 26:6515
Minella M, Bertinetti S, Hanna K, Minero C, Vione D (2019) Degradation of ibuprofen and phenol with a Fenton-like process triggered by zero-valent iron (ZVI-Fenton). Environ Res 179:108750. https://doi.org/10.1016/j.envres.2019.108750
Mohamed MH, Wilson LD, Pratt DY, Guo R, Wu C, Headley JV (2012) Evaluation of the accessible inclusion sites in copolymer materials containing beta-cyclodextrin. Carbohydr Polym 87:1241–1248. https://doi.org/10.1016/j.carbpol.2011.09.011
Molazadeh M, Ahmadzadeh H, Pourianfar HR, Lyon S, Rampelotto PH (2019) The use of microalgae for coupling wastewater treatment with CO2 biofixation. Front Bioeng Biotechnol 7:42. https://doi.org/10.3389/fbioe.2019.00042
Morillas-España A, Lafarga T, Sánchez-Zurano A, Acién-Fernández FG, González-López C (2022) Microalgae based wastewater treatment coupled to the production of high value agricultural products: Current needs and challenges. Chemosphere 291:132968
Morin-Crini N, Crini G (2013) Environmental applications of water-insoluble β-cyclodextrin-epichlorohydrin polymers. Prog Polym Sci 38:344–368. https://doi.org/10.1016/j.progpolymsci.2012.06.005
Morin-Crini N, Winterton P, Fourmentin S, Wilson LD, Fenyvesi É, Crini G (2018) Water-insoluble β-cyclodextrin-epichlorohydrin polymers for removal of pollutants from aqueous solutions by sorption processes using batch studies: a review of inclusion mechanism. Prog Polym Sci 78:1–23. https://doi.org/10.1016/j.progpolymsci.2017.07.004
Morin-Crini N, Fourmentin S, Fenyvesi É, Lichtfouse E, Torri G, Fourmentin M, Crini G (2021) 130 years of cyclodextrin discovery for health, food, agriculture, and the industry: a review. Environ Chem Lett 19:2581–2617. https://doi.org/10.1007/s10311-020-01156-w
Mueller NC, Braun J, Bruns J, Cerník M, Rissing P, Rickerby D, Nowack B (2012) Application of nanoscale zero valent iron (nZVI) for groundwater remediation in Europe. Environ Sci Pollut Res 19:550–558. https://doi.org/10.1007/s11356-011-0576-3
Muñoz R, Guieysse B (2006) Algal-bacterial processes for the treatment of hazardous contaminants: a review. Water Res 40:2799–2815
Murai S, Imajo S, Inumaru H, Takahashi K, Hattori K (1997) Adsorption and recovery of ionic surfactants by β-cyclodextrin polymer. J Colloid Int Sci 190:488–490. https://doi.org/10.1006/jcis.1997.4873
Murai S, Imajo S, Maki Y, Takahashi K, Hattori K (1996) Adsorption and recovery of nonionic surfactants by β-cyclodextrin polymer. J Colloid Int Sci 183:118–123. https://doi.org/10.1006/jcis.1996.0524
Murai S, Kinoshita K, Ishii S (2006) Removal of phenolic compounds from aqueous solution by beta-cyclodextrin polymer. Transactions Mat Res Soc Japan 31:977–980
Murcia-Salvador A, Pellicer JA, Fortea MI, Gomez-Lopez VM, Rodriguez-Lopez MI, Nunez-Delicado E, Gabaldón JA (2019) Adsorption of direct blue 78 using chitosan and cyclodextrins as adsorbents. Polymers 11:1003. https://doi.org/10.3390/polym11061003
Murray A, Öermeci B (2012) Application of molecularly imprinted and non-imprinted polymers for removal of emerging contaminants in water and wastewater treatment: a review. Environ Sci Poll Res 19:3820–3830. https://doi.org/10.1007/s11356-012-1119-2
Musaev K, Mirkhamitova D, Yarbekov A, Nurmanov S, Akbarov K, Ruzimuradov O (2019) Facile synthesis of SiO2-TiO2 photocatalyst nanoparticles for degradation of phenolic water pollutants. SN Appl Sci 1:1164. https://doi.org/10.1007/s42452-019-1192-y
Nabgan W, Saeed M, Jalil AA, Nabgan B, Gambo Y, Ali MW, Ikram M, Fauzi AA, Owgi AHK, Hussain I, Thahe AA, Hu X (2022) A state of the art review on electrochemical technique for the remediation of pharmaceuticals containing wastewater. Environ Res 210:112975
Nadtochenko VA, Kiwi J (1998) Photolysis of FeOH2+ and FeCl2+ in aqueous solution. Photodissociation kinetics and quantum yields. Inorg Chem 37:5233–5238
Narkis N, Bendavid B, Rotel MS (1985) Ozonation of non-ionic surfactants in aqueous-solutions. Water Sci Technol 17:1069–1080. https://doi.org/10.2166/wst.1985.0202
Nguyen THA, Oh SY (2019) Biochar-mediated oxidation of phenol by persulfate activated with zero-valent iron. J Chem Technol Biotechnol 94:3932–3940. https://doi.org/10.1002/jctb.6194
Ning B, Graham NJD, Zhang Y (2007a) Degradation of octylphenol and nonylphenol by ozone. Part i: Direct Reaction Chemosphere 68:1163–1172. https://doi.org/10.1016/j.chemosphere.2007.01.055
Ning B, Graham NJD, Zhang Y (2007b) Degradation of octylphenol and nonylphenol by ozone. Part II: Indirect Reaction Chemosphere 68:1173–1179. https://doi.org/10.1016/j.chemosphere.2007.01.056
Niu B, Cai J, Song W, Zhao G (2020) Novel electrochemical pretreatment for preferential removal of nonylphenol in industrial wastewater: biodegradability improvement and toxicity reduction. Environ Sci Technol 54:1258–1266. https://doi.org/10.1021/acs.est.9b03153
O’Carroll D, Sleep B, Krol M, Boparai H, Kocur C (2013) Nanoscale zero valent iron and bimetallic particles for contaminated site remediation. Adv Water Resour 51:104–122. https://doi.org/10.1016/j.advwatres.2012.02.005
Oh YC (2004) Photocatalytic degradation of organic contaminants in water. Iowa State University, UMI Number, p 3145675
Olaniyan LWB, Okoh OO, Mkwetshana NT, Okoh AI (2020) Environmental water pollution, endocrine interference and ecotoxicity of 4-tert-octylphenol: a review. Rev Environ Contamination Toxicol 248:81–109. https://doi.org/10.1007/398_2018_20
Ömeroğlu S, Murdoch FK, Sanin D (2015) Investigation of nonylphenol and nonylphenol ethoxylates in sewage sludge samples from a metropolitan wastewater treatment plant in Turkey. Talanta 131:650–655. https://doi.org/10.1016/j.talanta.2014.08.014
Osei AR, Konate Y, Abagale FK (2019) Pollutant removal and growth dynamics of macrophyte species for faecal sludge treatment with constructed wetland technology. Water Sci Technol 80:1145–1154. https://doi.org/10.2166/wst.2019.354
Oturan N, van Hullebusch ED, Zhang H, Mazeas L, Budzinski H, Le Menach K, Oturan MA (2015) Occurrence and removal of organic micropollutants in landfill leachates treated by electrochemical advanced oxidation processes. Environ Sci Technol 49:12187–12196. https://doi.org/10.1021/acs.est.5b02809
Pandis PK, Kalogirou C, Kanellu E, Vaitsis C, Savvidou MG, Sourkouni G, Zorpas AA, Argirusis C (2022) Key points of advanced oxidation processes (AOPs) for wastewater, organic pollutants and pharmaceutical waste treatment: A mini review. ChemEng 6:8
Parag R, Gogate PR, Pandit AB (2004) A review of imperative technologies for wastewater treatment II: hybrid methods. Adv Environ Res 8:553–597. https://doi.org/10.1016/S1093-0191(03)00031-5
Parlapiano M, Akyol C, Foglia A, Pisani M, Astolfi P, Eusebi AL, Fatone F (2021) Selective removal of contaminants of emerging concern (CECs) from urban water cycle via molecularly imprinted polymers (MIPs): Potential of upscaling and enabling reclaimed water reuse. J Environ Chem Eng 9:105051
Patyal V, Jaspal D, Tiwari AK, Khare K (2022) Constructed wetlands for removal of phosphorus from domestic wastewater - A patent review. Sustainable Water Manage 8:45
Pellicer JA, Rodríguez-López MI, Fortea MI, Lucas-Abellán M-R, López-Miranda S, Gómez-López VM, Semeraro CP, Fini P, Franco E, Ferrándiz M, Pérez E, Ferrándiz M, Núñez-Delicado E, Gabaldón JA (2019) Adsorption properties of β- and hydroxypropyl-β-cyclodextrins cross-linked with epichlorohydrin in aqueous solution. A sustainable recycling strategy in textile dyeing process. Polymers 11:252. https://doi.org/10.3390/polym1102252
Pelizzetti E, Minero C, Maurino V, Sclafani A, Hidaka H, Serpone N (1989) Photocatalytic degradation of nonylphenol ethoxylated surfactants. Environ Sci Technol 23:1380–1385. https://doi.org/10.1021/es00069a008
Pelizzetti E, Minero C, Hidaka H, Serpone N (1992) Photocatalytic purification and treatment of water and air. In: photocatalytic purification and treatment of water and air. Ollis DF and Al-Ekabi H (Eds.). New York: Elsevier 820 p
Poyatos JM, Muñio MM, Almecija MC, Torres JC, Hontoria E, Osorio F (2010) Advanced oxidation processes for wastewater treatment: state of the art. Water Air Soil Pollut 205:187. https://doi.org/10.1007/s11270-009-0065-1
Pirilä M, Saouabe M, Ojala S, Rathnayake B, Drault F, Valtanen A, Huuhtanen M, Brahmi R, Keiski RL (2015) Photocatalytic degradation of organic pollutants in wastewater. Topics Catalysis 58:1085–1099. https://doi.org/10.1007/s11244-015-0477-7
Priac A, Morin-Crini N, Druart C, Gavoille S, Bradu C, Lagarrigue C, Torri G, Winterton P, Crini G (2017) Alkylphenol and alkylphenol polyethoxylates in water and wastewater: a review of options for their elimination. Arabian J Chem 10:S3749–S3773. https://doi.org/10.1016/j.arabjc.2014.05.011
Qiang ZM, Nie YF, Ben WW, Qu JH, Zhang HQ (2013) Degradation of endocrine-disrupting chemicals during activated sludge process. Water Res 41:2341–2348. https://doi.org/10.1016/j.chemosphere.2012.11.069
Qin XM, Bai L, Tan Y, Li L, Song F, Wang Y (2019) β-Cyclodextrin-crosslinked polymeric adsorbent for simultaneous removal and stepwise recovery of organic dyes and heavy metal ions: fabrication, performance and mechanism. Chem Eng J 372:1007–1018. https://doi.org/10.1016/j.cej.2019.05.006
Rammohan G, Nadagouda MN (2013) Green photocatalysis for degradation of organic contaminants: a review. Current Org Chem 17:2338–2348. https://doi.org/10.2174/13852728113179990039
Redalje DG, Duerr EO, De la Noüe J, Mayzaud P, Nonomura AH, Cassin RC (1989) Algae as ideal waste removers: biochemical pathways. In: Huntley ME (ed) biotreatment of agricultural wastewater. CRC Press, Boca Raton, pp 91–110
Restivo J, Garcia-bordejé E, Órfão JJM, Pereira MFR (2016) Carbon nanofibers Doped with nitrogen for the continuous catalytic ozonation of organic pollutants. Chem Eng J 293:102–111. https://doi.org/10.1016/j.cej.2016.02.055
Restivo J, Órfão JJM, Pereira MFR, Garcia-bordejé E, Roche P, Bourdin D, Houssais B, Coste M, Derrouiche S (2013) Catalytic ozonation of organic micropollutants using carbon nanofibers supported on Monoliths. Chem Eng J 230:115–123. https://doi.org/10.1016/j.cej.2013.06.064
Ribeiro AR, Nunes OC, Pereira MFR, Silva AMT (2015) An overview on the advanced oxidation processes applied for the treatment of water pollutants defined in the recently launched Directive 2013/39/EU. Rev Environ Int 75:33–51. https://doi.org/10.1016/j.envint.2014.10.027
Ricky R, Shanthakumar S (2022) Phycoremediation integrated approach for the removal of pharmaceuticals and personal care products from wastewater -A review. J Environ Manage 302:113998
Rivas J, Gimeno O, Beltrán F (2009) Wastewater recycling: Application of ozone based treatments to secondary effluents. Chemosphere 74:854–859. https://doi.org/10.1016/j.chemosphere.2008.07.090
Rivera-Utrilla J, Sánchez-Polo M, Gómez-Serrano V, Álvarez PM, Alvim-Ferraz MCM, Dias JM (2011) Activated carbon modifications to enhance its water treatment applications. An Overview J Hazard Mater 187:1–23. https://doi.org/10.1016/j.jhazmat.2011.01.033
Rodríguez A, Rosal R, Perdigón-Melón JA, Mezcua M, Agüera A, Hernando MD, Letón P, Fernández-Alba AR, García-Calvo E (2008) Ozone-based technologies in water and wastewater treatment. Springer Verlag Berlin Heidelberg, Hdb Env Chem. https://doi.org/10.1007/698_5_103
Rodriguez S, Vasquez L, Costa D, Romero A, Santos A (2014) Oxidation of orange G by persulfate activated by Fe(II), Fe(III) and zero valent iron (ZVI). Chemosphere 101:86–92. https://doi.org/10.1016/j.chemosphere.2013.12.037
Rodriguez-Pena M, Barrera-Diaz CE, Frontana-Uribe BA, Roa-Morales G (2019) Nonylphenol degradation by simultaneous electrooxidation on BDD anode and oxidation by H2O2 in a continuous flow electrochemical reactor. Int J Electrochem Sci 14:4409–4419. https://doi.org/10.20964/2019.05.21
Romita R, Rizzi V, Semeraro P, Gubitosa J, Gabaldón JA, Gorbe MIF, López VMG, Cosma P, Fini P (2019) Operational parameters affecting the atrazine removal from water by using cyclodextrin based polymers as efficient adsorbents for cleaner technologies. Environ Technol Innovation 16:100454. https://doi.org/10.1016/j.eti.2019.100454
Romo A, Peñas FJ, Isasi JR (2004) Sorption of dibenzofuran derivatives from aqueous solutions by β-cyclodextrin polymers: an isosteric heat approach. J Colloid Int Sci 279:55–60. https://doi.org/10.1016/j.jcis.2004.06.043
Rule KL, Combe SDW, Ross D, Thornton A, Makropoulos CK, Rautiu R (2006) Sources of priority substances entering an urban wastewater catchment-trace organic chemicals. Chemosphere 63:581–591. https://doi.org/10.1016/j.chemosphere.2005.08.016
Safarzadeh-Amiri A, Bolton JR, Cater SR (1996) The use of iron in advanced oxidation processes. J Adv Oxid Technol 1:18–26
Salam MA, Fageeh O, Al-Thabaiti SA, Obaid AY (2015) Removal of nitrate ions from aqueous solution using zero-valent iron nanoparticles supported on high surface area nanographenes. J Mol Liq 212:708–715. https://doi.org/10.1016/j.molliq.2015.09.029
Salgueiro-Gonzalez N, Muniategui-Lorenzo S, Lopez-Mahia P, Prada-Rodriguez D (2017) Trends in analytical methodologies for the determination of alkylphenols and bisphenol A in water samples. Anal Chim Acta 962:1–14. https://doi.org/10.1016/j.aca.2017.01.035
Salomon KY, Claver NGH, Sylvain AK (2019) Nonylphenol and its ethoxylate in water environment. J Geography Environ Earth Sci 23:1–14. https://doi.org/10.9734/JGEESI/2019/v23i430186
Sancey B, Crini G (2012) Décontamination des effluents de traitement de surface par oxydation/bioadsorption sur cyclodextrine (in French). Techniques De L’ingénieur 154:1–12
Sancey B, Trunfio T, Charles J, Minary JF, Gavoille S, Badot PM, Crini G (2011) Heavy metal removal from industrial effluents by sorption on cross-linked starch: Chemical study and impact on water toxicity. J Environ Manage 92:765–772. https://doi.org/10.1016/j.jenvman.2010.10.033
Sanchez-Polo M, von Gunten U, Rivera-Utrilla J (2005) Efficiency of activated carbon to transform ozone into OH radicals: influence of operational parameters. Water Res 39:3189–3198. https://doi.org/10.1016/j.watres.2005.05.026
Saravanan M, Nam SE, Eom HJ, Lee DH, Rhee JS (2019) Long-term exposure to waterborne nonylphenol alters reproductive physiological parameters in economically important marine fish. Comparative Biochem Physiol C Toxicol Pharmacology 216:10–18. https://doi.org/10.1016/j.cbpc.2018.11.009
Sayed AEH, Kataoka C, Oda S, Kashiwada S, Mitani H (2018) Sensitivity of medaka (Oryzias latipes) to 4-nonylphenol subacute exposure; erythrocyte alterations and apoptosis. Environ Toxicol Pharmacol 58:98–104. https://doi.org/10.1016/j.etap.2017.12.023
Sayed AEH, Abd-Elkareem M, Abou Khalil NS (2019) Immunotoxic effects of 4-nonylphenol on Clarias gariepinus: cytopathological changes in hepatic melanomacrophages. Aquat Toxicol 207:83–90. https://doi.org/10.1016/j.aquatox.2018.12.002
Schaar H, Clara M, Gans O, Kreuzinger N (2010) Micropollutant removal during biological wastewater treatment and a subsequent ozonation step. Environ Pollut 158:1399–1404. https://doi.org/10.1016/j.envpol.2009.12.038
Schultze-Nobre L, Wiessner A, Bartsch C, Paschke H, Stefanakis AI, Aylward LA, Kuschk P (2017) Removal of dimethylphenols and ammonium in laboratory-scale horizontal subsurface flow constructed wetlands. Eng Life Sci 17:1224–1233. https://doi.org/10.1002/elsc.201600213
Sermon PA, Leadley JG, MacGibbon RM, Ruzimuradov O (2012) Tuning X/(TiO2)x–(SiO2)100–x (0 < x < 40) xerogel photocatalysts. Ionics 18:455–459. https://doi.org/10.1007/s11581-012-0686-z
Serpone N, Pellizetti E (1989) Photocatalysis. Fundamentals and applications. Wiley, New York
Serpone N, Terzian R, Hidaka H, Pelizzetti E (1994) Ultrasonic induced dehalogenation and oxidation of 2-, 3-, and 4-chlorophenol in air-equilibrated aqueous media. Similarities with irradiated semiconductor particulates. J Phys Chem 98:2634–2640. https://doi.org/10.1021/j100061a021
Setiyanto H, Adyatmika IM, Syaifullah MM, Zulfikar MA, Buchari (2018) Mediated electrochemical oxidation (MEO) process: a study on nonylphenol ethoxylates (NPE) oxidation in batch mode using cerium (IV) oxidant. In: Aisyah S, Samsudin A, AlJupri, Kusumawaty D, Nuraeni E, Yulianti K, Hasanah L, Rusyati L, Megasari R, Rosjanuardi R and Wiji (Eds.). 4th International Seminar of Mathematics, Science and Computer Science Education. IOP Publishing Ltd, Bristol, p UNSP 012201
Setiyanto H, Syaifullah MM, Adyatmika IM, Setyorini DA, Azis MY, Saraswaty V, Zulfikar MA (2021) Degradation of nonylphenol ethoxylate-10 (NPE-10) by mediated electrochemical oxidation (MEO) technology. Sains Malaysiana 50:373–381. https://doi.org/10.17576/jsm-2021-5002-09
Shao B, Hu J, Yang M, An W, Tao S (2005) Nonylphenol and nonylphenol ethoxylates in river water, drinking water, and fish tissues in the area of Chongqing, China. Arch Environ Contam Toxicol 48:467–473
Sharma R, Malaviya P (2022) Constructed wetlands for textile wastewater remediation: A review on concept, pollutant removal mechanisms, and integrated technologies for efficiency enhancement. Chemosphere 290:133358
Sherrard KB, Marriott PJ, Amiet RG, McCormick MJ, Colton R, Millington K (1996) Spectroscopic analysis of heterogeneous photocatalysis products of nonylphenol- and primary alcohol ethoxylate nonionic surfactants. Chemosphere 33:1921–1940. https://doi.org/10.1016/0045-6535(96)00292-5
Sikder MT, Rahman MM, Jakariya M, Hosokawa T, Kurasaki M, Saito T (2019) Remediation of water pollution with native cyclodextrins and modified cyclodextrins: a comparative overview and perspectives. Chem Eng J 355:920–941. https://doi.org/10.1016/j.cej.2018.08.218
Sivri S, Ustun GE (2020) Aygun A (2020) Electrooxidation of nonylphenol ethoxylate-10 (NP10E) in a continuous reactor by BDD anodes: optimisation of operating conditions. Int J Environ Anal Chem 10(2):456
Soares A, Guieysse B, Jefferson B, Cartmell E, Lester JN (2008) Nonylphenol in the environment: a critical review on occurrence, fate, toxicity and treatment in wastewaters. Environ Int 34:1033–1049. https://doi.org/10.1016/j.envint.2008.01.004
Soto AM, Justicia H, Wray JW, Sonnenschein C (1991) p-Nonyl-phenol: an estrogenic xenobiotic released from “modified” polystyrene. Environ Health Perspectives 92:167–173. https://doi.org/10.1289/ehp.9192167
Sousa H, Sousa CA, Simões LC, Simões M (2022) Microalgal-based removal of contaminants of emerging concern. J Hazard Mat 423:127153
Takeda S, Iida S, Chayama K, Tsuji H, Fukushi K, Wakida S (2000) Separation of bisphenol A and three alkylphenols by micellar electrokinetic chromatography. J Chromatogr A 895:213–218. https://doi.org/10.1016/S0021-9673(00)00666-X
Temiz K, Olmez-Hanci T, Arslan-Alaton I (2016) Zero-valent iron-activated persulfate oxidation of a commercial alkyl phenol polyethoxylate. Environ Technol 37:1757–1767. https://doi.org/10.1080/09593330.2015.1131751
Ternes TA, Stüber J, Herrmann N, McDowell D, Ried A, Kampmann M, Teiser B (2003) Ozonation: a tool for removal of pharmaceuticals, contrast media and musk fragrances from wastewater. Water Res 37:1976–1982. https://doi.org/10.1016/S0043-1354(02)00570-5
Tomei MC, Carozza NA (2015) Sequential anaerobic/anaerobic digestion for enhanced sludge stabilization: comparison of the process performance for mixed and waste sludge. Environ Sci Pollut Res 22:7271–7279. https://doi.org/10.1007/s11356-014-3130-2
Tomei MC, Mosca Angelucci D, Levantesi C (2016) Two-stage anaerobic and post-aerobic mesophilic digestion of sewage sludge: analysis of process performance and hygienization potentiality. Sci Total Environ 545–546:453–464. https://doi.org/10.1007/s11356-014-3130-2
Tomei MC, Angelucci DM, Mascolo G, Kunkel U (2019) Post-aerobic treatment to enhance the removal of conventional and emerging micropollutants in the digestion of waste sludge. Waste Manag 96:36–46. https://doi.org/10.1016/j.wasman.2019.07.013
Trujillo-Reyes J, Peralta-Vide JR, Gardea-Torresdey JL (2014) Supported and unsupported nanomaterials for water and soil remediation: are they a useful solution for worldwide pollution? J Hazard Mater 280:487–503. https://doi.org/10.1016/j.jhazmat.2014.08.029
Tsuji I, Kato H, Kobayashi H, Kudo A (2004) Photocatalytic H2 evolution reaction from aqueous solutions over band structure-controlled (AgIn)xZn2(1–x)S2 solid solution photocatalysts with visible-light response and their surface nanostructure. J Am Chem Soc 126:13406–13413. https://doi.org/10.1021/ja048296m
Umar M, Aziz HA (2013) Photocatalytic of organic pollutants in water. InTech Open Chapter 8:195–208. https://doi.org/10.5772/53699
Vatankhah H, Riley SM, Murray C, Quineones O, Xerxes Steirer K, Dickenson ERV, Christopher Bellona C (2019) Simultaneous ozone and granular activated carbon for advanced treatment of micropollutants in municipal wastewater effluent. Chemosphere 234:845–854. https://doi.org/10.1016/j.chemosphere.2019.06.082
Vazquez-Duhalt R, Marquez-Rocha F, Ponce Rivas E, Licea A, Viana MT (2005) Nonylphenol, an integrated vision of a pollutant. Scientific Review Appl Ecology Environ Res 4:1–25
Vences-Benitez JC, Martínez-Miranda V, Linares-Hernández I, Almazán-Sánchez PT, Vázquez-Mejía G (2017) Electrooxidation performance of aqueous solution of nonylphenol decaethoxylate and denim wastewater. Water Air Soil Pollut 228:393. https://doi.org/10.1007/s11270-017-3576-1
Venkatesan AK, Halden RU (2013) National inventory of alkylphenol ethoxylate compounds in U.S. sewage sludges and chemical fate in outdoor soil mesocosms. Environ Pollut 174:189–193. https://doi.org/10.1016/j.envpol.2012.11.012
Wang JX, Xie P, Guo NC (2007) Effects of nonylphenol on the growth and microcystin production of Microcystis strains. Environ Res 103:70–78
Wang L, Sun H, Wu Y, Huang G, Dai S (2009) Photodegradation of nonylphenol polyethoxylates in aqueous solution. Environ Chem 6:185–193. https://doi.org/10.1071/EN08101
Wang Q, Cissoko N, Zhou M, Xu X (2011) Effects and mechanism of humic acid on chromium(VI) removal by zero-valent iron (Fe0) nanoparticles. Phys Chem Earth 36:442–446
Wang Y, Wang Q, Zhan X, Wang F, Safdar M, He J (2013) Visible light driven type II heterostructures and their enhanced photocatalysis properties: a review. Nanoscale 5:8326–8339. https://doi.org/10.1039/C3NR01577G
Wang Y, Cao H, Chen L, Chen C, Duan X, Xie Y, Song W, Sun H, Wang S (2018) Tailored Synthesis of active reduced graphene oxides from waste graphite: structural defects and pollutant-dependent reactive radicals in aqueous organics decontamination. Appl Catal B Environ 229:71–80. https://doi.org/10.1016/j.apcatb.2018.02.010
Wang L, Xiao H, He N, Sun X, Duan S (2019) Biosorption and biodegradation of the environmental hormone nonylphenol by four marine microalgae. Sci Rep 9:5277. https://doi.org/10.1038/s41598-019-41808-8
Wert EC, Rosario-Ortiz FL, Snyder SA (2009) Effect of ozone exposure on the oxidation of trace organic contaminants in wastewater. Water Res 43:1005–1014. https://doi.org/10.1016/j.watres.2008.11.050
Wollmann F, Dietze S, Ackermann JU, Bley T, Walther T, Steingroewer J, Krujatz F (2019) Microalgae wastewater treatment: biological and technological approaches. Eng Life Sci 19:860–879. https://doi.org/10.1002/elsc.201900071
Xiao LL, Ching C, Ling YH, Nasiri M, Klemes MJ, Reineke TM, Helbling DE, Dichtel WR (2019) Cross-linker chemistry determines the uptake potential of perfluorinated alkyl substances by beta-cyclodextrin polymers. Macromolecules 52:3747–3752. https://doi.org/10.1021/acs.macromol.9b00417
Xie XW, Ma XG, Guo LH, Fan YM, Zeng GL, Zhang MY, Li J (2019) Novel magnetic multi-templates molecularly imprinted polymer for selective and rapid removal and detection of alkylphenols in water. Chem Eng J 357:56–65. https://doi.org/10.1016/j.cej.2018.09.080
Xin Y, Wang G, Zhu X, Gao M, Liu Y, Chen Q (2017) Photodegradation performance and mechanism of 4-nonylphenol by WO3/TiO2 and TiO2 nanotube array photoelectrodes. Environ Technol 38:3084–3092. https://doi.org/10.1080/09593330.2017.1290143
Xiong X, Sun B, Zhang J, Gao N, Shen J, Li J, Guan X (2014) Activating persulfate by Fe0 coupling with weak magnetic field: performance and mechanism. Water Res 62:53–62. https://doi.org/10.1016/j.watres.2014.05.042
Xu XR, Li XZ (2010) Degradation of azo dye orange G in aqueous solutions by persulfate with ferrous ion. Sep Purif Technol 72:105–111. https://doi.org/10.1016/j.seppur.2010.01.012
Xu YH, Chen HR, Zeng ZX, Lei B (2006) Investigation on mechanism of photocatalytic activity enhancement of nanometer cerium-doped titania. Appl Surf Sci 252:8565–8570. https://doi.org/10.1016/j.apsusc.2005.11.072
Xu GH, Xie XC, Qin L, Hu XJ, Zhang D, Xu J, Li D, Ji XW, Huang Y, Tu Y, Jiang L, Wei DY (2019) Simple synthesis of a swellable porous β-cyclodextrin-based polymer in the aqueous phase for the rapid removal of organic micro-pollutants from water. Green Chem 21:6062–6072. https://doi.org/10.1039/c9gc02422k
You X, Yang L, Zhou X, Zhang Y (2022) Sustainability and carbon neutrality trends for microalgae-based wastewater treatment: A review. Environ Res 209:112860
Yusof NA, Khairi NAS, Rahman SKA (2021) Molecularly imprinted polymer for water contaminants. Polymer nanocomposite-based smart materials. From Synthesis to application. Woodhead Publishing Series in Composites Science and Engineering, Chapter 12:211–233. https://doi.org/10.1016/B978-0-08-103013-4.00012-1
Zaytseva TB, Medvedeva NG (2019) Sorption and biodegradation of octyl- and nonylphenols by the cyanobacterium Planktothrix agardhii (Gomont) Anagn. & Komarek. Inland Water Biol 12:337–345. https://doi.org/10.1134/S1995082919030192
Zhao J, Hidaka H, Takamura H, Pelizzetti E, Serpone N (1993) Photodegradation of surfactants. 11. Zeta-potential measurements in the photocatalytic oxidation of surfactants in aqueous titania dispersions. Langmuir 9:1646–1650. https://doi.org/10.1021/la00031a008
Zhao J, Zhang Y, Quan X, Chen S (2010) Enhanced oxidation of 4-chlorophenol using sulfate radicals generated from zero-valent iron and peroxydisulfate at ambient temperature. Sep Purif Technol 71:302–307. https://doi.org/10.1016/j.seppur.2009.12.010
Zhou Z, Jiang JQ (2015) Treatment of selected pharmaceuticals by ferrate(VI): Performance, kinetic studies and identification of oxidation products. J Pharma Biomed 106:37–45. https://doi.org/10.1016/j.jpba.2014.06.032
Zhou GJ, Peng FQ, Yang B, Ying GG (2013) Cellular responses and bioremoval of nonylphenol and octylphenol in the freshwater green microalga Scenedesmus obliquus. Ecotoxicol Environ Safety 87:10–16. https://doi.org/10.1016/j.ecoenv.2012.10.002
Zhou GJ, Ying GG, Liu S, Zhou LJ, Chen ZF, Peng FQ (2014) Simultaneous removal of inorganic and organic compounds in wastewater by freshwater green microalgae. Environ Sci Processes 16:2018–2027. https://doi.org/10.1039/C4EM00094C
Zucker I, Mamane H, Cikurel H, Jekel M, Hübner U, Avisar D (2015) A hybrid process of biofiltration of secondary effluent followed by ozonation and short soil aquifer treatment for water reuse. Water Res 84:315–322. https://doi.org/10.1016/j.watres.2015.07.034
Acknowledgements
Nadia Morin-Crini and Grégorio Crini (Besançon, France) thanks the FEDER (Fonds Européen de Développment Régional) for its financial support (NIRHOFEX Program: “Innovative materials for wastewater treatment”), the Université de Franche-Comté for the research grant awarded to Guest Professor C. Bradu, and the Région Bourgogne Franche-Comté for the research grant awarded to Guest Researcher C. Cosentino. Ján Derco (Bratislava, Slovak Republic) thanks the Agency for Research and Development for the financial support (contract no APVV-0656-12). Olim Ruzimuradov thanks the Ministry of Innovative Development for the research project No FZ-2020092325. Helena Prosen (Ljubljana, Slovenia) and Borislav N. Malinović (Banja Luka, Bosnia and Herzegovina) acknowledge the financial support of Slovenian Research Agency (research programme P1-0153 and bilateral research project ARRS-BI-BA/19-20-040).
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Crini, G., Cosentino, C., Bradu, C. et al. Innovative technologies to remove alkylphenols from wastewater: a review. Environ Chem Lett 20, 2597–2628 (2022). https://doi.org/10.1007/s10311-022-01438-5
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DOI: https://doi.org/10.1007/s10311-022-01438-5