Experimental and computational assessment of 1,4-Dioxane degradation in a photo-Fenton reactive ceramic membrane filtration process

Abstract

• 1,4-Dioxane was degraded via the photo-Fenton reactive membrane filtration.

• Degradation efficiency and AQY were both enhanced in photocatalytic membrane.

• There is a tradeoff between photocatalytic degradation and membrane permeation flux.

• Degradation pathways of 1,4-Dioxane is revealed by DFT analysis.

The present study evaluated a photo-Fenton reactive membrane that achieved enhanced 1,4-Dioxane removal performance. As a common organic solvent and stabilizer, 1,4-Dioxane is widely used in a variety of industrial products and poses negative environmental and health impacts. The membrane was prepared by covalently coating photocatalyst of goethite (α-FeOOH) on a ceramic porous membrane as we reported previously. The effects of UV irradiation, H₂O₂ and catalyst on the removal efficiency of 1,4-Dioxane in batch reactors were first evaluated for optimized reaction conditions, followed by a systematical investigation of 1,4-Dioxane removal in the photo-Fenton membrane filtration mode. Under optimized conditions, the 1,4-Dioxane removal rate reached up to 16% with combination of 2 mmol/L H₂O₂ and UV₃₆₅ irradiation (2000 µW/cm²) when the feed water was filtered by the photo-Fenton reactive membrane at a hydraulic retention time of 6 min. The removal efficiency and apparent quantum yield (AQY) were both enhanced in the filtration compared to the batch mode of the same photo-Fenton reaction. Moreover, the proposed degradation pathways were analyzed by density functional theory (DFT) calculations, which provided a new insight into the degradation mechanisms of 1,4-Dioxane in photo-Fenton reactions on the functionalized ceramic membrane.

Graphical abstract

Keywords

Photo-Fenton / Ceramic membrane / 1,4-Dioxane / Goethite

References

[1] Adamson D T, Piña E A, Cartwright A E, Rauch S R, Anderson R H, Mohr T, Connor J A (2017). 1,4-Dioxane drinking water occurrence data from the third unregulated contaminant monitoring rule. Science of the Total Environment, 596: 236–245

[2] Ahmad R, Kim J K, Kim J H, Kim J (2019). Diethylene glycol-assisted organized TiO₂ nanostructures for photocatalytic wastewater treatment ceramic membranes. Water, 11(4): 750

[3] Alias N H, Jaafar J, Samitsu S, Matsuura T, Ismail A, Othman M, Rahman M A, Othman N H, Abdullah N, Paiman S H (2019). Photocatalytic nanofiber-coated alumina hollow fiber membranes for highly efficient oilfield produced water treatment. Chemical Engineering Journal, 360: 1437–1446

[4] Aryal R, Xia C, Liu J (2019). 1,4-Dioxane-contaminated groundwater remediation in the anode chamber of a microbial fuel cell. Water Environment Research, 91(11): 1537–1545

[5] Aziz A, Ibrahim S (2018). Preparation of activated carbon/N-doped titania composite for synergistic adsorption-photocatalytic oxidation of batik dye. MS&E, 358(1): 012014

[6] Barndõk H, Blanco L, Hermosilla D, Blanco Á (2016a). Heterogeneous photo-Fenton processes using zero valent iron microspheres for the treatment of wastewaters contaminated with 1,4-dioxane. Chemical Engineering Journal, 284: 112–121

[7] Barndõk H, Hermosilla D, Han C, Dionysiou D D, Negro C, Blanco Á (2016b). Degradation of 1,4-Dioxane from industrial wastewater by solar photocatalysis using immobilized NF-TiO₂ composite with monodisperse TiO₂ nanoparticles. Applied Catalysis B: Environmental, 180: 44–52

[8] Barndõk H, Cortijo L, Hermosilla D, Negro C, Blanco Á (2014). Removal of 1,4-Dioxane from industrial wastewaters: Routes of decomposition under different operational conditions to determine the ozone oxidation capacity. Journal of Hazardous Materials, 280: 340–347

[9] Beckett M A, Hua I (2000). Elucidation of the 1,4-Dioxane decomposition pathway at discrete ultrasonic frequencies. Environmental Science & Technology, 34(18): 3944–3953

[10] Beckett M A, Hua I (2003). Enhanced sonochemical decomposition of 1,4-Dioxane by ferrous iron. Water Research, 37(10): 2372–2376

[11] Berger T, Regmi C, Schäfer A, Richards B (2020). Photocatalytic degradation of organic dye via atomic layer deposited TiO₂–ceramic membranes in single-pass flow-through operation. Journal of Membrane Science: 118015

[12] Biniaz P, Makarem M A, Rahimpour M R (2019). Membrane reactors. In: Benaglia M, Puglisi A, eds. Catalyst Immobilization: Methods and Applications. Hoboken: Wiley, 307–324

[13] Chabalala M B (2016). Preparation of doped nanotitanium dioxide (TIO₂) immobilized on polyethersulphone (PES) nanofiberes for photocatalytic degradation of water pollutants. Master’s thesis. Johannesburg: University of Johannesburg

[14] Chakraborty S, Loutatidou S, Palmisano G, Kujawa J, Mavukkandy M O, Al-Gharabli S, Curcio E, Arafat H A (2017). Photocatalytic hollow fiber membranes for the degradation of pharmaceutical compounds in wastewater. Journal of Environmental Chemical Engineering, 5(5): 5014–5024

[15] Cheremisinoff N P (2017). Groundwater Remediation: A Practical Guide for Environmental Engineers and Scientists. Hoboken: John Wiley & Sons

[16] Chiou C H, Wu C Y, Juang R S (2008). Influence of operating parameters on photocatalytic degradation of phenol in UV/TiO₂ process. Chemical Engineering Journal, 139(2): 322–329

[17] Chitra S, Paramasivan K, Cheralathan M, Sinha P K (2012). Degradation of 1,4-Dioxane using advanced oxidation processes. Environmental Science and Pollution Research International, 19(3): 871–878

[18] Choi J Y, Lee Y J, Shin J, Yang J W (2010). Anodic oxidation of 1,4-Dioxane on boron-doped diamond electrodes for wastewater treatment. Journal of Hazardous Materials, 179(1–3): 762–768

[19] Coleman H, Vimonses V, Leslie G, Amal R (2007). Degradation of 1,4-Dioxane in water using TiO₂ based photocatalytic and H₂O₂/UV processes. Journal of Hazardous Materials, 146(3): 496–501

[20] De Angelis L, De Cortalezzi M M F (2016). Improved membrane flux recovery by Fenton-type reactions. Journal of Membrane Science, 500: 255–264

[21] De Clercq J, Van De Steene E, Verbeken K, Verhaege M (2010). Electrochemical oxidation of 1,4-Dioxane at boron-doped diamond electrode. Journal of Chemical Technology and Biotechnology (Oxford, Oxfordshire), 85(8): 1162–1167

[22] Ding Y, Sun W, Cao L, Yang J (2016). A spontaneous catalytic membrane reactor to dechlorinate 2,4,6-TCP as an organic pollutant in wastewater and to reclaim electricity simultaneously. Chemical Engineering Journal, 285: 573–580

[23] EPA, U.S. (2006). Treatment Technologies for 1,4-Dioxane: Fundamentals and Field Applications. Cincinnati: Office of Solid Waste and Emergency Response, EPA

[24] EPA, U.S. (2017). Technical Fact Sheet for 1, 4-dioxane: EPA 505-F-17-011. Washington: Federal Facilities Restoration and Reuse Office, EPA

[25] Fu W, Zhang W (2018). Microwave-enhanced membrane filtration for water treatment. Journal of Membrane Science, 568: 97–104

[26] Gu Y, Favier I, Pradel C, Gin D L, Lahitte J F, Noble R D, Gómez M, Remigy J C (2015). High catalytic efficiency of palladium nanoparticles immobilized in a polymer membrane containing poly (ionic liquid) in Suzuki–Miyaura cross-coupling reaction. Journal of Membrane Science, 492: 331–339

[27] Guo Y, Xu B, Qi F (2016). A novel ceramic membrane coated with MnO₂–Co₃O₄ nanoparticles catalytic ozonation for benzophenone-3 degradation in aqueous solution: fabrication, characterization and performance. Chemical Engineering Journal, 287: 381–389

[28] He J, Ma W, Song W, Zhao J, Qian X, Zhang S, Jimmy C Y (2005). Photoreaction of aromatic compounds at α-FeOOH/H₂O interface in the presence of H₂O₂: Evidence for organic-goethite surface complex formation. Water Research, 39(1): 119–128

[29] Hwangbo M, Claycomb E C, Liu Y, Alivio T E, Banerjee S, Chu K H (2019). Effectiveness of zinc oxide-assisted photocatalysis for concerned constituents in reclaimed wastewater: 1,4-Dioxane, trihalomethanes, antibiotics, antibiotic resistant bacteria (ARB), and antibiotic resistance genes (ARGs). Science of the Total Environment, 649: 1189–1197

[30] Jasmann J R, Borch T, Sale T C, Blotevogel J (2016). Advanced electrochemical oxidation of 1,4-Dioxane via dark catalysis by novel titanium dioxide (TiO₂) pellets. Environmental Science & Technology, 50(16): 8817–8826

[31] Johns M M, Marshall W E, Toles C A (1998). Agricultural by-products as granular activated carbons for adsorbing dissolved metals and organics. Journal of Chemical Technology & Biotechnology Biotechnology, 71(2): 131–140

[32] Kamaludin R, Puad A S M, Othman M H D, Kadir S H S A, Harun Z (2019). Incorporation of N-doped TiO₂ into dual layer hollow fiber (DLHF) membrane for visible light-driven photocatalytic removal of reactive black 5. Polymer Testing, 78: 105939

[33] Karges U, Becker J, Püttmann W (2018). 1,4-Dioxane pollution at contaminated groundwater sites in western Germany and its distribution within a TCE plume. Science of the Total Environment, 619: 712–720

[34] Klečka G M, Gonsior S J (1986). Removal of 1,4-Dioxane from wastewater. Journal of Hazardous Materials, 13(2): 161–168

[35] Kleine J, Peinemann K V, Schuster C, Warnecke H J (2002). Multifunctional system for treatment of wastewaters from adhesive-producing industries: Separation of solids and oxidation of dissolved pollutants using doted microfiltration membranes. Chemical Engineering Science, 57(9): 1661–1664

[36] Lee K C, Beak H J, Choo K H (2015). Membrane photoreactor treatment of 1, 4-Dioxane-containing textile wastewater effluent: Performance, modeling, and fouling control. Water Research, 86: 58–65

[37] Lee K C, Choo K H (2013). Hybridization of TiO₂ photocatalysis with coagulation and flocculation for 1,4-Dioxane removal in drinking water treatment. Chemical Engineering Journal, 231: 227–235

[38] Li S, Zhang G, Peng W, Zheng H, Zheng Y (2016). Microwave-enhanced Mn-Fenton process for the removal of BPA in water. Chemical Engineering Journal, 294: 371–379

[39] Li Y, Yeung K L (2019). Polymeric catalytic membrane for ozone treatment of DEET in water. Catalysis Today, 331: 53–59

[40] Liang L, Zhang J, Feng P, Li C, Huang Y, Dong B, Li L, Guan X (2015). Occurrence of bisphenol A in surface and drinking waters and its physicochemical removal technologies. Frontiers of Environmental Science & Engineering, 9(1): 16–38

[41] Liu G, Zhu D, Zhou W, Liao S, Cui J, Wu K, Hamilton D (2010). Solid-phase photocatalytic degradation of polystyrene plastic with goethite modified by boron under UV-vis light irradiation. Applied Surface Science, 256(8): 2546–2551

[42] Liu H, Chen T, Frost R L (2014). An overview of the role of goethite surfaces in the environment. Chemosphere, 103: 1–11

[43] Lyman W J, Reehl W F, Rosenblatt D H (1990). Handbook of Chemical Property Estimation Methods.Washington, DC: American Chemical Society

[44] Maekawa J, Mae K, Nakagawa H (2016). Degradation of 1,4-Dioxane by the ferrioxalate-mediated photo-Fenton process using UV or white LED irradiation. Journal of Chemical Engineering of Japan, 49(3): 305–311

[45] Mao J, Quan X, Wang J, Gao C, Chen S, Yu H, Zhang Y (2018). Enhanced heterogeneous Fenton-like activity by Cu-doped BiFeO₃ perovskite for degradation of organic pollutants. Frontiers of Environmental Science & Engineering, 12(6): 10

[46] Marenich A V, Cramer C J, Truhlar D G (2009). Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. Journal of Physical Chemistry B, 113(18): 6378–6396

[47] Martijn B J, Fuller A L, Malley J P, Kruithof J C (2010). Impact of IX-UF pretreatment on the feasibility of UV/H₂O₂ treatment for degradation of NDMA and 1,4-Dioxane. Ozone Science and Engineering, 32(6): 383–390

[48] Maurino V, Calza P, Minero C, Pelizzetti E, Vincenti M (1997). Light-assisted 1,4-dioxane degradation. Chemosphere, 35(11): 2675–2688

[49] Mcelroy A C, Hyman M R, Knappe D R (2019). 1,4-Dioxane in drinking water: Emerging for forty years and still unregulated. Current Opinion in Environmental Science & Health, 7: 117–125

[50] Mcguire M J, Suffet I H, Radziul J V (1978). Assessment of unit processes for the removal of trace organic compounds from drinking water. Journal-American Water Works Association, 70(10): 565–572

[51] Merayo N, Hermosilla D, Cortijo L, Blanco Á (2014). Optimization of the Fenton treatment of 1,4-Dioxane and on-line FTIR monitoring of the reaction. Journal of Hazardous Materials, 268: 102–109

[52] Miao X, Dai H, Chen J, Zhu J (2018). The enhanced method of hydroxyl radical generation in the heterogeneous UV-Fenton system with α-FeOOH as catalyst. Separation and Purification Technology, 200: 36–43

[53] Miao Y, Johnson N W, Gedalanga P B, Adamson D, Newell C, Mahendra S (2019). Response and recovery of microbial communities subjected to oxidative and biological treatments of 1,4-Dioxane and co-contaminants. Water Research, 149: 74–85

[54] Mohr T K, Stickney J A, Diguiseppi W H (2016). Environmental investigation and remediation: 1,4-Dioxane and other solvent stabilizers. Florida: CRC Press

[55] Moustakas N, Katsaros F, Kontos A, Romanos G E, Dionysiou D, Falaras P (2014). Visible light active TiO₂ photocatalytic filtration membranes with improved permeability and low energy consumption. Catalysis Today, 224: 56–69

[56] Nomura Y, Fukahori S, Fujiwara T J J O H M (2020). Removal of 1,4-Dioxane from landfill leachate by a rotating advanced oxidation contactor equipped with activated carbon/TiO₂ composite sheets. Journal of Hazardous Materials, 383: 121005

[57] Otitoju T A, Jiang D, Ouyang Y, Elamin M A M, Li S (2020). Photocatalytic degradation of Rhodamine B using CaCu₃Ti₄O₁₂ embedded polyethersulfone hollow fiber membrane. Journal of industrial and engineering chemistry, 83: 145–152

[58] Otto M, Nagaraja S (2007). Treatment technologies for 1,4-Dioxane: Fundamentals and field applications. Remediation Journal: The Journal of Environmental Cleanup Costs, Technologies & Techniques, 17(3): 81–88

[59] Papageorgiou S, Katsaros F, Favvas E, Romanos G E, Athanasekou C, Beltsios K, Tzialla O, Falaras P (2012). Alginate fibers as photocatalyst immobilizing agents applied in hybrid photocatalytic/ultrafiltration water treatment processes. Water Research, 46(6): 1858–1872

[60] Qing W, Li X, Shao S, Shi X, Wang J, Feng Y, Zhang W, Zhang W (2019). Polymeric catalytically active membranes for reaction-separation coupling: A review. Journal of Membrane Science, 583: 118–138

[61] Qing W, Liu F, Yao H, Sun S, Chen C, Zhang W (2020). Functional catalytic membrane development: A review of catalyst coating techniques. Advances in Colloid and Interface Science, 282: 102207

[62] Romanos G, Athanasekou C, Likodimos V, Aloupogiannis P, Falaras P (2013). Hybrid ultrafiltration/photocatalytic membranes for efficient water treatment. Industrial & Engineering Chemistry Research, 52(39): 13938–13947

[63] Romanos G E, Athanasekou C, Katsaros F, Kanellopoulos N, Dionysiou D, Likodimos V, Falaras P (2012). Double-side active TiO₂-modified nanofiltration membranes in continuous flow photocatalytic reactors for effective water purification. Journal of Hazardous Materials, 211: 304–316

[64] Rosenfeldt E J, Linden K G, Canonica S, Von Gunten U (2006). Comparison of the efficiency of OH radical formation during ozonation and the advanced oxidation processes O₃/H₂O₂ and UV/H₂O₂. Water Research, 40(20): 3695–3704

[65] Scaratti G, Basso A, Landers R, Alvarez P J, Puma G L, Moreira R F (2018). Treatment of aqueous solutions of 1,4-Dioxane by ozonation and catalytic ozonation with copper oxide (CuO). Environmental Technology, 39: 1–13

[66] Son H S, Choi S B, Khan E, Zoh K D (2006). Removal of 1,4-Dioxane from water using sonication: Effect of adding oxidants on the degradation kinetics. Water Research, 40(4): 692–698

[67] Son H S, Im J K, Zoh K D (2009). A Fenton-like degradation mechanism for 1,4-Dioxane using zero-valent iron (Fe⁰) and UV light. Water Research, 43(5): 1457–1463

[68] Stefan M I, Bolton J R (1998). Mechanism of the degradation of 1,4-Dioxane in dilute aqueous solution using the UV/hydrogen peroxide process. Environmental Science & Technology, 32(11): 1588–1595

[69] Stepien D K, Diehl P, Helm J, Thoms A, Püttmann W (2014). Fate of 1,4-Dioxane in the aquatic environment: From sewage to drinking water. Water Research, 48(1): 406–419

[70] Suh J H, Mohseni M (2004). A study on the relationship between biodegradability enhancement and oxidation of 1,4-Dioxane using ozone and hydrogen peroxide. Water Research, 38(10): 2596–2604

[71] Sun M, Lopez-Velandia C, Knappe D R (2016). Determination of 1,4-Dioxane in the Cape Fear River watershed by heated purge-and-trap preconcentration and gas chromatography–mass spectrometry. Environmental Science & Technology, 50(5): 2246–2254

[72] Sun S, Yao H, Fu W, Hua L, Zhang G, Zhang W (2018). Reactive photo-Fenton ceramic membranes: Synthesis, characterization and antifouling performance. Water Research, 144: 690–698

[73] Sun S, Yao H, Fu W, Xue S, Zhang W (2020). Enhanced degradation of antibiotics by photo-Fenton reactive membrane filtration. Journal of Hazardous Materials, 386: 121955

[74] Tian G P, Wu Q Y, Li A, Wang W L, Hu H Y (2017). Promoted ozonation for the decomposition of 1,4-Dioxane by activated carbon. Water Science and Technology: Water Supply, 17(2): 613–620

[75] Tseng D H, Juang L C, Huang H H (2012). Effect of oxygen and hydrogen peroxide on the photocatalytic degradation of monochlorobenzene in aqueous suspension. International Journal of Photoenergy, 2012: 328526

[76] Varanasi L, Coscarelli E, Khaksari M, Mazzoleni L R, Minakata D (2018). Transformations of dissolved organic matter induced by UV photolysis, Hydroxyl radicals, chlorine radicals, and sulfate radicals in aqueous-phase UV-Based advanced oxidation processes. Water Research, 135: 22–30

[77] Wang J, Wu Z, Li T, Ye J, Shen L, She Z, Liu F (2018). Catalytic PVDF membrane for continuous reduction and separation of p-nitrophenol and methylene blue in emulsified oil solution. Chemical Engineering Journal, 334: 579–586

[78] Wei S, Zeng C, Lu Y, Liu G, Luo H, Zhang R (2019). Degradation of antipyrine in the Fenton-like process with a La-doped heterogeneous catalyst. Frontiers of Environmental Science & Engineering, 13(5): 66

[79] Westermann T, Melin T (2009). Flow-through catalytic membrane reactors: Principles and applications. Chemical Engineering and Processing: Process Intensification, 48(1): 17–28

[80] Xu X, Liu S, Cui Y, Wang X, Smith K, Wang Y (2019). Solar-driven removal of 1,4-Dioxane using WO₃/ng-Al₂O₃ nano-catalyst in water. Catalysts, 9(4): 389

[81] Yabuki Y, Yoshida G, Daifuku T, Ono J, Banno A J J O W, Technology E (2018). Biological treatment of 1,4-Dioxane in wastewater from landfill by indigenous microbes attached to flowing carriers. Journal of Water and Environment Technology, 16(6): 245–255

[82] Youn N K, Heo J E, Joo O S, Lee H, Kim J, Min B K (2010). The effect of dissolved oxygen on the 1,4-Dioxane degradation with TiO₂ and Au–TiO₂ photocatalysts. Journal of Hazardous Materials, 177(1–3): 216–221

[83] Zeng Q, Dong H, Wang X, Yu T, Cui W (2017). Degradation of 1, 4-Dioxane by hydroxyl radicals produced from clay minerals. Journal of Hazardous Materials, 331: 88–98

[84] Zhang S, Gedalanga P B, Mahendra S (2017). Advances in bioremediation of 1,4-Dioxane-contaminated waters. Journal of Environmental Management, 204: 765–774

[85] Zhao Y, Truhlar D G (2008). The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: Two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theoretical Chemistry Accounts, 120(1–3): 215–241

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