Occurrence of bisphenol A in surface and drinking waters and its physicochemical removal technologies

Abstract

Bisphenol A (BPA), an endocrine disrupting compound, has caused wide public concerns due to its wide occurrence in environment and harmful effects. BPA has been detected in many surface waters and drinking water with the maximum concentrations up to tens of µg·L^-1. The physicochemical technology options in eliminating BPA can be divided into four categories: oxidation, advanced oxidation, adsorption and membrane filtration. Each removal option has its own limitation and merits in removing BPA. Oxidation and advanced oxidation generally can remove BPA efficiently while they also have some drawbacks, such as high cost, the generation of a variety of transformation products that are even more toxic than the parent compound and difficult to be mineralized. Only few advanced oxidation methods have been reported to be able to mineralize BPA completely. Therefore, it is important not only to identify the major initial transformation products but also to assess their estrogenic activity relative to the parent compounds when oxidation methods are employed to remove BPA. Without formation of harmful by-products, physical separation methods such as activated carbon adsorption and membrane processes are able to remove BPA in water effluents and thus have potential as BPA removal technologies. However, the necessary regeneration of activated carbon and the low BPA removal efficiency when the membrane became saturated may limit the application of activated carbon adsorption and membrane processes for BPA removal. Hybrid processes, e.g. combining adsorption and biologic process or combining membrane and oxidation process, which can achieve simultaneous physical separation and degradation of BPA, will be highly preferred in future.

Keywords

Bisphenol A (BPA) / occurrence / conventional oxidation / advanced oxidation / adsorption / membrane filtration

References

[1] Krishnan P, Le H, Lee S H, Gelerinter E. Further EPR studies of molecular motions in polymer/plasticizer mixtures. Journal of Polymer Science. Part B, Polymer Physics, 1993, 31(13): 1885–1890

[2] Von Reppert-Bismarck J, EU to Ban Bisphenol A in Baby Bottles in 2011, Reuters. Nov., 25. 2010

[3] Vandenberg L N, Hauser R, Marcus M, Olea N, Welshons W V. Human exposure to Bisphenol A (BPA). Reproductive Toxicology (Elmsford, N.Y.), 2007, 24(2): 139–177

[4] Kolpin D W, Furlong E T, Meyer M T, Thurman E M, Zaugg S D, Barber L B, Buxton H T. Pharmaceuticals, hormones, and other organic wastewater contaminants in U.S. streams, 1999-2000: a national reconnaissance. Environmental Science and Technology, 2002, 36(6): 1202–1211

[5] Rodriguez-Mozaz S, de Alda M J, Barceló D. Monitoring of estrogens, pesticides and BPA in natural waters and drinking water treatment plants by solid-phase extraction-liquid chromatography-mass spectrometry. Journal of Chromatography A, 2004, 1045(1-2): 85–92

[6] Fromme H, Küchler T, Otto T, Pilz K, Müller J, Wenzel A. Occurrence of phthalates and bisphenol A and F in the environment. Water Research, 2002, 36(6): 1429–1438

[7] Staples C A, Williams J B, Blessing R L, Varineau P T. Measuring the biodegradability of nonylphenol ether carboxylates, octylphenol ether carboxylates, and nonylphenol. Chemosphere, 1999, 38(9): 2029–2039

[8] Céspedes R, Lacorte S, Raldúa D, Ginebreda A, Barceló D, Piña B. Distribution of endocrine disruptors in the Llobregat River Basin (Catalonia, NE Spain). Chemosphere, 2005, 61(11): 1710–1719

[9] González-Casado A, Navas N, del Olmo M, Vílchez J L. Determination of BPA in water by micro liquid-liquid extraction followed by silylation and gas chromatography-mass spectrometry analysis. Journal of Chromatographic Science, 1998, 36(11): 565–569

[10] Ribeiro C, Pardal M Â, Martinho F, Margalho R, Tiritan M E, Rocha E, Rocha M J. Distribution of endocrine disruptors in the Mondego River Estuary, Portugal. Environmental Monitoring and Assessment, 2009, 149(1-4): 183–193

[11] Ribeiro C, Tiritan M E, Rocha E, Rocha M J. Seasonal and spatial distribution of several endocrine-disrupting compounds in the Douro River Estuary, Portugal. Archives of Environmental Contamination and Toxicology, 2009, 56(1): 1–11

[12] Jonkers N, Kohler H P E, Dammshäuser A, Giger W. Mass flows of endocrine disruptors in the Glatt River during varying weather conditions. Environmental Pollution, 2009, 157(3): 714–723

[13] Ko E J, Kim K W, Kang S Y, Kim S D, Bang S B, Hamm S Y, Kim D W. Monitoring of environmental phenolic endocrine disrupting compounds in treatment effluents and river waters, Korea. Talanta, 2007, 73(4): 674–683

[14] Pojana G, Gomiero A, Jonkers N, Marcomini A. Natural and synthetic endocrine disrupting compounds (EDCs) in water, sediment and biota of a coastal lagoon. Environment International, 2007, 33(7): 929–936

[15] Boyd G R, Palmeri J M, Zhang S, Grimm D A. Pharmaceuticals and personal care products (PPCPs) and endocrine disrupting chemicals (EDCs) in stormwater canals and Bayou St. John in New Orleans, Louisiana, USA. Science of the Total Environment, 2004, 333(1-3): 137–148

[16] Xue X, Wu F, Deng N.Determination of endocrine disrupting compounds in rivers and lakes of Wuhan City, China. Journal of Luoyang University, 2005, 20(4): 33–36 (in Chinese)

[17] Gong J, Ran Y, Chen D, Yang Y, Ma X. Occurrence and environmental risk of endocrine-disrupting chemicals in surface waters of the Pearl River, South China. Environmental Monitoring and Assessment, 2009, 156(1-4): 199–210

[18] Li Z, Li D.Distribution characteristics of BPA in Shihwa Lake and nearby creeks. Transactions of Oceanology and Limnology, 2004, 2: 30–35 (in Chinese)

[19] Zhao J L, Ying G G, Wang L, Yang J F, Yang X B, Yang L H, Li X. Determination of phenolic endocrine disrupting chemicals and acidic pharmaceuticals in surface water of the Pearl Rivers in South China by gas chromatography-negative chemical ionization-mass spectrometry. Science of the Total Environment, 2009, 407(2): 962–974

[20] Gong J, Ran Y, Yang Y, Chen D Y. Contamination of estrogenic compounds in the surface water of Guangzhou reach of the Pearl River. Environmental Chemistry, 2008, 2(27): 242–244 (in Chinese)

[21] Kang J H, Kondo F. BPA in the surface water and freshwater snail collected from rivers around a secure landfill. Bulletin of Environmental Contamination and Toxicology, 2006, 76(1): 113–118

[22] Hashimoto S, Horiuchi A, Yoshimoto T, Nakao M, Omura H, Kato Y, Tanaka H, Kannan K, Giesy J P. Horizontal and vertical distribution of estrogenic activities in sediments and waters from Tokyo Bay, Japan. Archives of Environmental Contamination and Toxicology, 2005, 48(2): 209–216

[23] Schmidt R, Brockmeyer R. Vorkommen und Verhalten von Expektorantien, Analgetika, Xylometazolin und deren Metaboliten in Gewässern und bei der Uferfiltration. Vom Wasser, 2002, 98: 37–54

[24] Kuch H M, Ballschmiter K. Determination of endocrine-disrupting phenolic compounds and estrogens in surface and drinking water by HRGC-(NCI)-MS in the picogram per liter range. Environmental Science and Technology, 2001, 35(15): 3201–3206

[25] Loos R, Hanke G, Umlauf G, Eisenreich S J. LC-MS-MS analysis and occurrence of octyl- and nonylphenol, their ethoxylates and their carboxylates in Belgian and Italian textile industry, waste water treatment plant effluents and surface waters. Chemosphere, 2007, 66(4): 690–699

[26] Alum A, Yoon Y, Westerhoff P, Abbaszadegan M. Oxidation of BPA, 17β-estradiol, and 17α-ethynyl estradiol and byproduct estrogenicity. Environmental Toxicology, 2004, 19(3): 257–264

[27] Lee J, Park H, Yoon J. Ozonation characteristics of bisphenol A in water. Water Environment and Technology, 2003, 24(2): 241–248

[28] Deborde M, Rabouan S, Duguet J P, Legube B. Kinetics of aqueous ozone-induced oxidation of some endocrine disruptors. Environmental Science and Technology, 2005, 39(16): 6086–6092

[29] Deborde M, Rabouan S, Mazellier P, Duguet J P, Legube B. Oxidation of BPA by ozone in aqueous solution. Water Research, 2008, 42(16): 4299–4308

[30] Garoma T, Matsumoto S. Ozonation of aqueous solution containing BPA: effect of operational parameters. Journal of Hazardous Materials, 2009, 167(1-3): 1185–1191

[31] Garoma T, Matsumoto S, Wu Y, Klinger R. Removal of BPA and its reaction-intermediates from aqueous solution by ozonation. Ozone Science and Engineering, 2010, 32(5): 338–343

[32] Gultekin I, Mavrov V, Ince N H. Degradation of BPA by ozonation. Journal of Advanced Oxidation Technologies, 2009, 12(2): 242–248

[33] Waldemer R H, Tratnyek P G. Kinetics of contaminant degradation by permanganate. Environmental Science and Technology, 2006, 40(3): 1055–1061

[34] Yang J J. Determination of trace permanganate and oxidation of BPA by permanganate. Dissertation for the Master Degree. Harbin: Harbin Institute of Technology, 2008: 32–35

[35] Jiang J, Pang S Y, Ma J. Role of ligands in permanganate oxidation of organics. Environmental Science and Technology, 2010, 44(11): 4270–4275

[36] Shao X L, Ma J, Wen G, Yang J J. Oxidation of estrone by permanganate: reaction kinetics and estrogenicity removal. Chinese Science Bulletin, 2010, 55(9): 802–808

[37] Lee Y, Um I H, Yoon J. Arsenic(III) oxidation by iron(VI) (ferrate) and subsequent removal of arsenic(V) by iron(III) coagulation. Environmental Science and Technology, 2003, 37(24): 5750–5756

[38] Li C, Li X Z, Graham N. A study of the preparation and reactivity of potassium ferrate. Chemosphere, 2005, 61(4): 537–543

[39] Lee Y, Yoon J, von Gunten U. Kinetics of the oxidation of phenols and phenolic endocrine disruptors during water treatment with ferrate (Fe(VI)). Environmental Science and Technology, 2005, 39(22): 8978–8984

[40] Li C, Li X Z, Graham N, Gao N Y. The aqueous degradation of BPA and steroid estrogens by ferrate. Water Research, 2008, 42(1-2): 109–120

[41] Zhang P, Zhang G, Dong J, Fan M, Zeng G. Bisphenol A oxidative removal by ferrate (Fe (VI)) under a weak acidic condition. Separation and Purification Technology, 2011, 84(1): 46–51

[42] Deborde M, von Gunten U. Reactions of chlorine with inorganic and organic compounds during water treatment-Kinetics and mechanisms: a critical review. Water Research, 2008, 42(1-2): 13–51

[43] Hu J Y, Aizawa T, Ookubo S. Products of aqueous chlorination of BPA and their estrogenic activity. Environmental Science and Technology, 2002, 36(9): 1980–1987

[44] Gallard H, Leclercq A, Croué J P. Chlorination of BPA: kinetics and by-products formation. Chemosphere, 2004, 56(5): 465–473

[45] Yamamoto T, Yasuhara A. Chlorination of BPA in aqueous media: formation of chlorinated bisphenol A congeners and degradation to chlorinated phenolic compounds. Chemosphere, 2002, 46(8): 1215–1223

[46] Torres R A, Pétrier C, Combet E, Carrier M, Pulgarin C. Ultrasonic cavitation applied to the treatment of bisphenol A. Effect of sonochemical parameters and analysis of BPA by-products. Ultrasonics Sonochemistry, 2008, 15(4): 605–611

[47] Torres R A, Abdelmalek F, Combet E, Pétrier C, Pulgarin C. A comparative study of ultrasonic cavitation and Fenton’s reagent for BPA degradation in deionised and natural waters. Journal of Hazardous Materials, 2007, 146(3): 546–551

[48] Torres R A, Pétrier C, Combet E, Moulet F, Pulgarin C. BPA mineralization by integrated ultrasound-UV-iron (II) treatment. Environmental Science and Technology, 2007, 41(1): 297–302

[49] Gültekin I, Ince N H. Ultrasonic destruction of BPA: the operating parameters. Ultrasonics Sonochemistry, 2008, 15(4): 524–529

[50] Guo Z, Feng R. Ultrasonic irradiation-induced degradation of low-concentration bisphenol A in aqueous solution. Journal of Hazardous Materials, 2009, 163(2-3): 855–860

[51] Mahamuni N N, Adewuyi Y G. Advanced oxidation processes (AOPs) involving ultrasound for waste water treatment: a review with emphasis on cost estimation. Ultrasonics Sonochemistry, 2010, 17(6): 990–1003

[52] Tsai W T, Lee M K, Su T Y, Chang Y M. Photodegradation of BPA in a batch TiO₂ suspension reactor. Journal of Hazardous Materials, 2009, 168(1): 269–275

[53] Watanabe N, Horikoshi S, Kawabe H, Sugie Y, Zhao J, Hidaka H. Photodegradation mechanism for BPA at the TiO₂/H₂O interfaces. Chemosphere, 2003, 52(5): 851–859

[54] Guo C, Ge M, Liu L, Gao G, Feng Y, Wang Y. Directed synthesis of mesoporous TiO₂ microspheres: catalysts and their photocatalysis for BPA degradation. Environmental Science and Technology, 2010, 44(1): 419–425

[55] Xie Y B, Li X Z. Degradation of BPA in aqueous solution by H₂O₂-assisted photoelectrocatalytic oxidation. Journal of Hazardous Materials, 2006, 138(3): 526–533

[56] Fukahori S, Iguchi Y, Ichiura H, Kitaoka T, Tanaka H, Wariishi H. Effect of void structure of photocatalyst paper on VOC decomposition. Chemosphere, 2007, 66(11): 2136–2141

[57] Wang R, Ren D, Xia S, Zhang Y, Zhao J. Photocatalytic degradation of BPA using immobilized TiO₂ and UV illumination in a horizontal circulating bed photocatalytic reactor (HCBPR). Journal of Hazardous Materials, 2009, 169(1-3): 926–932

[58] Tao H, Hao S, Chang F, Wang L, Zhang Y, Cai X, Zeng J S D. Photodegradation of BPA by Titana Nanoparticles in Mesoporous MCM-41. Water, Air, and Soil Pollution, 2011, 214(1): 491–498

[59] Horikoshi S, Hidaka H, Serpone N. Environmental remediation by an integrated microwave/UV illumination technique: VI. A simple modified domestic microwave oven integrating an electrodeless UV-Vis lamp to photodegrade environmental pollutants in aqueous media. Journal of Photochemistry and Photobiology A Chemistry, 2004, 161(2): 221–225

[60] Wang G, Wu F, Zhang X, Luo M, Deng N. Enhanced TiO₂ photocatalytic degradation of bisphenol E by β-cyclodextrin in suspended solutions. Journal of Photochemistry and Photobiology A Chemistry, 2006, 133(1-3): 85–91

[61] Kaneco S, Rahman M A, Suzuki T, Katsumata H, Ohta K. Optimization of solar photocatalytic degradation conditions of BPA in water using titanium dioxide. Journal of Photochemistry and Photobiology A Chemistry, 2004, 163(3): 419–424

[62] Subagio D P, Srinivasan M, Lim M, Lim T T. Photocatalytic degradation of BPA by nitrogen-doped TiO₂ hollow sphere in a vis-LED photoreactor. Applied Catalysis B: Environmental, 2010, 95(3–4): 414–422

[63] Wang Y, Wang X, Li C M. Electrocatalysis of Pd–Co supported on carbon black or ball-milled carbon nanotubes towards methanol oxidation in alkaline media. Applied Catalysis B: Environmental, 2010, 99(1): 229–234

[64] Yang J, Dai J, Li J. Synthesis, characterization and degradation of BPA using Pr, N co-doped TiO₂ with highly visible light activity. Applied Surface Science, 2011, 257(21): 8965–8973

[65] Zhou D, Wu F, Deng N, Xiang W. Photooxidation of BPA in water in the presence of ferric and carboxylate salts. Water Research, 2004, 38(19): 4107–4116

[66] Liu Y, Deng L, Chen Y, Wu F, Deng N. Simultaneous photocatalytic reduction of Cr(VI) and oxidation of BPA induced by Fe(III)-OH complexes in water. Journal of Hazardous Materials, 2007, 139(2): 399–402

[67] Zhan M, Yang X, Xian Q, Kong L. Photosensitized degradation of BPA involving reactive oxygen species in the presence of humic substances. Chemosphere, 2006, 63(3): 378–386

[68] Wang C, Zhu L, Song C, Shan G, Chen P. Characterization of photocatalyst Bi_3.84W_0.16O_6.24 and its photodegradation on BPA under simulated solar light irradiation. Applied Catalysis B: Environmental, 2011, 105(1-2): 229–236

[69] Rosenfeldt E J, Linden K G. Degradation of endocrine disrupting chemicals BPA, ethinyl estradiol, and estradiol during UV photolysis and advanced oxidation processes. Environmental Science and Technology, 2004, 38(20): 5476–5483

[70] Chen B, Yang C, Goh N K. Photolysis pathway of nitroaromatic compounds in aqueous solutions in the UV/H₂O₂ process. Journal of Environmental Sciences (China), 2006, 18(6): 1061–1064

[71] Chen P J, Kullman S W, Hinton D E, Linden K G. Comparisons of polychromatic and monochromatic UV-based treatments of BPA in water via toxicity assessments. Chemosphere, 2007, 68(6): 1041–1049

[72] Chen P J, Linden K G, Hinton D E, Kashiwada S, Rosenfeldt E J, Kullman S W. Biological assessment of BPA degradation in water following direct photolysis and UV advanced oxidation. Chemosphere, 2006, 65(7): 1094–1102

[73] Irmak S, Erbatur O, Akgerman A. Degradation of 17β-estradiol and BPA in aqueous medium by using ozone and ozone/UV techniques. Journal of Hazardous Materials, 2005, 126(1-3): 54–62

[74] Rivas F J, Carbajo M, Beltrán F, Gimeno O, Frades J. Comparison of different advanced oxidation processes (AOPs) in the presence of perovskites. Journal of Hazardous Materials, 2008, 155(3): 407–414

[75] Katsumata H, Kawabe S, Kaneco S, Suzuki T, Ohta K. Degradation of BPA in water by the photo-Fenton reaction. Journal of Photochemistry and Photobiology A Chemistry, 2004, 162(2): 297–305

[76] Inoue M, Masuda Y, Okada F, Sakurai A, Takahashi I, Sakakibara M. Degradation of BPA using sonochemical reactions. Water Research, 2008, 42(6-7): 1379–1386

[77] Torres R A, Sarantakos G, Combet E, Pétrier C, Pulgarin C. Sequential helio-photo-Fenton and sonication processes for the treatment of BPA. Journal of Photochemistry and Photobiology A Chemistry, 2008, 199(2): 197–203

[78] Neamţu M, Frimmel F H. Degradation of endocrine disrupting BPA by 254 nm irradiation in different water matrices and effect on yeast cells. Water Research, 2006, 40(20): 3745–3750

[79] Huang Y F, Huang Y H. Behavioral evidence of the dominant radicals and intermediates involved in BPA degradation using an efficient Co²⁺/PMS oxidation process. Journal of Hazardous Materials, 2009, 167(1-3): 418–426

[80] Torres-Palma R A, Nieto J I, Combet E, Pétrier C, Pulgarin C. An innovative ultrasound, Fe²⁺ and TiO₂ photoassisted process for BPA mineralization. Water Research, 2010, 44(7): 2245–2252

[81] Huang Y F, Huang Y H. Identification of produced powerful radicals involved in the mineralization of BPA using a novel UV-Na₂S₂O₈/H₂O₂-Fe(II,III) two-stage oxidation process. Journal of Hazardous Materials, 2009, 162(2-3): 1211–1216

[82] Pan B, Lin D, Mashayekhi H, Xing B. Adsorption and hysteresis of BPA and 17α-ethinyl estradiol on carbon nanomaterials. Environmental Science and Technology, 2008, 42(15): 5480–5485

[83] Nakanishi A, Tamai M, Kawasaki N, Nakamura T, Tanada S. Adsorption characteristics of BPA onto carbonaceous materials produced from wood chips as organic waste. Journal of Colloid and Interface Science, 2002, 252(2): 393–396

[84] Bautista-Toledo I, Ferro-García M A, Rivera-Utrilla J, Moreno-Castilla C, Vegas Fernández F J. BPA removal from water by activated carbon. Effects of carbon characteristics and solution chemistry. Environmental Science and Technology, 2005, 39(16): 6246–6250

[85] Tsai W T, Lai C W, Su T Y. Adsorption of BPA from aqueous solution onto minerals and carbon adsorbents. Journal of Hazardous Materials, 2006, 134(1-3): 169–175

[86] Liu G, Ma J, Li X, Qin Q. Adsorption of BPA from aqueous solution onto activated carbons with different modification treatments. Journal of Hazardous Materials, 2009, 164(2-3): 1275–1280

[87] Asada T, Oikawa K, Kawata K, Ishihara S, Iyobe T, Yamada A. Study of removal effect of BPA and beta-estradiol by porous carbon. Journal of Health Science, 2004, 50(6): 588–593

[88] Sui Q, Huang J, Liu Y, Chang X, Ji G, Deng S, Xie T, Yu G. Rapid removal of BPA on highly ordered mesoporous carbon. Journal of Environmental Sciences (China), 2011, 23(2): 177–182

[89] Yoon Y, Westerhoff P, Snyder S A, Esparza M. HPLC-fluorescence detection and adsorption of BPA, 17β-estradiol, and 17α-ethynyl estradiol on powdered activated carbon. Water Research, 2003, 37(14): 3530–3537

[90] Mao M, Liu Z, Wang T, Yu B, Wen X, Yang K, Zhao C. Polysulfone‐activated carbon hybrid particles for the removal of BPA. Separation Science and Technology, 2006, 41(3): 515–529

[91] Pan J, Yao H, Li X, Wang B, Huo P, Xu W, Ou H, Yan Y. Synthesis of chitosan/γ-Fe₂O₃/fly-ash-cenospheres composites for the fast removal of BPA and 2,4,6-trichlorophenol from aqueous solutions. Journal of Hazardous Materials, 2011, 190(1-3): 276–284

[92] Matsushita K, Shimada M, Okayama T. Adsorption properties of BPA on activated carbon prepared from wastepaper. Sen'i Gakkaishi, 2009, 65(11): 287–291

[93] Zhang Y, Causserand C, Aimar P, Cravedi J P. Removal of BPA by a nanofiltration membrane in view of drinking water production. Water Research, 2006, 40(20): 3793–3799

[94] Dong B, Wang L, Gao N. The removal of BPA by ultrafiltration. Desalination, 2008, 221(1-3): 312–317

[95] Dong B, Chu H, Wang L, Xia S, Gao N. The removal of BPA by hollow fiber microfiltration membrane. Desalination, 2010, 250(2): 693–697

[96] Wu S, Dong B, Huang Y. Adsorption of BPA by polysulphone membrane. Desalination, 2010, 253(1–3): 22–29

[97] Liu L, Zheng G, Yang F. Adsorptive removal and oxidation of organic pollutants from water using a novel membrane. Chemical Engineering Journal, 2010, 156(3): 553–556

[98] Kim J H, Kim S, Lee C H, Kwon H H, Lee S. A novel nanofiltration hybrid system to control organic micro-pollutants: application of dual functional adsorbent/catalyst. Desalination, 2008, 231(1–3): 276–282

[99] Chin S S, Lim T M, Chiang K, Fane A G. Factors affecting the performance of a low-pressure submerged membrane photocatalytic reactor. Chemical Engineering Journal, 2007, 130(1): 53–63

[100] Zhang T, Zhang X, Yan X, Ng J, Wang Y, Sun D D. Removal of BPA via a hybrid process combining oxidation on β-MnO₂ nanowires with microfiltration. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2011, 392(1): 198–204

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Grant Nos. 21077029 and 11175244), the Foundation of the State Key Laboratory of Pollution Control and Resource Reuse, China (PCRRY11001), and the Shanghai Rising-Star Program (12QA1403500).

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