265
Views
26
CrossRef citations to date
0
Altmetric
Original Articles

A Critical Review of the Formation of Mono- and Dicarboxylated Metabolic Intermediates of Alkylphenol Polyethoxylates during Wastewater Treatment and Their Environmental Significance

, , , &
Pages 199-238 | Published online: 02 Mar 2010

REFERENCES

  • Ackermann , G. E. , Schwaiger , J. , Negele , R. D. and Fent , K. 2002 . Effects of long-term nonylphenol exposure on gonadal development and biomarkers of estrogenicity in juvenile rainbow trout (Oncorhynchus mykiss) . Aquat. Toxicol. , 60 : 203 – 221 .
  • AEA Technology Environment . 2004 . The environmental and economic costs and social consequences of reducing levels of dangerous substances discharged from waste water treatment works in the Yorkshire water region , Oxford, , England : Author . A report produced for Yorkshire Water
  • Ahel , M. , Conrad , T. and Giger , W. 1987 . Persistent organic chemicals in sewage effluents 3. Determinations of nonylphenoxy carboxylic acids by high-resolution gas-chromatography mass/spectrometry and high-performance liquid chromatography . Environ. Sci. Technol. , 21 : 697 – 703 .
  • Ahel , M. , Giger , W. and Koch , M. 1994a . Behaviour of alkylphenol polyethoxylate surfactants in the aquatic environment – I Occurrence and transformation in sewage treatment . Water. Res. , 28 : 1131 – 1142 .
  • Ahel , M. , Giger , W. and Schaffner , C. 1994b . Behaviour of alkylphenol polyethoxylate surfactants in the aquatic environment—II Occurrence and transformation in rivers . Water. Res. , 28 : 1143 – 1152 .
  • Ahel , M. , Hrsak , D. and Giger , W. 1994c . Aerobic transformation of short-chain alkylphenol polyethoxylates by mixed bacterial cultures . Arc. Environ. Contam. Toxicol. , 26 : 540 – 548 .
  • Ahel , M. , Schaffner , C. and Giger , W. 1996 . Behaviour of alkylphenol polyethoxylate surfactants in the aquatic environment—III. Occurrence and elimination of their persistent metabolites during infiltration of river water to groundwater . Water Res. , 30 : 37 – 46 .
  • Ahel , M. , Scully , F. E. , Hoigne , J. and Giger , W. 1994d . Photochemical degradation of nonylphenol and nonylphenol polyethoxylates in natural waters . Chemosphere , 28 : 1361 – 1368 .
  • Ahel , M. , Giger , W. , Molnar , E. and Ibric , S. 2000 . Determination of nonylphenol polyethoxylates and their lipophilic metabolites in sewage effluents by normal-phase high-performance liquid chromatography and fluorescence detection . Croatica Chem. Acta. , 73 : 209 – 227 .
  • APE Research Council . 2004 . Regulatory status of alkylphenols and their ethoxylates in the United States, Canada and the European Union , Washington, DC : Author .
  • Ashfield , L. A. , Pottinger , T. G. and Sumpter , J. P. 1988 . Exposure of female juvenile rainbow trout to alkylphenolic compounds results in modification to growth and ovosomatic index . Environ. Toxicol. Chem. , 17 : 679 – 686 .
  • Ball , H. A. and Reinhard , M. 1985 . “ Discharge of halogenated octylphenol polyethoxylate residues in a chlorinated secondary effluent ” . In Water chlorination: Chemistry, environmental impact and health effects , Edited by: Jolley , R. L. vol. 5 , 1505 – 1514 . Chelsea, MI : Lewis .
  • Ball , H. A. , Reinhard , M. and McCarty , P. L. 1989 . Biotransformation of halogenated and nonhalogenated octylphenol polyethoxylate residues under aerobic and anaerobic conditions . Environ. Sci. Technol. , 23 : 951 – 961 .
  • Barber , L. B. , Brown , G. K. and Zaugg , S. D. 2000 . Potential endocrine disrupting organic chemicals in treated municipal wastewater and river water . Analysis of Environmental Endocrine Disruptors ACS Symposium Series , 747 : 97 – 124 .
  • Bennie , T. D. 1999 . Review of the environmental occurrence of alkylphenols and alkylphenol ethoxylates . Water Qual. Res. J. Canada. , 34 : 79 – 122 .
  • Bennie , T. D. , Burnison , K. , Cureton , P. , Davidson , N. , Rawn , T. and Servos , M. R. 2001 . Uncertainties associated with assessing the risk of an endocrine active substance in the Canadian environment . Water Qual. Res. J. Canada. , 36 : 319 – 330 .
  • Birkett , J. W. and Lester , J. N. 2002 . Endocrine disrupters in wastewater and sludge treatment processes. , Boca Raton, FL : CRC Press .
  • Cefic . 2002 . Chemistry sectors: Detergents. CESIO surfactants statistics for Western Europe , Brussels : Author .
  • Chang , B. V. , Yu , C. H. and Yuan , S. Y. 2004 . Degradation of nonylphenol by anaerobic microorganisms from river sediment . Chemosphere. , 55 : 493 – 500 .
  • Cheng , C. Y. , Wu , C. Y. , Wang , C. H. and Ding , W. H. 2006a . Determination and distribution characteristics of degradation products of nonylphenol polyethoxylates in the rivers of Taiwan . Chemosphere , 65 : 2275 – 2281 .
  • Cheng , C. Y. , Li , W. R. , Chang , J. W. , Wu , H. C. and Ding , W. H. 2006b . Synthesis and determination of dicarboxylic degradation products of nonylphenol polyethoxylates by gas chromatography–mass spectrometry . J. Chromatogr. A. , 1127 : 246 – 253 .
  • Chiu , T. Y. , Lara Dominguez , M. V. and James , A. E. 2006 . Critical flux and rejection behaviour of non-circular-channelled membranes. Influence of some operating conditions . Sep. Purif. Technol. , 50 : 212 – 219 .
  • Clara , M. , Strenn , B. , Gans , O. , Martinez , E. , Kreuzinger , N. and Kroiss , H. 2005 . Removal of selected pharmaceuticals, fragrances and endocrine disrupting compounds in a membrane bioreactor and conventional wastewater treatment plants . Water Res. , 39 : 4797 – 4807 .
  • Comber , M. H. I. , Williams , T. D. and Stewart , K. M. 1993 . The effects of nonylphenol on Daphnia magna . Water Res. , 27 : 273 – 276 .
  • Conn , K. E. , Barber , L. B. , Brown , G. K. and Siegrist , R. L. 2006 . Occurrence and fate of organic contaminants during onsite wastewater treatment . Environ. Sci. Technol. , 40 : 7358 – 7366 .
  • DiCorcia , A. , Samperi , R. and Marcomini , E. 1994 . Monitoring aromatic surfactants and their biodegradation intermediates in raw and treated sewages by solid-phase extraction and liquid chromatography . Environ. Sci. Technol. , 28 : 850 – 858 .
  • DiCorcia , A. , Constantino , A. , Crescenzi , C. , Marinoni , E. and Samperi , R. 1998a . Characterization of recalcitrant intermediates from biotransformation of the branched alkyl side chain of nonylphenol ethoxylate surfactants . Environ. Sci. Technol. , 32 : 2401 – 2409 .
  • DiCorcia , A. , Crescenzi , C. , Marcomini , E. and Samperi , R. 1998b . Liquid chromatography-electrospray-mass spectrometry as a valuable tool for characterizing biodegradation intermediates of branched alcohol ethoxylate surfactants . Environ. Sci. Technol. , 32 : 711 – 718 .
  • DiCorcia , A. , Cavallo , R. , Crescenzi , C. and Nazzari , M. 2000 . Occurrence and abundance of dicarboxylated metabolites of nonylphenol polyethoxylate surfactants in treated sewages . Environ. Sci. Technol. , 34 : 3914 – 3919 .
  • Ding , W. H. and Chen , C. T. 1999 . Analysis of nonylphenol polyethoxycarboxylates and their related metabolites by on-line derivatization and ion-trap gas chromatography-mass spectrometry . J. Chromatogr. A. , 862 : 113 – 120 .
  • Ding , W. H. and Tzing , S. H. 1998 . Analysis of nonylphenol polyethoxylates and their degradation products in river water and sewage effluent by gas chromatography-ion trap (tandem) mass spectrometry with electron impact and chemical ionization . J. Chromatogr. A. , 824 : 79 – 90 .
  • Ding , W. H. , Fujita , Y. , Aeschimann , R. and Reinhard , M. 1996 . Identification of organic residues in tertiary effluents by GC/EI-MS, GC-CI-MS and GC-TSQ-MS . Fresenius J. Anal. Chem. , 354 : 48 – 55 .
  • Ding , W. H. , Tzing , S. H. and Lo , J. H. 1999 . Occurrence and concentrations of aromatic surfactants and their degradation products in river waters of Taiwan . Chemosphere. , 38 : 2597 – 2606 .
  • Duarte , C. L. , Sampa , M. H. O. , Rela , P. R. , Oikawa , H. and Silveira , G. G. 2002 . Advanced oxidation process by electron-beam irradiation-induced decomposition of pollutants in industrial effluents . Radiat. Phys. Chem. , 63 : 647 – 651 .
  • Dussault , E. B. , Sherry , J. P. , Lee , H. B. , Burnison , B. K. , Bennie , D. T. and Servos , M. R. 2005 . In vivo estrogenicity of nonylphenol and its ethoxylates in the Canadian environment . Hum. Ecol. Risk Assess. , 11 : 353 – 364 .
  • Dutta , A. P. January 15 2008 . Authorities clueless: Carcinogen NP in a large number of products in India January 15 , Down To Earth magazine
  • Environment Canada and Health Canada . 2001 . Priority substances list assessment report: Nonylphenol and its ethoxylates Retrieved February 8, 2010, from http://www.hc-sc.gc.ca/ewh-semt/alt_formats/hecs-sesc/pdf/pubs/contaminants/psl2-lsp2/nonylphenol/nonylphenol_e.pdf(Report no. EN40-215-/57E, 98)
  • European Commission . 2000 . Water framework directive (2000/60/EC): Establishing a framework for community action in the field of water policy , Brussels : Author .
  • European Commission . 2002 . “ European chemicals bureau ” . In 4-Nonylphenol (branched) and nonylphenol: European Union risk assessment report Retrieved February 8, 2010, from http://ecbjrcit/existingchemicals/(Report no. EUR 20387 EN)
  • European Commission . 2003a . Directive 2003/53/EC of the European Parliament and of the Counil of 18 June 2003, amending for the 26th time Council Directive 76/769/EEC relating to restrictions on the marketing and use of certain dangerous substances and preparations (nonylphenol, nonylphenol ethoxylate and cement) Retrieved February 21, 2010, from http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2003:178:0024:0027:en:PDF
  • European Commission . 2003b . Integrated pollution prevention and control: Reference document on best available techniques for the textile industry Retrieved February 8, 2010, from http://www.jrc.es/pub/english.cgi/0/733169
  • Ferguson , P. L. and Brownawell , B. J. 2003 . Degradation of nonylphenol ethoxylates in estuarine sediment under aerobic and anaerobic conditions . Environ. Toxicol. Chem. , 22 : 1189 – 1199 .
  • Ferguson , P. L. , Iden , R. C. and Brownawell , J. B. 2000 . Analysis of alkylphenol ethoxylate metabolites in the aquatic environment using liquid chromatography-electrospray mass spectrometry . Environ. Sci. Technol. , 72 : 4322 – 4330 .
  • Ferguson , P. L. , Iden , R. C. and Brownawell , J. B. 2001 . Distribution and fate of neutral alkylphenol ethoxylate metabolites in a sewage-impacted urban estuary . Environ. Sci. Technol. , 35 : 2428 – 2435 .
  • Field , J. A. and Reed , R. L. 1996 . Nonylphenol polyethoxylate carboxylate metabolites of non-ionic surfactants in U. S. paper mill effluents, municipal sewage treatment plant effluents, and river waters . Environ. Sci. Technol. , 30 : 3544 – 3550 .
  • Field , J. A. and Reed , R. L. 1999 . Subcritical (hot) water/ethanol extraction of nonylphenol polyethoxy carboxylates from industrial and municipal sludges . Environ. Sci. Technol. , 33 : 2782 – 2787 .
  • Frassinetti , S. , Isoppo , A. L. , Corti , A. and Allini , G. V. 1996 . Bacterial attack of nonionic aromatic surfactants: Comparison of degradative capabilities of new isolates from nonylphenol polyethoxylate polluted waste waters . Environ. Techol. , 17 : 199 – 213 .
  • Fujii , K. , Urano , N. , Ushio , H. , Satomi , M. , Iida , H. Ushio-Sata , N. 2000 . Profile of a nonylphenol-degrading microflora and its potential for bioremedial applications . J. Biochem. , 128 : 909 – 916 .
  • Fujita , Y. and Reinhard , M. 1997 . Identification of metabolites from the biological transformation of the nonionic surfactant residue octylphenoxy acid and its brominated analog . Environ. Sci. Technol. , 31 : 1518 – 1524 .
  • Fujita , M. , Ike , M. , Mori , K. , Kaku , H. , Sakaguchi , Y. Asano , M. 2000 . Behaviour of nonylphenol ethoxylates in sewage treatment plants in Japan – Biotransformation and ecotoxicity . Water Sci. Technol. , 42 : 23 – 30 .
  • Fukushima , M. and Tatsumi , K. 2001 . Degradation pathways of pentachlorophenol by photo-fenton systems in the presence of iron(III), humic acid, and hydrogen peroxide . Environ. Sci. Technol. , 35 : 1771 – 1778 .
  • Garcia-Reyero , N. , Requena , V. , Petrovic , M. , Fischer , B. , Hansen , P. Diaz , A. 2004 . Estrogenic potential of halogenated derivatives of nonylphenol ethoxylates and carboxylates . Environ. Toxicol. Chem. , 23 : 705 – 711 .
  • Gehringer , P. , Eschweiler , H. , Weiss , S. and Reemtsma , T. 2005 . Decomposition of aqueous naphthalene 1,5-disulfonic acid by means of oxidation processes . Ozone Sci. Eng. , 28 : 437 – 443 .
  • Gibson , R. , Wang , M. J. , Padgett , E. and Beck , A. J. 2005 . Analysis of 4-nonylphenols, phthalates, and polychlorinated biphenyls in soils and biosolids . Chemosphere. , 61 : 1336 – 1344 .
  • Giger , W. , Stephanou , E. and Schaffner , C. 1981 . Persistent organic chemicals in sewage effluents. I. Identifications of nonylphenols and nonylphenolethoxylates by glass capillary gas chromatography/mass spectrometry . Chemosphere , 10 : 1253 – 1263 .
  • Giger , W. , Brunner , P. H. and Schaffner , C. 1984 . 4-Nonylphenol in sewage sludge: Accumulation of toxic metabolites from non-ionic surfactants . Science. , 225 : 623 – 625 .
  • Giger , W. , Ahel , M. , Koch , M. , Laubscher , H. U. , Schaffner , C. and Schneider , J. 1987 . Behaviour of alkylphenol polyethoxylate surfactants and of nitrilotriacetate in sewage treatment . Water Sci. Technol. , 19 : 449 – 460 .
  • González , S. , Petrovic , M. and Barcelo , D. 2007 . Removal of a broad range of surfactants from municipal wastewater-Comparison between membrane bioreactor and conventional activated sludge treatment . Chemosphere. , 67 : 335 – 343 .
  • Gray , M. A. and Metcalfe , C. D. 1997 . Induction of testis-ova in Japanese medaka (Oryzias latipes) exposed to p-nonylphenol . Environ. Toxicol. Chem. , 16 : 1082 – 1086 .
  • Gross , B. , Montgomery-Brown , J. , Naumann , A. and Reinhard , M. 2004 . Occurrence and fate of pharmaceuticals and alkylphenol ethoxylate metabolites in an effluent-dominated river and wetland . Environ. Toxicol. Chem. , 23 : 2074 – 2083 .
  • Gutsche , C. D. and Pasto , J. D. 1975 . Fundamentals of organic chemistry , London : Prentice-Hall .
  • Haag , W. R. and Hoigne , J. 1985 . Photo-sensitized oxidation in natural water via OH radicals . Chemosphere. , 12 : 1659 – 1671 .
  • Hayashi , S. , Saito , S. , Kim , J. H. , Nishimura , O. and Sudo , R. 2005 . Aerobic biodegradation behavior of nonylphenol polyethoxylates and their metabolites in the presence of organic matter . Environ. Sci. Technol. , 39 : 5626 – 5633 .
  • Hill , W. J. , Baum , J. S. and Feigl , M. D. 1993 . Chemistry and life: An introduction to general, organic, and biological chemistry, , 4th Ed , Upper Saddle River, NJ : Prentice-Hall .
  • Hoai , P. M. , Tsunoi , S. , Ike , M. , Inui , N. , Tanaka , M. and Fujita , M. 2004 . Dicarboxylic degradation products of nonylphenol polyethoxylates: Synthesis and identification by gas chromatography-mass spectrometry using electron and chemical ionization modes . J. Chromatogr. A. , 1061 : 115 – 121 .
  • Hoai , P. M. , Tsunoi , S. , Ike , M. , Sei , K. , Lu , X. Tanaka , M. 2006 . Dicarboxylic degradation products of nonylphenol polyethoxylates determination and structural elucidation in water samples by solid-phase extraction and GC–MS after methylation . J. Chromatogr. A. , 1103 : 125 – 132 .
  • ICIS Chemical Business Americas . 2007 . Overview of the U. S. nonylphenol sector, Focus on Surfactants 4 2007
  • Ike , M. , Asano , M. , Belkada , F. D. , Tsunoi , S. , Tanaka , M. and Fujata , M. 2002 . Degradation of biotransformation products of nonylphenol ethoxylates by ozonation and UV/TiO2 treatment . Water Sci. Technol. , 46 : 127 – 132 .
  • Ikehata , K. and El-Din , M. 2004 . Gamal. Degradation of recalcitrant surfactants in wastewater by ozonation and advanced oxidation processes: a review . Ozone: Sci. Eng. , 26 : 327 – 343 .
  • Isobe , T. and Takada , H. 2004 . Determination of degradation products of alkylphenol polyethoxylates in municipal wastewaters and rivers in Tokyo, Japan . Environ. Toxicol. Chem. , 23 : 599 – 605 .
  • Isobe , T. , Nishiyama , H. , Nakashima , H. and Takada , H. 2001 . Distribution and behaviour of nonylphenol, octylphenol, and nonylphenol monoethoxylate in Tokyo Metropolitan Area: Their association with aquatic particles and sedimentary distributions . Environ. Sci. Technol. , 35 : 1041 – 1049 .
  • Ito , Y. , Takahashi , M. , Mizukoshi , A. , Asami , M. and Aizawa , T. Analytical methods for nonylphenol ethoxylates and their degradation products . Annual Meeting of Japan Society on Water Environment . Tokyo.
  • Jobling , S. and Sumpter , P. J. 1993 . Detergent components in sewage effluent are weakly oestrogenic to fish: An in vitro study using rainbow trout (Oncorhynchus mykiss) hepatocytes . Aquat. Toxicol. , 27 : 361 – 372 .
  • Jobling , S. , Sheahan , D. , Osborne , A. J. , Matthiessen , P. and Sumpter , P. J. 1996 . Inhibition of testicular growth in rainbow trout (Oncorhynchus mykiss) exposed to estrogenic alkylphenolic chemicals . Environ. Toxicol. Chem. , 15 : 194 – 202 .
  • John , D. M. and White , G. F. 1998 . Mechanism for biotransformation of nonylphenol polyethoxylates to xenoestrogens in Pseudomonas putida . J. Bacteriol. , 180 ( 17 ) : 4332 – 4338 .
  • Johnson , C. A. and Sumpter , P. J. 2001 . Removal of endocrine-disrupting chemicals in activated sludge treatment works . Environ. Sci. Technol. , 35 : 4697 – 4703 .
  • Jones , O. A. H. , Green , P. G. , Voulvoulis , N. and Lester , J. N. 2007 . Questioning the excessive use of advanced treatment to remove organic micropollutants from wastewater . Environ. Sci. Technol. , 41 : 5085 – 5089 .
  • Jonkers , N. , Knepper , T. P. and De Voogt , P. 2001 . Aerobic biodegradation studies of nonylphenol ethoxylates in river water using liquid chromatography-electrospray tandem mass spectrometry . Environ. Sci. Technol. , 35 : 335 – 340 .
  • Kimura , K. , Amy , G. , Drewes , J. E. , Heberer , T. , Kim , T. U. and Watanabe , Y. 2003 . Rejection of organic micropollutants (disinfection by-products, endocrine disrupting compounds, and pharmaceutically active compounds) by NF/RO membranes . J. Membr. Sci. , 227 : 113 – 121 .
  • Kinae , N. , Hashizume , T. , Makita , T. , Tomita , T. , Kimura , I. and Kanamori , H. 1981 . Studies on the toxicity of pulp and paper mill effluents. I. Mutagenicity of the sediment samples derived from kraft paper mills . Water Res. , 15 : 17 – 24 .
  • Knepper , T. P. , Barcelo , D. and De Voogt , P. 2003 . Analysis and fate of surfactants in the aquatic environment, 40 , Amsterdam : Elsevier .
  • Koh , Y. K. K. , Lester , J. N. and Scrimshaw , M. D. 2005 . The fate and behaviour of alkylphenols and their polyethoxylates in an activated sludge plant . Bull. Environ. Contam. Toxicol. , 75 : 1098 – 1106 .
  • Kolpin , D. W. , Furlong , E. T. , Meyer , M. T. , Thurman , E. M. , Zaugg , S. D. Barber , L. D. 2002 . Pharmaceuticals, hormones, and other organic wastewater contaminants in U. S. streams, 1999–2000: A national reconnaissance . Environ. Sci. Technol. , 36 : 1202 – 1211 .
  • Komori , K. , Okayasu , Y. , Yasojima , M. , Suzuki , Y. and Tanaka , H. 2006 . Occurrence of nonylphenol, nonylphenol ethoxylate surfactants and nonylphenol carboxylic acids in wastewater in Japan . Water Sci. Technol. , 53 : 27 – 33 .
  • Langford , K. H. and Lester , J. N. 2003 . “ Fate and behavior of endocrine disrupters in wastewater treatment processes ” . In Endocrine disrupters in wastewater and sludge treatment processes , Edited by: Birkett , J. W. and Lester , J. N. Boca Raton, FL : CRC Press .
  • Langford , K. H. , Scrimshaw , M. D. and Lester , J. N. 2004 . Analytical methods for the determination of alkylphenolic surfactants and polybrominated diphenyl ether in wastewaters and sewage sludges. II Method development . Environ. Technol. , 25 : 975 – 985 .
  • Langford , K. H. , Scrimshaw , M. D. , Birkett , J. W. and Lester , J. N. 2005a . The partitioning of alkylphenolic surfactants and polybrominated diphenyl ether flame retardants in activated sludge batch tests . Chemosphere , 61 : 1221 – 1230 .
  • Langford , K. H. , Scrimshaw , M. D. , Birkett , J. W. and Lester , J. N. 2005b . Degradation of nonylphenolic surfactants in activated sludge batch tests . Water Res. , 39 : 870 – 876 .
  • Lee , H. B. and Peart , T. E. 1998 . Occurrence and elimination of nonylphenol ethoxylates and metabolites in municipal wastewater and effluents . Water Qual. Res. J. Canada. , 33 : 389 – 402 .
  • Lee , H. B. , Weng , J. , Peart , T. E. and Maguire , R. J. 1998 . Occurrence of alkylphenoxyacetic acids in Canadian sewage treatment plant effluents . Water Qual. Res. J. Canada. , 33 : 19 – 29 .
  • Lester , J. N. and Edge , D. 2001 . “ Chapter 5—Sewage and sewage sludge treatment ” . In Pollution, causes, effects and control, , 4th ed. , Edited by: Harrison , R. M. 113 – 144 . London : Royal Society of Chemistry .
  • Liu , X. , Tani , A. , Kimbara , K. and Kawai , F. 2006 . Metabolic pathway of xenoestrogenic short ethoxy chain-nonylphenol to nonylphenol by aerobic bacteria, Ensifer sp. strain AS08 and Pseudomonas sp. strain AS90 . Appl. Microbiol. Biotechnol. , 72 : 552 – 559 .
  • Loos , R. , Hanke , G. , Umlauf , G. and Eisenreich , S. J. 2007 . 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. , 66 : 690 – 699 .
  • Maeda , S. and Mikami , I. 1988 . Degradation of the non-ionic surfactant (polyoxyethylene-p-nonylphenyl ether) by Pseudomonas species . J. Water Wastes , 30 : 1056 – 1063 .
  • Maki , H. , Fujita , M. and Fujiwara , Y. 1996 . Identification of final biodegradation product of nonylphenol ethoxylate (NPE) by river microbial consortia . Bull. Environ. Contam. Toxicol. , 57 : 881 – 887 .
  • Maki , H. , Masuda , N. , Furiwara , Y. , Ike , M. and Fujita , M. 1994 . Degradation of alkylphenol ethoxylates by Psuedomonas sp strain TR01 . Appl. Environ. Microbiol. , 60 : 2265 – 2271 .
  • Maki , H. , Okamura , H. , Aoyama , I. and Fujita , M. 1998 . Halogenation and toxicity of the biodegradation products of a nonionic surfactant, nonylphenol ethoxylate . Environ. Toxicol. Chem. , 17 : 650 – 654 .
  • Mann , A. H. and Reid , V. W. 1971 . Biodegradation of synthetic detergents. Evaluation by community trial. Part 2: Alcohol and alkylphenol ethoxylates . J. Amer. Oil Chem. Soc. , 48 : 794 – 797 .
  • Mansour , M. , Feicht , E. A. , Behechti , A. and Scheunert , I. 1997 . Experimental approaches to studying the photostability of selected pesticides in water and soil . Chemosphere. , 35 : 39 – 50 .
  • Manzano , M. A. , Perales , J. A. , Sales , D. and Quiroga , J. M. 1998 . Effect of concentration on the biodegradation of a nonylphenol polyethoxylate in river water . Bull. Environ. Contam. Toxicol. , 61 : 489 – 496 .
  • Manzano , M. A. , Perales , J. A. , Sales , D. and Quiroga , J. M. 1999 . The effect of temperature on the biodegradation of a nonylphenol polyethoxylate in river . Water Res. , 33 : 2593 – 2600 .
  • Marcomini , A. , Pavoni , B. , Sfriso , A. and Orio , A. A. 1990 . Persistent metabolites of alkylphenol polyethoxylates in the marine environment . Mar. Chem. , 29 : 307 – 323 .
  • Maruyama , K. , Yuan , M. and Otsu , A. 2000 . Seasonal changes in ethylene oxide chain length of poly(oxyethylene)alkylphenol ether nonionic surfactants in three main rivers in Tokyo . Environ. Sci Technol. , 34 : 343 – 348 .
  • Mayer , T. , Bennie , D. , Rosa , F. , Rekas , G. , Palabrica , V. and Schachtschneider , J. 2007 . Occurrence of alkylphenolic substances in a Great Lakes coastal marsh, Cootes Paradise, ON, Canada . Environ. Pollut. , 147 : 683 – 690 .
  • McLeese , D. W. , Zitko , V. , Sergeant , D. B. , Burridge , L. and Metcalfe , C. D. 1981 . Lethality and accumulation of alkylphenols in aquatic fauna . Chemosphere , 10 : 723 – 730 .
  • Minamiyama , M. , Ochi , S. and Suzuki , Y. 2006 . Fate of nonylphenol polyethoxylates and nonylphenoxy acetic acids in an anaerobic digestion process for sewage sludge treatment . Water Sci. Technol. , 53 : 221 – 226 .
  • Montgomery-Brown , J. and Reinhard , M. 2003 . Occurrence and behaviour of alkylphenol polyethoxylates in the environment . Environ. Eng. Sci. , 20 ( 5 ) : 471 – 486 .
  • Montgomery-Brown , J. , Drewes , J. E. , Fox , P. and Reinhard , M. 2003 . Behavior of alkylphenol polyethoxylate metabolites during soil aquifer treatment . Water Res. , 37 : 3672 – 3681 .
  • Moraes , M. C. F. , Romanelli , M. F. , Sena , H. C. , Pasqualini da Silva , G. , Sampa , M. H. O. and Borrely , S. I. 2004 . Whole acute toxicity removal from industrial and domestic effluents treated by electron beam radiation: emphasis on anionic surfactants . Radiat. Phys. Chem. , 71 : 461 – 463 .
  • Nakada , N. , Yasojima , M. , Okayasu , Y. , Komori , K. , Tanaka , H. and Suzuki , Y. 2006 . Fate of oestrogenic compounds and identification of oestrogenicity in a wastewater treatment process . Water Sci. Technol. , 53 : 51 – 63 .
  • Nghiem , L. D. and Schaäfer , A. I. 2006 . Critical risk points of nanofiltration and reverse osmosis processes in water recycling applications . Desalination. , 187 : 303 – 312 .
  • Nguyen , M. H. and Sigoillot , J. C. 1997 . Isolation from coastal sea water and characterization of bacterial strains involved in non-ionic surfactant degradation . Biodegradation. , 7 : 369 – 375 .
  • Nimrod , A. C. and Benson , W. H. 1998 . Reproduction and development of Japanese Medaka following an early life stage exposure to xenoestrogens . Aquat. Toxicol. , 44 : 141 – 156 .
  • Organisation for Economic Co-operation and Development . 1980 . Test guideline for ready biodegradability: Modified sturm test , Paris : Author . (Document 301-B)
  • Petrovic , M. and Barcelo , D. 2001 . Determination of phenolic xenoestrogens in environmental samples by liquid chromatography with mass spectrometric detection . J. AOAC Int. , 84 : 1074 – 1085 .
  • Petrovic , M. , Diaz , A. , Ventura , F. and Barcelo , D. 2001 . Simultaneous determination of halogenated derivatives of alkylphenol ethoxylates and their metabolites in sludges, river sediments, and surface, drinking, and wastewaters by liquid chromatography-mass spectrometry . Anal. Chem. , 73 : 5886 – 5895 .
  • Petrovic , M. , Sole , M. , Lopez de Alda , M. J. and Barcelo , D. 2002a . Endocrine disruptors in sewage treatment plants, receiving river waters, and sediments: Integration of chemical analysis and biological effects on feral carp . Environ. Toxicol. Chem. , 21 : 2146 – 2156 .
  • Petrovic , M. , Eljarrat , E. , Lopez de Alda , M. J. and Barcelo , D. 2002b . Recent advances in the mass spectrometric analysis related to endocrine disrupting compounds in aquatic environmental samples . J. Chromatogr. A. , 974 : 23 – 51 .
  • Petrovic , M. , Gehringer , P. , Eschweiler , H. and Barcelo , D. 2004 . LC-MS-(MS) determination of oxidative degradation products of nonylphenol ethoxylates, carboxylates and nonylphenols in water . Water Sci. Technol. , 50 : 227 – 234 .
  • Petrovic , M. , Gehringer , P. , Eschweiler , H. and Barcelo , D. 2007 . Radiolytic decomposition of multi-class surfactants and their biotransformation products in sewage treatment plant effluents . Chemosphere. , 66 : 114 – 122 .
  • Purdom , C. E. , Hardiman , P. A. , Bye , V. J. , Eno , N. C. , Tyler , C. R. and Sumpter , J. P. 1994 . Estrogenic effects from sewage treatment works . Chem Ecol. , : 8275 – 8285 .
  • Reinhard , M. , Goodman , N. and Morkelmans , K. E. 1982 . Occurrence of brominated alkylphenol polyethoxy carboxylates in mutagenic wastewater concentrates . Environ. Sci. Technol. , 16 : 351 – 362 .
  • Renner , R. 1997 . European bans on surfactant trigger transatlantic debate . Environ. Sci. Technol. , 31 : 316A – 320A .
  • Routledge , E. J. and Sumpter , J. P. 1997 . Structural features of alkylphenolic chemicals associated with estrogenic activity . J. Biol. Chem. , 272 : 3280 – 3288 .
  • Sato , H. , Shibata , A. , Wang , Y. , Yoshikawa , H. and Tamura , H. 2001 . Characterization of biodegradation intermediates of non-ionic surfactants by matrix-assisted laser desorption/ionization-mass spectrometry 1. Bacterial biodegradation of octylphenol polyethoxylate under aerobic conditions . Polym. Degrad. Stab. , 74 : 69 – 75 .
  • Sato , H. , Shibata , A. , Wang , Y. , Yoshikawa , H. and Tamura , H. 2003 . Characterization of biodegradation intermediates of nonionic surfactants by MALDI-MS. 2. Oxidative biodegradation profiles of uniform octylphenol polyethoxylate in 18O-labeled water . Biomacromolecules. , 4 : 46 – 51 .
  • Schroder , H. F. 2001 . Tracing of surfactants in the biological wastewater treatment process and the identification of their metabolites by flow injection-mass spectrometry and liquid chromatography-mass spectrometry and -tandem mass spectrometry . J. Chromatogr. A. , 926 : 127 – 150 .
  • Servos , M. R. , Maguire , R. J. , Bennie , D. T. , Lee , H.-B. , Cureton , P. M. Davidson , N. 2000 . Supporting document for nonylphenol and its ethoxylates. National Water Research Institute 00-029, 1–217 , Burlington, Ontario, , Canada : Environment Canada .
  • Shang , D. Y. , Macdonald , R. W. and Ikonomou , M. G. 1999 . Persistence of nonylphenol ethoxylate surfactants and their primary degradation products in sediments from near a municipal outfall in the Strait of Georgia, British Columbia, Canada . Environ. Sci. Technol. , 33 : 1366 – 1372 .
  • Sheahan , D. , Cliffe , S. , Jobling , S. , Harries , J. , Hurst , M. Morris , S. 2002 . The identification of estrogenic substances in sewage treatment works effluents. Part ll: Industrial effluents , Bristol, , England : Environment Agency .
  • Sole , M. , Lopez de Alda , M. J. , Castillo , M. , Porte , C. , Ledegaard-Pedersen , K. and Barcelo , D. 2000 . Estrogenicity determination in sewage treatment plants and surface waters from the Catalonian area (NE Spain) . Environ. Sci. Technol. , 34 : 5076 – 5083 .
  • Spengler , P. , Korner , W. and Metzger , J. W. 2001 . Substances with estrogenic activity in effluents of sewage treatment plants in southwestern Germany. 1. Chemical analysis . Environ. Toxicol. Chem. , 20 : 2133 – 2141 .
  • Staples , C. A. , Williams , J. B. , Blessing , R. L. and Varineau , P. T. 1999 . Measuring the biodegradability of nonylphenol ether carboxylates, octylphenol ether carboxylates and nonylphenol . Chemosphere. , 38 : 2029 – 2039 .
  • Staples , C. A. , Naylor , C. G. , Williams , J. B. and Gledhhill , W. E. 2001 . Ultimate biodegradation of alkylphenol ethoxylates surfactants and their biodegradation intermediates . Environ. Toxicol. Chem. , 20 : 2450 – 2455 .
  • Stephanou , E. and Giger , W. 1982 . Persistent organic chemicals in sewage effluents. 2. Quantitative determinations of nonylphenol and nonylphenol ethoxylates by glass capillary gas chromatography . Environ. Sci. Technol. , 16 : 800 – 805 .
  • Stiff , M. J. , Rootham , R. C. and Culley , G. E. 1973 . The effect of temperature on the removal of non-ionic surfactants during small scale activated-sludge sewage treatment-I. Comparison of alcohol ethoxylates with a branched-chain alkyl phenol ethoxylate . Water Res. , 7 : 1003 – 1010 .
  • Sumpter , J. P. 2002 . “ Endocrine disruption in the aquatic environment ” . In The handbook of environmental chemistry, part M, endocrine disrupters part II , Edited by: Metzler , M. vol. 3 , 271 – 289 . Berlin & Heidelberg, , Germany : Springer-Verlag .
  • Szymanski , A. , Wyrwas , B. , Szymanowska , M. and Lukaszewski , Z. 2001 . Determination of short-chained polyethoxylate(ethylene glycols) and ethylene glycol in environmental samples . Water Res. , 35 : 3599 – 3604 .
  • Szymanski , A. , Wyrwas , B. and Lukaszewski , Z. 2003 . Determination of non-ionic surfactants and their biotransformation by-products adsorbed on alive activated sludge . Water Res. , 37 : 281 – 288 .
  • Tanghe , T. , Devriese , G. and Verstraete , W. 1998 . Nonylphenol degradation in lab-scale activated sludge units is temperature dependent . Water Res. , 32 : 2889 – 2896 .
  • Tanghe , T. , Dhooge , V. and Verstrate , W. 1999 . Isolation of a bacterial strain able to degrade branched nonylphenol . Appl. Environ. Microbiol. , 65 : 746 – 751 .
  • Tarrant , H. , Llewellyn , N. , Lyons , A. , Tattersall , N. , Wylde , S. Mouzakitis , G. 2005 . Endocrine disruptors in the Irish aquatic environment (Final report) , Ireland : Environmental Protection Agency . ERTDI Report 32
  • Terzic , S. , Matosic , M. , Ahel , M. and Mijatovic , I. 2005 . Elimination of aromatic surfactants from municipal wastewaters: comparison of conventional activated sludge treatment and membrane biological reactor . Water Sci. Technol. , 51 : 447 – 453 .
  • Ushida , Y. , Takahara , Y. and Ohta , H. 2003 . Sphingobium amiense sp. nov., a novel nonylphenol-degrading bacterium isolated from a river sediment . Inter. J. Syst. Evol. Microbiol. , 53 : 2045 – 2048 .
  • van Ginkel , C. G. 1996 . Complete degradation of xenobiotic surfactants by consortia of aerobic microorganisms . Biodegradation , 7 : 151
  • Ventura , F. , Figueras , A. , Caixach , J. , Espadaler , I. , Romero , J. Guardiola , J. 1988 . Characterization of polyethoxylated surfactants and their brominated derivatives formed at the water treatment plant of Barcelona by GC/MS and FAB mass spectrometry . Water Res. , 22 : 1211 – 1217 .
  • Ventura , F. , Caixach , J. , Romero , J. , Espadaler , I. and Rivera , J. 1992 . New methods for the identification of surfactants and their acidic metabolites in raw and drinking water: FAB-MS and MS/MS . Water Sci. Technol. , 26 : 257 – 264 .
  • Wagener , S. and Schink , B. 1988 . Fermentative degradation of nonionic surfactants and polyethylene glycol by enrichment cultures and by pure cultures of homoacetogenic and propionate-forming bacteria . Appl. Environ. Microbiol. , 54 : 561 – 565 .
  • Wang , L. , Wu , Y. , Sun , H. , Xu , J. and Dai , S. 2006 . Distribution and dissipation pathways of nonylphenol polyethoxylates in the Yellow River: Site investigation and lab-scale studies . Environ. Int. , 32 : 907 – 914 .
  • Water Technology International Corporation . 1998 . Interim report: Characterisation of selected Canadian sewage treatment plants for the occurrence, fate and release of endocrine disrupting compounds , Burlington, Ontario : Environment Canada . Report prepared for the National Water Research Institute, Environment Canada, April 1998
  • White , R. , Jobling , S. , Hoare , S. A. , Sumpter , J. P. and Parker , M. G. 1994 . Environmentally persistent alkylphenolic compounds are estrogenic . Endocrinology. , 135 : 175 – 182 .
  • Zepp , R. G. , Schlotzhauer , P. F. and Sink , R. 1985 . Photosensitized transformations involving electronic-energy transfer in natural waters role of humic substances . Environ. Sci. Technol. , 19 : 74 – 81 .
  • Zhang , J. , Yang , M. , Qiao , Y. , Zhang , Y. and Chen , M. 2007 . Biodegradation of nonylphenoxy carboxylates mixtures in two microcosms . Sci Tot Environ. , 388 : 392 – 397 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.