C8- and C9-Alkylphenols and Ethoxylates: I. Identity, Physical Characterization, and Biodegradation Pathways Analysis

REFERENCES

• Ahel , M and Giger , W . 1993a . Aqueous solubility of alkylphenols and alkylphenol polyethoxylates . Chemosphere , 26 : 1461 – 70 .
   Web of Science ®Google Scholar
• Ahel , M and Giger , W . 1993b . Partitioning of alkylphenols and alkylphenol polyethoxylates between water and organic solvents . Chemosphere , 26 : 1471 – 8 .
   Web of Science ®Google Scholar
• Ahel , M , Giger , W and Schaffner , C . 1994 . Behavior of alkylphenol polyethoxylate surfactants in the aquatic environment—II. Occurrence and transformation in rivers . Water Res , 28 : 1143 – 52 .
   Web of Science ®Google Scholar
• APERC (Alkylphenols and Ethoxylates Research Council) . 2006 . Alkylphenols and Alkylphenol Ethoxylates-Product Uses , Washington, DC, USA : Alkylphenols and Ethoxylates Research Council . Available at http://www.aperc.org/productinfo.htm
   Google Scholar
• Bidleman , T F and Renberg , L . 1985 . Determination of vapor pressures of chloroguaiacols, chloroveratroles, and nonylphenol by gas chromatography . Chemosphere , 14 : 1475 – 81 .
   Web of Science ®Google Scholar
• Burgess , R M , Pelletier , M C Gunderson , J L . 2005 . Effects of different forms of organic carbon on the partitioning and bioavailability of nonylphenol . Environ Toxicol Chem , 24 : 1609 – 17 .
   PubMed Web of Science ®Google Scholar
• Chang , B V , Yu , C H and Yuan , S Y . 2004 . Degradation of nonylphenol by anaerobic microorganisms from river sediments . Chemosphere , 55 : 493 – 500 .
   PubMed Web of Science ®Google Scholar
• Corvini , P FX , Vinken , R Hommes , G . 2004 . Degradation of the radioactive and non-labelled branched 4(3′,5′-dimethyl-3′-heptyl)-phenol nonylphenol isomer by Sphingomonas TTNP3 . Biodegradation , 15 : 9 – 18 .
   PubMed Web of Science ®Google Scholar
• Corvini , P FX , Meesters , R and Mundt , M . 2007 . Contribution to the detection and identification of oxidation metabolites of nonylphenol in Sphingomonas sp. Strain TTNP3 . Biodegradation , 18 : 233 – 45 .
   PubMed Web of Science ®Google Scholar
• Dachs , J , Van Ry , D A and Eisenreich , S J . 1999 . Occurrence of estrogenic nonylphenols in the urban and coastal atmosphere of the lower Hudson river estuary . Environ Sci Technol , 33 : 2676 – 9 .
   Web of Science ®Google Scholar
• DiCorcia , A , Costantino , A Crescenzi , C . 1998 . Characterization of recalcitrant intermediates from biotransformation of the branched alkyl side chain of nonylphenol ethoxylate surfactants . Environ Sci Technol , 32 : 2401 – 9 .
   Web of Science ®Google Scholar
• Doucette , W J . 2005 . Determination of Octanol-Water Partition Coefficients for NP, NPE4 and NPE9 Using the Slow-Stir Method , Logan, UT, USA : Utah State University . Report to the Alkylphenols and Ethoxylates Research Council, Washington, DC, USA
   Google Scholar
• Duering , R A , Krahe , S and Gath , S . 2002 . Sorption behavior of nonylphenol in terrestrial soils . Environ Sci Technol , 36 : 4052 – 7 .
   PubMed Web of Science ®Google Scholar
• EC (Environment Canada) . 2007 . Ecological Categorization of Substances on the Domestic Substance List; Categorization Decisions Available at http://www.ec.gc.ca/substances/ese/eng/dsl/cat_index.cfm (Completed in September 2006)
   Google Scholar
• EC (European Commission) . 2002 . European Union Risk Assessment Report: 4-Nonylphenol (Branched) and Nonylphenol: Final Report. Available at http://ecb.jrc.it/DOCUMENTS/Existing-Chemicals/RISK_ASSESSMENT/REPORT/
   Google Scholar
• EC and HC (Environment Canada and Health Canada) . 2001 . Priority Substances List Assessment Report: Nonylphenol and its Ethoxylates. Available at www.ec.gc.ca/ccebl/eng/final/index_ehtml
   Google Scholar
• Ekelund , R , Granmo , A and Magnusson , K . 1993 . Biodegradation of 4-nonylphenol in seawater and sediment . Environ Pollut , 79 : 59 – 61 .
   PubMed Web of Science ®Google Scholar
• Field , J . 1996 . Sorption of NPECs to EPA River Sediments Draft Report for Chemical Manufacturers Association, Oregon State University, Corvallis, OR, USA, available from the Alkylphenols and Ethoxylates Research Council, Washington, DC, USA
   Google Scholar
• Franska , M , Franski , R Szymanski , A . 2003 . A central fission pathway in alkylphenol ethoxylate biodegradation . Water Res , 37 : 1005 – 14 .
   PubMed Web of Science ®Google Scholar
• Gabriel , F LP , Giger , W Guenther , K . 2005a . Differential degradation of nonylphenol isomers by Sphingomonas xenophaga Bayram . Applied Environ Micro , 71 : 1123 – 9 .
   PubMed Web of Science ®Google Scholar
• Gabriel , F LP , Heidlberger , A Rentsch , D . 2005b . A novel metabolic pathway for degradation of 4-nonylphenol environmental contaminants by Sphingomonas xenophaga Bayram . J Biol Chem , 280 : 15526 – 33 .
   PubMed Web of Science ®Google Scholar
• Huntsman Corporation . 1998a . Technical Bulletin for Nonylphenol (NP), Austin, TX, USA, available from the Alkylphenols and Ethoxylates Research Council, Washington, DC, USA
   Google Scholar
• Huntsman Corporation . 1998b . Technical Bulletin for Surfonic N-31.5 (NPE3), Austin, TX, USA, available from the Alkylphenols and Ethoxylates Research Council, Washington, DC, USA
   Google Scholar
• Huntsman Corporation . 1999a . Technical Bulletin for Surfonic N-10 (NPE1.5), Austin, TX, USA, available from the Alkylphenols and Ethoxylates Research Council, Washington, DC, USA
   Google Scholar
• Huntsman Corporation . 1999b . Technical Bulletin for Surfonic N-40 (NPE4), Austin, TX, USA, available from the Alkylphenols and Ethoxylates Research Council, Washington, DC, USA
   Google Scholar
• Huntsman Corporation . 1999c . Technical Bulletin for Surfonic N-95 (NPE9.5), Austin, TX, USA, available from the Alkylphenols and Ethoxylates Research Council, Washington, DC, USA
   Google Scholar
• Huntsman Corporation . 1999d . Technical Bulletin for Surfonic N-300 (NPE30), Austin, TX, USA, available from the Alkylphenols and Ethoxylates Research Council, Washington, DC, USA
   Google Scholar
• John , D F and White , G F . 1998 . Mechanism for biotransformation of nonylphenol polyethoxylates to xenoestrogens in Pseudomonas putida . J Bacteriol , 180 : 4332 – 8 .
   PubMed Web of Science ®Google Scholar
• John , D M , House , W A and White , G E . 2000 . Environmental fate of nonylphenol ethoxylates: Differential adsorption of homologs to components of river sediment . Environ Toxicol Chem , 19 : 293 – 300 .
   Web of Science ®Google Scholar
• Jonkers , N , Knepper , T P and DeVoogt , P . 2001 . Aerobic biodegradation studies of nonylphenol ethoxylates in river water using liquid chromatography-electrospray tandem mass spectrometry . Environ Sci Technol , 35 : 335 – 40 .
   PubMed Web of Science ®Google Scholar
• Kawai , F . 2002 . Microbial degradation of polyethers . Appl Microbiol Biotechnol , 58 : 30 – 8 .
   PubMed Web of Science ®Google Scholar
• Klecka , G M , Zabik , J Woodburn , K . 2007 . Exposure analysis of C8- and C9-alkylphenol, alkylphenol ethoxylates and their metabolites in surface water systems within the United States . Hum Ecol Risk Assess , 13 : 792 – 822 .
   Web of Science ®Google Scholar
• Lalah , J O , Schramm , K W Henkelmann , B . 2003 . The dissipation, distribution and fate of a branched 14C-nonylphenol isomer in lake water/sediment systems . Environ Pollut , 122 : 195 – 203 .
   PubMed Web of Science ®Google Scholar
• Mackay , D . 2001a . A Review of the Environmental Fate of Nonylphenol and Related Substances Canadian Environmental Modeling Center; Trent University, Peterborough, ON, Canada. Report to the Alkylphenols and Ethoxylates Research Council, Washington, DC, USA
   Google Scholar
• Mackay , D . 2001b . Multimedia Models: The Fugacity Approach, , 2nd Edition , Boca Raton, FL, USA : Lewis Publishers .
   Google Scholar
• Maguire , R J . 1999 . Review of the persistence of nonylphenol and nonylphenol ethoxylates in aquatic environments . Water Qual Res J Canada , 34 : 37 – 78 .
   Web of Science ®Google Scholar
• Maki , H , Masuda , N Fujiwara , Y . 1994 . Degradation of alkylphenol ethoxylates by Pseudomonas sp. Strain TR01 . Appl Environ Microbiol , 60 : 2265 – 71 .
   PubMed Web of Science ®Google Scholar
• McLeese , D W , Zitko , V Sergeant , D B . 1981 . Lethality and accumulation of alkylphenols in aquatic fauna . Chemosphere , 10 : 723 – 30 .
   Web of Science ®Google Scholar
• Merck . 2006 . The Merck Index, , 14th Edition , Edited by: O'Neil , M J . Whitehouse Station, NJ, USA : Merck & Co. .
   Google Scholar
• Montgomery-Brown , J and Reinhard , M . 2003 . Occurrence and behavior of alkylphenol polyethoxylates in the environment . Environ Engineering Sci , 20 : 471 – 86 .
   Web of Science ®Google Scholar
• Naylor , C G . 2006 . Personal communication on vapor pressure of NP, NPE and NPEC. Austin, TX, USA
   Google Scholar
• Naylor , C G , Staples , C A Klecka , G M . 2006 . Biodegradation of [14C] ring-labeled nonylphenol ethoxylate . Arch Environ Contam Toxicol , 51 : 11 – 20 .
   PubMed Web of Science ®Google Scholar
• Pearce , B A and Heydeman , M T . 1980 . Metabolism of di(ethylene glycol)[2-(2′-hydroxy)ethanol] and other short poly(ethylene glycols) by gram-negative bacteria . J Gen Microbiol , 118 : 21 – 7 .
   Google Scholar
• Salanitro , J P and Diaz , L A . 1995 . Anaerobic biodegradability testing of surfactants . Chemosphere , 30 : 813 – 30 .
   PubMed Web of Science ®Google Scholar
• Schick , M . 1967 . Nonionic Surfactants, vol 1. Surfactant Science Series , New York, NY, USA : Marcel Dekker, Inc. .
   Google Scholar
• Servos , M R . 1999 . Review of the aquatic toxicity, estrogenic responses and bioaccumulation of alkylphenols and alkylphenol polyethoxylates . Water Qual Res J Canada , 34 : 123 – 77 .
   Web of Science ®Google Scholar
• Staples , C A , Naylor , C G Williams , J B . 2001 . Ultimate biodegradability of C8- and C9-alkylphenol ethoxylate degradation intermediates . Environ Toxicol Chem , 20 : 2450 – 5 .
   PubMed Web of Science ®Google Scholar
• Staples , C , Mihaich , E Carbone , J . 2004 . A weight of evidence analysis of the chronic ecotoxicity of nonylphenol ethoxylates, nonylphenol ether carboxylates, and nonylphenol . Human Ecol Risk Assess , 10 : 999 – 1017 .
   Web of Science ®Google Scholar
• Swisher , R D . 1987 . Surfactant Biodegradation, , 2nd Edition, Revised and Expanded , New York, NY, USA : Marcel Dekker, Inc. .
   Google Scholar
• Talmage , S S . 1994 . Environmental and Human Safety of Major Surfactants—Alcohol and Alkylphenol Ethoxylates , Boca Raton, FL, USA : Lewis Publishers .
   Google Scholar
• Tanghe , T , Dhooge , W and Verstraete , W . 2000 . Formation of the metabolic intermediate 2,4,4-trimethyl-2-pentanol during incubation of a shape Sphingomonas sp. strain with the xeno-estrogenic octylphenol . Biodegradation , 11 : 11 – 9 .
   PubMed Web of Science ®Google Scholar
• Thiele , B , Heinke , V Kleist , E . 2004 . Contribution to the structural elucidation of 10 isomers of technical p-nonylphenol . Environ Sci Technol , 38 : 3405 – 11 .
   PubMed Web of Science ®Google Scholar
• UKEA (United Kingdom Environment Agency) . 2005 . Environmental Risk Evaluation Report: 4-tert-Octylphenol. London, UK
   Google Scholar
• USEPA (U. S. Environmental Protection Agency) . 1996 . RM-1 Document for Para-Nonylphenol. Washington, DC, USA
   Google Scholar
• USEPA . 2000 . EPISuite: Estimation Program Interface (EPI) Suite, Version 3.12 Washington, DC, USA
   Google Scholar
• van Ginkel , C G . 1996 . Complete degradation of xenobiotic surfactants by consortia of aerobic microorganisms . Biodegradation , 7 : 151 – 64 .
   PubMed Web of Science ®Google Scholar
• Van Ry , D A , Dachs , J Gigliotti , C L . 2000 . Atmospheric seasonal trends and environmental fate of alkylphenols in the lower Hudson River estuary . Environ Sci Technol , 34 : 2410 – 7 .
   Web of Science ®Google Scholar
• Weston RF, Inc. 1990a . Determination of the Water Solubility of 4-Nonylphenol , Washington, DC, USA : Roy F. Weston, Inc., Lionville, PA, USA, available from the Alkylphenols and Ethoxylates Research Council . Final Report for Chemical Manufacturers Association, Study No. 90-042
   Google Scholar
• Weston RF, Inc. 1990b . Determination of the Soil Adsorption Isotherm of 4-Nonylphenol , Washington, DC, USA : Roy F. Weston, Inc., Lionville, PA, USA, available from the Alkylphenols and Ethoxylates Research Council . Final Report for Chemical Manufacturers Association, Study No. 90-041
   Google Scholar
• Wheeler , T F , Heim , J R LaTorre , M R . 1997 . Mass spectral characterization of p-nonylphenol isomers using high-resolution capillary GC-MS . J Chromatographic Sci , 35 : 19 – 30 .
   Web of Science ®Google Scholar
• White , G F , Russell , N J and Tidswell , E C . 1996 . Bacterial scission of ether bonds . Microbiol Rev , 60 : 216 – 32 .
   PubMedGoogle Scholar
• Ying , G G , Williams , B and Kookana , R . 2002 . Environmental fate of alkylphenols and alkylphenol ethoxylates—A review . Environ International , 28 : 215 – 26 .
   PubMed Web of Science ®Google Scholar