Using Quantitative Structure–Activity Relationships to Support the Assessment of the Environmental Fate and Aquatic Toxicity of a Series of Methacrylic Acid Esters

REFERENCES

• Archer , G . 1990 . A Hydrolysis Study of 14C-Methyl Methacrylate , Painesville, OH, , USA : Ricerca, Inc . 3181-88-0211-EF-001
   Google Scholar
• Bailey , H C , Liu , D HW and Javitz , H A . Time/toxicity relationships in short term static, dynamic and plug-flow bioassays . Aquatic Toxicology and Hazard Assessment: Eighth symposium . Edited by: Bahner , R C and Hansen , D J . pp. 193 – 212 . American Society for Testing and Materials . ASTM STP 891
   Google Scholar
• BASF AG . 2003 . Material Safety Data Sheet (91/155/EEC) Methyl methacrylate Ludwigshafen, , Germany
   Google Scholar
• Bauer , W . 1990 . “ Methacrylic Acid and Derivatives ” . In Ullmann's Encyclopedia of Industrial Chemistry, , 5th edit , Edited by: Elvers , B . Vol. A 16 , 441 – 52 . Weinheim, , Germany : VCH Verlagsgesellschaft GmbH .
   Google Scholar
• Beilstein's . 1976 . Handbuch der Organischen Chemie, , 4th ed , 1518 – 9 . Berlin, Heidelberg : Springer Verlag .
   Google Scholar
• Bowman , J H . 1990a . Acute Flow-Through Toxicity of Glacial Methacrylic Acid to Rainbow Trout (Salmo gairdneri) , Columbia, MO, , USA : ABC Laboratories, Inc .
   Google Scholar
• Bowman , J H . 1990b . Acute Flow-Through Toxicity of Methyl Methacrylate to Rainbow Trout (Salmo gairdneri) , Columbia, MO, , USA : ABC Laboratories, Inc .
   Google Scholar
• Burgess , D . 1990a . Acute Flow-Through Toxicity of Methacrylic Acid to Daphnia magna , Columbia, MO, , USA : ABC Laboratories, Inc .
   Google Scholar
• Burgess , D . 1990b . Acute Flow-Through Toxicity of Methyl Methacrylate to Daphnia magna , Columbia, MO, , USA : ABC Laboratories, Inc .
   Google Scholar
• Christensen , K P . 1995 . i-Butyl Methacrylate—Determination of the Sorption and Desorption Properties , Wareham, MA, , USA : Springborn Laboratories . Report No. 94-12-5609
   Google Scholar
• CITI (Japanese Chemicals Inspection and Testing Institute) . 1992 . Biodegradation and Bioaccumulation—Data of Existing Chemicals Based on the CSCL Tokyo, , Japan
   Google Scholar
• Comber , M HI and Long , K WJ . 1999 . Methacrylic Acid: Determination of the Toxicity to the Green Alga Selenastrum capricornutum in Closed Vessels , Brixham, Devon, , UK : Brixham Environmental Laboratory, Zeneca Limited .
   Google Scholar
• Deusch , N . 2006 . Determination of the Melting Point and Boiling Point of Isobutyl Methacrylate by Differential Scanning Calorimetry , Darmstadt, , Germany : Evonik Röhm GmbH . AN-AP-ST 07/03
   Google Scholar
• DiToro , D M , Zarba , C S Hansen , D J . 1991 . Technical basis for the equilibrium partitioning method for establishing sediment quality criteria . Environ Toxicol Chem , 11 : 1541 – 83 .
   Google Scholar
• Douglas , M T and Bell , G . 1992 . Assessment of Ready Biodegradability of Methacrylic Acid (Closed Bottle Test) , Huntingdon, Cambridgeshire, , England, UK : Huntingdon Research Centre Ltd. . MPA 1(a)/91332, 6.1.92
   Google Scholar
• EC (European Commission) . 2003 . Brussels, , Belgium Technical Guidance Document in Support of Commission Directive 93/67/EEC on Risk Assessment for New Notified Substances and Commission Regulation (EC) No. 1488/94 on Risk Assessment for Existing Substances. Part II. ECSC-EC-EAEC
   Google Scholar
• ECETOC (European Centre for Ecotoxicology and Toxicology of Chemicals) . 1995 . Joint Assessment of Commodity Chemicals, Methyl methacrylate. No. 30, ISSN-0773-6339-30, Brussels, Belgium
   Google Scholar
• Forbis , A D . 1990 . Acute Toxicity of Methyl Methacrylate to Selenastrum capricornutum Printz , Columbia, MO, , USA : ABC Laboratories, Inc .
   Google Scholar
• Hardies , D E . 1990 . Adsorption and Desorption of Methacrylic Acid to Soils , Painesville, OH, , USA : Ricerca, Inc . 3184-88-0213-EF-001
   Google Scholar
• Hardies , D E . 1991 . Adsorption and Desorption of Methyl Methacrylate to Soils to Soils , Painesville, OH, , USA : Ricerca, Inc . 3183-88-0212-EF-001
   Google Scholar
• Hoberg , J R . 2002a . Ethyl Methacrylate—Toxicity to the Freshwater Green Alga, Pseudokirchneriella subcapitata , Wareham, MA, , USA : Springborn Smithers Laboratories . 13536.6124
   Google Scholar
• Hoberg , J R . 2002b . Isobutyl Methacrylate—Toxicity to the Freshwater Green Alga, Pseudokirchneriella subcapitata , Wareham, MA, , USA : Springborn Smithers Laboratories . 13536.6125
   Google Scholar
• Jaworska , J S , Hunter , R S and Schultz , T W . 1995 . Quantitative structure-activity relationships and volume fraction analysis for selected esters . Arch Environ Contam Toxicol , 29 : 86 – 93 .
   PubMed Web of Science ®Google Scholar
• Jones , O . 2002 . Using Physiologically Based Pharmacokinetic Modeling to Predict the Pharmacokinetics and Toxicity of Methacrylate Esters , England, , UK : A Thesis submitted to Univ. of Manchester for the degree of Doctor of Philosophy University of Manchester .
   Google Scholar
• Kent , S J , Morris , D S and Cornish , S K . 1993 . n-Butyl methacrylate: Acute Toxicity to Daphnia Magna , Brixham, Devon, , UK : Brixham Environmental Laboratory, Zeneca Limited .
   Google Scholar
• Kikushima , E . 1998a . Alkyl Methacrylate (C = 2–20), n-Butyl Methacrylate, Physicochemical Analysis of Material Number K-670C, CERI (Chemicals Evaluation and Research Institute) Kurume Laboratory Test No. 80670CK, 19-14, Chuo-machi, Kurume-Shi, Fukuoka-prefecture, Japan
   Google Scholar
• Kikushima , E . 1998b . Alkyl Methacrylate (C = 2–20), n-Butyl methacrylate Determination of the Partition Coefficient of Material Number K-670C, CERI (Chemicals Evaluation and Research Institute) Kurume Laboratory, Test No. 80670CK, 19-14, Chuo-machi, Kurume-Shi, Fukuoka-prefecture, Japan
   Google Scholar
• Kikushima , E . 1998c . Alkyl Methacrylate (C = 2–20), 2-Ethylhexyl methacrylate Physicochemical Analysis of Material Number K-670D, CERI (Chemicals Evaluation and Research Institute) Kurume Laboratory, Test No. 80670DK, 19-14, Chuo-machi, Kurume-Shi, Fukuoka-prefecture, Japan
   Google Scholar
• Kikushima , E . 1998d . Alkyl Methacrylate (C = 2–20), 2-Ethylhexyl methacrylate Determination of the Partition Coefficient of Material Number K-670D, CERI (Chemicals Evaluation and Research Institute) Kurume Laboratory, Test No. 80670DK, 19-14, Chuo-machi, Kurume-Shi, Fukuoka-prefecture, Japan
   Google Scholar
• Kirk-Othmer . 1981 . “ Methacrylic Acid and Derivates ” . In Encyclopedia of Chemical Technology, , 3rd ed. , Vol. 15 , 346 – 76 . 685 New York, NY, , USA : John Wiley and Sons .
   Google Scholar
• Klimisch , H J , Andreae , M and Tillmann , U . 1997 . A systematic approach for evaluating the quality of experimental toxicological and ecotoxicological data . Regulatory Toxicol Pharmacol , 25 : 1 – 5 .
   PubMed Web of Science ®Google Scholar
• Lange , J . 2004 . Lauryl Methacrylate: Water solubility , Sarstedt, , Germany : Dr. U. Noack-Laboratorien . (Generator column method): Study no. CPW 93803
   Google Scholar
• Luskin , L S . 1971 . “ Acrylic acid, methacrylic acid, and the related esters ” . In Vinyl and Diene Monomers , Edited by: Leonard , E C . Vol XXIV , 105 – 205 . New York, NY, , USA : John Wiley and Sons . Part 1, chapter 3
   Google Scholar
• Lyman , W J , Reehl , W F and Rosenblatt , D H . 1982 . Handbook of Chemical Property Estimation Methods , New York, NY, , USA : McGraw-Hill Book Company .
   Google Scholar
• Mackay , D . 2001 . Multimedia Models: The Fugacity Approach, , 2nd ed , Boca Raton, FL, , USA : Lewis Publishers .
   Google Scholar
• Mead , C . 1995 . Empicryl 6068: Assessment of the Ready Biodegradability CO2 Evolution Test (Modified Sturm test) of Empicryl 6068 , Derby, , UK : Safepharm Laboratories, Inc .
   Google Scholar
• Miller , D E . 1989 . A Hydrolysis Study of 14C-Ethyl Methacrylate , Painesville, OH, , USA : Ricerca Inc. . 3191-88-0206-EF-001
   Google Scholar
• MoE (Ministry of the Environment, Japan) . 1998a . Fish(Oryzias latipes) Acute Toxicity Study with n-Butyl Methacrylate According to the OECD-Guideline 203 , Kureha Special Laboratory Co., Ltd. . Test No.1997-SEI13, 16 Ochiai, Nishiki-machi, Iwaki-city, Fukushima-prefecture, Japan
   Google Scholar
• MoE . 1998b . Acute Daphnia magna Toxicity Study with n-Butyl Methacrylate According to the OECD-Guideline 202 , Kureha Special Laboratory Co., Ltd. . Test No.1997-SEI11, 16 Ochiai, Nishiki-machi, Iwaki-city, Fukushima-prefecture, Japan
   Google Scholar
• MoE. 1998c . Chronic Daphnia magna Toxicity Study with n-Butyl Methacrylate According to the OECD-Guideline 211 , Kureha Special Laboratory Co., Ltd. . Test No.1997-SEI20, 16 Ochiai, Nishiki-machi, Iwaki-city, Fukushima-prefecture, Japan
   Google Scholar
• MoE. 1998d . Algae Toxicity Study with n-Butyl Methacrylate According to the OECD-Guideline 201 , Kureha Special Laboratory Co., Ltd. . Test No.1997-SEI10, 16 Ochiai, Nishiki-machi, Iwaki-city, Fukushima-prefecture, Japan
   Google Scholar
• MoE . 1998e . Chronic Daphnia magna Toxicity Study with 2-Ethylhexyl Methacrylate According to the OECD-Guideline 211 , Mitsubishi Chemical Safety Institute Ltd. Yokohama Laboratory . Test No.7B763G, 1000 Kamoshida, Aoba-Ku, Yokohama, Kanagawa-prefecture, Japan
   Google Scholar
• Mori , H . 1998a . Alkyl Methacrylate (C = 2–20), n-Butyl methacrylate according to the OECD-Guideline 301C Biodegradation Test of Material Number K-670C. CERI (Chemicals Evaluation and Research Institute) Kurume Laboratory, Test No. 20670C, 19-14. Chuo-machi, Kurume-Shi, Fukuoka-prefecture, Japan
   Google Scholar
• Mori , H . 1998b . Alkyl Methacrylate (C = 2–20), 2-Ethylhexyl Methacrylate According to the OECD-Guideline 301C Biodegradation Test of Material Number K-670D, CERI (Chemicals Evaluation and Research Institute) Kurume Laboratory, Test No. 20670D, 19-14. Chuo-machi, Kurume-Shi, Fukuoka-prefecture, Japan
   Google Scholar
• Morris , D S , Comber , M HI and Cornish , S K . 1993a . n-Butyl Methacrylate: Determination of Octanol Water Partition Coefficient, Brixham Environmental Laboratory , Brixham, Devon, , UK : Zeneca Limited .
   Google Scholar
• Morris , D S , Caunter , J E and Penwell , A J . 1993b . n-Butyl Methacrylate: Acute Toxicity to Fathead Minnow (Pimephales promelas) , Brixham, Devon, , UK : Brixham Environmental Laboratory, Zeneca Limited .
   Google Scholar
• Nemec , J W and Kirch , L S . 1984 . Kirk-Othmer Encyclopedia of Chemical Technology, , 3rd ed , vol 15–26 , 347 – 71 . 723 New York, NY, , USA : John Wiley and Sons .
   Google Scholar
• Noack , M . 2005 . Dodecyl Methacrylate: Daphnia Magna STRAUS Reproduction Test (Semi-Static, 21 d) Limit Test. Study no. DRE93801. Dr. U. Noack-Laboratorien, Sarstedt, Germany
   Google Scholar
• OECD (Organization of Economic Cooperation and Development) . 2006 . OECD Guidelines for the Testing of Chemicals Paris, , France Available at http://new.sourceoecd.org/ Guideline 201, Freshwater Alga and Cyanobacteria, Growth Inhibition Test. Adopted 23 March 2006
   Google Scholar
• Parkerton , T F and Konkel , W J . 2000 . Application of quantitative structure-activity relationships for assessing the aquatic toxicity of phthalate esters . Ecotoxicol Environ Safety , 45 : 61 – 78 .
   PubMed Web of Science ®Google Scholar
• Partheil , G . 1964 . Versuche zur Destillation VI, VB 64/21 , Darmstadt, , Germany : Evonik Röhm GmbH .
   Google Scholar
• Partheil , G . 1966 . Zur Destillation 27, VB 66/38 , Darmstadt, , Germany : Evonik Röhm GmbH .
   Google Scholar
• Partheil , G . 1969 . Zur Destillation 38, VB 69/48 , Darmstadt, , Germany : Evonik Röhm GmbH .
   Google Scholar
• Putt , A E . 1995a . Methacrylic Acid—The Chronic Toxicity to Daphnia magna under Flow-Through Conditions , Wareham, MA, , USA : Springborn Laboratories, Inc . 95-8-6069
   Google Scholar
• Putt , A E . 1995b . Ethyl Methacrylate—Acute Toxicity to Daphnids (Daphnia magna) under Flow-Through Conditions , Wareham, MA, , USA : Springborn Laboratories Inc . 95-1-5665
   Google Scholar
• Putt , A E . 1995c . Ethyl Methacrylate—Chronic Toxicity to Daphnia Magna under Flow-Through Conditions , Wareham, MA, , USA : Springborn Laboratories Inc . 95-8-6066
   Google Scholar
• Putt , A E . 1995d . n-Butyl methacrylate—The Chronic Toxicity to Daphnia Magna under Flow-Through Conditions , Wareham, MA, , USA : Springborn Smithers Laboratories . 95-8-6067
   Google Scholar
• Putt , A E . 1995e . i-Butyl Methacrylate—Acute Toxicity to Daphnids (Daphnia Magna) under Flow-Through Conditions , Wareham, MA, , USA : Springborn Laboratories . 95-4-5815
   Google Scholar
• Putt , A E . 1997 . The Chronic Toxicity to Daphnia Magna under Flow-Through Conditions , Wareham, MA, , USA : Springborn Laboratories. Inc . 96-12-6804
   Google Scholar
• Rehberg , C E and Fisher , C H . 1948 . Properties of monomeric and polymeric alkyl acrylates and methacrylates . Ind Eng Chem , 40 : 1429 – 33 .
   Google Scholar
• Reinert , K H . 1987 . Aquatic toxicity of acrylates and methacrylates: Quantitative structure-activity relationships based on Kow and LC50 . Regulatory Toxicol Pharmacol , 7 : 384 – 9 .
   PubMedGoogle Scholar
• Sandmeyer , E E and Kirwin , C J Jr. 1981 . Patty's Industrial Hygiene and Toxicology, , 3rd ed , vol 2A , 2291 – 302 . New York, NY, , USA : John Wiley & Sons Inc .
   Google Scholar
• Sangster , J . 1989 . Octanol-water partition coefficients of simple organic compounds . J Phys Chem Ref Data , 18 : 1170
   Google Scholar
• Schäfers , C . 2002a . Early Life Stage Toxicity of Methacrylic Acid to Zebrafish (Danio rerio) , Schmallenberg-Grafschaft, , Germany : Fraunhofer Institute for Molecular Biology and Applied Ecology . RÖH-027/4-18
   Google Scholar
• Schäfers , C . 2002b . Early Life Stage Toxicity of Methyl Methacrylate to Zebrafish (Danio rerio) , Schmallenberg-Grafschaft, , Germany : Fraunhofer Institute for Molecular Biology and Applied Ecology . RÖH-028/4-18
   Google Scholar
• Schäfers , C . 2003 . 2-Ethylhexyl Methacrylate: Daphnia magna, Reproduction Test in Closed Vessels , Schmallenberg-Grafschaft, , Germany : Fraunhofer Institut für Molekularbiologie und angewandte Oekologie . MPA-001/4-21
   Google Scholar
• Schäfers , C . 2006 . Fish Bioconcentration of 2-Ethylhexyl Methacrylate According to the OECD-Guideline 305 , Schmallenberg-Grafschaft, , Germany : Fraunhofer Institute for Molecular Biology and Applied Ecology . MPA-001/4-10
   Google Scholar
• Scheerbaum , D . 2005 . Dodecyl Methacrylate: Alga, Growth Inhibition Test with Desmodesmus subspicatus , Sarstedt, , Germany : Dr. U. Noack-Laboratorien . 72 h. Study no. SSO93801
   Google Scholar
• Smyth , D V and Long , K WJ . 1999 . Methyl, Ethyl and Isobutyl Methacrylate: Determination of Toxicity to the Green Alga Selenastrum capricornutum, Brixham Environmental Laboratory , Brixham, Devon, , UK : Zeneca Limited .
   Google Scholar
• Smyth , D V , Morris , D S and Cornish , S K . 1993 . n-Butyl Methacrylate: Toxicity to Green Alga Selenastrum capricornutum , Brixham, Devon, , UK : Brixham Environmental Laboratory, Zeneca Limited .
   Google Scholar
• Sousa , J V . 1995a . Ethyl Methacrylate—Acute Toxicity to Rainbow Trout (Oncorhynchus mykiss) under Flow-Through Conditions , Wareham, MA, , USA : Springborn Laboratories Inc . 94-12-5606
   Google Scholar
• Sousa , J V . 1995b . i-Butyl Methacrylate: Acute Toxicity to Rainbow Trout (Oncorhynchus mykiss) under Flow-Through Conditions , Wareham, MA, , USA : Springborn Laboratories . 94-11-5562
   Google Scholar
• Thiebaud , H . 1994a . Méthacrylate de ethyle, toxicité aigue vis-à-vis des daphnies Centre d'application de Levallois unpublished study on behalf of Elf Atochem, cited in: ECETOC (1996) joint assessment of commodity chemicals No. 36, ISSN-0773-6339-36
   Google Scholar
• Thiebaud , H . 1994b . Méthacrylate de butyle, toxicité aigue vis-à-vis des daphnies; Centre d'application de Levallois unpublished study on behalf of Elf Atochem cited in: ECETOC (1996) joint assessment of commodity chemicals No. 36, ISSN-07736339-36
   Google Scholar
• Thiebaud , H . 1994c . Méthacrylate de isobutyle, toxicité aigue vis-à-vis des daphnies; Centre d'application de Levallois unpublished study on behalf of Elf Atochem cited in: ECETOC (1996) joint assessment of commodity chemicals No. 36, ISSN-0773-6339-36
   Google Scholar
• Thiébaud , H and Moncel , N . 1995a . Methacrylate D'Ethyle Détermination de la Biodégradabilité Facile Essai en Fioles Fermées [Determination of ready biodegradability; closed bottle test] Report no. 58167. Elf Atochem Centre d'Application de Levallois, France. March 1, 1995
   Google Scholar
• Thiébaud , H and Moncel , N . 1995b . Methacrylate De Butyle—Détermination de la Biodégradabilité Facile Essai en Fioles Fermées [Determination of ready biodegradability; closed bottle test] Report no. 58162. Elf Atochem Centre d'Application de Levallois, France. February 28, 1995
   Google Scholar
• Thiébaud , H and Moncel , N . 1995c . Methacrylate D'Isobutyle: Détermination de la biodégradabilité facile essai en fioles fermées , France : Elf Atochem Centre d'Application de Levallois . Report no. 58168. March 1, 1995
   Google Scholar
• UNEP (United Nations Environment Programme) . 2001 . Stockholm Convention on Persistent Organic Pollutants Geneva, , Switzerland October
   Google Scholar
• USEPA (US Environmental Protection Agency) . 1984 . Estimating Concern “Levels” for Concentrations of Chemical Substances in the Environment , Washington, DC, , USA : Environmental Health Branch, Health and Environmental Review Division . Report
   Google Scholar
• USEPA . 2000 . Interim Guidance for Using Ready and Inherent Biodegradability Tests to Derive Input Data for Multimedia Models and Wastewater Treatment Plants (WWT) Models (9/1/2000) Washington, DC, , USA Available at http://www.epa.gov/opptintr/exposure/docs/halflife.htm
   Google Scholar
• USEPA . 2007 . EPISuite. Estimation Program Interface (EPI) Suite Version 3.20. Including submodels MBPWIN v1.42, HENRYWIN v3.10, KOWWIN v1.67, ECOSAR v0.99h, PCKOCWIN v1.66, BIOWIN v4.10, BCFWIN v2.17, and AOPWIN v1.92 Washington, DC, , USA
   Google Scholar