Theoretical investigation on the kinetics and mechanisms of hydroxyl radical-induced transformation of parabens and its consequences for toxicity: Influence of alkyl-chain length

Water Research

Volumn 91, Issue , 2016, Pages 77-85

  Gao, Yanpeng ^a,b   Ji, Yuemeng ^a   Li, Guiying ^a   An, Taicheng ^a  

^a GUANGZHOU INSTITUTE OF GEOCHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Advanced oxidative degradation; Aquatic toxicity; Parabens; Photochemical transformation; Theoretical calculation

Indexed keywords

ABSTRACTING; AQUATIC ORGANISMS; DEGRADATION; SURFACE WATERS; TOXICITY;

ADVANCED OXIDATIVE DEGRADATION; ALKYL CHAIN LENGTHS; AQUATIC TOXICITY; DEGRADATION PRODUCTS; EMERGING ORGANIC CONTAMINANTS; HYDROXYL RADICALS; OH -; OXIDATIVE DEGRADATION; PHOTOCHEMICAL TRANSFORMATIONS; THEORETICAL CALCULATIONS;

ALGAE;

4 HYDROXYBENZOIC ACID ESTER; ETHYL PARABEN; HYDROXYL RADICAL; METHYL PARABEN; PROPYL PARABEN; WATER POLLUTANT;

ALGA; CRUSTACEAN; DEGRADATION; ECOTOXICOLOGY; FISH; HYDROXYL RADICAL; ORGANIC POLLUTANT; OXIDANT; OXIDATION; PARABEN; PHOTOCHEMISTRY; REACTION KINETICS; SURFACE WATER; THEORETICAL STUDY; TOXICITY; TRANSFORMATION;

AQUATIC ENVIRONMENT; AQUATIC SPECIES; ARTICLE; DAPHNIA; DENSITY FUNCTIONAL THEORY; ECOTOXICITY; GREEN ALGA; KINETICS; OXIDATION; PHOTOCHEMISTRY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; ANIMAL; CHEMICAL MODEL; CHEMISTRY; DRUG EFFECTS; FISH; METABOLISM; OXIDATION REDUCTION REACTION; TOXICITY; WATER POLLUTANT;

CHLOROPHYTA; DAPHNIA;

ANIMALS; CHLOROPHYTA; DAPHNIA; FISHES; HYDROXYL RADICAL; KINETICS; MODELS, CHEMICAL; OXIDATION-REDUCTION; PARABENS; WATER POLLUTANTS, CHEMICAL;

EID: 84954232606     PISSN: 00431354     EISSN: 18792448     Source Type: Journal    
DOI: 10.1016/j.watres.2015.12.056     Document Type: Article

References (63)

1. An T.C., An J.B., Gao Y.P., Li G.Y., Fang H.S., Song W.H. Photocatalytic degradation and mineralization mechanism and toxicity assessment of antivirus drug acyclovir: experimental and theoretical studies. Appl. Catal. B Environ. 2015, 164:279-287.
2. An T.C., Fang H.S., Li G.Y., Wang S.L., Yao S.D. Experimental and theoretical insights into photochemical transformation kinetics and mechanisms of aqueous propylparaben and risk assessment of its degradation products. Environ. Toxicol. Chem. 2014, 33(8):1809-1816.
3. An T.C., Gao Y.P., Li G.Y., Kamat P.V., Peller J., Joyce M.V. Kinetics and mechanism of (OH)-O-center dot mediated degradation of dimethyl phthalate in aqueous solution: experimental and theoretical studies. Environ. Sci. Technol. 2014, 48(1):641-648.
4. An T.C., Sun L., Li G.Y., Gao Y.P., Ying G.G. Photocatalytic degradation and detoxification of o-chloroaniline in the gas phase: mechanistic consideration and mutagenicity assessment of its decomposed gaseous intermediate mixture. Appl. Catal. B Environ. 2011, 102(1-2):140-146.
5. An T.C., Yang H., Li G.Y., Song W.H., Cooper W.J., Nie X.P. Kinetics and mechanism of advanced oxidation processes (AOPs) in degradation of ciprofloxacin in water. Appl. Catal. B Environ. 2010, 94(3-4):288-294.
6. Barone V., Cossi M. Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model. J. Phys. Chem. A 1998, 102(11):1995-2001.
7. Berkowitz J., Ellison G.B., Gutman D. Three methods to measure RH bond energies. J. Phys. Chem. 1994, 98(11):2744-2765.
8. 2/UV system. Ozone Sci. Eng. 2012, 34(5):354-358.
9. Boxall A.B.A., Sinclair C.J., Fenner K., Kolpin D., Maund S.J. Peer reviewed: when synthetic chemicals degrade in the environment. Environ. Sci. Technol. 2004, 38(19):368A-375A.
10. Brezonik P.L., Fulkerson-Brekken J. Nitrate-induced photolysis in natural waters: controls on concentrations of hydroxyl radical photo-intermediates by natural scavenging agents. Environ. Sci. Technol. 1998, 32(19):3004-3010.
11. Calafat A.M., Ye X.Y., Wong L.Y., Bishop A.M., Needham L.L. Urinary concentrations of four parabens in the US population: NHANES 2005-2006. Environ. Health Perspect. 2010, 118(5):679-685.
12. Casoni D., Sarbu C. The lipophilicity of parabens estimated on reverse phases chemically bonded and oil-impregnated plates and calculated using different computation methods. J. Sep. Sci. 2009, 32(14):2377-2384.
13. Collins F.C., Kimball G.E. Diffusion-controlled reaction rates. J. Colloid Sci. 1949, 4(4):425-437.
14. Daghrir R., Dimboukou-Mpira A., Seyhi B., Drogui P. Photosonochemical degradation of butyl-paraben: optimization, toxicity and kinetic studies. Sci. total Environ. 2014, 490:223-234.
15. Darbre P.D., Harvey P.W. Paraben esters: review of recent studies of endocrine toxicity, absorption, esterase and human exposure, and discussion of potential human health risks. J. Appl. Toxicol. 2008, 28(5):561-578.
16. DeMatteo M.P., Poole J.S., Shi X.F., Sachdeva R., Hatcher P.G., Hadad C.M., Platz M.S. On the electrophilicity of hydroxyl radical: a laser flash photolysis and computational study. J. Am. Chem. Soc. 2005, 127(19):7094-7109.
17. Dobbins L.L., Usenko S., Brain R.A., Brooks B.W. Probabilistic ecological hazard assessment of parabens using daphnia magna and pimephales promelas. Environ. Toxicol. Chem. 2009, 28(12):2744-2753.
18. Dong M.M., Rosario-Ortiz F.L. Photochemical formation of hydroxyl radical from effluent organic matter. Environ. Sci. Technol. 2012, 46(7):3788-3794.
19. ECOSAR http://www.epa.gov/oppt/newchems/tools/21ecosar.htm.
20. EU WHITE PAPER Strategy for a Future Chemicals Policy COM 2001, 88 final. http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=COM:2001:0088:FIN:EN:PDF.
21. 2 and risk assessment of its degradation products. Environ. Sci. Technol. 2013, 47(6):2704-2712.
22. Fang X.W., Schuchmann H.P., von Sonntag C. The reaction of the OH radical with pentafluoro-, pentachloro-, pentabromo- and 2,4,6-triiodophenol in water: electron transfer vs. addition to the ring. J. Chem. Soc. Perkin Trans. 2000, 2(7):1391-1398.
23. Frisch M.J., Truck G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery J.A., Stratmann J.R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Boboul A.G., Stefnov B.B., Liu G., Liaschenko A., Piskorz P., Komaromi L., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Gonzalez C., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S., Pople J.A. 2003, Guassian, Inc., Pittsburgh, PA., GAUSSIAN 03.
24. Gao Y., An T., Fang H., Ji Y., Li G. Computational consideration on advanced oxidation degradation of phenolic preservative, methylparaben, in water: mechanisms, kinetics, and toxicity assessments. J. Hazard. Mater. 2014, 278(0):417-425.
25. Gao Y., Ji Y., Li G., An T. Mechanism, kinetics and toxicity assessment of OH-initiated transformation of triclosan in aquatic environments. Water Res. 2014, 49:360-370.
26. Hatipoglu A., Vione D., Yalcin Y., Minero C., Cinar Z. Photo-oxidative degradation of toluene in aqueous media by hydroxyl radicals. J. Photochem. Photobiol. A Chem. 2010, 215(1):59-68.
27. Jones O.A.H., Voulvoulis N., Lester J.N. Aquatic environmental assessment of the top 25 english prescription pharmaceuticals. Water Res. 2002, 36(20):5013-5022.
28. Karpuzoglu E., Holladay S.D., Gogal R.M. Parabens: potential impact of low-affinity estrogen receptor binding chemicals on human health. J. Toxicol. Environ. Health Part B Crit. Rev. 2013, 16(5):321-335.
29. Kasprzyk-Hordern B., Dinsdale R.M., Guwy A.J. The occurrence of pharmaceuticals, personal care products, endocrine disruptors and illicit drugs in surface water in South Wales, UK. Water Res. 2008, 42(13):3498-3518.
30. Kuş N., Bayari S.H., Fausto R. Methylparaben isolated in solid Argon: structural characterization and UV-Induced conversion into methylparaben radical and isomeric ketenes. J. Phys. Chem. B 2013, 117(43):13543-13555.
31. Leal L.H., Vieno N., Temmink H., Zeeman G., Buisman C.J.N. Occurrence of xenobiotics in gray water and removal in three biological treatment systems. Environ. Sci. Technol. 2010, 44(17):6835-6842.
32. Liao C.Y., Lee S., Moon H.B., Yamashita N., Kannan K. Parabens in sediment and sewage sludge from the United States, Japan, and Korea: spatial distribution and temporal trends. Environ. Sci. Technol. 2013, 47(19):10895-10902.
33. Liao C.Y., Liu F., Kannan K. Occurrence of and dietary exposure to parabens in foodstuffs from the United States. Environ. Sci. Technol. 2013, 47(8):3918-3925.
34. 2: multivariable experimental design and mechanism. Appl. Catal. B-Environmental 2009, 88(1-2):32-41.
35. Liu F., Xu M.Y., Chen X.J., Yang Y.G., Wang H.J., Sun G.P. Novel strategy for tracking the microbial degradation of azo dyes with different polarities in living cells. Environ. Sci. Technol. 2015, 49(19):11356-11362.
36. Liu J.L., Wong M.H. Pharmaceuticals and personal care products (PPCPs): a review on environmental contamination in China. Environ. Int. 2013, 59:208-224.
37. Madden J.C., Enoch S.J., Hewitt M., Cronin M.T.D. Pharmaceuticals in the environment: good practice in predicting acute ecotoxicological effects. Toxicol. Lett. 2009, 185(2):85-101.
38. Minakata D., Li K., Westerhoff P., Crittenden J. Development of a group contribution method to predict aqueous phase hydroxyl radical (HO center dot) reaction rate constants. Environ. Sci. Technol. 2009, 43(16):6220-6227.
39. Monod A., Doussin J.F. Structure-activity relationship for the estimation of OH-oxidation rate constants of aliphatic organic compounds in the aqueous phase: alkanes, alcohols, organic acids and bases. Atmos. Environ. 2008, 42(33):7611-7622.
40. Okuno Y. Theoretical investigation of the mechanism of the Baeyer-Villiger reaction in nonpolar solvents. Chem. A Eur. J. 1997, 3(2):212-218.
41. Peng X.Z., Yu Y.J., Tang C.M., Tan J.H., Huang Q.X., Wang Z.D. Occurrence of steroid estrogens, endocrine-disrupting phenols, and acid pharmaceutical residues in urban riverine water of the Pearl River Delta, South China. Sci. Total Environ. 2008, 397(1-3):158-166.
42. Plumlee M.H., McNeill K., Reinhard M. Indirect photolysis of perfluorochemicals: hydroxyl radical-initiated oxidation of N-ethyl perfluorooctane sulfonamido acetate (N-EtFOSAA) and other Perfluoroalkanesulfonamides. Environ. Sci. Technol. 2009, 43(10):3662-3668.
43. Prasse C., Wagner M., Schulz R., Ternes T.A. Oxidation of the antiviral drug acyclovir and its biodegradation product carboxy-acyclovir with ozone: kinetics and identification of oxidation products. Environ. Sci. Technol. 2012, 46(4):2169-2178.
44. Ramaswamy B.R., Kim J.W., Isobe T., Chang K.H., Amano A., Miller T.W., Siringan F.P., Tanabe S. Determination of preservative and antimicrobial compounds in fish from Manila Bay, Philippines using ultra high performance liquid chromatography tandem mass spectrometry, and assessment of human dietary exposure. J. Hazard. Mater. 2011, 192(3):1739-1745.
45. Sánchez-Martín J., Beltrán-Heredia J., Domínguez J.R. Advanced photochemical degradation of emerging pollutants: methylparaben. Water Air Soil Pollut. 2013, 224(5).
46. Salvito D.T., Senna R.J., Federle T.W. A framework for prioritizing fragrance materials for aquatic risk assessment. Environ. Toxicol. Chem. 2002, 21(6):1301-1308.
47. Sanderson H., Johnson D.J., Wilson C.J., Brain R.A., Solomon K.R. Probabilistic hazard assessment of environmentally occurring pharmaceuticals toxicity to fish, daphnids and algae by ECOSAR screening. Toxicol. Lett. 2003, 144(3):383-395.
48. Schwarzenbach R.P., Egli T., Hofstetter T.B., von Gunten U., Wehrli B. Global water pollution and human health. Annu. Rev. Environ. Resour. 2010, 35:109-136. 35.
49. Schwarzenbach R.P., Escher B.I., Fenner K., Hofstetter T.B., Johnson C.A., von Gunten U., Wehrli B. The challenge of micropollutants in aquatic systems. Science 2006, 313(5790):1072-1077.
50. Smith K.W., Souter I., Dimitriadis I., Ehrlich S., Williams P.L., Calafat A.M., Hauser R. Urinary paraben concentrations and ovarian aging among women from a fertility center. Environ. Health Perspect. 2013, 121(11-12):1299-1305.
51. Steter J.R., Rocha R.S., Dionisio D., Lanza M.R.V., Motheo A.J. Electrochemical oxidation route of methyl paraben on a boron-doped diamond anode. Electrochimica Acta 2014, 117:127-133.
52. Tay K.S., Rahman N.A., Abas M.R.B. Kinetic studies of the degradation of parabens in aqueous solution by ozone oxidation. Environ. Chem. Lett. 2010, 8(4):331-337.
53. Tay K.S., Rahman N.A., Bin Abas M.R. Ozonation of parabens in aqueous solution: kinetics and mechanism of degradation. Chemosphere 2010, 81(11):1446-1453.
54. Terasaki M., Makino M., Tatarazako N. Acute toxicity of parabens and their chlorinated by-products with Daphnia magna and Vibrio fischeri bioassays. J. Appl. Toxicol. 2009, 29(3):242-247.
55. Tunkel J., Mayo K., Austin C., Hickerson A., Howard P. Practical considerations on the use of predictive models for regulatory purposes. Environ. Sci. Technol. 2005, 39(7):2188-2199.
56. Wang D., Bolton J.R., Hofmann R. Medium pressure UV combined with chlorine advanced oxidation for trichloroethylene destruction in a model water. Water Res. 2012, 46(15):4677-4686.
57. Wenk J., von Gunten U., Canonica S. Effect of dissolved organic matter on the transformation of contaminants induced by excited triplet states and the hydroxyl radical. Environ. Sci. Technol. 2011, 45(4):1334-1340.
58. Yamamoto H., Tamura I., Hirata Y., Kato J., Kagota K., Katsuki S., Yamamoto A., Kagami Y., Tatarazako N. Aquatic toxicity and ecological risk assessment of seven parabens: individual and additive approach. Sci. Total Environ. 2011, 410:102-111.
59. Yamamoto H., Watanabe M., Hirata Y., Nakamura Y., Nakamura Y., Kitani C., Sekizawa J., Uchida M., Nakamura H., Kagami Y., Koshio M., Hirai N., Tatarazako N. Preliminary ecological risk assessment of butylparaben and benzylparaben -1. Removal efficiency in wastewater treatment, acute/chronic toxicity for aquatic organisms, and effects on medaka gene expression. Environ. Sci. 2007, 14:73-87.
60. 2: a case of sulfa drugs. Catal. Today 2010, 153(3-4):200-207.
61. Yu J.C., Kwong T.Y., Luo Q., Cai Z.W. Photocatalytic oxidation of triclosan. Chemosphere 2006, 65(3):390-399.
62. Zhang S.Y., Chen J.W., Qiao X.L., Ge L.K., Cai X.Y., Na G.S. Quantum chemical investigation and experimental verification on the aquatic photochemistry of the sunscreen 2-phenylbenzimidazole-5-sulfonic acid. Environ. Sci. Technol. 2010, 44(19):7484-7490.
63. Zhou J., Chen J.W., Liang C.H., Xie Q., Wang Y.N., Zhang S.Y., Qiao X.L., Li X.H. Quantum chemical investigation on the mechanism and kinetics of PBDE photooxidation by center dot OH: a case study for BDE-15. Environ. Sci. Technol. 2011, 45(11):4839-4845.