Behavior of stable carbon isotope of phthalate acid esters during photolysis under ultraviolet irradiation

Chemosphere

Volumn 92, Issue 11, 2013, Pages 1557-1562

  Peng, Xuewei ^a,b   Li, Xianguo ^a   Feng, Lijuan ^a  

^a Ocean University of China   (China)

^b WEIFANG UNIVERSITY   (China)

Author keywords

Compound specific isotope analysis; Pathway; Photolysis; Phthalic acid ester

Indexed keywords

CARBON; CARBOXYLIC ACIDS; ESTERS; GAS CHROMATOGRAPHY; IRRADIATION; ISOTOPES; MASS SPECTROMETRY; MOLECULES; PHASE INTERFACES; PHOTOLYSIS; RATE CONSTANTS;

COMPOUND SPECIFIC ISOTOPE ANALYSIS; IN-LABORATORY EXPERIMENTS; ISOTOPE RATIO MASS SPECTROMETRY; KINETIC ISOTOPE EFFECTS; PATHWAY; PHTHALIC ACID ESTERS; STABLE CARBON ISOTOPE FRACTIONATIONS; ULTRAVIOLET IRRADIATIONS;

PHOTODEGRADATION;

CARBON 13; PHTHALIC ACID DIBUTYL ESTER; PHTHALIC ACID DIMETHYL ESTER; PHTHALIC ACID DIOCTYL ESTER; STABLE ISOTOPE;

BIODEGRADATION; CARBON ISOTOPE; COMBUSTION; ISOTOPIC FRACTIONATION; ISOTOPIC RATIO; LABORATORY METHOD; MOLECULAR ANALYSIS; PHTHALATE; STABLE ISOTOPE; ULTRAVIOLET RADIATION;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; MINERALIZATION; PH; PHOTODEGRADATION; PHOTOLYSIS; TOTAL ORGANIC CARBON; ULTRAVIOLET IRRADIATION;

EID: 84880698970     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2013.04.029     Document Type: Article

References (41)

1. Alborzfar M., Escande K., Allen S.J. Removal of 3,4-dichlorobut-1-ene using ozone oxidation. Water Res. 2000, 34:2963-2970.
2. Balabanovich A.I., Schnabel W. On the photolysis of phthalic acid dimethyl and diethyl ester: a product analysis study. J. Photochem. Photobiol., A 1998, 113:145-153.
3. Barlow N., Phillips S., Wallace D., Sar M., Gaido K., Foster P. Quantitative changes in gene expression in fetal rat testes following exposure to di(n-butyl) phthalate. Toxicol. Sci. 2003, 73:431-441.
4. Burrows H.D., Canle L.M., Santaballa J.A., Steenken S. Reaction pathways and mechanisms of photodegradation of pesticides. J. Photochem. Photobiol., B 2002, 67:71-108.
5. Canonica S., Hoigné J. Enhanced oxidation of methoxy phenols at micromolar concentration photosensitized by dissolved natural organic material. Chemosphere 1995, 30:2365-2374.
6. Chang B.V., Yang C.M., Cheng C.H., Yuan S.Y. Biodegradation of phthalate esters by two bacteria strains. Chemosphere 2004, 55:533-538.
7. Chen J.W., Quan X., Schramm K.W., Kettrup A., Yang F.L. Quantitative structure-property relationships (QSPRs) on direct photolysis of PCDDs. Chemosphere 2001, 45:151-159.
8. Courbet C., Rivière A., Jeannottat S., Rinaldi S., Hunkeler D., Bendjoudi H., de Marsily G. Complementing approaches to demonstrate chlorinated solvent biodegradation in a complex pollution plume: mass balance, PCR and compound-specific stable isotope analysis. J. Contam. Hydrol. 2011, 126:315-329.
9. 2 Environ. Environ. Technol. 2003, 24:479-489.
10. Djebbar K.E., Zertal A., Debbache N., Sehili T. Comparison of diuron degradation by direct UV photolysis and advanced oxidation processes. J. Environ. Manage. 2008, 88:1505-1512.
11. Ejlertsson J., Alnervik M., Jonsson S., Svensson B. Influence of water solubility, side-chain degradability, and side-chain structure on the degradation of phthalic acid esters under methanogenic conditions. Environ. Sci. Technol. 1997, 31:2761-2764.
12. Elsner M., Zwank L., Hunkeler D., Schwarzenbach R.P. A new concept linking observable stable isotope fractionation to transformation pathways of organic pollutants. Environ. Sci. Technol. 2005, 39:6896-6916.
13. Faure G. Principles of Isotope Geology 1986, John Wiley and Sons, New York.
14. Gavala H.N., Alatriste-Mondragon F., Iranopour R., Ahring B.K. Biodegradation of phthalate esters during the mesophilic anaerobic digestion of sludge. Chemosphere 2003, 52:673-682.
15. Giam C.S., Atlas E., Powers M.A., Leonard J.E. Phthalic acid esters. Handbook of Environmental Chemistry. Part C 1984, vol. 3:67-140. Springer-Verlag, New York, Berlin.
16. Griebler C., Safinowski M., Vieth A., Richnow H.H., Meckenstock R.U. Combined application of stable carbon isotope analysis and specific metabolites determination for assessing in situ degradation of aromatic hydrocarbons in a tar oil-contaminated aquifer. Environ. Sci. Technol. 2004, 38:617-631.
17. Harrington R.R., Poulson S.R., Drever J.I., Colberg P.J.S., Kelly E.F. Carbon isotope systematics of monoaromatic hydrocarbons: vaporization and adsorption experiments. Org. Geochem. 1999, 30:765-775.
18. Hartenbach A., Hofstetter T.B., Tentscher P.R., Canonica S., Berg M., Schwarzenbach R.P. Carbon, hydrogen, and nitrogen isotope fractionation during light-induced transformations of atrazine. Environ. Sci. Technol. 2008, 42:7751-7756.
19. Hu X., Zhang K., Zhone B., Wu D. Photodegradation of phthalic acid esters in water. J. Sichuan Univ. 2003, 34:300-302.
20. Huff J.E., Kluwe W.M. Phthalate esters carcinogenicity in F344/N rats and B6C3F1 mice. Prog. Clin. Biol. Res. 1984, 141:137-154.
21. Hunkeler D., Aravena R., Butler B.J. Monitoring microbial dechlorination of tetrachloroethene (PCE) in groundwater using compound-specific stable carbon isotope ratios: microcosm and field studies. Environ. Sci. Technol. 1999, 33:2733-2738.
22. Huskey W.P. Enzyme mechanism from isotope effects 1991, 37-72. CRC Press, Boca Raton, FL. P.F. Cook (Ed.).
23. Imfeld G., Nijenhuis I., Nikolausz M., Zeiger S., Paschke H., Drangmeister J., Grossmann J., Richnow H.H., Weber S. Assessment of in situ degradation of chlorinated ethenes and bacterial community structure in a complex contaminated groundwater system. Water Res. 2008, 42:871-882.
24. Lau T.K., Chu W., Graham N. The degradation of endocrine disruptor di-n-butyl phthalate by UV irradiation: a photolysis and product study. Chemosphere 2005, 60:1045-1053.
25. Lesser L.E., Johnson P.C., Aravena R., Spinnler G.E., Bruce C.L., Salanitro J.P. An evaluation of compound-specific isotope analyses for assessing the biodegradation of MTBE at Port Hueneme, CA. Environ. Sci. Technol. 2008, 42:6637-6643.
26. Meckenstock R.U., Morasch B., Griebler C., Richnow H.H. Stable isotope fractionation analysis as a tool to monitor biodegradation in contaminated aquifers. J. Contam. Hydrol. 2004, 75:215-255.
27. Morasch B., Hunkeler D., Zopfi J., Temime B., Höhener P. Intrinsic biodegradation potential of aromatic hydrocarbons in an alluvial aquifer - potentials and limits of signature metabolite analysis and two stable isotope-based techniques. Water Res. 2011, 45:4459-4469.
28. Muneer M., Theurich J., Bahnemann D. Titanium dioxide mediated photocatalytic degradation of 1,2-diethyl phthalate. J. Photochem. Photobiol., A 2001, 143:213-219.
29. Niu J.F., Chen J.W., Martens D., Henkelmann B., Quan X., Yang F., Seidlitz H.K., Schramm K.W. The role of UV-B on the degradation of PCDD/Fs and PAHs sorbed on surfaces of spruce (Picea abies (L.) Karst) needles. Sci. Total Environ. 2004, 322:231-241.
30. Peng X., Li X. Compound-specific isotope analysis for aerobic biodegradation of phthalate acid esters. Talanta 2012, 97:445-449.
31. Peng X., Feng L., Li X. Pathway of diethyl phthalate photolysis in sea-water determined by gas chromatography-mass spectrometry and compound-specific isotope analysis. Chemosphere 2013, 90:220-226.
32. 13C values) of polybrominated diphenyl ethers and their UV-transformation products. Environ. Pollut. 2011, 159:2706-2712.
33. Saeger V.W., Tucker E.S. Biodegradation of phthalic acid esters in river water and activated sludge. Appl. Environ. Microbiol. 1976, 31:29-34.
34. Scholz N. Ecotoxicity and biodegradation of phthalate monoesters. Chemosphere 2003, 53:921-926.
35. Schwarzenbach R.P., Gschwend P.M., Imboden D.M. Environmental Organic Chemistry 2003, John Wiley & Sons, New York, p. 1311. second ed.
36. Shiner, V.J., Wilgis, F.P. 1992. In: Buncel, E., Saunders, W.H. (Eds.), Isotopes in organic chemistry, Heavy atom isotope effects, vol. 8. Amsterdam, London, New York, Tokyo, pp. 239-335.
37. Staples C.A., Adams W.J., Parkerton T.F., Gorsuch J.W., Biddinger G.R., Reinert K.H. Aquatic toxicity of eighteen phthalate esters. Environ. Toxicol. Chem. 1997, 16:875-891.
38. Tiehm A., Schmidt K.R., Pfeifer B., Heidinger M., Ertl S. Growth kinetics and stable carbon isotope fractionation during aerobic degradation of cis-1,2-dichloroethene and vinyl chloride. Water Res. 2008, 42:2431-2438.
39. 2. J. Hazard. Mater. 2007, 139:132-139.
40. 2 process. J. Hazard. Mater. 2009, 162:954-959.
41. 2-UV reaction system. Water Res. 2008, 42:1413-1420.