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Fenton degradation of dialkylphthalates: products and mechanism

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Abstract

Contamination of wastewater by organic pollutants is a major worldwide issue. For instance plastic additives such as phthalates are found in wastewater. Efficient techniques are thus needed to clean wastewaters. The Fenton reaction involving H2O2 and Fe(II) salts can be used to treat polluted water. During the Fenton reaction pollutants are decomposed directly by hydroxyl radicals. In some cases toxic by-products are produced. Here dimethyl phthalate, diethyl phthalate, and dipropyl phthalate by-products formed during the Fenton reaction were studied. Fenton degradation of selected phthalates yielded numerous transformation products such as hydroxylated phthalates. The hydroxylation reaction occurred at the aromatic ring of phthalates and yielded mono- and dihydroxylated phthalates. For monohydroxylated phthalate, 3-hydroxy- and 4-hydroxydialkylphthalates are the main transformation products. In addition to hydroxylated derivatives, aliphatic chain degraded mono- and dihydroxylated phthalates were also detected.

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References

  • Behnke W, Hollander W, Koch W, Nolting F, Zetzsch C (1988) A smog chamber for studies of the photochemical degradation of chemicals in the presence of aerosols. Atmos Environ 22:1113–1120

    Article  CAS  Google Scholar 

  • da Silva G, Bozzelli JW, Asatryan R (2009) Hydroxyl radical initiated oxidation of s-triazine: hydrogen abstraction is faster than hydroxyl addition. J Phys Chem A 113:8596–8696

    Article  CAS  Google Scholar 

  • Galyashin VN, El’kin YN, Rozynov BV, Kuz’min NM (1983) Mass spectra of hydroxyl-substituted methyl esters of benzecarboxylic acids with different numbers of carboxyl groups. Russ Chem B+ 32:1851–1857

    Article  Google Scholar 

  • Huang WB, Chen CY (2010) Photocatalytic degradation of diethyl phthalate (DEP) in water using TiO2. Water Air Soil Pollut 207:349–355

    Article  CAS  Google Scholar 

  • Huang PC, Tien CJ, Sun YM, Hsieh CY, Lee CC (2008) Occurrence of phthalates in sediment and biota: relationship to aquatic factors and the biota-sediment accumulation factor. Chemosphere 73:539–544

    Article  CAS  Google Scholar 

  • Ikehata K, El-Din MG (2006) Aqueous pesticide degradation by hydrogen peroxide/ultraviolet irradiation and fenton-type advanced oxidation processes: a review. J Environ Eng Sci 5:81–135

    Article  CAS  Google Scholar 

  • Ikehata K, Naghashkar NJ, El-Din MG (2006) Degradation of aqueous pharmaceuticals by ozonation and advanced oxidation processes: a review. Ozone-Sci Eng 28:353–414

    Article  CAS  Google Scholar 

  • Jung JY, Oh BS, Kim KS, Koga M, Shinohara R, Kang JW (2010) The degradation of diethyl phthalate (DEP) during ozonation: oxidation by-products study. J Water Health 8:290–298

    Article  CAS  Google Scholar 

  • Nakai M, Tabira Y, Asai D, Yakabe Y, Shimyozu T, Noguchi M, Takatsuki M, Shimohigashi Y (1999) Binding characteristics of dialkyl phthalates for the estrogen receptor. Biochem Biophy Res Co 254:311–314

    Article  CAS  Google Scholar 

  • Nakrst J, Cistan M, Tišler T, Zagorc-Končan J, Gotvajn AZ (2010) Feasibility of Fenton’s oxidation for removal of estrogens from aqueous solutions. Acta Chim Slov 57:90–99

    CAS  Google Scholar 

  • Oehlmann J, Oetken M, Schulte-Oehlmann U (2008) A critical evaluation of the environmental risk assessment for plasticizer in the freshwater environment in Europe, with special emphasis on bisphenol A and endocrine disruption. Environ Res 108:140–149

    Article  CAS  Google Scholar 

  • Pant N, Shukla M, Patel DK, Shukla Y, Mathur N, Gupta YK, Saxena DK (2008) Correlation of phthalate exposures with semen quality. Toxicol Appl Pharm 231:112–116

    Article  CAS  Google Scholar 

  • Parveen M, Inoue A, Ise R, Tanji M, Kiyama R (2008) Evaluation of estrogenic activity of phthalate esters by gene expression profiling using a focused microarray (ESTRARRAY). Environ Toxicol Chem 27:1416–1425

    Article  CAS  Google Scholar 

  • Satoh AY, Trosko JE, Masten SJ (2007) Methylene blue dye test for rapid qualitative detection of hydroxyl radicals formed in a Fenton’s reaction aqueous solution. Environ Sci Technol 41:2881–2887

    Article  CAS  Google Scholar 

  • Tay KS, Rahman NA, Abas MRB (2010) Ozonation of a mixture of dialkylphthlates in aqueous solution. J Chem Technol Biot 85:726–729

    Article  CAS  Google Scholar 

  • Trujillo D, Font X, Sánchez A (2006) Use of fenton reaction for the treatment of leachate from composting of different wastes. J Hazard Mater 138:201–204

    Article  CAS  Google Scholar 

  • Xu B, Gao NY, Cheng H, Xia SJ, Rui M, Zhao DD (2009a) Oxidative degradation of dimethyl phthalate (DMP) by UV/H2O2 process. J Hazard Mater 162:954–959

    Article  CAS  Google Scholar 

  • Xu XR, Li SX, Li XY, Gu JD, Chen F, Li XZ, Li HB (2009b) Degradation of n-butyl benzyl phthalate using TiO2/UV. J Hazard Mater 164:527–532

    Article  CAS  Google Scholar 

  • Yang GP, Zhao XK, Sun XJ, Lu XL (2005) Oxidative degradation of diethyl phthalate by photochemically-enhanced Fenton reaction. J Hazard Mater 126:112–118

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This research was supported financially by the Malaysia Toray Science Foundation (MTSF), Ministry of Higher Education Malaysia (FRGS-FP018-2008C) and University of Malaya (PS354-2010A).

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Authors and Affiliations

  1. Environmental Research Group, Department of Chemistry, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia

    Kheng Soo Tay, Noorsaadah Abd Rahman & Mhd Radzi Bin Abas

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  1. Kheng Soo Tay
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  2. Noorsaadah Abd Rahman
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  3. Mhd Radzi Bin Abas
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Correspondence to Kheng Soo Tay.

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Tay, K.S., Rahman, N.A. & Abas, M.R.B. Fenton degradation of dialkylphthalates: products and mechanism. Environ Chem Lett 9, 539–546 (2011). https://doi.org/10.1007/s10311-011-0317-3

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  • DOI: https://doi.org/10.1007/s10311-011-0317-3

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