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The photosensitized oxidation of mixture of parabens in aqueous solution

  • Application of Sustainable Technologies for The Removal of Environmental Contaminants Before Reuse
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Abstract

The work presents results of studies on the photosensitized oxidation of mixture of five parabens (methyl-, ethyl-, propyl-, n-butyl-, and benzylparaben) in aqueous solution. Aluminum phthalocyanine chloride tetrasulfonic acid and xenon lamp simulating solar radiation were used as a photosensitizer and a light source, respectively. The purpose was to investigate the influence of inhibitory effect compounds present in the mixture on the reaction rate. The influence of the addition of second photosensitizer on the parabens degradation rate was investigated. The effect of additives: tert-butanol - hydroxyl radical scavenger and sodium azide - singlet oxygen scavenger on reaction course was also determined. The transformation products formed during the photosensitized oxidation process were analyzed by UPLC-MS/MS. The efficiency of photosensitized oxidation of parabens with natural sunlight irradiation in the central Poland was checked.

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References

  • Aalto TR, Firman MC, Rigler NE (1953) p-Hydroxybenzoic acid esters as preservatives. J Am Pharm Assoc Am PharmAssoc (Baltim) 42(8):449–457

    Article  CAS  Google Scholar 

  • Albero B, Pérez RA, Sánchez-Brunete C, Tadeo JL (2012) Occurrence and analysis of parabens in municipal sewage sludge from wastewater treatment plants in Madrid (Spain). J Hazard Mater 239–240:48–55

    Article  Google Scholar 

  • Andersen FA (2008) Final report on the safety assessment of methylparaben, ethylparaben, isopropylparaben, isobutylparaben and benzylparaben as used in cosmetic products. Int J Toxicol 27(suppl 4):1–82

    Google Scholar 

  • Andersen HR, Lundsbye M, Wedel HV, Eriksson E, Ledin A (2007) Estrogenic personal care products in a greywater reuse system. Water Sci Technol 56:45–49

    Article  CAS  Google Scholar 

  • Barr L, Metaxas G, Harbach CA, Savoy LA, Darbre PD (2012) Measurement of paraben concentrations in human breast tissue at serial locations across the breast from axilla to sternum. J Appl Toxicol 32(3):219–232

    Article  CAS  Google Scholar 

  • Bazin I, Gadal A, Touraud E, Roig B (2010) Hydroxy benzoate preservatives (parabens) in the environment: data for environmental toxicity assessment. In: Fatta-Kassinos D, Bester K, Kummerer K (eds) Xenobiotics in the urban water cycle: mass flows, environmental processes, mitigation and treatment strategies. Part II. Springer, Netherlands, pp 245–257

    Chapter  Google Scholar 

  • Calafat AM, Ye X, Wong LY, Bishop AM, Needham LL (2010) Urinary concentrations of four parabens in the U.S. population: NHANES 2005–2006. Environ Health Perspect 118(5):679–685

    Article  CAS  Google Scholar 

  • Castelain F, Castelain M (2012) Parabens: a real hazard or a scare story? Eur J Dermatol 22(6):723–727

    CAS  Google Scholar 

  • Cavalcante RP, da Rocha Sandim L, Bogo D, Barbosa AML, Osugi ME, Blanco M, de Oliveira SC, de Fatima Cepa Matos M, Machulek A Jr, Ferreira VS (2013) Application of Fenton, photo-Fenton, solar photo-Fenton and UV/H2O2 to degradation of the antineoplastic agent mitoxantrone and toxicological evaluation. Environ Sci Pollut Res 20:2352–2361

    Article  CAS  Google Scholar 

  • Chen Y, Liang Q, Zhou D, Wang Z, Tao T, Zuo Y (2013a) Photodegradation kinetics, products and mechanism of timolol under simulated sunlight. J Hazard Mater 252–253:220–226

    Google Scholar 

  • Chen Y, Zhang K, Zuo Y (2013b) Direct and indirect photodegradation of estriol in the presence of humic acid, nitrate and iron complexes in water solutions. Sci Total Environ 463–464:802–809

    Article  Google Scholar 

  • Darbre PD, Aljarrah A, Miller WR, Coldham NG, Sauer MJ, Pope GS (2004) Concentrations of parabens in human breast tumours. J Appl Toxicol 24:5–13

    Article  CAS  Google Scholar 

  • Domínguez JR, Muñoz MJ, Palo P, González T, Peres JA, Cuerda-Correa EM (2014) Fenton advanced oxidation of emerging pollutants: parabens. Int J Energy Environ Eng 5:89–98

    Article  Google Scholar 

  • Feng X, Chen Y, Fang Y, Wang X, Wang Z, Tao T, Zuo Y (2014) Photodegradation of parabens by Fe(III)-citrate complexes at circumneutral pH: matrix effect and reaction mechanism. Sci Total Environ 472:130–136

    Article  CAS  Google Scholar 

  • Filby AL, Neuparth T, Thorpe KL, Owen R, Galloway TS, Tyler CR (2007) Health impacts of estrogens in the environment, considering complex mixture effects. Environ Health Perspect 115(12):1704–1710

    Article  CAS  Google Scholar 

  • Gryglik D, Miller JS, Ledakowicz S (2004) Solar energy utilization in degradation of 2-chlorophenol by immobilized photosensitizers. Sol Energy 77(5):615–623

    Article  CAS  Google Scholar 

  • Gryglik D, Lach M, Miller JS (2009) The aqueous photosensitized degradation of butylparaben. Photochem Photobiol Sci 8:549–555

    Article  CAS  Google Scholar 

  • Kamaraj M, Ranjith KS, Rajeshwari S, Rajendra KRT, Hasna AS (2014) Photocatalytic degradation of endocrine disruptor Bisphenol-A in the presence of prepared CexZn1 − xO nanocomposites under irradiation of sunlight. J Environ Sci. Article in press

  • Liao C, Kannan K (2014) Concentrations and composition profiles of parabens in currency bills and paper products including sanitary wipes. Sci Total Environ 475:8–15

    Article  CAS  Google Scholar 

  • Ma WL, Wang L, Guo L, Liu LY, Qi H, Zhu NZ, Gao CJ, Li JF, Kannan K (2013) Urinary concentrations of parabens in Chinese young adults: implications for human exposure arch. Environ Contam Toxicol 65:611–618

    Article  CAS  Google Scholar 

  • Maroga MV, Héquet V, Andrès Y, Gru Y, Colin R, Doña-Rodríguez JM, Pastrana-Martínez LM, Silva AMT, Leleu M, Tindall AJ, Mateos S, Falaras P (2015) Photocatalytic degradation of estradiol under simulated solar light and assessment of estrogenic activity. Appl Catal B Environ 162:437–444

    Article  Google Scholar 

  • Remucal CK (2014) The role of indirect photochemical degradation in the environmental fate of pesticides: a review. Environ Sci Process Impacts 16:628–653

    Article  CAS  Google Scholar 

  • Routledge EJ, Parker J, Odum J, Ashby J, Sumpter JP (1998) Some alkyl hydroxy benzoate preservatives (parabens) are estrogenic. Toxicol Appl Pharmacol 153(1):12–19

    Article  CAS  Google Scholar 

  • Sandanger TM, Huber S, Moe MK, Braathen T, Leknes H, Lund E (2011) Plasma concentrations of parabens in postmenopausal women and self-reported use of personal care products: the NOWAC postgenome study. J Expo Sci Environ Epidemiol 21(6):595–600

    Article  CAS  Google Scholar 

  • Schlumpf M, Kypke K, Wittassek M, Angerer J, Mascher H, Mascher D, Vökt C, Birchler M, Lichtensteiger W (2010) Exposure patterns of UV filters, fragrances, parabens, phthalates, organochlor pesticides, PBDEs, and PCBs in human milk: Correlation of UV filters with use of cosmetics. Chemosphere 81(10):1171–1183

    Article  CAS  Google Scholar 

  • Shirai S, Suzuki Y, Yoshinaga J, Shiraishi H, Mizumoto Y (2013) Urinary excretion of parabens in pregnant Japanese women. Reprod Toxicol 35:96–101

    Article  CAS  Google Scholar 

  • Soni MG, Carabin IG, Burdock GA (2005) Review: safety assessment of esters of p-hydroxybenzoic acid (parabens). Food Chem Toxicol 43(7):985–1015

    Article  CAS  Google Scholar 

  • Steter JR, Rocha RS, Dionísio D, Lanza MRV, Motheo AJ (2014) Electrochemical oxidation route of methyl paraben on a boron-doped diamond anode. Electrochim Acta 117:127–133

    Article  CAS  Google Scholar 

  • Tay KS, Rahman NA, Mhd. Abas RB (2010) Kinetic studies of the degradation of parabens in aqueous solution by ozone oxidation. Environ Chem Lett 8:331–337

    Article  CAS  Google Scholar 

  • Thorpe KL, Maack G, Benstead R, Tyler CR (2009) Estrogenic wastewater treatment works effluents reduce egg production in fish. Environ Sci Technol 43(8):2976–2982

    Article  CAS  Google Scholar 

  • Vialaton D, Richard C (2002) Phototransformation of aromatic pollutants in solar light: photolysis versus photosensitized reactions under natural water conditions. Aquat Sci 64:207–215

    Article  CAS  Google Scholar 

  • Wang L, Wu Y, Zhang W, Kannan K (2013) Characteristic profiles of urinary p-hydroxybenzoic acid and its esters (parabens) in children and adults from the United States and China. Environ Sci Technol. doi:10.1021/es304659r

    Google Scholar 

  • Weschler CJ, Nazaroff WW (2014) Dermal uptake of organic vapors commonly found in indoor air. Environ Sci Technol 48(2):1230–1237

    Article  CAS  Google Scholar 

  • Yazar K, Johnsson S, Lind ML, Boman A, Liden C (2011) Preservatives and fragrances in selected consumer-available cosmetics and detergents. Contact Dermatitis 64(5):265–272

    Article  CAS  Google Scholar 

  • Ye X, Bishop AM, Reidy JA, Needham LL, Calafat AM (2006a) Parabens as urinary biomarkers of exposure in humans. Environ Health Perspect 114(12):1843–1846

    CAS  Google Scholar 

  • Ye X, Kuklenyik Z, Bishop AM, Needham LL, Calafat AM (2006b) Quantification of the urinary concentrations of parabens in humans by on-line solid phase extraction-high performance liquid chromatography-isotope dilution tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 844:3–9

    Article  Google Scholar 

  • Zuo Y, Zhang K, Zhou S (2013) Determination of estrogenic steroids and microbial and photochemical degradation of 17a-ethinylestradiol (EE2) in lake surface water, a case study. Environ Sci Process Impacts 15:1529–1535

    Article  CAS  Google Scholar 

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Acknowledgments

Marta Gmurek acknowledges the support from Foundation for Polish Science within the START scholarship.

Conflict of interest

The authors declare that there is no any actual or potential conflict of interest including any financial, personal, or other relationships with other people or organizations within 3 years of beginning the submitted work that could inappropriately influence, or be perceived to influence, their work.

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Authors and Affiliations

  1. Faculty of Civil Engineering, Architecture and Environmental Engineering, Lodz University of Technology, Al. Politechniki 6, 90-924, Lodz, Poland

    D. Gryglik

  2. Faculty of Process and Environmental Engineering, Lodz University of Technology, ul. Wólczańska 213, 90-924, Lodz, Poland

    M. Gmurek

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  1. D. Gryglik
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  2. M. Gmurek
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Correspondence to D. Gryglik.

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Responsible editor: Roland Kallenborn

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Gryglik, D., Gmurek, M. The photosensitized oxidation of mixture of parabens in aqueous solution. Environ Sci Pollut Res 25, 3009–3019 (2018). https://doi.org/10.1007/s11356-014-4059-1

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  • DOI: https://doi.org/10.1007/s11356-014-4059-1

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