Advertisement

Occurrence of Personal Care Products and Transformation Processes in Chlorinated Waters

  • Mariana M. de Oliveira e Sá
  • Margarida S. Miranda
  • Joaquim C. G. Esteves da SilvaEmail author
Chapter
Part of the The Handbook of Environmental Chemistry book series (HEC, volume 36)

Abstract

Personal care products (PCPs) have been found in surface water, wastewater, tap water, and swimming pool water. The chlorine used in the disinfection process of water reacts with these compounds generating chlorinated byproducts that may possess enhanced toxicity.

In the case of swimming pool water chlorine also reacts with organic material released by swimmers such as amino acids and other nitrogen compounds yielding chlorinated compounds. Besides this organic material, sunscreen cosmetics used by swimmers are also released into pool water and react with chlorine. UV-Filters 2-ethylhexyl-p-dimethylaminobenzoate (EHDPABA), benzophenone-3 (BP-3), benzophenone-4 (BP-4), 2-ethylhexyl-4-methoxycinnamate (EHMC), and 4-tert-butyl-4′-methoxy-dibenzoylmethane (BDM) are known to suffer an electrophilic aromatic substitution of one or two atoms of hydrogen per one or two chlorine atoms leading to mono- and di-chlorinated byproducts. It has also been observed the presence of halobenzoquinones (HBQs) in pool water that results from the chlorination of UV-filters such as BDM, octocrylene, and terephthalilidene dicamphor sulfonic acid. The chlorination of some parabens has also been studied. It is known that some of the formed chlorinated byproducts are genotoxic. In this chapter we present a review on the work done so far to determine the stability of PCPs in chlorinated water and to identify the chlorinated byproducts.

Keywords

Chlorinated byproducts Chlorination Personal care products UV-filters 

References

  1. 1.
    Poiger T, Buser H-R, Balmer ME et al (2004) Occurrence of UV filter compounds from sunscreens in surface waters: regional mass balance in two Swiss lakes. Chemosphere 55:951–963CrossRefGoogle Scholar
  2. 2.
    Giokas DL, Sakkas VA, Albanis TA (2004) Determination of residues of UV-filters in natural waters by solid-phase extraction coupled to liquid chromatography-photodiode array detection and gas chromatography–mass spectrometry. J Chromatogr A 1026:289–293CrossRefGoogle Scholar
  3. 3.
    Sui Q, Huang J, Deng S et al (2011) Seasonal variation in the occurrence and removal of pharmaceuticals and personal care products in different biological wastewater treatment processes. Environ Sci Technol 45:3341–3348CrossRefGoogle Scholar
  4. 4.
    Westerhoff P, Yoon Y, Snyder S, Wert E (2005) Fate of endocrine-disruptor, pharmaceutical, and personal care product chemicals during simulated drinking water treatment processes. Environ Sci Technol 39:6649–6663CrossRefGoogle Scholar
  5. 5.
    Onesios KM, Yu JT, Bouwer EJ (2009) Biodegradation and removal of pharmaceuticals and personal care products in treatment systems: a review. Biodegradation 20:441–466CrossRefGoogle Scholar
  6. 6.
    Lakind JS (2010) The good, the bad, and the volatile: can we have both healthy pools and healthy people? Environ Sci Technol 44:3205–3210CrossRefGoogle Scholar
  7. 7.
    Santos AJ, Miranda MS, Esteves da Silva JCG (2012) The degradation products of UV-filters in aqueous and chlorinated aqueous solutions. Water Res 46:3167–3176CrossRefGoogle Scholar
  8. 8.
    Buth JM, Arnold WA, McNeill K (2007) Unexpected products and reaction mechanisms of the aqueous chlorination of cimetidine. Environ Sci Technol 41:6228–6233CrossRefGoogle Scholar
  9. 9.
    Richardson SD, DeMarini DM, Kogevinas M et al (2010) What’s in the pool? A comprehensive identification of disinfection byproducts and assessment of mutagenicity of chlorinated and brominated swimming pool water. Environ Health Perspect 118:1523–1530CrossRefGoogle Scholar
  10. 10.
    Plewa MJ, Wagner ED, Mitch WA (2011) Comparative mammalian cell cytotoxicity of water concentrates from disinfected recreational pools. Environ Sci Technol 45:4159–4165CrossRefGoogle Scholar
  11. 11.
    Barbot E, Moulin P (2008) Swimming pool water treatment by ultrafiltration-adsorption process. J Membr Sci 314:50–57CrossRefGoogle Scholar
  12. 12.
    Anipsitakis GP, Tufano TP, Dionysiou DD (2008) Chemical and microbial decontamination of pool water using activated potassium peroxymonosulfate. Water Res 42:2899–2910CrossRefGoogle Scholar
  13. 13.
    Bond T, Goslan EH, Parsons SA, Jefferson B (2012) A critical review of trihalomethane and haloacetic acid formation from natural organic matter surrogates. Environ Technol Rev 1:93–113CrossRefGoogle Scholar
  14. 14.
    Li J, Blatchley ER III (2007) Volatile disinfection byproduct formation resulting from chlorination of organic-nitrogen precursors in swimming pools. Environ Sci Technol 41:6732–6739CrossRefGoogle Scholar
  15. 15.
    Kanan A, Karanfil T (2011) Formation of disinfection byproducts in indoor swimming pool water: the contribution from filling water natural organic matter and swimmer body fluids. Water Res 45:926–932CrossRefGoogle Scholar
  16. 16.
    Shah AD, Mitch WA (2011) Halonitroalkanes, halonitriles, haloamides, and n-itrosamines: a critical review of nitrogenous disinfection byproduct formation pathways. Environ Sci Technol 46:119–131CrossRefGoogle Scholar
  17. 17.
    Shen R, Andrews SA (2011) Demonstration of 20 pharmaceuticals and personal care products (PPCPs) as nitrosamine precursors during chloramine disinfection. Water Res 45:944–952CrossRefGoogle Scholar
  18. 18.
    Negreira N, Canosa P, Rodriguéz I et al (2008) Study of some UV-filters stability in chlorinated water and identification of halogenated by-products by gas chromatography–mass spectrometry. J Chromatogr A 1178:206–214CrossRefGoogle Scholar
  19. 19.
    Salvador A, Chisvert A (2005) Sunscreen analysis. A critical survey on UV-filters determination. Anal Chim Acta 537:1–14CrossRefGoogle Scholar
  20. 20.
    Duirk SE, Bridenstine DR, Leslie DC (2013) Reaction of benzophenone UV-filters in the presence of aqueous chlorine: kinetics and chloroform formation. Water Res 47:579–587CrossRefGoogle Scholar
  21. 21.
    Sakkas VA, Giokas DL, Lambropoulou DA et al (2003) Aqueous photolysis of the sunscreen agent octyl-dimethyl-p-aminobenzoic acid. Formation of disinfection byproducts in chlorinated swimming pool water. J Chromatogr A 1016:211–222CrossRefGoogle Scholar
  22. 22.
    Negreira N, Rodriguéz I, Rodil R, Cela R (2012) Assessment of benzophenone-4 reactivity with free chlorine by liquid chromatography quadrupole time-of-flight mass spectrometry. Anal Chim Acta 743:101–110CrossRefGoogle Scholar
  23. 23.
    Santos AJ, Crista DMA, Miranda MS et al (2013) Degradation of UV-filters 2-ethylhexyl-4-methoxycinnamate and 4-tert-butyl-4′-methoxydibenzoylmethane in chlorinated water. Environ Chem 10:127–134CrossRefGoogle Scholar
  24. 24.
    Wang W, Qian Y, Boyd JM et al (2013) Halobenzoquinones in swimming pool waters and their formation from personal care products. Environ Sci Technol 47:3275–3282Google Scholar
  25. 25.
    Zhao Y, Qin F, Boyd JM et al (2010) Characterization and determination of chloro- and bromo-benzoquinones as new chlorination disinfection byproducts in drinking water. Anal Chem 82:4599–4605CrossRefGoogle Scholar
  26. 26.
    Canosa P, Rodríguez I, Rubí E et al (2006) Formation of halogenated byproducts of parabens in chlorinated water. Anal Chim Acta 575:106–113CrossRefGoogle Scholar
  27. 27.
    Hrudey SE (2009) Chlorination disinfection by-products, public health risk tradeoffs and me. Water Res 43:2057–2092CrossRefGoogle Scholar
  28. 28.
    Villanueva CM, Cantor KP, Grimalt JO et al (2007) Bladder cancer and exposure to water disinfection byproducts through ingestion, bathing, showering, and swimming in pools. Am J Epidemiol 165:148–156CrossRefGoogle Scholar
  29. 29.
    Kogevinas M, Villanueva CM, Font-Ribera L et al (2010) Genotoxic effects in swimmers exposed to disinfection byproducts in indoor swimming pools. Environ Health Perspect 118:1531–1537CrossRefGoogle Scholar
  30. 30.
    Liviac D, Wagner ED, Mitch WA et al (2010) Genotoxicity of water concentrates from recreational pools after various disinfection methods. Environ Sci Technol 44:3527–3532CrossRefGoogle Scholar
  31. 31.
    Lourencetti C, Grimalt JO, Marco E et al (2012) Trihalomethanes in chlorine and bromine disinfected swimming pools: air-water distributions and human exposure. Environ Int 45:59–67CrossRefGoogle Scholar
  32. 32.
    Gago-Ferrero P, Alonso MB, Bertozzi CP et al (2013) First determination of UV-filters in marine mammals. Octocrylene levels in franciscana dolphins. Environ Sci Technol 47:5619–5625CrossRefGoogle Scholar
  33. 33.
    Díaz-Cruz MS, Llorca M, Barceló D (2008) Organic UV-filters and their photodegradates, metabolites and disinfection byproducts in the aquatic environment. Trends Anal Chem 27:873–887CrossRefGoogle Scholar
  34. 34.
    Subedi B, Du B, Chambliss CK et al (2012) Occurrence of pharmaceuticals and personal care products in German fish tissue: a national study. Environ Sci Technol 46:9047–9054CrossRefGoogle Scholar
  35. 35.
    Nieuwenhuijsen MJ, Martinez D, Grellier J et al (2010) Chlorination disinfection byproducts in drinking water and congenital anomalies: review and meta-analyses. Environ Health Perspect 117:1486–1493CrossRefGoogle Scholar
  36. 36.
    Zwiener C, Richardson SD, de Marini DM et al (2007) Drowning in disinfection byproducts? Assessing swimming pool water. Environ Sci Technol 41:363–372CrossRefGoogle Scholar
  37. 37.
    Xiao F, Zhang X, Zhai H et al (2012) New halogenated disinfection byproducts in swimming pool water and their permeability across skin. Environ Sci Technol 46:7112–7119CrossRefGoogle Scholar

Copyright information

© Springer International Publishing Switzerland 2014

Authors and Affiliations

  • Mariana M. de Oliveira e Sá
    • 1
  • Margarida S. Miranda
    • 1
  • Joaquim C. G. Esteves da Silva
    • 1
    Email author
  1. 1.Department of Chemistry and Biochemistry, Faculty of Sciences, Centro de Investigação em Química (CIQ)University of PortoPortoPortugal

Personalised recommendations