Advertisement

Identification of 3-(trifluoromethyl)phenol as the malodorous compound in a pollution incident in the water supply in Catalonia (N.E. Spain)

  • Jordi QuintanaEmail author
  • Alejandra Hernández
  • Francesc Ventura
  • Ricard Devesa
  • Maria Rosa Boleda
Research Article
  • 36 Downloads

Abstract

A study of organic compounds that caused a serious taste and odor episode of water supply in two residential areas in Catalonia (N.E. Spain) was carried out. Sweet and paint/solvent odor were the main descriptors used by consumers. Some cases of sickness and nausea were also associated with drinking water consumption by the consumers. Closed-loop stripping analysis (CLSA) combined with sensory gas chromatography and gas chromatography mass spectrometry detection were used to study the problem. As a result, 3-(trifluoromethyl)phenol (CAS number 98-17-9) was for the first time identified as a responsible of an odor incident in drinking water. Concentration levels of this compound were up to 17,000 ng/L in groundwater and up to 600 ng/L in distributed water. Odor threshold in water for 3-(trifluoromethyl)phenol was determined as 13 ng/L (45 °C).

Keywords

3-(trifluoromethyl)anisole Sensory-GC Olfactory detection Bad odor event Water quality CAS 98-17-9 Odor threshold 

Notes

Acknowledgements

We are grateful to Dr. Auguste Bruchet for his explanations about past episodes in France involving fluoro-related compounds and to M.J. Domínguez-Cereijo for the details of the distribution system and sampling coordination. We are also grateful to all our colleagues of the Analytical Organic Chemistry Department for dealing with the daily work and spending time to move forward this study. We would also like to thank you I. Pérez and all the members and volunteers of the panel.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

11356_2019_4635_MOESM1_ESM.docx (93 kb)
ESM 1 (DOCX 93.1 kb)

References

  1. ASTM (2011) E679-04(2011) Standard practice for determination of odor and taste thresholds by a forcedchoice ascending concentration series method of limits, ASTM International, West Conshohocken.  https://doi.org/10.1520/E0679-04R11
  2. Baird RB, Eaton AD, Rice EW (2017) Standard methods for the examination of water and wastewater, 23th edn. Washington DC (USA)Google Scholar
  3. Balci M, Çelik M, Gültekin MS (2006) Methods of molecular transformations. Compounds with two carbonheteroatom bonds. Quinones and heteroatom analogues. Vol 28, In: Griesbeck AG (ed) Houben-Weyl. Science of synthesis. George Thieme Verlag, StuttgartGoogle Scholar
  4. Benanou D, Acobas F, de Roubin MR, David F, Sandra P (2003) Analysis of off-flavors in the aquatic environment by stir bar sorptive extraction–thermal desorption–capillary GC/MS/olfactometry. Anal Bioanal Chem 376:69–77.  https://doi.org/10.1007/s00216-003-1868-3 CrossRefGoogle Scholar
  5. Bentley R (2006) The nose as a stereochemist. Enantiomers and Odor. Chem Rev 106:4099–4112.  https://doi.org/10.1021/cr050049t CrossRefGoogle Scholar
  6. Boleda MR, Diaz A, Martí I, Martin-Alonso J, Matía L, Romero J, Ventura F (2007) A review of taste and odour events in Barcelona’s drinking water area (1990-2004). Water Sci Technol 55:217–221CrossRefGoogle Scholar
  7. Bruchet A (1999) Solved and unsolved cases of taste and odor episodes in the files of inspector Cluzeau. Water Sci Technol 40:15–21.  https://doi.org/10.1016/S0273-1223(99)00532-6 CrossRefGoogle Scholar
  8. Bruchet A, Hochereau C (1999) Solved and unsolved cases of taste and odor episodes in the files of inspector Cluzeau. Water Sci Technol 40:15–21.  https://doi.org/10.1016/S0273-1223(99)00532-6
  9. Capel PD, Giger W, Reichert P, Wanner O (1988) Accidental input of pesticides into the Rhine River. Environ Sci Technol 22:992–997.  https://doi.org/10.1021/es00174a001 CrossRefGoogle Scholar
  10. Crane R, Moore K, Fielding M (1996) Formation and occurrence of bromophenols, iodophenols, bromoanisoles and iodoanisoles in drinking water: an investigation of taste and odour potential. UKWIR report DW-05, UK Water Industry Research Ltd, LondonGoogle Scholar
  11. Curtis RF et al (1972) 2,3,4,6-Tetrachloroanisole association with musty taint in chickens and microbiological formation. Nature 235:223–224CrossRefGoogle Scholar
  12. Czerny M, Brueckner R, Kirchhoff E, Schmitt R, Buettner A (2011) The influence of molecular structure on odor qualities and odor detection thresholds of volatile alkylated phenols. Chem Senses 36:539–553.  https://doi.org/10.1093/chemse/bjr009 CrossRefGoogle Scholar
  13. Devesa R, Cardeñoso R, Matia L, Ventura F, Salvatella N (2004) The panel of Aigües de Barcelona: 15 years of history. Water Sci Technol 49:145–151CrossRefGoogle Scholar
  14. Diaz A, Fabrellas C, Ventura F, Galceran MT (2005) Determination of the odor threshold concentrations of chlorobrominated anisoles in water. J Agric Food Chem 53:383–387.  https://doi.org/10.1021/jf049582k CrossRefGoogle Scholar
  15. Ding JP, Tao ZQ, Fan L, Yang SY (2009) Synthesis and properties of fluorinated biphenyl-type epoxy resin. J Appl Polym Sci 113:1429–1437.  https://doi.org/10.1002/app.29912 CrossRefGoogle Scholar
  16. European Chemicals Agency (2018) Information on chemicals. https://echa.europa.eu/information-on-chemicals. Accessed 2 Apr 2019
  17. Gallagher DL, Phetxumphou K, Smiley E, Dietrich AM (2015) Tale of two isomers: complexities of human odor perception for cis- and trans-4-methylcyclohexane methanol from the chemical spill in West Virginia. Environ Sci Technol 49:1319–1327.  https://doi.org/10.1021/es5049418 CrossRefGoogle Scholar
  18. Guadagni DG, Buttery RG (1978) Odor threshold of 2,3,6-trichloroanisole in water. J Food Sci 43:1346–1347.  https://doi.org/10.1111/j.1365-2621.1978.tb15311.x CrossRefGoogle Scholar
  19. Jáuregui O, Galceran MT (2001) Chapter 6 phenols. In: Kleiböhmer W (ed) Handbook of analytical separations, vol 3. Elsevier Science B.V., Atlanta, pp 175–236.  https://doi.org/10.1016/S1567-7192(01)80009-7
  20. Jin C-l, Zhang Z-h (2010) The improved synthesis of 3-trifluoromethyl phenol. Shandong Chemical Industry 5(22–23):30Google Scholar
  21. Jin J-m, Wang G-l, Shi J-h, Yan W (2007) Preparation advances of trifluoromethyl phenol. Technology & Development of Chemical Industry 2:27–29Google Scholar
  22. Mallevialle J, Suffet IH (1987) Identification and treatment of tastes and odors in drinking water. AWWA Research Foundation, Lyonnaise des eaux, DenverGoogle Scholar
  23. McGuire MJ, Krasner SW, Hwang CJ, Izaguirre G (1981) Closed-loop stripping analysis as a tool for solving taste and odor problems. J Am water Works Assoc. 10:530–537.  https://doi.org/10.1002/j.1551-8833.1981.tb04784.x
  24. McGuire MJ, Suffet IH, Rosen J (2014) Consumer panel estimates of odor thresholds for crude 4-methylcyclohexanemethanol. J Am Water Works Assoc 106:E445–E458CrossRefGoogle Scholar
  25. Montiel A, Rigal S, Welté B (1999) Study of the origin of musty taste in the drinking water supply. Water Sci Technol 40:171–177.  https://doi.org/10.1016/S0273-1223(99)00554-5 CrossRefGoogle Scholar
  26. Moore JW, Ramamoorthy S (1984) Organic chemicals in natural waters: applied monitoring and impact assessment. Springer Verlag, New YorkCrossRefGoogle Scholar
  27. Munch JW (1995) Method 524.2: Measurement of purgeable organic compounds in water by capillary column gas chromatography/mass spectrometry. U.S. Environmental Protection Agency, CincinnatiGoogle Scholar
  28. Piriou P, Devesa R, De Lalande M, Glucina K (2009) European reassessment of MIB and geosmin perception in drinking water. J Water Supply Res Technol AQUA 58:532–538.  https://doi.org/10.2166/aqua.2009.124 CrossRefGoogle Scholar
  29. Quintana J, Vegué L, Martin-Alonso J, Paraira M, Boleda MR, Ventura F (2016) Odor events in surface and treated water: the case of 1,3-dioxane related compounds. Environ Sci Technol 50:62–69.  https://doi.org/10.1021/acs.est.5b03409 CrossRefGoogle Scholar
  30. Siegemund G (2005) Aromatic compounds with fluorinated side-chains. In: Siegemund G, Schwertfeger W, Feiring A, Smart B, Behr F, Vogel H, McKusick B (eds) Ullmann’s encyclopedia of industrial chemistry. Wiley-VCH Verlag GmbH & Co., Zurich.  https://doi.org/10.1002/14356007.a11_349
  31. Suffet IH, Anselme C, Mallevialle J (1995) Advances in taste-and-odor treatment and control. AWWA Research Foundation and Lyonnaise des Eaux, DenverGoogle Scholar
  32. Unger TA (1996) Pesticide synthesis handbook. Noyes Publications, Park RidgeGoogle Scholar
  33. van Gemert LJ (2011) Odour thresholds. Compilation of odour threshold values in air and water, 2nd edn. Oliemans Punter & Partners BV, ZeistGoogle Scholar
  34. Ventura F, Matia L, Romero J, Boleda MR, Martí I, Martín J (1995) Taste and odor events in Barcelona’s water supply. Water Sci Technol 31:63–68CrossRefGoogle Scholar
  35. Ventura F, Romero J, Parés J (1997) Determination of dicyclopentadiene and its derivatives as compounds causing odors in groundwater supplies. Environ Sci Technol 31:2368–2374.  https://doi.org/10.1021/es960987y CrossRefGoogle Scholar
  36. WHO (2011) Guidelines for drinking-water quality, 4th edn. World Health Organization, Geneva http://apps.who.int/iris/bitstream/10665/44584/1/9789241548151_eng.pdf. Accessed 2 Apr 2019Google Scholar
  37. Young WF, Horth H, Crane R, Ogden T, Arnott M (1996) Taste and odour threshold concentrations of potential potable water contaminants. Water Res 30:331–340.  https://doi.org/10.1016/0043-1354(95)00173-5 CrossRefGoogle Scholar
  38. Zhai Y-E, Shi D-Q (2013) Synthesis and herbicidal activity of 2-alkyl(aryl)-4-amino-3-[alkyl(alkoxy)carbonyl]-5-cyano-6-[(3-trifluoromethyl)phenoxy]-pyridines. J Heterocyclic Chem 50:1039–1042.  https://doi.org/10.1002/jhet.1591 Google Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Aigües de BarcelonaEmpresa Metropolitana de Gestió del Cicle Integral de l’Aigua, S.A.BarcelonaSpain
  2. 2.Department of Environmental ChemistryInstitute of Environmental Assessment and Water Research – Spanish Council for Scientific Research (IDAEA-CSICBarcelonaSpain

Personalised recommendations