Skip to main content

Advertisement

Log in

Decontamination of polycyclic aromatic hydrocarbons and nonylphenol from sewage sludge using hydroxypropyl-β-cyclodextrin and evaluation of the toxicity of leachates

  • Research Article
  • Published:
Environmental Science and Pollution Research Aims and scope Submit manuscript

Abstract

A decontamination technique based in cyclodextrin extraction has been developed to eliminate nonylphenol (NP) and 16 polycyclic aromatic hydrocarbons (PAHs; the US Environmental Protection Agency priority pollutants list) from sewage sludge. In a first step, PAHs and NP were characterised in six sludges to determine contamination levels according to limit values proposed by the European Union Sludge Directive draft. There were few variations in the total PAHs content with levels of 1.88 to 3.05 mg kg−1. Three-ring PAHs predominated, but fluoranthene and pyrene were also present. None of the sludge exceeded the PAHs limit proposed by the European Union’s draft Directive. On the contrary, NP content in four of the six sludges was over the recommended limits of 50 mg kg-1 for NP ethoxylates. With the aim of obtaining NP values below the concentration limits proposed to use the sewage sludge as agricultural amendments, a preliminary study using hydroxypropyl-β-cyclodextrin (HPBCD) extractions as a decontamination technique was carried out. About 90 % of NP content was removed with only one extraction with HPBCD, whereas after three sequential extractions using an aqueous solution without HPBCD, the NP extraction percentage was less than 1 %. Simultaneously, PAHs extraction percentages obtained with HPBCD were also much higher than when aqueous solution was used, especially in the case of two- and three-ring PAHs. Finally, the potential environmental hazard of HPBCD leachates to aquatic organisms (Daphnia magna) was tested. These results indicate that the treatment of sewage sludge with cyclodextrin could allow their safe use as fertiliser in agriculture.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  • Abad E, Martínez K, Planas C, Palacios O, Caixach J, Rivera J (2005) Priority organic pollutant assessment of sludges for agricultural purposes. Chemosphere 51:1358–1369

    Article  Google Scholar 

  • Alexander M (2000) Aging, bioavailability, and overestimation of risk from environmental pollutants. Environ Sci Technol 34:4259–4265

    Article  CAS  Google Scholar 

  • Aparicio I, Santos JL, Alonso E (2009) Limitation of the concentration of organic pollutants in sewage sludge for agricultural purposes: a case study in South Spain. Waste Manag 29:1747–1753

    Article  CAS  Google Scholar 

  • ASTM (1999) Standard methods for measuring the toxicity of sediment-associated contaminants with freshwater invertebrates. E 1706-95b. In: Annual book of ASTM standards. ASTM, Philadelphia, pp. 65–68

  • Badr T, Hanna K, de Brauer C (2004) Enhanced solubilization and removal of naphthalene and phenanthrene by cyclodextrins from two contaminated soils. J Hazard Mat B112:215–223

    Article  Google Scholar 

  • Barata C, Alañón P, Gutierrez-Alonso S, Riva MC, Fernández C, Tarazona JV (2008) A Daphnia magna feeding bioassay as a cost effective and ecological relevant sublethal toxicity test for environmental risk assessment of toxic effluents. Sci Tot Environ 405:78–86

    Article  CAS  Google Scholar 

  • Blanchard M, Teil MJ, Ollivon L, Legenti L, Chevreuil M (2004) Polycyclic aromatic hydrocarbons and polychlorobiphenyls in wastewater and sewage sludges from the Paris area (France). Environ Res 95:184–197

    Article  CAS  Google Scholar 

  • Burgess RM, Pelletier MC, Gundersen JL, Perron MM, Ryba SA (2005) Effects of different forms of organic carbon on the partitioning and bioavailability of nonylphenol. Environ Toxicol Chem 24:1609–1617

    Article  CAS  Google Scholar 

  • Campos B, Piña B, Fernández-Sanjuán M, Lacorte S, Barata C (2012) Enhanced offspring production in Daphnia magna clones exposed to serotonin reuptake inhibitors and 4-nonylphenol. Stage- and food-dependent effects. Aquat Toxicol 109:100–110

    Article  CAS  Google Scholar 

  • Céspedes R, Lacorte S, Ginebreda A, Barceló D (2008) Occurrence and fate of alkylphenols and alkylphenol ethoxylates in sewage treatment plants and impact on receiving waters along the Ter River (Catalonia, NE Spain). Environ Pollut 153:384–392

    Article  Google Scholar 

  • Comber MHI, Williams TD, Stewart KM (1993) The effects of nonylphenol on Daphnia magna. Water Res 27:273–276

    Article  CAS  Google Scholar 

  • Dai JY, Xu MQ, Chen JP, Yang XP, Ke ZS (2007) PCDD/F, PAH and heavy metals in the sewage sludge from six wastewater treatment plants in Beijing, China. Chemosphere 66:353–361

    Article  CAS  Google Scholar 

  • European Union (1986) Council Directive 86/278/ECC: protection of the environment, and in particular of the soil, when sewage sludge is used in agriculture. Official Journal L 181:6–12

  • European Union (2000) EC working document on sludge, 3rd draft: 27 April 2000. ENV.E.3/LM, European Union, Brussels, Belgium

  • European Union (2003) Council Directive 2003/53/EC of the European Parliament and the Council of 18 June 2003 amending for the 26th time Council Directive 76/769/EEC relating to restrictions on the marketing and use of certain dangerous substances and preparations (nonylphenol, nonylphenol ethoxylate and cement). Official Journal of the European Union 17.7.2003. L 178/24

  • Fenyvesi E, Gruiz K, Verstichel S, De Wilde B, Leitgib L, Csabai K, Szaniszlo N (2005) Biodegradation of cyclodextrins in soil. Chemosphere 60:1001–1008

    Article  CAS  Google Scholar 

  • Fenyvesi E, Molnár M, Letigib L, Gruiz K (2009) Cyclodextrin-enhanced soil-remediation technologies. Land Contam Reclam 17:585–597

    Article  Google Scholar 

  • Fernández-Sanjuán M, Rigol A, Sahuquillo A, Rodríguez-Cruz S, Lacorte S (2009) Determination of alkylphenols and alkylphenol ethoxylates in sewage sludge: effect of simple pre-treatment. Anal Bioanal Chem 394:1525–1533

    Article  Google Scholar 

  • Ginés JM, Pérez-Martínez JI, Arias MJ, Moyano JR, Morillo E, Ruiz-Conde A, Sánchez-Soto PJ (1996) Inclusión of the herbicide 2,4-dichlorophenoxyacetic acid (2,4-D) with beta-cyclodextrin by different processing methods. Chemosphere 33:321–334

    Article  Google Scholar 

  • Gómez J, Alcantara MT, Pazos M, Sanromán MA (2010) Soil washing using cyclodextrins and their recovery by application of electrochemical technology. Chem Eng J 159:53–57

    Article  Google Scholar 

  • Gómez-Rico MF, Font R, Aracil I, Fullana A (2007) Analysis of organic pollutants in sewage sludges from the Valencian Community (Spain). Environ Contam Toxicol 52:306–316

    Article  Google Scholar 

  • González MM, Martín J, Santos JL, Aparicio I, Alonso E (2010) Occurence and risk assessment of nonylphenol and nonylphenol ethoxylates in sewage sludge from different convencional treatment processes. Sci Total Environ 408:563–570

    Article  Google Scholar 

  • Gould S, Scott R (2005) 2-Hydroxypropyl-β-cyclodextrin (HP-β-CD): a toxicology review. J Food Chem Toxicol 43:1451–1459

    Article  CAS  Google Scholar 

  • Hajdu C, Gruiz K, Fenyvesi E, Nagy ZM (2011) Application of cyclodextrins in environmental bioassays for soil. J Incl Phenom Macrocycl Chem 70:307–313

    Article  CAS  Google Scholar 

  • Hartnik T, Jensen J, Hermens JLM (2008) Nonexhaustive b-cyclodextrin extraction as a chemical tool to estimate bioavailability of hydrophobic pesticides for earthworms. Environ Sci Technol 42:8419–8425

    Article  CAS  Google Scholar 

  • Ifelebuegu AO (2011) The fate and behavior of selected endocrine disrupting chemicals in full scale wastewater and sludge treatment unit processes. Int J Environ Sci Technol 8:245–254

    Article  CAS  Google Scholar 

  • Kawasaki N, Araki M, Nakamura T, Tanada S (2001) Inclusión behavior of 4-nonylphenol into cyclodextrin derivates. J Colloid Interf Sci 238:215–218

    Article  CAS  Google Scholar 

  • Khadhar S, Higashi T, Hamdi H, Matsuyama S, Charef A (2010) Distribution of 16 EPA-priority polycyclic aromatic hydrocarbons (PAHs) in sludges collected from nine Tunisian wastewater treatment plants. J Hazard Mater 183:98–102

    Article  CAS  Google Scholar 

  • Kiss T, Fenyvwsi F, Pasztor N, Feher P, Varadi J, Kocsan R, Szente L, Fenyvesi E, Szabo G, Vecsernyes M, Bacskay I (2007) Cytotoxicity of different types of methylated β-cyclodextrins and ionic derivatives. Pharmazie 62:557–558

    CAS  Google Scholar 

  • Laturnus F, Arnold K, Gron C (2007) Organic contaminants from sewage sludge applied to agricultural soils. Environ Sci Pollut Res 14:53–60

    Article  CAS  Google Scholar 

  • Lian J, Liu JX, Wei YS (2009) Fate of nonylphenol polyethoxylates and their metabolites in four Beijing wastewater treatment plants. Sci Total Environ 407:4261–4268

    Article  CAS  Google Scholar 

  • Martínez E, Gros M, Lacorte S, Barceló D (2004) Simplified procedures for the análisis of polycyclic aromatic hydrocarbons in water, sediments and mussels. J Chromatogr A 1047:181–188

    Google Scholar 

  • McAllister L, Semple KT (2010) Measurement of bioaccesibility of organic pollutants in soil. In: S.P. Cummings (ed) Bioremediation, methods in molecular biology, vol. 599. Humana Press, New York, pp. 1–14

  • Miégle C, Dugay J, Hennion MC (2003) Optimization, validation and comparison of various extraction techniques for the trace determination of polycyclic aromatic hydrocarbons in sewage sludges by liquid chromatography coupled to diode-array and fluorescence detection. J Chromatogr A 995:87–97

    Article  Google Scholar 

  • Minamiyama M, Ochi S, Suzuki Y (2006) Fate of nonylphenol polyethoxylates and nonylphenoxy acetic acids in an anaerobic digestion process for sewage sludge treatment. Water Sci Technol 53:221–226

    Article  CAS  Google Scholar 

  • Morillo E, Maqueda C, Reinoso R, Undabeytia T (2002) Effect of two organic amendements on norflurazone retention and release by soils of different characteristics. Environ Sci Technol 36:4319–4325

    Article  CAS  Google Scholar 

  • Morillo E, Romero AS, Madrid L, Villaverde J, Maqueda C (2008) Characterization and sources of PAHs and potentially toxic metals in urban environments of Seville (South Spain). Water Air Soil Pollut 187:41–51

    Article  CAS  Google Scholar 

  • Morillo E, Sánchez-Trujillo MA, Moyano JR, Villaverde J, Gómez-Pantoja ME, Pérez-Martínez JI (2012) Enhanced solubilization of six PAHs by three synthetic cyclodextrins for remediation applications. Molecular modeling of the inclusion complexes. Plos ONE. doi:10.1371/journal.pone.0044137

    Google Scholar 

  • Navarro A, Endo S, Gocht T, Barth JAC, Lacorte S, Barceló D, Grathwohl P (2009) Sorption of alkylphenols on Ebro River sediments: comparing isotherms with field observations in river water and sediments. Environ Pollut 157:698–703

    Article  CAS  Google Scholar 

  • Olah J, Cserhati T, Szejtli J (1998) β-cyclodextrin enhanced biological detoxification of industrial wastewaters. Water Res 22:1345–1351

    Article  Google Scholar 

  • Oleszczku P (2008) Aplication of hydroxypropyl[β]cyclodextrin to evaluation of polycyclic aromatic hydrocarbon losses during sewage sludges composting. J Environ Sci Health A 43:10–17

    Article  Google Scholar 

  • Oleszczuk P (2007) Changes of polycyclic aromatic hydrocarbons during composting of sewage sludges with different properties and PAHs content. Chemosphere 67:582–591

    Article  CAS  Google Scholar 

  • Oleszczuk P (2009) Application of three methods used for the evaluation of polycyclic aromatic hydrocarbons (PAHs) bioaccesibility for sewage sludge composting. Bioresource Technol 100:413–420

    Article  CAS  Google Scholar 

  • Olmstead AW, LeBlanc GA (2005) Joint action of polycyclic aromatic hydrocarbons: predictive modeling of sublethal toxicity. Aquat Toxicol 75:253–262

    Article  CAS  Google Scholar 

  • Pérez S, Guillamón M, Barceló D (2001) Quantitative analysis of polycyclic aromatic hydrocarbons in sewage sludge from wastewater treatment plants. J Chromatogr A 938:57–65

    Article  Google Scholar 

  • Petitgirard A, Djehiche M, Persello J, Fievet P, Fatin-Roge N (2009) PAH contaminated soil remediation by reusing an aqueous solution of cyclodextrins. Chemosphere 75:714–718

    Article  CAS  Google Scholar 

  • Pousada-Ferradas Y, Seoane-Labandeira S, Mora-Gutierrez A, Nunez-Delgado (2012) A risk of water pollution due to ash-sludge mixtures: column trials. Int J Environ Sci Technol 9:21–29

    Article  CAS  Google Scholar 

  • Rhodes AH, McAllister LE, Semple KT (2010) Linking desorption kinetics to phenanthrene biodegradation in soil. Environ Pollut 158:1348–1353

    Article  CAS  Google Scholar 

  • Semple KT, Doick KJ, Wick LY, Harms H (2007) Microbial interactions with organic contaminants in soil: definitions, processes and measurement. Environ Pollut 150:166–176

    Article  CAS  Google Scholar 

  • Shen RY, Luo YM, Zhang GY, Teng Y, Li ZG, Wu LH (2007) Contamination of PAHs in sludge samples from the Yangtze River delta area. Pedosphere 17:373–382

    Article  CAS  Google Scholar 

  • Soares A, Guieysse B, Jefferson B, Cartmell E, Lester JN (2008) Nonylphenol in the environment: a critical review on occurrence, fate, toxicity and treatment in wastewaters. Environ Int 34:1033–1049

    Article  CAS  Google Scholar 

  • Sun H, Gu X (2005) Comprehensive toxicity study of nonylphenol and short-chain nonylphenol polyethoxylates on Daphnia magna. Bull Environ Contam Toxicol 75:677–683

    Article  CAS  Google Scholar 

  • Villar P, Callejón M, Alonso E, Jiménez JC, Guiraúm A (2006) Temporal evolution of polycyclic aromatic hydrocarbons (PAHs) in sludge from wastewater treatment plants, comparison between PAHs and heavy metals. Chemosphere 64:535–541

    Article  CAS  Google Scholar 

  • Villaverde J (2007) Time-dependent sorption of norflurazon in four different soils: use of β-cyclodextrin solutions for remediation of pesticide-contaminated soils. J Hazard Mater 142:184–190

    Article  CAS  Google Scholar 

  • Villaverde J, Pérez-Martínez JI, Maqueda C, Ginés JM, Morillo E (2005a) Inclusión complexes of alpha- and gamma-cyclodextrins and the herbicide norflurazon: I. Preparation and characterization. II. Enhanced solubilisation and removal from soils. Chemosphere 60:656–664

    Article  CAS  Google Scholar 

  • Villaverde J, Maqueda C, Morillo E (2005b) Improvement of the desorption of the herbicide norflurazon from soils via complexation with β-cyclodextrin. J Agric Food Chem 53:5366–5372

    Article  CAS  Google Scholar 

  • Villaverde J, Posada-Baquero R, Rubio-Bellido M, Láiz L, Sáiz-Jimenez C, Sánchez-Trujillo MA, Morillo E (2012) Enhanced mineralisation of diuron using a cyclodextrin-based bioremediation technology. J Agric Food Chem 60:9941–9947

    Article  CAS  Google Scholar 

  • Wacker Chemie (2103) CawasolW7 HPMaterial Safety data Sheet. http://www.wacker.com/cms/en/productsmarkets/products/product.jsp?product=8971

  • Ying GG (2006) Fate, behavior and effects of surfactants and their degradation products in the environment. Environ Int 32:417–431

    Article  CAS  Google Scholar 

  • Zar JH (1996) Bioestatistical analysis. Bioestatistical analysis. Prentice-Hall, Upper Saddle River

    Google Scholar 

Download references

Acknowledgements

Support from projects CTM2006-04626 and CTM2009-07335, Spanish Ministry of Science and Innovation (co-funded by Fondo Europeo de Desarrollo Regional, FEDER), are greatly appreciated. M.A. Sánchez-Trujillo acknowledges a research contract from Consejo Superior de Investigaciones Científicas (CSIC, JAEPre 0800763) cofinanced by Fondo Social Europeo (FSE).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Esmeralda Morillo.

Additional information

Responsible editor: Philippe Garrigues

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sánchez-Trujillo, M.A., Lacorte, S., Villaverde, J. et al. Decontamination of polycyclic aromatic hydrocarbons and nonylphenol from sewage sludge using hydroxypropyl-β-cyclodextrin and evaluation of the toxicity of leachates. Environ Sci Pollut Res 21, 507–517 (2014). https://doi.org/10.1007/s11356-013-1930-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11356-013-1930-4

Keywords

Navigation