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Photodegradation of the Endocrine-Disrupting Chemical 4-Nonylphenolin Biosolids Applied to Soil

Kang Xia* and Chang Yoon Jeong

Abstract plication of biosolids. 4-Nonylphenol has been fre-quently detected in a wide range of environmental sam-There is increasing concern about the environmental fate and im-ples (Shang et al., 1999; Dachs et al., 1999; Sole et al.,pact of biosolids-associated anthropogenic organic chemicals, among

which 4-nonylphenol (4-NP) is one of the most studied chemicals. 2000; Kolpin et al., 2002; Ferguson et al., 2003). Signifi-This is primarily because 4-NP is an endocrine disruptor and has cant levels (50–200 �g kg�1) of 4-NP have been foundbeen frequently detected in environmental samples. Due to its high in sediments of rivers that receive surface runoff fromhydrophobicity, 4-NP has high affinity for biosolids. Land application biosolids-amended land (Sole et al., 2000). Marcominiof 4-NP–containing biosolids could potentially introduce large quanti- et al. (1989) observed an 80% reduction of 4-NP in theties of this chemical into the environment. A laboratory experiment top 5 cm of soil 30 d after biosolids were spread on thewas conducted to investigate the effect of artificial sunlight on 4-NP

soil surface (13.5 dry Mg ha�1 yr�1). The remaining 4-NPdegradation in biosolids applied to soil. When exposed to artificialin the soil stayed at a fairly constant level (100 �g kg�1)sunlight for 30 d, the top-5-mm layer of biosolids showed a 55%even 320 d after the application. The levels of 4-NP inreduction of 4-NP, while less than 15% of the 4-NP was degradeddeeper soil profiles were not investigated in the studywhen the biosolids were kept in the dark. Our results indicate that

sensitized photolysis reaction plays an important role in reducing the by Marcomini et al. (1989). Vikelsøe et al. (2002) investi-levels of 4-NP in land-applied biosolids. Surface application rather gated 4-NP levels along soil profiles to a depth of 60 cmthan soil incorporation of biosolids could be effective in reducing in a Danish field receiving biosolids application (17 drybiosolids-associated organic chemicals that can be degraded through Mg ha�1 yr�1) for 25 yr. Even six years after ceasingphotolysis reactions. However, the risks of animal ingestion, foliar biosolids application in this field, they found significantdeposition, and runoff should also be evaluated when biosolids are concentrations of 4-NP, ranging from 500 to 5000 �gapplied on the soil surface.

kg�1, along the soil profiles. Those levels exceeded thecurrent recommended Danish soil quality criteria of 10�g kg�1 for 4-NP (Jensen et al., 1997). Different from

The endocrine disruptor 4-NP is one of the major the study by Marcomini et al. (1989) in which biosolidsanaerobic degradation metabolites of nonylphenol were surface-applied, biosolids were incorporated into

polyethoxylates (NPnEOs), nonionic surfactants that soil through conventional cultivation during the applica-are widely used as industrial detergents, emulsifiers, tion in the field investigated by Vikelsøe et al. (2002).wetting agents, and dispersing agents (Maguire, 1999; The plow depth was not noted in the study by VikelsøeThiele et al., 1997). Detailed molecular structures for et al. (2002). None of the above-cited studies attempted4-NP and NPnEOs can be found in a review article by to explore the mechanisms for the transformation ofMaguire (1999). Due to its high hydrophobicity (log 4-NP in soil systems. We hypothesize that biosolids ap-KOW � approximately 4.48, log KOC � approximately plication methods may have a significant impact on the3.97) (Ahel and Giger, 1993; Rolf-Alexander et al., fate of 4-NP in soil.2002), large quantities of 4-NP are found in biosolids, Surface application and soil incorporation are fre-which consist of high levels of organic matter. The levels quently used for biosolids disposal in the United Statesof 4-NP in biosolids were found to be from a few mg (USEPA, 1999). Compared with soil incorporation, bio-kg�1 up to several thousand mg kg�1 (Maguire, 1999; solids are exposed to more sunlight and oxygen whenGuardia et al., 2001; Keller et al., 2003; Xia and Pillar, they are surface-applied. Research (Faust and Holgne,2003). Land application of biosolids is one of the most 1987; Pelizzetti et al., 1989; Ahel et al., 1994) has showncommon ways of biosolids disposal and is expected to that under aerobic conditions 4-NP in natural waterincrease as other disposal options become more expen- degrades rapidly mainly due to sensitized photolysissive or heavily regulated (USEPA, 1999). Given that by dissolved organic matter, while direct photolysis isthe annual production of biosolids in the United States comparatively slow. Sensitized (indirect) photolysis is ais projected to increase sharply to about 47 million Mg transformation of a given xenobiotic compound initi-(50% of which will be land-disposed) within the next ated through light absorption by other chemicals presentdecade (USEPA, 1999), several thousand Mg of 4-NP in the system. Direct photolysis is a process in which acould be released to the environment through land ap- given compound undergoes transformation due to its

absorption of light (Schwarzenbach et al., 1993). It isK. Xia, Department of Crop and Soil Sciences, 3111 Plant Sciences believed that dissolved organic matter–derived organicBuilding, University of Georgia, Athens, GA 30602. C.Y. Jeong, De- peroxy radicals (ROO·) formed in natural water underpartment of Renewable Resources, University of Louisiana, P.O. Box

sunlight can react with 4-NP (Faust and Holgne, 1987;44650, Lafayette, LA 70504. Received 9 Sept. 2003. *Correspondingauthor ([email protected]). Schwarzenbach et al., 1993), a sensitized photolysis reac-

Published in J. Environ. Qual. 33:1568–1574 (2004). ASA, CSSA, SSSA Abbreviations: HPLC, high performance liquid chromatography;

4-NP, 4-nonylphenol; NPnEO, nonylphenol polyethoxylate.677 S. Segoe Rd., Madison, WI 53711 USA

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XIA & JEONG: PHOTODEGRADATION OF ENDOCRINE DISRUPTOR IN SOIL 1569

num foil, were run simultaneously. One-millimeter headspacetion. The half-life of 4-NP in the surface layer of naturalwas kept in each cell and air was pumped at a constant ratewaters was estimated in the range of 0.6 to 29 d (Faustthrough the headspace to maintain aerobic conditions. Theand Holgne, 1987; Ahel et al., 1994). Research by Peliz-outgoing air from each cell was bubbled through a small bottlezetti et al. (1989) demonstrated a complete photocata-containing 10 mL hexane to trap volatilized 4-NP. Every day,lytic degradation of 4-NP within an hour after it was the hexane in each bottle was collected for analysis of 4-NP.

exposed to UV light (wavelength �340 nm) and TiO2 in Ten milliliters of fresh hexane was immediately added intowater. Although research has shown photodegradation each bottle after the collection. Each collected hexane solutionof 4-NP in aqueous systems, no information has been was evaporated to dryness under N2, redissolved in 0.5 mLfound on how sunlight affects the degradation of 4-NP methanol, then analyzed for 4-NP using high performance

liquid chromatography (HPLC). The water contents (10%in biosolids that are applied to soil. Photodegradationweight base) of the samples were monitored by weighing eachmay contribute to the fast reduction of 4-NP observedcell unit daily and kept at their original levels by adding waterby Marcomini et al. (1989) in soils receiving biosolidswhen needed. For comparison, photodegradation of 4-NP inthrough surface application. The objective of the presenta 10-mL solution containing 6.6 mg L�1 4-NP and 5 mg L�1

study was to use laboratory-constructed soil profiles tofulvic acid (International Humic Substances Society Standardinvestigate the potential of 4-NP photodegradation in IS103F) was also investigated under similar experimental con-

biosolids spread on the soil surface, incorporated with ditions as that for biosolids. The carbon concentration in thesoil, and applied below the soil surface. fulvic acid solution was similar to that in typical surface water

(Faust and Holgne, 1987). All experiments were run in trip-licate.Materials and Methods

Biosolids, Compost, and Soil Samples Sample Extraction and CleanupFreshly produced biosolids and compost of biosolids were Before extraction for 4-NP and NPnEOs, solid samples

collected from a wastewater treatment plant located in north- taken from each layer of the cell units were freeze-dried andeastern Kansas. This treatment plant, operated using activated ground to a fine powder. Loss of 4-NP from the samplessludge systems, serves a city with 150 000 people. It also re- did not occur during freeze-drying and grinding. Freeze-driedceives wastewater from several medium-scale industries. The samples (2–5 g) were extracted with hexane and acetone (1:1,wastewater treatment capacity of the plant is approximately volume ratio) on an accelerated solvent extraction system4.5 � 104 m3 d�1 (12 million gallon d�1). The activated sludge (Model 200ASE; Dionex, Sunnyvale, CA) using a single staticis partially dewatered on a belt filter press, producing approxi- cycle (20 min, 100�C, 10 342 kPa [1500 psi]). Water samplesmately 10 000 kg wet biosolids per day. The biosolids produced were extracted for 4-NP with 10 mL hexane using a liquid–are immediately transferred to lagoons and composted for up liquid extraction method. Extracts of solid samples and waterto two months before they are applied on land. The average samples were then evaporated to dryness under N2 (50�C),water contents in the biosolids and compost are 85 and 23%, redissolved in 1 mL methanol, and stored at �10�C until analy-respectively. The biosolids were collected on three different sis. For both solid samples and water samples, 4-tert-butylphe-days and then composited. Compost samples were collected nol, sublimed (Sigma Chemical, St. Louis, MO) and 2,4,6-from different compost lagoons and then composited. Biosolids tribromophenol (Sigma Chemical) were used as surrogateand compost samples were kept frozen until the conduction standard and internal standard, respectively, for quality con-of 4-NP photodegradation experiments. Soil used for this study trol purposes.was a Kennebec silt loam (fine-silty, mixed, mesic CumulicHapludolls), an agricultural soil collected from Manhattan, Analysis of 4-Nonylphenol and Nonylphenol PolyethoxylatesKS. The organic matter content of the soil is 2.8%. The soil by High Performance Liquid Chromatography and Gasconsists of (weight percent) montmorillonite (37%), kaolinite Chromatography–Mass Spectrometry(8%), mica (27%), and montmorillonite-mica (27%).

The concentrations of 4-nonylphenol and NPnEOs wereanalyzed, respectively, via reverse phase and normal phaseExperimental Setup HPLC with a diode array detector (DAD) and a fluorescencedetector (FLD). The presence of 4-NP and NPnEOs (n �Appropriate amounts of biosolids, compost, or biosolids

and soil mix (1:1 weight ratio, equivalent to application of 1–4) in each sample was confirmed using gas chromatographywith mass spectrometry detector (GC–MS). Technical-gradebiosolids at a rate of approximately 120 dry Mg ha�1 to the

top 1 cm of soil) were distributed homogeneously in the cell 4-NP purchased from Sigma Chemical, pure NP1EO andNP2EO purchased from Ehrenstorfer Labs (Augsburg, Ger-shown in Fig. 1. Two types of cells (6- and 11-mm-thick)

were constructed. One cell could hold a sample with a 5-mm many), and Surfonic N-95 donated by Mr. Carter Naylor(Huntsman Corp., Austin, TX) were used as standards. Thethickness and the other could hold a sample with a 10-mm

thickness. The cell loaded with a 5-mm-thick sample was Surfonic N-95, with an average of 9.5 ethoxy units, consistsof a mixture of NPnEOs with n � 2 to 16 (Keller et al., 2003).placed on top of a cell, which was loaded with a 10-mm-thick

sample to form a cell unit. The two cells were pressed together A Hewlett-Packard (Palo Alto, CA) 1050 HPLC equippedwith a DAD and a FLD was used for sample analysis. Injec-by fold-back clips placed along the border of the cells. Each

cell unit was irradiated with the cell containing a 5-mm-thick tions (5 �L) were passed through a 25-�L sample loop. Theanalytical column was kept at 40�C. The DAD was operatedsample facing the light for 0.5 h, 12 h, 4 d, 10 d, 20 d, and

30 d at 25�C in a temperature-controlled growth chamber under the following conditions: signal � 277 nm, bandwidth �40 nm, and reference � 350 nm. Data were collected fromfitted with lamps simulating the September sunlight radiation

(approximately 2 kWh m�2 d�1) as measured in Manhattan, the FLD at excitation � � 230 nm, emission � � 301 nm, andpmtgain � 6. A 124- � 4-mm LiChrospher 100-RP-18e columnKS. A sheet of aluminum foil was attached beneath each cell

unit to avoid irradiation through the bottom plate by scattering with a particle size of 5 �m (Agilent Technologies, SantaClarita, CA) was used for the reverse-phase HPLC. A metha-light. Dark controls, cell units completely wrapped with alumi-

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1570 J. ENVIRON. QUAL., VOL. 33, JULY–AUGUST 2004

Fig. 1. Schematic diagram for the cell used in the photodegradation study (modified from Balmer et al., 2000). Pyrex glass is adequate for ourexperiment in which near-soil-surface sunlight (terrestrial light) (wavelength � 290 nm; Schwarzenbach et al., 1993) is of interest. Pyrex glassdoes not completely block UV light between 290 and 325 nm. It is more transparent to UV light with wavelength � 325 nm than quartz.

nol and water mixture (8:2) was used as the mobile phase at a light exposure and seemed to continue to drop withflow rate of 1.5 mL min�1. Normal phase HPLC used a 4.6- � time. Contrary to what was observed for the top-5-mm100-mm Hypersil APS column (Agilent Technologies) with a layer, the 4-NP concentrations in the bottom-10-mmparticle size of 5 �m. A flow rate of 1.5 mL min�1 was used layer biosolids in the cell units that were exposed tofor the mobile phase (hexane to water to isopropanol ratio �78:2:20, 50:3:47, and 0:3:97 at 0–3, 3–22, and 22–23 min, respec-tively).

A Hewlett-Packard 6890 Series GC–MS was used to con-firm the presence of 4-NP and NPnEOs (n � 1–4) in thebiosolids and water extracts. The GC–MS used a Model 5972quadrupole mass selective detector and was operated in theelectron impact mode using helium as the carrier gas (88.9kPa [12.9 psi]; 1.1 mL min�1). A 30-m � 0.25-mm � 0.25-�mHP-5MS column was used under the following conditions(Marcomini et al., 1989; De Voogt et al., 1997). The initialcolumn temperature was held at 100�C for 0.5 min and thenincreased to 320�C at a rate of 10�C min�1. The temperaturewas finally maintained at 320�C for 5 min. Injections (1 �L)were in the splitless mode with the injector temperature at200�C and interface line temperature at 250�C. Published spec-tra (Stephanou and Ginger, 1982), 4-NP, NP1EO, and NP2EOstandards, and commercial surfactant mixtures were used inthe confirmation of 4-NP and NPnEOs (n � 1–4) in the ex-tractants.

Results and DiscussionThe initial concentrations of 4-NP in the biosolids,

compost, and biosolids and soil (1:1) mixture used forthis experiment were 937, 125, and 430 mg kg�1, respec-tively. Our results suggest that volatilization due to con-tinuous air flow through each cell during the entireexperimental period was insignificant. Figure 2 showsthat when the cell units were kept in the dark for 30 dthe levels of 4-NP decreased slowly, only about 10 to15% of the initial concentrations, in the surface- andbottom-layer biosolids (top 5 mm and bottom 10 mm,

Fig. 2. Concentrations of 4-nonylphenol (4-NP) in biosolids in top-respectively). A rapid decrease was observed for 4-NP5-mm and bottom-10-mm layers exposed (solid circle) and unex-in the top-5-mm layer of biosolids when the cell units posed (solid triangle) to artificial sunlight. The term C/Ci is the

were exposed to artificial sunlight. The 4-NP concentra- concentration ratio of 4-NP at each sampling point to its initial con-centration.tion in this layer dropped about 55% within 30 d of

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light decreased at the same slow rate as that in the tion, 4-NP may be sorbed tightly onto the organic matterin biosolids and, therefore, is less available for micro-biosolids that were not exposed to artificial sunlightorganisms. Our study has shown a Kd value of approxi-(Fig. 2). Similar results were observed for 4-NP in themately 2000 mL g�1 for 4-NP on the biosolids used incompost (Fig. 3). Figure 4 shows that artificial sunlightthis study. Our observed degradation rates of 4-NP inhad no effect on the degradation of the parent com-samples that were not exposed to artificial sunlight werepounds (NPnEOs) of 4-NP in the top-5-mm layer ofmuch slower than what have been presented in severalbiosolids and, therefore, no new 4-NP was formed inrecent studies in which soil samples, soil and uncontami-our samples during the experimental period. Our resultsnated biosolids mixture samples, or marine sedimentare in agreement with the findings from the study con-samples were spiked with 4-NP (Topp and Starratt,ducted by Ahel et al. (1994), in which significant photol-2000; Hesselsøe et al., 2001; Gejlsbjerg et al., 2001; Yingysis reactions were not detected for NPnEOs. The insig-and Kookana, 2003). The 4-NP reductions varying fromnificant photodegradation of NPnEOs may be due to30 to 95% of original levels within the 30-d period weretheir lack of reactivity with dissolved organic matter–observed in these studies. It has been well-documentedderived organic peroxy radicals (ROO·) (Ahel et al.,that faster degradation rate is in general observed for1994).an organic chemical when it is freshly added to a soilPrevious studies have indicated that certain micro-matrix than when it is sequestered in a soil due to pro-organisms could degrade 4-NP in pure culture when 4-NPlonged chemical–soil contact time (aging) (Hatzingerwas the only carbon and energy source (Tanghe et al.,and Alexander, 1995; Kelsey et al., 1997; Alexander,1999; Fujii et al., 2000; Vallini et al., 2001). The half-2000). During the wastewater treatment processes, 4-NPlife of 4-NP in these microbial culture varied from 4 tomolecules may have moved into sites within the biosolids7 d. However, in biosolids the role of microorganismsmatrix (an “aging” process) that are not readily accessedmay not be as significant as in pure culture because ofby microorganisms, resulting in the slower microbialthe large quantities of other available carbon sourcesdegradation observed in our study compared with thatfor microorganisms in biosolids. No information hasobserved in the above-cited experiments, which usedbeen found on whether 4-NP can be cometabolized withfreshly spiked samples.the presence of other available carbon sources. In addi-

Our results suggest that sunlight plays an importantrole in degrading 4-NP in biosolids. The 4-NP degrada-tion rate in the top-5-mm layer of biosolids exposed toartificial sunlight was almost five times as fast as thatin the samples without light exposure. It has been shownthat photolysis depth in soils is only limited to a depthup to 2 mm (Hebert and Miller, 1990) and, therefore,artificial light had almost no impact on 4-NP in thebottom-10-mm layer biosolids. When the biosolids wereincorporated with soil by mixing with soil at 1:1 weightratio, 30% of 4-NP was degraded in the top-5-mm layerwithin 30 d of light exposure (Fig. 5), a rate slower thanthat for the biosolids-only samples (Fig. 2). This mayhave been due to the fact that soil particles blocked someof the light from reaching biosolids particles, resulting inless photolysis reaction for 4-NP in biosolids. Previousresearch has shown sensitized photolysis of 4-NP bydissolved organic matter in natural waters (Faust andHolgne, 1987; Ahel et al., 1994). Our results shown inFig. 6 further prove this reaction. A complete reductionof 4-NP was achieved within 6 d (144 h) in a solutioncontaining 5 mg L�1 fulvic acid when the solution wasexposed to artificial sunlight. Although microbial degra-dation was likely to be retarded due to the strong sorp-tion and “aging” of 4-NP in biosolids, the association of4-NP with organic matter microsites in biosolids mighthave increased the effectiveness of sensitized photolysisreaction when the 4-NP–containing biosolids were ex-posed to light.

Our laboratory study suggests that surface applicationof biosolids on soil could be effective in reducing biosol-

Fig. 3. Concentrations of 4-nonylphenol (4-NP) in compost in top- ids-associated organic chemicals that can be degraded5-mm and bottom-10-mm layers exposed (solid circle) and unex- through photolysis reactions. However, since water isposed (solid triangle) to artificial sunlight. The term C/Ci is the

an important factor for the photolysis reaction, wetconcentration ratio of 4-NP at each sampling point to its initial con-centration. rather than dry biosolids should be applied. Surface-

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Fig. 4. Levels of nonylphenol polyethoxylates (NPnEOs) in the top-5-mm layer of biosolids exposed (open triangle) and unexposed (open circle)to artificial sunlight.

broadcasting on sunny days might be a better approach rapid decrease of 4-NP within 30 d was observed in afield on which biosolids were thinly spread onto thethan broadcasting on overcast days. The results from

the field investigation by Marcomini et al. (1989) sup- surface of the soil at multiple times per year. Sunlightcould rapidly degrade 4-NP before it has a chance toport the conclusion from our laboratory study. An initial

Fig. 5. Concentrations of 4-nonylphenol (4-NP) in soil and biosolids mixture (1:1 weight ratio) in the top-5-mm layer exposed (solid circle) andunexposed (solid triangle) to artificial sunlight. The term C/Ci is the concentration ratio of 4-NP at each sampling point to its initial concentration.

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Fig. 6. Photolysis of 4-nonylphenol (4-NP) in a solution containing fulvic acid at 5 mg L�1. The term C/Ci is the concentration ratio of 4-NP ateach sampling point to its initial concentration.

Hesselsøe, M., D. Jensen, K. Skals, T. Olesen, P. Moldrup, P. Roslev,be incorporated into soil and/or leached down the soilG.K. Mortensen, and K. Henriksen. 2001. Degradation of 4-nonyl-profile. 4-Nonylphenol was observed to be more persis-phenol in homogeneous and nonhomogeneous mixtures of soil and

tent when biosolids were incorporated into soils through sewage sludge. Environ. Sci. Technol. 35:3695–3700.cultivation (Vikelsøe et al., 2002). Jensen, J., H.L. Kristensen, and J.J. Scott-Fordsmand. 1997. Soil qual-

ity criteria for selected compounds. Working Rep. 83. Danish Envi-ron. Protection Agency, Copenhagen.Acknowledgments

Keller, H., K. Xia, and A. Bhandari. 2003. Occurrence and transforma-The experiments of this research were conducted at the tion of estrogenic nonylphenol polyethoxylates and their metabo-

lites in three northeast Kansas wastewater treatment plants. Period.Department of Agronomy at Kansas State University. TheHazard. Toxic Radioactive Waste Manage. 7:203–213.research was financially supported by the Kansas Center for

Kelsey, J.W., B.D. Kottler, and M. Alexander. 1997. Selective chemicalAgricultural Resources and the Environment (KCARE) andextractants to predict bioavailability of soil-aged organic chemicals.the Kansas Agricultural Experiment Station.Environ. Sci. Technol. 31:214–217.

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Xia, K., and G.D. Pillar. 2003. Anthropogenic organic chemicals inResponse, Washington, DC.biosolids from selected wastewater treatment plants in GeorgiaVallini, G., S. Frassinetti, F. D’Andrea, G. Catelani, and M. Agnolucci.and South Carolina. p. 806–809. In K. Hatcher (ed.) Proc. 20032001. Biodegradation of 4-(1-nonyl)phenol by axenic cultures of the Georgia Water Res. Conf. 23–24 Apr. 2003. Univ. of Georgia Press,

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