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Odor Events in Surface and Treated Water: The Case of 1,3-Dioxane Related Compounds Jordi Quintana,† Lídia Vegué,† Jordi Martín-Alonso,† Miquel Paraira,† M. Rosa Boleda,*,† and Francesc Ventura‡ †

Aigües de Barcelona, Empresa Metropolitana de Gestió del Cicle Integral de l’Aigua, S.A. General Batet, 1-7, 08028 Barcelona, Spain Institute of Environmental Assessment and Water ResearchSpanish Council for Scientific Research (IDAEA-CSIC), Department of Environmental Chemistry, Jordi Girona 18, 08034 Barcelona, Spain

‡

S Supporting Information *

ABSTRACT: A study has been carried out to identify the origin of the odorous compounds at trace levels detected in surface waters and in Barcelona’s tap water (NE Spain) which caused consumer complaints. The malodorous compounds were 2,5,5-trimethyl-1,3-dioxane (TMD) and 2-ethyl-5,5dimethyl-1,3-dioxane (2EDD) which impart a distinctive sickening or olive-oil odor to drinking water at low ng/L levels. Flavor profile analysis (FPA) or threshold odor number (TON) were used for organoleptic purposes. Levels up to 749 ng/L for TMD and 658 ng/L for 2EDD were measured at the entrance of the drinking water treatment plant. Three wastewater treatment plants (WWTPs) using industrial byproducts coming from resin manufacturing plants to promote codigestion were found to be the origin of the event. Corrective measures were applied, including the prohibition to use these byproducts for codigestion in the WWTPs involved. A similar event was already recorded in the same area 20 years ago.

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INTRODUCTION Water safety and quality are basic requirements of water utility companies. One of the most frequent consumer complaints is related to taste and odor problems in tap water because it is perceived as hazardous for human consumption. The worldwide primary cause of these episodes in waters are mainly related to metabolites released from algal blooms.1 Geosmin and 2-methy-isoborneol (MIB) imparting earthy and musty odors to water are among the most cited compounds in the literature causing off-flavors.2−4 Apart from compounds of natural origin, disinfection byproducts formed during water treatment processes,5,6 chemicals leached from pipes,7 or industrial and sewage effluents or leachates from poor waste disposals are examples of anthropogenic compounds which can also contribute to many off-flavor episodes.8−10 At present, different analytical techniques such as liquid− liquid extraction (LLE), purge and trap (PT), solid-phase microextraction (SPME), stir-bar sorptive extraction (SBSE), or closed loop stripping analysis (CLSA) coupled to GC-MS instruments have proven to be suitable for the analysis of taste and odor compounds at the ng/L level.11−13 For the study of odor events, water companies usually use the two-of-five test,14 the attribute rating test,15 or the flavor profile analysis (FPA),16,17 among others. The FPA method is widely used as a sensory technique in studying tastes and odors in water, which assesses the overall taste and odor characteristics of the sample when information about the specific compounds that cause the odor is not available. In order to © XXXX American Chemical Society

improve the knowledge about which compounds are responsible for the flavor profile, gas chromatography with olfactometric detection (GC-OD) is needed. This technique combines the odor evaluation of the individual GC peaks eluting from a chromatographic column at an olfactory detector outlet and the chemical identification of the odorous compounds by GC-MS. Applications of the GC-OD technique in solving taste and odor episodes in water have been reported.9,18,19 Since 1977, two groups of chemical compounds, 2-alkyl-5,5dimethyl-1,3-dioxanes and 2-alkyl-4-methyl-1,3-dioxolanes (alkyl chain: R = H to i-C4H9) (see chemical structures and acronyms in Figure S1, Supporting Information) intermittently appear in the literaturemajor incidents in the 1990sas the compounds responsible for bad taste and odor in different aquatic environmental compartments.20−27 These groups of chemical compounds are unintended reaction products present in wastes from resin manufacturing plants that use glycols (i.e., neopentylglycol, polypropylene glycol) as raw material for acidcatalyzed polyesterification processes. Consumer complaints and odor incidents in tap waters noticed in Philadelphia (U.S.A.),28 Barcelona (Spain),11,29 Worcester (U.K.),30 and Buenos Aires (Argentina)31 were caused by 2-ethyl-5,5Received: July 29, 2015 Revised: November 16, 2015 Accepted: November 23, 2015

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DOI: 10.1021/acs.est.5b03409 Environ. Sci. Technol. XXXX, XXX, XXX−XXX

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Environmental Science & Technology

Figure 1. Sources of drinking water of Barcelona city and most important polluting inputs influencing the quality of surface water in the lower course of Llobregat River.

located in the mouth of Llobregat River can be operated during long drought periods, but usually no more than 1% of water is therein produced. In the last section of the Llobregat River, DWTP1 (6 m3/s) located in Sant Joan Despi ́ supplies Barcelona city and DWTP2 (4 m3/s) located in Abrera, preferentially supplies the surrounding areas. The Ter River raw water is transported through a 120 km long pipeline and treated in DWTP3. In general, DWTP1 and DWTP2 supply treated water to the West part of the city, whereas DWTP3 supplies the East part. Since 2012, a 12-km pipe has been able to transport bidirectionally 4 m3/s between both sources according to the supply needs. Consequently, water from different origins is blended and therefore different tap water qualities can be found in Barcelona. Improvement of Llobregat River Water Quality. Whereas Ter River raw water is only affected by agricultural pollution, Llobregat River is a very stressed river due to densely industrialized and inhabited areas along the banks of the river and the presence of salt mines in its upper course. This salinity confers a characteristic salty taste to its treated water. Llobregat River is a Mediterranean-climate river where flows are very irregular, and the water availability and demand are out-ofphase. DWTP1 and DWTP2 are extremely exposed to human and industrial activities, being the Anoia River and Rubi ́ stream, both tributaries of the Llobregat River, the two main spots of industrial pollution contribution. In 1960s and 1970s, to improve the quality of the surface water at the collection point

dimethyl-1,3-dioxane (2EDD) and/or 2-ethyl-4-methyl-1,3dioxolane (2E4MDL). Sickening, latex paint, varnish, olive oil, sweet fruity or green apple are among the descriptors used by panelists to describe the incidents involving 2EDD and 2E4MDL with threshold odors established in 5−10 ng/L for both compounds.28,32 Table S1 (see Supporting Information, SI) chronologically summarizes the different incidents caused by 1,3-dioxanes and 1,3-dioxolane derivatives described in the literature. The aim of this study is to investigate the origin of the new series of odor incidents in 2013−2014 in surface and treated water from Barcelona’s drinking water treatment plant (DWTP1) which were primarily assigned to dioxanes and dioxolanes, taking advantage of the knowledge of the events happening in 1993.

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EXPERIMENTAL SECTION A summary of materials, analytical methods (CLSA, TON, FPA), and instruments used (GC-MS, GC-OD) are provided in the SI. Site Description. Description of the Llobregat Basin. The Llobregat and Ter rivers (see Figure 1), situated in the south and north of the city of Barcelona (NE Spain), respectively, supply most of Barcelona (51.5% and 40%, respectively) and surrounding areas (2.9 million inhabitants) with drinking water. Groundwater of Llobregat and Besòs rivers (7% and 0.5%, respectively) are also used. A desalination plant (1.90 m3/s) B


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sand, predisinfection with chlorine dioxide is followed by coagulation and sedimentation, and the clarified water is driven by gravity through the open sand filters. The groundwater from the aquifer of the Llobregat River is then incorporated at the sand filters output. At this point, the water production is split into a conventional refining treatment including ozonization followed by filtering through granular activated carbon (GAC), and an advanced treatment using membrane technology. In the advanced process, the blended groundwater and sand filtered water flow to several chambers where the ultrafiltration (UF) membrane equipment is placed. Following the UF, the water is disinfected with ultraviolet radiation and pumped to reverse osmosis (RO) racks. The water produced by this path needs to be remineralized with calcium carbonate. Both conventional and advanced treatments of produced water are blended in a chamber where a final disinfection using chlorine is performed. The usual percentage of advanced treatment using membrane technology is the 40−50% of final treated water. Wastewater Treatments Plants in the Llobregat River. Several wastewater treatment plants are located in the last 100 km of the Llobregat River, some of them close to DWTP1 (see Figure 1 and Scheme 1). Several effluents with minor industrial pollution impact dump directly into the river. However, the most polluted effluents (WWTP1, WWTP2, and WWTP3) lead to water diversion systems built to preserve the quality of surface water collection of DWTP1. These WWTPs are equipped with fundamental treatment processes such as mechanical pretreatment with coarse particle screening, an aerated grit-removal tank, a primary clarifier and a biological treatment stage with activated sludge. All of them have secondary treatment which includes nitrogen removal and, in most cases, phosphorus removal (except WWTP2). WWTP1 is the greatest one, and it is designed to serve 375 000 population equivalents and treat an influent flow of 0.74 m3/s (Scheme 2). Additionally, only WWTP1 has a tertiary treatment to improve the quality of effluent water which consists in a flocculation tank proximal to sand filters. In some of them (WWTP1, WWTP3, and WWTP5), the sludge is treated to obtain biogas to be used in power cogeneration plants in order to take profit of the sludge waste, to generate energy from a renewable source, to recycle biodegradable organic residues, and to diminish the environmental impact of methane emissions, thus reducing the energy needs of WWTPs to a more sustainable value. To promote a better yield in methane production,

of DWTP1, especially in drought periods or because industrial spills, both tributaries were diverted (90%). Several bypass channel systems parallel to the Llobregat River were constructed, and agricultural channel systems were also used to collect the surface water of these two tributaries. In 1980s and 1990s, industrial and urban effluents were connected to the WWTPs systems (Scheme 1). These protection systems do not Scheme 1. Sampling Points along the Final Course of the Llobregat Rivera

a

Sampling points from 1 to 5 correspond to surface water. Sampling points from 6 to 9 correspond to bypass pollution system. Sampling points from 10 to 15 correspond to effluents and influents of WWTPs.

always work properly, either because of rain episodes or because of unsuitable maintenance, causing a severe drop in water quality in the surface water entering the DWTP1. Description of DWTP1 Process. In order to reduce the level of organic and inorganic precursors of disinfection byproducts as well as to reduce the salt content of the raw water, several improvements have been applied in DWTP1 in recent times (see Scheme S1). After an initial removal of gravel and coarse Scheme 2. Diagram of WWTP1 Treatmenta

a

Solid line denotes the water treatment. Broken line denotes the sludge treatment. Bold line denotes the pathway of dioxane compounds which origin is the industrial byproducts for co-digestion process. C


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respectively, which odors were similar and in agreement with the whole odor of the samples and described as dioxane-like odor by most veteran analysts. Even though it is known that sample preconcentration can modify the odor’s perception in FPA of water samples, in our case the same odor descriptor was obtained in water samples and OD analysis of CLSA extracts. The same CLSA extracts were then injected into a GC/MS to obtain the full spectrum of each odorous compound (see Figure S3, C to F). While the NIST library did not match any result search in agreement with the mass spectra of the compounds of interest, the mass spectra of TMD, 2EDD, 2iPMD, and 2iBMD described in the 1993 episode were concordant with them. No 2-alkyl-4-methyl-1,3-dioxolanes were identified. At that time, standards were not available and were synthesized.11 Now, facing the impossibility of a new and quick synthesis for these four compounds, the old standards were used only for qualitative purposes. They were injected on both GC/FID/OD and GC/MS obtaining the same odor profiles and mass spectra as those found in water samples. Quantifications were calculated by the response factor method by using 1-chlorohexane34 as an internal standard and applying the recovery efficiencies for used CLSA filters.11 Investigation of the Origin of the Odor Events. As described previously, the final course of Llobregat River is plenty of industrial and urban wastewater infrastructures with countless interconnections between them. A simplified scheme is depicted in Scheme 1 showing the most relevant sampling points. Llobregat and Anoia River Samples (Sampling Points 1 to 6). The first sampling campaign was carried out at sampling points 2 and 3 of the Llobregat River (Scheme 1). At sampling point 2, TMD was found with levels up to 204 ng/L, which allowed for us to discard contributions from WWTP 4 and 5, and placed the origin of the problem downstream. At sampling point 3, concentrations of TMD were 666 ng/L. The observed increase of TMD concentration was consistent with a possible overflow from the pipeline (sampling point 9) which collects all the diverted waters of the bypass system (90% Anoia river and 100% Rubi stream) into the river. Later analysis of point 9 confirmed this fact. Lower values were measured for 2iBMD and 2iPMD. During the odor episode, TMD was the main 1,3-dioxane derivative identified with maximum values of 423, 1007, and 738 ng/L, respectively in sampling points 1−3. The second most concentrated compound was 2EDD with levels up to 25, 401, and 658 ng/L for the same sampling points. Lower values (up to 131 ng/L in sampling point 1) were measured for 2iBMD and even lower (≤23 ng/L) for 2iPMD. As odor in sampling point 2 was detected, any of the WWTPs located upstream of this point could be at least partially responsible for the odor event. Because industrial influent of WWTP3 was responsible for the 1993 odor event,11 sampling efforts were focused on the Anoia River (sampling points 5 and 6). While no dioxanes were measured in point 5, WWTP3 effluents were the origin of malodorous compounds detected in point 6 which reached maximum levels up to 447 ng/L, 427 ng/L and 585 ng/L for TMD, 2EDD, and 2iBMD, respectively, thus contributing to the odor event. Pipeline Samples (Sampling Points 7 to 9). Sampling of diverted waters of the Anoia and Rubi bypass system were carried out. A strong odor intensity matched with that described in the DWTP1 being TMD the most intense by far of all 1,3-dioxane derivatives found. Levels up to 5697 ng/L

addition of cosubstrates conveys the production of more gas and, consequently, more electricity at only a marginal additional cost. These cosubstrates can be added at the codigestion process as methanolic or glycolate solutions containing several types of industrial residues in order to allow a better waste management.

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RESULTS AND DISCUSSION Background. In 1993, a resin manufacturing plant polluted the Tordera aquifer (NE Spain) with 1,3-dioxane and 1,3dioxolane derivatives. The aquifer is used as a water supply reserve by several coastal villages. The pollution caused hundreds of consumer complaints for water bad taste and odor (see Figure 1). Several months later, a commercial hazardous waste management facility placed several kilometers upstream of the Barcelona’s DWTP1 which is located in the Llobregat River (different catchment) accepted several tanks loads of the above-mentioned resin from the manufacturing plant containing mostly byproducts of the process. The treatment carried out in the waste management facility was not able to remove the problematic compounds but the treated wastewater was discharged directly to the Llobregat River which was subsequently polluted with the malodorous components and caused a shutdown of the DWTP1 with maximum measured levels at its entrance of 312 ng/L for 2EDD. This error of procedure was similar to that incident reported in Philadelphia’s tap water.28 Barcelona’s DWTP was unable to remove efficiently these compounds and peak values of 49 ng/L of 2EDD in treated water were measured.11 Description of the Odor Event. Table S2 displays the timeline of the event. On October 3rd and 4th, 2013, a rising number of customers complained about the bad odor of their tap water, mainly drinking water coming from the DWTP1 area of influence. Customers described the odor as sweet solvent or nail polish, whereas trained panelists in DWTP1 defined it as dioxane-like odor. The TON analysis of the odor profile along the plant process showed the presence of an intense odor in raw water and in the sand filtration step, lower intense odor in the ozonization and GAC filter steps, whereas no odor was noticed neither in the advanced treatment (UF+RO) steps nor in the groundwater. This coincides with the documented substantial reduction of concentrations of potent odorous compounds in full-scale treatment plants by RO treatment. Average rejections of 90%, 95% and 86% for MIB, geosmin and 2,4,6-trichloroanisole, respectively by RO membranes have been reported.33 Finally, blended water from conventional and advanced treatments presented a low intensity odor as well as in the genuine distributed water leading to the DWTP1 shutdown. From this moment, use of surface water was avoided, and groundwater was exclusively used as raw water (see Scheme S1) after ensuring its good organoleptic quality. TON analyses of groundwater before and after GAC filtration were performed. Unfortunately, the odor remained intense in the groundwater treated water because desorption of odorous compounds from GAC occurred. New GAC filters were installed to replace the old ones containing the adsorbed odorous compounds to avoid undesired desorptions and to restore the production of drinking water as soon as possible. Identification of Compounds Responsible of the Events. CLSA extracts were injected into the GC/FID/OD to identify the compounds that could be responsible of the odor. Analysts identified by sniffing four peaks (see Figure S2, peaks 1−4) at retention times of 13.4, 16.7, 18.8, and 19.0 min, D


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Figure 2. F-EEM fluorescence spectra for sampling points 2, 9, and 3 during the second week (parts A, B, and C, respectively) and during the 20th week (parts D, E, and F, respectively) at the same sampling points.

were measured for TMD and up to 1040 ng/L for 2EDD both in sampling point 8 (Table S3 and Scheme 1). Less concentrated and positive samples were observed for 2iPMD and 2iBMD, whereas no 1,3-dioxolane derivatives were found. Effluents of Wastewater Samples (Sampling Points 10 to 14). Five wastewater effluents were monitored. Analysis of WWTP1 effluents (sampling point 14), the closest to DWTP1, presented the strongest odor intensities. Levels up to 1757 ng/ L and 837 ng/L for TMD and 2EDD, respectively, were measured. Again, no 1,3-dioxolane derivatives were found. Moreover, the GC/FID/OD chromatographic profiles obtained from sampling points 9 and 14 were very similar (see Figure S2, C), TMD being the main compound. Taking into account

these results, we hypothesized that the focus of the episode was placed in the WWTP1 process, where industrial byproducts were used in the codigestion of sludge in order to increase the production of biogas and improve the efficiency of the sludge treatment process (Scheme 2). To confirm that these industrial byproducts used in the codigestion process were the origin of the contamination, influent and effluent water samples (sampling points 15 and 14 respectively) were analyzed along the WWTP1. Concentrations of all the dioxanes analyzed were lower in effluents than in influents except for TMD, so contamination was located inside the WWTP1. TMD was only found once in influents at a very low concentration, but it always appeared at high concenE


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to poor infrastructure maintenance of the retaining wall at the beginning of pipeline (sampling point 9), a significant fraction of the effluent overflowed to the surface water of Llobregat River upstream of DWTP1. A request to the authorities to repair the retaining wall and to prevent this undesirable overflow was made. Once repaired (week 16, Table S3) concentrations of odorous compounds in the WWTP1 effluent decreased to 35 ng/L for TMD, the sole dioxane compound being identified. As a result, the quality of the surface wàter at the catchment of DWTP1 improved considerably. The influence of the WWTP1 effluent over the quality of surface water, as well as the presence of dioxane related compounds, disappeared when the retaining wall was repaired. Complementary qualitative analyses of dissolved organic matter (DOM) by fluorescence excitation−emission matrix spectroscopy (F-EEM) were performed upstream and downstream of the point of overflow as well as at the point of discharge of this pipe (sampling points 2, 3, and 9, respectively) at the beginning and at the end of odor episode (weeks 2 and 20) (Figure 2). In the first episode, fluorescence spectra of river sampling point 3 was very similar to the discharge point of the pipe (sampling point 9)a lower intensity is caused by a dilution effect of the river flow. This result demonstrated an important overflow from sampling point 8 (Scheme 1) to the Llobregat River before sampling point 3. However, in the second episode, fluorescence spectra of sampling points 2 and 3 are very similar, thus proving an absence of overflow from sampling point 8. According to the regions description of DOM,36 increments of 32% in fulvic acid-like region, 289% in soluble microbial byproduct-like region and 215% in the humic acid-like region in the sampling point 3 respect the sampling point 2 were observed during the second week, whereas both spectra were quite similar in the same regions at the same sampling points in the 20th week. As soon as analysts did not detect any odor by the FPA, the DWTP1 began to treat the surface water again. Previously, all GAC filters were changed to new ones to improve the elimination efficiency of dioxanes during treatment and to avoid undesired desorptions in used GAC filters. Environmental Implications. It has been proven that alkyl-1,3-dioxane compounds are present in the effluents of some WWTPs and introduced in the sludge treatment via a codigestion process. The presence of these compounds in the surface water can occur due to a poor maintenance of the wastewater system collection. The river dilution may not be enough to reduce the analytical concentrations of these compounds to not detected levels by FPA. Although these compounds are not legislated as contaminants in any directive water framework, their presence and their organoleptic properties challenge drinking water treatment. Advanced treatment with ultrafiltration and reverse osmosis membranes allowed alkyl-1,3-dioxane compound removal from treated water. Conventional treatment with ozonation and GAC process can also remove these compounds, but a good management of these filters is needed to improve the efficiency of elimination.

trations in effluents. Qualitative analysis of some batches of these industrial byproducts were carried out by LLE-GC-MS (results not shown) arising a single peak of TMD, this result being consistent with the effluent analysis of WWTP1, where TMD was always the main compound. Focusing attention in the chromatographic profiles, TMD is always the main compound in effluent profiles but seldom in influents. Industrial byproducts containing dioxane residues are added in the codigestion step. Then, the sludge digested is dehydrated to obtain a minimum volume for solid disposal. The purge of sludge dehydration is incorporated into the wastewater treatment process before the biological step for its further treatment as wastewater (Scheme 2). Once it was proven that the origin of dioxanes in the DWTP1 catchment was due to the byproducts added in the codigestion process in WWTP1, this type of industrial residue was banned for this purpose (from the ninth week onward) and it was mandatory to use only certified dioxane-free industrial residues. A similar incident was recorded in Germany (Stepien et al.)35 when 1,4-dioxane was present in methanol industrial byproducts used in the postanoxic denitrification step. In that case the management of WWTP forced the companies who supplied these residues to remove the 1,4-dioxane by stripping. However, in our case, effluent samples from WWTP1 still presented odor problems due to the time residence of compounds in the digester, which was expected to be approximately one month. This fact explains why the concentrations of dioxanes dropped very slowly during that period (from the 10th to the 22nd week, Table S3). Although the concentration of dioxanes decreased progressively in the WWTP1 effluent, the odor detection still remained in the catchment of DWTP1. A new sampling campaign was done involving all WWTPs. Effluents of WWTP2 and WWTP4 were dioxane-free; however, TMD reached levels up to 12 216 ng/L and 7715 ng/L in WWTP5 and WWTP3 effluents. The second most concentrated compound was 2EDD, with maximum levels of 587 ng/L and 792 ng/L in WWTP5 and WWTP3 effluents, respectively. Both WWTPs used the same cogeneration process as WWTP1 and the same industrial residues. As WWTP1, the same policy of dioxane-free industrial residues was applied for those facilities. Their effluents were monitored regularly but their levels dropped slowly because the regeneration of sewage sludge was elapsed between 30 and 40 days, depending on the capacity of the digesters. The odor event detected in the catchment of DWTP1 was attributed to a unique operating problem in the codigestion process of several WWTPs located in the last course of the Llobregat River. Table S3 displays both the concentration levels and odor intensities in all sampling points along the 24 weeks of monitoring until the end of event. According to Table S3, TMD is the compound that shows the highest values of concentration in most of samples. Likewise, it is the compound to which panelists attributed the highest odor intensities. Therefore, TMD is the compound that contributes the most to this odor episode. Effluents from WWTP1 pour into pipe (sampling points 7 and 8 in Scheme 1) together with other sewer pipes which are collected in a pool prior to be discharged downstream of DWTP1 by another pipeline (sampling point 9). However, the results of the overall sampling showed a contamination of catchment water in DWTP1 as a result of unexpected presence of compounds from the WWTP1 effluent. At that time and due

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ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.est.5b03409. F


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(15) Dietrich, A. M.; Whelton, A. J.; Hoehn, R. C.; Anderson, R.; Wille, M. The attribute rating test for sensory analysis. Water Sci. Technol. 2004, 49, 61−68. (16) APHA; ASSA; WEF, Section 2170: Section 2170: Flavor Profile Analysis. In Standard Methods for the Examination of Water and Wastewater, 20th ed.; Washington DC, 1998. (17) Suffet, I. H.; Brady, B. M.; Bartels, J. H. M.; Burlingame, G.; Malleviale, J.; Yohe, T. Development of the flavor profile analysis method into a standard method for sensory analysis of water. Water Sci. Technol. 1988, 20, 1−9. (18) Benanou, D.; Acobas, F.; de Roubin, M. R.; David, F.; Sandra, P. Analysis of off-flavors in the aquatic environment by stir bar sorptive extraction-thermal desortion-capillary GC/MS/olfactometry. Anal. Bioanal. Chem. 2003, 376, 69−77. (19) Hochereau, C.; Bruchet, A. Design and application of GC-sniff/ MS system for solving taste and odour episodes in drinking water. Water Sci. Technol. 2004, 49, 81−88. (20) Loy Jr, E. W.; Brown, D. W.; Myron Stephenson, J. H.; Little, J. A., Use of wastewater discharge compliance monitoring data. In Identification and Analysis of Organic Pollutants in Water; Keith, L. H., Ed.; Ann Arbor Science Publishing: Ann Arbor, MI, 1977; pp 499− 516. (21) Mantica, E.; Botta, D.; Castellani Pirri, L., Pollution conditions of the aquifer beneath a plant producing alkyd resins. In Organic Micropollutants in the Aquatic Environment; Bjorseth, A., Angeletti, G., Eds.; D. Reidel Publish. Co.: Dordrecht (Holland), 1986, pp 89−106. (22) Bruchet, A.; Khiari, D. In Advances in Taste and Odor Treatment Control; AWWA Research Foundation and Lyonnaise des Eaux; Denver, CO. 1995, 321−349. (23) Gittelman, T. S.; Luitweiler, P.; Staudte, P. B. Tastes and odors in treated water from algae, urea and industrial chemicals in source waters. Proceedings of the AWWA Water Quality Technology Conference, Boston, MA, 1996. (24) Botta, D.; Dancelli, E.; Mantica, E. A case history of contamination by polychloro-1,3-butadiene congeners. Environ. Sci. Technol. 1996, 30 (2), 453−462. (25) Noblet, J.; Schweitzer, L.; Ibrahim, E.; Stolzenbach, K. D.; Zhou, L.; Suffet, I. H. Evaluation of a taste and odor incident on the Ohio River. Water Sci. Technol. 1999, 40 (6), 185−193. (26) Schweitzer, L.; Noblet, J.; Ye, Q.; Ruth, E.; Suffet, I. H. The environmental fate and mechanism of formation of 2-ethyl-5,5dimethyl-1,3-dioxane (2EDD). A malodorous contaminant in drinking water. Water Sci. Technol. 1999, 40 (6), 217−224. (27) Franchini, M.; Marton, D.; Tapparo, A. Headspace gas chromatographic determination of 2-alkyl-5,5-dimethyl-1,3-dioxane derivatives in wastewaters of a polyester resin plant. Analyst 2001, 126 (4), 469−471. (28) Preti, G.; Gittelman, T. S.; Staudte, P. B.; Luitweiler, P. Letting the Nose Lead the Way Malodorous Components in Drinking Water. Anal. Chem. 1993, 65 (15), 699A−702A. (29) Ventura, F.; Matia, L.; Romero, J.; Boleda, M. R.; Martí, I.; Martín, J. Taste and odor events in Barcelona’s water supply. Water Sci. Technol. 1995, 31 (11), 63−68. (30) Fowle, S. E.; Constantine, C. E.; Fone, D.; McCloskey, B. An epidemiological study after a water contamination incident near Worcester, England in April 1994. Journal of Epidemiology and Community Health (1979-) 1996, 50 (1), 18−23. (31) Bruchet, A.; Hochereau, C.; Campos, C. An acute taste and odour episode solved by olfactory GC-MS. Water Sci. Technol. 2007, 55 (5), 223−230. (32) Schweitzer, L.; Noblet, J.; Ruth, E.; Suffet, I. H. The formation, stability, and odor characterization of 2-ethyl-4-methyl-1,3-dioxolane (2-EMD). Water Sci. Technol. 1999, 40 (6), 293−298. (33) Agus, E.; Lim, M. H.; Zhang, L.; Sedlak, D. L. Odorous Compounds in Municipal Wastewater Effluent and Potable Water Reuse Systems. Environ. Sci. Technol. 2011, 45 (21), 9347−9355. (34) Romero, J.; Manero, I.; Laso, J. Validation of Geosmin and 2Methyl-i-Borneol Analysis by CLSA-GC-FID Method to Obtain ISO17025 Accreditation. J. Chromatogr. Sci. 2007, 45 (7), 439−446.

Tables S1−S3, Scheme S2, and Figures S1−S3, together with analytical methods and instrumentation used (PDF)

AUTHOR INFORMATION

Corresponding Author

*Phone: +34 933422635; fax: +34 933422666; e-mail: [email protected] (M.R.B.). Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS We are grateful to colleagues of Water Quality Management Division (J. M. Agulló, M. Ganzer), panelists and sampling team (A. Cabeza), and co-workers of Analytical Organic Chemistry Department (S. Cruz and G. Carrera).

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REFERENCES

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Environmental Science & Technology (35) Stepien, D. K.; Diehl, P.; Helm, J.; Thoms, A.; Püttmann, W. Fate of 1,4-dioxane in the aquatic environment: From sewage to drinking water. Water Res. 2014, 48 (0), 406−419. (36) Chen, W.; Westerhoff, P.; Leenheer, J. A.; Booksh, K. Fluorescence Excitation−Emission Matrix Regional Integration to Quantify Spectra for Dissolved Organic Matter. Environ. Sci. Technol. 2003, 37 (24), 5701−5710.

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