Release of nitrosamines and nitrosamines precursors from scrap tires

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Release of nitrosamines and nitrosamines precursors from scrap tires Wilson Beita-Sandí, Meric Selbes, Mahmut Selim ERSAN, and Tanju Karanfil Environ. Sci. Technol. Lett., Just Accepted Manuscript • DOI: 10.1021/acs.estlett.9b00172 • Publication Date (Web): 20 Mar 2019 Downloaded from http://pubs.acs.org on March 21, 2019

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Environmental Science & Technology Letters

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Release of Nitrosamines and Nitrosamines Precursors from Scrap Tires

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Wilson Beita–Sandí§, †, *, Meric Selbes¥, Mahmut S. Ersan§, ⊥ and Tanju Karanfil§

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§Department

of Environmental Engineering and Earth Sciences, Clemson University, Anderson,

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SC 29625, United States †Research

Center of Environmental Pollution (CICA), University of Costa Rica, 2060 San José,

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Costa Rica

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¥Hazen ⊥Water

and Sawyer, Fairfax, VA 22030, United States

Quality Research and Development Division, Southern Nevada Water Authority, Las Vegas, NV 89193, United States

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*Corresponding author:

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Email: [email protected] Phone: +506.2511.8204

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ACS Paragon Plus Environment


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Abstract

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Materials used during manufacturing of tires can be a source of nitrosamines and/or their

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precursors. Here, we examined the leaching of nitrosamines and nitrosamine precursors from scrap

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tires under different test conditions. Tire chips of different sizes and crumb rubber were exposed

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to leaching solutions with pH values ranging from 4.0 to 10.0. Leachate collected from tires were

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analyzed for nitrosamines. Leachates were oxidized with chloramine, ozone or ozone followed by

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chloramine to quantify the amount of nitrosamine precursors. While N-nitrosodimethylamine

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(NDMA) and N-nitrosomorpholine (NMOR) constituted more than 90% of nitrosamines, N-

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nitrosodibutylamine (NDBA) and N-nitrosopyrrolidine (NPYR) were also detected in the

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leachates. Chloramination of the leachate was found to form additional NDMA, NMOR and other

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nitrosamines. While ozonation alone did not lead to formation of NDMA or NMOR, lower

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formation of NDMA and NMOR observed when ozonation followed by chloramination as

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compared to only chloramination. This suggests that ozonation reduced the reactivity of

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nitrosamine precursors leaching from scrap tires. Furthermore, leaching of NDMA and NMOR

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precursors were higher at lower pH conditions, which can be attributed to higher solubility of

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protonated amines. From an environmental standpoint, these results suggest that water in contact

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with tire scraps (such as in urban runoff, bed media for ballast water and wastewater treatment,

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ground cover for playgrounds) may potentially contain nitrosamines and nitrosamine precursors,

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and the amount of precursor leaching may change with the size of the tire scraps.

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1. Introduction

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Approximately 290 million scrap tires are generated each year in the United States (US) with about

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10% disposed annually in landfills.1 Disposed tires are a troublesome source of waste in the

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environment due to their non–biodegradable and mixed composition (e.g., carbon black, elastomer

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compounds, steel cord, and several other organic and inorganic constituents).2 One approach to

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deal with the disposal/stockpiling of scrap tires is reusing or recycling them in different

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applications (e.g., replacement for mineral aggregates in manufacturing concrete,3 bed media for

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ballast water and wastewater treatment,4–7 drainage layer in green roofs,8,9 production of activated

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carbon10 and ground cover in playgrounds11). However, the use of scrap tires is of concern because

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they can potentially release toxic substances.12–14

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In this study, we investigated the leaching of nitrosamines and their precursors from scrap tires in

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contact with water. Nitrosamines with near–ubiquitous presence in many environmental matrices

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(e.g., tobacco, personal care products, food) gained significant attention as many of them are

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suspected of being human carcinogens.15–20 Drinking water facilities in the US increased the use

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of chloramination to reduce the formation of trihalomethanes and haloacetic acids; however, one

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unintended consequence of chloramination was the formation of nitrosamines.21 Nitrosamines can

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also formed during ozonation of water.22–25 Furthermore, use of ozone prior to chloramines can

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change the overall reactivity of nitrosamine precursors.23

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The first report of nitrosamines linked to rubber and rubber products was the discovery of both N-

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nitrosodimethylamine (NDMA) and N-nitrosomorpholine (NMOR) in air samples collected in

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rubber and tire manufacturing plants in concentrations up to 1,060 g/m3 and 4,700 g/m3,

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respectively.15,26–28 Both nitrosamines were also detected in the air from the interior of new



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automobiles, with the maximum amount found in the spare tire well area.26 Nitrosamines in the

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rubber industry are formed due to the extensive use of vulcanization agents. 17,27–29

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Additionally, tire wear particles (TWPs) emissions from the friction of tires on the road from

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automobile traffic constitute one of the most relevant sources for both airborne and non–airborne

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rubber emissions.30 Non-airborne emissions make up 90–99.9% of the total TWPs emissions and

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can be found deposited on the road or at the road side.30–32 For a single passenger tire, reported

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estimations of TWPs were in the range of 0.006–0.09 g/km.33 In road runoff, concentrations of

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TWPs may range from 0.3 to 197 mg/L.34 Runoff water contacted with reused/recycled tires or

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surface runoff from the road or road side would likely transport TWPs to surface waters sources,

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leading to its pollution with a wide range of compounds (e.g., polycyclic aromatic hydrocarbons,

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total petroleum hydrocarbons, metals and sulfur).30,35 Also, recent estimates indicate that tire

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materials account for up to 60% of plastics released into the environment.36

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An increase in urbanization will likely increase the reliance of drinking water treatment plants

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(DWTPs) on water sources impacted by anthropogenic activities. Consequently, constituents

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leaching from tires (in use, TWPs, scrap, reused/recycled or stockpiled) can end up in water

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sources, and thus, there is a need for understanding the potential significance and impact of such

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materials on the formation of nitrosamines. The objectives of this paper were to investigate (i) the

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contribution of tire–constituents and (ii) the effects of pH and contact time on the release of

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nitrosamines and nitrosamine precursors. Leaching experiments from scrap tires were followed

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with chloramination, ozonation and ozonation followed by chloramination (commonly used

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oxidants in DWTPs).

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2. Materials and methods


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Leaching experiments. Crumb rubbers (0.141–0.238 cm = 8x14 US mesh) and tire chips

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(i.e., 2.5 cm x 2.5 cm and 10 cm x 5 cm) were rinsed with distilled and deionized water (DDW)

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prior to experiments to remove the apparent dirt, sand, grit and other foreign particles. The

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preparation of the tire material is reported elsewhere.14 Samples of the crumb rubber and tire chips

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of 50 g were placed in amber borosilicate bottles and filled with 1 L of DDW. The bottles were

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tumbled at room temperature (22 C ± 1 C) for 12 h and 24 h. The leaching of nitrosamines and

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their precursors was investigated in at pH 4, 7 and 10. The pH was adjusted using only NaOH or

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HCl ACS grade. Scrap tires were separated from the water using 0.45 mm pre-washed polyether

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sulfonate filter and the leachates were tested for nitrosamines.

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Nitrosamines analysis. Scrap tires leachates were analyzed for the occurrence of N-

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nitrosodibutylamine (NDBA), N-nitrosodiethylamine (NDEA), NDMA, N-nitrosodipropylamine

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(NDPA), N-nitrosomethylethylamine (NMEA), NMOR, N-nitrosopiperidine (NPIP), N-

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nitrosopyrrolidine (NPYR) following the US EPA method 521 with minor modifications.37.

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Formation potential (FP) of leachates were tested during chloramination (NH2Cl), ozonation (O3)

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and ozonation followed by chloramination (O3/NH2Cl). Monochloramine preparation is described

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in Text S1 of the Supporting Information. In the FP tests, pH of leachate samples was adjusted to

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8.0 with 8 mM borate buffer and dosed with 100 mg Cl2/L preformed monochloramine. Ozone

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was generated using a bench–scale ozone generator as described elsewhere.38 Ozonation was

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achieved by adding 1 mg O3/mg dissolved organic carbon (DOC) to water samples buffered at pH

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8.0 (borate buffer, 8 mM) and contacted for 5 min. After that, samples were analyzed for

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nitrosamines (O3 treatment) and chloraminated for measuring nitrosamines FP (O3/NH2Cl

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treatment). While occurrence and O3 treated samples were immediately analyzed for nitrosamines,

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all chloraminated samples were held at room temperature (20–21 C) in the dark for five days. At



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the end of five days, samples were quenched with anhydrous sodium thiosulfate and analyzed for

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nitrosamines. Additional details about DOC, dissolved nitrogen (DN) and other analytical methods

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are provided in Text S3 and Table S2 of the Supporting Information.

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3. Results and Discussion

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Water quality analysis results of the leaching solutions collected at the end of 24 h contact

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time is presented in Table 1. In all of the cases, DOC leaching was higher than the other measured

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parameters including DN, nitrite, nitrate and ammonia. Based on the nitrite, nitrate and ammonia

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concentrations measured in the leachates, dissolved organic nitrogen (DON) concentrations were

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calculated by subtracting ammonia, nitrite and nitrate from DN concentrations. This indicates that

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dominant DN species were nitrogenous organic compounds (i.e., DON). Leaching of DON was

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correlated to nitrosamines formation in some studies.39

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Scrap tires leached NMOR, NDMA, NDPA and NPYR in the crumb rubber but only

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NMOR and NDMA in the tire chips (Table S3). NMOR had the highest concentration among the

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nitrosamines leached from tires. The concentrations of nitrosamines were higher in the crumb

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rubber and decreased with increasing tire size. Some nitrosamines can be formed during the

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vulcanization process of the production of rubber, which includes chemicals such as tetramethyl

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thiuram disulfide, zinc-diethyldithiocarbamate and morpholinomercaptobenzothiazole. For

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instance, NDMA and NMOR were reported in air samples collected from rubber–manufacturing

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plants.26,40,41

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Occurrence of NMOR or NMOR precursors in source waters have only been scarcely

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examined.42,43 Nonetheless, the source of NMOR precursors was not identified in such studies.

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While Glover et al.44 identified that wastewater effluents can be source of NMOR and NMOR

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precursors, there may be other sources. The findings of our work indicate that it is possible that


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NMOR or its precursors can be found in source waters which are not influenced by wastewater

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effluent and that, they can be present in urban runoff water that is in contact with tire rubbers.

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TWPs concentrations in runoff water were reported to be in the range of 0.3–197 mg/L.34 Based

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on these concentrations of TWPs, an approximation of the concentrations of nitrosamines that can

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be found in runoff water indicates that the formation potential of NDMA and NMOR during

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chloramination would be in the range of 3–1850 ng/L depending on the size of the TWPs. In the

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literature, NDMA was detected ranging from 80 to 115 ng/L in urban drainage.42 However,

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additional research is needed to further characterize and quantify the leaching of NDMA and

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NMOR and their precursors from the TWPs.

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Overall, these findings indicate that TWPs could be a potential source of nitrosamines and

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their precursors in runoff water. In addition to the runoff water, crumb rubber and tire chips can

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potentially be a source of nitrosamine and nitrosamine precursors in applications such as, bed

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media for ballast water treatment, bed media for wastewater treatment,4–7 drainage layer in green

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roofs,8,9 and ground cover in playgrounds11. In these applications, water is likely to be in contact

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with crumb rubber or tire chips for a shorter time at a large water to solids ratio. While the release

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of nitrosamines and nitrosamine precursors are likely to be lower, from an environmental

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standpoint, these applications could be a source of nitrosamines and nitrosamine precursor source.

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Leachate samples were oxidized to understand the nitrosamines formation potentials. Table

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2 shows the concentration (nmol/g tire) of the nitrosamines formed after the NH2Cl and ozonation

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O3/NH2Cl treatments. After NH2Cl treatment, NDMA formation from the crumb rubber was the

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highest among the nitrosamines analyzed followed by NMOR. The formation of the rest of

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nitrosamines (i.e., NPIP, NDEA, NPYR, NDBA, NMEA and NDPA) was relatively low. This

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indicates that compounds with pyrrole and pyridine structures also leached from tires. It is not



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surprising to see that higher NDMA and NMOR formation was observed from crumb as the

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concentration of DOC and DN were higher than tire chips.

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The vulcanization of the rubber frequently uses mixtures of accelerators that contain

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secondary amines (e.g., diethyldithiocarbamate).45,46 Thus, it is likely that such amines can lead to

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the formation of nitrosamines following chloramination. Formation of NDMA or NMOR indicates

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that secondary, tertiary or quaternary amines with dimethylamine or morpholine moieties were

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leached from the scrap tires. Rubber seals and gaskets from certain distribution system piping

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materials leached NDMA and its precursors in oxidant–free water and formed more NDMA after

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chloramination.47,48 In those studies, increasing contact times (i.e., stagnation period) with these

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materials resulted in further increases in NDMA levels. NDMA levels resulting from leaching pipe

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materials were within the range of 10–25 ng/L.47

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The order of nitrosamine formation was different when the leachate was O3/NH2Cl treated

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(Table 2). In this case, NMOR formation was the highest in the crumb rubber leachates followed

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by NMDA. Other nitrosamines were ≤ 6.8 nmol/g tire in both treatments. Ozonation of waters

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containing amides can lead to formation of NDMA.22 However, NDMA and NMOR

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concentrations measured after O3 treatment (Table S4) were comparable to the occurrence

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concentrations (Table S3) within the range of analytical error (10–20%). This indicates that

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ozonation did not lead to the formation of additional nitrosamines. After chloramination,

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concentrations of NDMA FP and NMOR FP were 126 and 81 nmol/g tire, respectively. NDMA

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FP decreased to 24 nmol/g tire while NMOR FP formed up to 155 nmol/g tire after O3/NH2Cl

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(Figure 1).

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Hydroxyl radicals formed during ozonation can lead to transformation or removal of

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nitrosamines and their precursors.22,23 In the present study, ozonation was conducted using a single


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O3 dose. Ozone residual or hydroxyl radicals may have been consumed by other organics present

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in the leachate since DOC concentrations were relatively high in these samples (i.e., above 5 mg/L

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as C). Further research is warranted to investigate the effect of ozone on nitrosamines leaching

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from tires. For both crumb rubber and tire chips, NDMA FP after O3 treatment was found lower

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than NH2Cl treatment. This indicates that ozonation transformed some of the NDMA precursors

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into less reactive precursors. Ozonation reduced NDMA formation below 2 nmol/g of tire which

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corresponded to ~98% lower than chloramine FP. On the contrary, NMOR FPs were higher after

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O3/NH2Cl than after NH2Cl treatment. For instance, NMOR FP increased from 81 to 155 nmol/g

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tire, 6.4 to 11.5 nmol/g tire, and 1.7 to 4.3 nmol/g tire for crumb rubber, 2.5 cm x 2.5 cm and 10

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cm x 5 cm, respectively. Ozonation possibly transformed some of the compounds into more

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reactive forms, thus increasing NMOR formation. These results indicated that ozonation

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commonly used at drinking water treatment plants can lead to higher NMOR formation while

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lowering NDMA formation.

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The effects of pH and contact time on the leaching on NDMA precursors were tested.

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Aggregate water quality parameters (i.e., DOC) are presented in Table S5 and NDMA formation

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results are shown in Figure S1. Leaching of NDMA precursors was only 10% higher when the

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contact time was doubled from 12 h to 24 h. Additional experiments with crumb rubber showed

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that NDMA and NMOR continued to leach after three sequential leaching cycles (Figure S2).

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Leaching of organics continued as long as the tires were in contact with water.14 However, leaching

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rate of organics decreased over time which could explain the findings of our study. Leaching of

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NDMA precursors were higher at lower pH conditions (Figure S1). While DN concentrations were

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comparable among the three pH conditions, DOC leaching increased between 20–25% with

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increasing contact time. Leaching of higher NDMA precursors can be potentially explained by the



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structure of amines. Amines can get protonated at pH below its pKa, thus resulting in a cation. In

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general, ionic compounds have a higher solubility than their non-ionic forms.49 In other words, at

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low pH conditions, amine gets protonated and becomes soluble; and at high pH, amines get

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deprotonated their solubility decreases. Given that most amine-based NDMA precursors have pKa

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values between 8 and 11 (e.g., 8.2 for ranitidine, 9.8 for trimethylamine, 10.3 for N,N-dimethyl-

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isopropylamine, 10.6 for DMA)23,50, it is not unexpected to see higher NDMA precursor leach

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under acidic conditions. In our study, increasing NDMA precursor leaching when pH is reduced

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from 7.0 to 4.0 indicates that there may be some other amines in tires that have pKa values within

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this range. Further research is necessary to investigate some of the amines leaching from tires.

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This study showed that organics leaching from tires can lead to formation of nitrosamines

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(especially NDMA and NMOR), and that the amount leached depended on the tire size and

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leaching conditions. Formation of nitrosamines can be higher in drinking water supplies under the

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influence of TWPs. For example, a source water impacted by an urban runoff could potentially

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experience higher NDMA and NMOR formation after a rain event. NDMA, NMOR and NPYR

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were present in a storm water runoff sample collected after a first–flush rain event.51 We previously

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reported that rainwater did not impact the level of NDMA precursors.52 However, these samples

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were collected from mainly rural areas. Further research is necessary to assess the impact of tire

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leachates on drinking water supplies.

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Associated Content

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Supporting Information The Supporting Information is available free of charge on the ACS Publications website at DOI. Texts S1−S3, Figure S1–S2, Tables S1−S5 and supplemental references.

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Table 1. Water quality analysis of scrap tires at the end of 24 h contact time. Parameter

Crumb rubber

2.5 cm x 2.5 cm

10 cm x 5 cm

Ammonia (mg/L as NH4+)

0.13

0.04

0.07

DN (mg/L as N)

1.1

0.5

0.6

DOC (mg/L as C)

21

11

10

DON (mg/L as N)

1.0

0.5

0.5

Nitrate (mg/L as NO3–)

< MRL

< MRL

< MRL

Nitrite (mg/L as NO2–)

< MRL

< MRL

< MRL

1.15

1.01

1.96

0.2412

0.1106

0.1962

SUVA254 (L/mg ∙ m) UV254 Absorbance (cm–1) 369 370 371

Table 2. Nitrosamines formation in scrap tires leachate after NH2Cl and O3/NH2Cl. Experimental conditions: pH = 7.0, contact time = 24 h, [NH2Cl] = 100 mg/L as Cl2. Concentration (nmol/g tire) Nitrosamine NH2Cl O3/NH2Cl Crumb 2.5 cm x 10 cm x 5 Crumb 2.5 cm x 10 cm x 5 rubber 2.5 cm cm rubber 2.5 cm cm NDMA 126 60 66 24 14 24 NMOR 81 6.4 1.7 155 12 4.3 NPIP 6.8 0.5 0.4 3.6 0.3 0.2 NDEA 1.4 0.6 0.5 0.6 0.3 0.3 NPYR 2.0 < MRL < MRL < MRL < MRL < MRL NDBA 1.4 0.7 0.5 1.1 0.5 0.4 NMEA 0.3 0.1 0.7 < MRL < MRL < MRL NDPA 0.1 < MRL < MRL < MRL < MRL < MRL



373 374 375 376 377 378 379 380 381 382 383 384 385 386 387 388 389 390 391 392 393 394

Figure 1. Effect of scrap tire size on the formation of A) NDMA and B) NMOR during leaching experiments in water. Leaching experimental conditions: pH = 7.0, contact time = 24 h.


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Release of nitrosamines and nitrosamines precursors from scrap tires

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