Study of some UV filters stability in chlorinated water and identification of halogenated by-products by gas chromatography–mass spectrometry

Negreira, Noelia; Canosa, P.; Rodrı́guez, I.; Ramil, M.; Rubí, E.; Cela, R.

doi:10.1016/j.chroma.2007.11.057

Cited by 105 publications

(84 citation statements)

References 29 publications

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“…This compromise the products' efficiency, since the UV-filters lose their photoprotective properties and photodegradation reactions may change their physical properties, namely the maximum absorption wavelength and absorbance coefficient (Díaz-Cruz et al, 2008;Serpone et al, 2002). Considering that these compounds are added to personal care products and applied frequently and in large quantities, it is essential to study their transformation products, since they can accumulate in human skin, posing a threat to human health, and afterwards will end up in the environment (Negreira et al, 2008).…”

Section: Environmental Degradation and Transformation Productsmentioning

confidence: 99%

“…The high sample volumes in this procedure, usually from 100 mL (Goksoyr et al, 2009;Liu et al, 2010) up to 1.0 L (Kameda et al, 2011;Liu et al, 2011) is the main disadvantage of this technique. Because UV-filters are relatively polar, the great majority of authors use intermediate polarity solvents like dichloromethane (DCM) (Goksoyr et al, 2009;Kameda et al, 2011;Lambropoulou et al, 2002;Tashiro and Kameda, 2013) or ethyl acetate (EA) (Arukwe et al, 2012;Balmer et al, 2005;da Silva et al, 2015;Negreira et al, 2008;Poiger et al, 2004) to extract water samples. However, Rodil et al (2012) used a more polar solvent, methanol (MeOH), which is justified by the complex mixture analysed, containing not only very polar UV-filters (like PBSA and BP4), but also other polar compounds like pharmaceuticals and herbicides.…”

Section: Extraction Techniques For Water Analysismentioning

confidence: 99%

“…As a result, the interference of endogenous materials is prevented by increasing the retention times during the reversed-phase chromatographic run (Ho and Ding, 2012). Several reagents have been steadily developed for this purpose, such as N-methyl-N-(trimethylsilyl)trifluoroacetamide (MSTFA) (Jeon et al, 2006;Negreira et al, 2009;Zhang and Lee, 2012a), N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA) (Román et al, 2011;Tarazona et al, 2010) and N-methyl-N-(tert-butyldimethylsilyl)trifluoroacetamide (MTB-STFA) (Negreira et al, 2008). These studies were conducted under high temperatures (60 o C) and for at least 30 min of reaction time.…”

Section: Chromatographic Analysismentioning

confidence: 99%

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Advances in analytical methods and occurrence of organic UV-filters in the environment — A review

Ramos

Homem

Alves

et al. 2015

Science of The Total Environment

262

110

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UV-filters are a group of compounds designed mainly to protect skin against UVA and UVB radiation, but they are also included in plastics, furniture, etc., to protect products from light damage. Their massive use in sunscreens for skin protection has been increasing due to the awareness of the chronic and acute effects of UV radiation. Some organic UV-filters have raised significant concerns in the past few years for their continuous usage, persistent input and potential threat to ecological environment and human health. UV-filters end up is wastewater and because wastewater treatment plants are not efficient in removing them, lipophilic compounds tend to sorb onto sludge and hydrophilics end up in river water, contaminating the existing biota. To better understand the risk associated with UV-filters in the environment a thorough review regarding their physicochemical properties, toxicity and environmental degradation, analytical methods and their occurrence was conducted.Higher UV-filter concentrations were found in rivers, reaching 0.3 mg/L for the most studied family, the benzophenone derivatives. Concentrations in the ng to µg/L range were also detected for the paminobenzoic acid, cinnamate, crylene and benzoyl methane derivatives in lake and sea water.Although at lower levels (few ng/L), UV-filters were also found in tap and groundwater. Swimming pool water is also a sink for UV-filters and its chlorine by-products, at the µg/L range, highlighting the benzophenone and benzimidazole derivatives. Soils and sediments are not frequently studied, but concentrations in the µg/L range have already been found especially for the benzophenone and crylene derivatives. Aquatic biota is frequently studied and UV-filters are found in the ng/g-dw range with higher values for fish and mussels. It has been concluded that more information regarding UVfilter degradation studies both in water and sediments is necessary and environmental occurrences should be monitored more frequently and deeply. SEHSDT -sequential extraction with high-speed dispersion tool; SLE -solid-liquid extraction; SPEsolid-phase extraction; SPF -sun protection factor; SPLE -selective pressurized liquid extraction;SPMDs -semipermeable membrane devices; SPME -solid phase microextraction; TD -thermal desorption; TCE -tetrachloroethylene; THF -tetrahydrofuran; Tl -toluene; UPLC -ultraperformance liquid chromatography; USE -ultrasound extraction; UV -ultraviolet; WTP -water treatment plant; WWTP -wastewater treatment plant 4

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Section: Environmental Degradation and Transformation Productsmentioning

confidence: 99%

Section: Extraction Techniques For Water Analysismentioning

confidence: 99%

Section: Chromatographic Analysismentioning

confidence: 99%

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Advances in analytical methods and occurrence of organic UV-filters in the environment — A review

Ramos

Homem

Alves

et al. 2015

Science of The Total Environment

262

110

View full text Add to dashboard Cite

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“…The formation mechanisms and potential ecological or health risk of DBPs should be paid more attention, which would provide scientific reference for optimizing disinfection operating parameters. The substitution and cleavage of two benzene rings of BP-3 and BP-4 in chlorination disinfection have been reported (Negreira et al, 2008(Negreira et al, , 2012Xiao et al, 2013). Bromoform was found to be generated from BP-3 during the chlorination of seawater swimming pools (Manasfi et al, 2015).…”

Section: Introductionmentioning

confidence: 92%

Transformation pathways and acute toxicity variation of 4-hydroxyl benzophenone in chlorination disinfection process

et al. 2016

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h i g h l i g h t s7 transformation products in 4HB chlorination disinfection system were identified. Transformation pathways of 4HB during chlorination disinfection were proposed. Acute toxicity increased after chlorination due to the formation of 3,5-dichloro-4HB. The transformation mechanisms of 4HB can be repeated in ambient water matrices. a r t i c l e i n f o a b s t r a c tBenzophenones compounds (BPs) are widely used as UV filters, and have been frequently found in multiple environmental matrices. The residual of BPs in water would cause potential threats on ecological safety and human health. Chlorination disinfection is necessary in water treatment process, in which many chemicals remained in water would react with disinfectant chlorine and form toxic byproducts. By using ultra performance liquid phase chromatography quadrupole time of flight mass spectrometer (UPLC-QTOF-MS), nuclear magnetic resonance (NMR), the transformation of 4-hydroxyl benezophenone (4HB) with free available chlorine (FAC) was characterized. Eight major products were detected and seven of them were identified. Transformation pathways of 4HB under acid, neutral, and alkaline conditions were proposed respectively. The transformation mechanisms involved electrophilic chlorine substitution of 4HB, Baeyer-Villiger oxidation of ketones, hydrolysis of esters and oxidative breakage of benzene ring. The orthogonal experiments of pH and dosages of disinfectant chlorine were conducted. The results suggested that pH conditions determined the occurrence of reaction types, and the dosages of disinfectant chlorine affected the extent of reactions. Photobacterium assay demonstrated that acute toxicity had significant increase after chlorination disinfection of 4HB. It was proved that 3,5-dichloro-4HB, one of the major transformation products, was responsible for the increasing acute toxicity after chlorination. It is notable that, 4HB at low level in real ambient water matrices could be transformed during simulated chlorination disinfection practice. Especially, two major products 3-chloro-4HB and 3,5-dichloro-4HB were detected out, implying the potential ecological risk after chlorination disinfection of 4HB.

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“…In particular, BP9 (2,3,4-tri-hydroxyl-BP) had the smallest ATFP (0.04) among all the tested compounds. Considering the possible transformation mechanisms of BP-type UV filters in chlorination treatment, the diphenyl ketone would be oxidized to phenyl benzoate ester, which would be further hydrolyzed to benzoic acid and phenolic derivatives in the chlorination system (Negreira et al, 2008(Negreira et al, , 2012. Onodera and some other researchers have suspected that chlorinated acetic acid and maleic acids are formed from the destruction of the aromatic ring by chlorine in water (Onodera et al, 1984;Norwood et al, 1980).…”

Section: Toxicity With Significant Decreasementioning

confidence: 99%

Acute toxicity formation potential of benzophenone-type UV filters in chlorination disinfection process

Liu

Chen

Wei

et al. 2014

Journal of Environmental Sciences

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a b s t r a c tBenzophenones (BPs) are a class of widely used UV filters, which have been frequently detected within multiple environmental matrices. Disinfection is a necessary process in water treatment processes. The transformation behaviors and toxicity changes of 14 BP-type UV filters during chlorination disinfection treatment were investigated in this study. A new index, the acute toxicity formation potential, was proposed to evaluate the toxicity changes and potential risks of BP-type UV filters during chlorination treatment. It was found that 13 of 14 BP-type UV filters exhibited toxicity decreases in the chlorination disinfection process, more or less, while one showed a toxicity increase. The toxicity changes were dependent on substitution effects, such that 2,4-di-hydroxylated or 3-hydroxylated BPs exhibited significant toxicity decreases after chlorination treatment due to the ready cleavage of the aromatic ring. Importantly, the acute toxicity changes could be duplicated in an ambient water matrix.

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Study of some UV filters stability in chlorinated water and identification of halogenated by-products by gas chromatography–mass spectrometry

Cited by 105 publications

References 29 publications

Advances in analytical methods and occurrence of organic UV-filters in the environment — A review

Advances in analytical methods and occurrence of organic UV-filters in the environment — A review

Transformation pathways and acute toxicity variation of 4-hydroxyl benzophenone in chlorination disinfection process

Acute toxicity formation potential of benzophenone-type UV filters in chlorination disinfection process

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