Oxidation of benzophenone-3 in aqueous solution by potassium permanganate: kinetics, degradation products, reaction pathways, and toxicity assessment.
Intermediate products
KMnO4
Mechanisms
Toxicity assessment
UV filters
Journal
Environmental science and pollution research international
ISSN: 1614-7499
Titre abrégé: Environ Sci Pollut Res Int
Pays: Germany
ID NLM: 9441769
Informations de publication
Date de publication:
Jun 2021
Jun 2021
Historique:
received:
26
10
2020
accepted:
08
02
2021
pubmed:
19
2
2021
medline:
2
7
2021
entrez:
18
2
2021
Statut:
ppublish
Résumé
Benzophenone-3 (BP-3) is used in a wide range of personal care products and plastics to resist ultraviolet light, which has aroused considerable public concern due to its endocrine-disrupting effects. In this work, we systematically investigated the chemical oxidation process of BP-3 by KMnO
Identifiants
pubmed: 33599933
doi: 10.1007/s11356-021-12913-x
pii: 10.1007/s11356-021-12913-x
doi:
Substances chimiques
Benzophenones
0
Water Pollutants, Chemical
0
Potassium Permanganate
00OT1QX5U4
Water
059QF0KO0R
oxybenzone
95OOS7VE0Y
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
31301-31311Subventions
Organisme : National Natural Science Foundation of China
ID : No. 21607073
Organisme : National Natural Science Foundation of China
ID : 21876082
Organisme : Fundamental Research Funds for the Central Universities
ID : No. 14380137
Références
Abdelraheem WHM, He X, Duan X, Dionysiou DD (2015) Degradation and mineralization of organic UV absorber compound 2-phenylbenzimidazole-5-sulfonic acid (PBSA) using UV-254 nm/H2O2. J Hazard Mater 282:233–240. https://doi.org/10.1016/j.jhazmat.2014.07.041
doi: 10.1016/j.jhazmat.2014.07.041
Balmer ME, Buser HR, Müller MD, Poiger T (2005) Occurrence of some organic UV filters in wastewater, in surface waters, and in fish from Swiss lakes. Environ Sci Technol 39:953–962. https://doi.org/10.1021/es040055r
doi: 10.1021/es040055r
Blair RM, Fang H, Branham WS, Hass BS, Dial SL, Moland CL, Tong W, Shi L, Perkins R, Sheehan DM (2000) The estrogen receptor relative binding affinities of 188 natural and xenochemicals: structural diversity of ligands. Toxicol Sci 54:138–153. https://doi.org/10.1093/toxsci/54.1.138
doi: 10.1093/toxsci/54.1.138
Bu L, Shi Z, Zhou S (2017) Enhanced degradation of Orange G by permanganate with the employment of iron anode. Environ Sci Pollut Res 24:388–394. https://doi.org/10.1007/s11356-016-7777-8
doi: 10.1007/s11356-016-7777-8
Calafat AM, Wong LY, Ye X, Reidy JA, Needham LL (2008) Concentrations of the sunscreen agent benzophenone-3 in residents of the United States: National Health and Nutrition Examination Survey 2003–2004. Environ Health Perspect 116:893–897. https://doi.org/10.1289/ehp.11269
doi: 10.1289/ehp.11269
Cao W, Yu Y, Wei J, Al-Basher G, Pan X, Li B, Xu X, Alsultan N, Chen J, Qu R, Wang Z (2020) KMnO4-mediated reactions for hexachlorophene in aqueous solutions: direct oxidation, self-coupling, and cross-coupling. Chemosphere 259:127422. https://doi.org/10.1016/j.chemosphere.2020.127422
doi: 10.1016/j.chemosphere.2020.127422
Careghini A, Mastorgio AF, Saponaro S, Sezenna E (2015) Bisphenol A, nonylphenols, benzophenones, and benzotriazoles in soils, groundwater, surface water, sediments, and food: a review. Environ Sci Pollut Res 22:5711–5741. https://doi.org/10.1007/s11356-014-3974-5
doi: 10.1007/s11356-014-3974-5
Chen J, Qu R, Pan X, Wang Z (2016) Oxidative degradation of triclosan by potassium permanganate: kinetics, degradation products, reaction mechanism, and toxicity evaluation. Water Res 103:215–223. https://doi.org/10.1016/j.watres.2016.07.041
doi: 10.1016/j.watres.2016.07.041
Coronado M, De Haro H, Deng X, Rempel MA, Lavado R, Schlenk D (2008) Estrogenic activity and reproductive effects of the UV-filter oxybenzone (2-hydroxy-4-methoxyphenyl-methanone) in fish. Aquat Toxicol 90:182–187. https://doi.org/10.1016/j.aquatox.2008.08.018
doi: 10.1016/j.aquatox.2008.08.018
Díaz-Cruz MS, Barceló D (2009) Chemical analysis and ecotoxicological effects of organic UV-absorbing compounds in aquatic ecosystems. Trends Anal Chem 28:708–717. https://doi.org/10.1016/j.trac.2009.03.010
doi: 10.1016/j.trac.2009.03.010
Díaz-Cruz MS, Gago-Ferrero P, Llorca M, Barceló D (2012) Analysis of UV filters in tap water and other clean waters in Spain. Anal Bioanal Chem 402:2325–2333. https://doi.org/10.1007/s00216-011-5560-8
doi: 10.1007/s00216-011-5560-8
Du J, Sun B, Zhang J, Guan X (2012) Parabola-like shaped pH-rate profile for phenols oxidation by aqueous permanganate. Environ Sci Technol 46:8860–8867. https://doi.org/10.1021/es302076s
doi: 10.1021/es302076s
Fent K, Zenker A, Rapp M (2010) Widespread occurrence of estrogenic UV-filters in aquatic ecosystems in Switzerland. Environ Pollut 158:1817–1824. https://doi.org/10.1016/j.envpol.2009.11.005
doi: 10.1016/j.envpol.2009.11.005
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam MJ, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas OV, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09 (Revision A.02). Gaussian, Inc., Wallingford
Gago-Ferrero P, Badia-Fabregat M, Olivares A, Piña B, Blánquez P, Vicent T, Caminal G, Díaz-Cruz MS, Barceló D (2012) Evaluation of fungal-and photo-degradation as potential treatments for the removal of sunscreens BP3 and BP1. Sci Total Environ 427:355–363. https://doi.org/10.1016/j.scitotenv.2012.03.089
doi: 10.1016/j.scitotenv.2012.03.089
Gago-Ferrero P, Demeestere K, Díaz-Cruz MS, Barceló D (2013a) Ozonation and peroxone oxidation of benzophenone-3 in water: effect of operational parameters and identification of intermediate products. Sci Total Environ 443:209–217. https://doi.org/10.1016/j.scitotenv.2012.10.006
doi: 10.1016/j.scitotenv.2012.10.006
Gago-Ferrero P, Díaz-Cruz MS, Barceló D (2011) Fast pressurized liquid extraction with in-cell purification and analysis by liquid chromatography tandem mass spectrometry for the determination of UV filters and their degradation products in sediments. Anal Bioanal Chem 400:2195–2204. https://doi.org/10.1007/s00216-011-4951-1
doi: 10.1007/s00216-011-4951-1
Gago-Ferrero P, Mastroianni N, Silvia Diaz-Cruz MS, Barcelo D (2013b) Fully automated determination of nine ultraviolet filters and transformation products in natural waters and wastewaters by on-line solid phase extraction-liquid chromatography-tandem mass spectrometry. J Chromatogr A 1294:106–116. https://doi.org/10.1016/j.chroma.2013.04.037
doi: 10.1016/j.chroma.2013.04.037
Giokas DL, Salvador A, Chisvert A (2007) UV filters: from sunscreens to human body and the environment. Trends Anal Chem 26:360–374. https://doi.org/10.1016/j.trac.2007.02.012
doi: 10.1016/j.trac.2007.02.012
Gong P, Yuan H, Zhai P, Xue Y, Li H, Dong W, Mailhot G (2015) Investigation on the degradation of benzophenone-3 by UV/H2O2 in aqueous solution. Chem Eng J 277:97–103. https://doi.org/10.1016/j.cej.2015.04.078
doi: 10.1016/j.cej.2015.04.078
Guo Y, Lin Q, Xu B, Qi F (2016) Degradation of benzophenone-3 by the ozonation in aqueous solution: kinetics, intermediates and toxicity. Environ Sci Pollut Res 23:7962–7974. https://doi.org/10.1007/s11356-015-5941-1
doi: 10.1007/s11356-015-5941-1
Jiang J, Pang S, Ma J (2009) Oxidation of triclosan by permanganate (Mn (VII)): importance of ligands and in situ formed manganese oxides. Environ Sci Technol 43:8326–8331. https://doi.org/10.1021/es901663d
doi: 10.1021/es901663d
Jiang J, Pang S, Ma J (2010) Role of ligands in permanganate oxidation of organics. Environ Sci Technol 44:4270–4275. https://doi.org/10.1021/es100038d
doi: 10.1021/es100038d
Jiang J, Pang S, Ma J, Liu H (2012) Oxidation of phenolic endocrine disrupting chemicals by potassium permanganate in synthetic and real waters. Environ Sci Technol 46:1774–1781. https://doi.org/10.1021/es2035587
doi: 10.1021/es2035587
Kunisue T, Chen Z, Louis GMB, Sundaram R, Hediger ML, Sun L, Kannan K (2012) Urinary concentrations of benzophenone-type UV filters in U.S. women and their association with endometriosis. Environ Sci Technol 46:4624–4632. https://doi.org/10.1021/es204415a
doi: 10.1021/es204415a
Liao C, Kannan K (2014) Widespread occurrence of benzophenone-type UV light filters in personal care products from China and the United States: an assessment of human exposure. Environ Sci Technol 48:4103–4109. https://doi.org/10.1021/es405450n
doi: 10.1021/es405450n
Liu H, Yao J, Wang L, Wang X, Qu R, Wang Z (2019) Effective degradation of fenitrothion by zero-valent iron powder (Fe0) activated persulfate in aqueous solution: kinetic study and product identification. Chem Eng J 358:1479–1488. https://doi.org/10.1016/j.cej.2018.10.153
doi: 10.1016/j.cej.2018.10.153
Liu Y, Ying G, Shareef A, Kookana RS (2011) Photostability of the UV filter benzophenone-3 and its effect on the photodegradation of benzotriazole in water. Environ Chem 8:581–588. https://doi.org/10.1071/en11068
doi: 10.1071/en11068
Liu Y, Ying G, Shareef A, Kookana RS (2012) Biodegradation of the ultraviolet filter benzophenone-3 under different redox conditions. Environ Toxicol Chem 31:289–295. https://doi.org/10.1002/etc.749
doi: 10.1002/etc.749
Luo S, Gao L, Wei Z, Spinney R, Dionysiou DD, Hu WP, Chai L, Xiao R (2018) Kinetic and mechanistic aspects of hydroxyl radical-mediated degradation of naproxen and reaction intermediates. Water Res 137:233–241. https://doi.org/10.1016/j.watres.2018.03.002
doi: 10.1016/j.watres.2018.03.002
Manasfi T, Storck V, Ravier S, Demelas C, Coulomb B, Boudenne JL (2015) Degradation products of benzophenone-3 in chlorinated seawater swimming pools. Environ Sci Technol 49:9308–9316. https://doi.org/10.1021/acs.est.5b00841
doi: 10.1021/acs.est.5b00841
Morohoshi K, Yamamoto H, Kamata R, Shiraishi F, Koda T, Morita M (2005) Estrogenic activity of 37 components of commercial sunscreen lotions evaluated by in vitro assays. Toxicol in Vitro 19:457–469. https://doi.org/10.1016/j.tiv.2005.01.004
doi: 10.1016/j.tiv.2005.01.004
Negreira N, Canosa P, Rodriguez I, Ramil M, Rubi E, Cela R (2008) Study of some UV filters stability in chlorinated water and identification of halogenated by-products by gas chromatography-mass spectrometry. J Chromatogr A 1178:206–214. https://doi.org/10.1016/j.chroma.2007.11.057
doi: 10.1016/j.chroma.2007.11.057
Pan X, Chen J, Wu N, Qi Y, Xu X, Ge J, Wang X, Li C, Qu R, Sharma VK, Wang Z (2018a) Degradation of aqueous 2,4,4'-Trihydroxybenzophenone by persulfate activated with nitrogen doped carbonaceous materials and the formation of dimer products. Water Res 143:176–187. https://doi.org/10.1016/j.watres.2018.06.038
doi: 10.1016/j.watres.2018.06.038
Pan X, Yan L, Li C, Qu R, Wang Z (2017) Degradation of UV-filter benzophenone-3 in aqueous solution using persulfate catalyzed by cobalt ferrite. Chem Eng J 326:1197–1209. https://doi.org/10.1016/j.cej.2017.06.068
doi: 10.1016/j.cej.2017.06.068
Pan X, Yan L, Qu R, Wang Z (2018b) Degradation of the UV-filter benzophenone-3 in aqueous solution using persulfate activated by heat, metal ions and light. Chemosphere 196:95–104. https://doi.org/10.1016/j.chemosphere.2017.12.152
doi: 10.1016/j.chemosphere.2017.12.152
Pang S, Jiang J, Gao Y, Zhou Y, Huangfu X, Liu Y, Ma J (2014) Oxidation of flame retardant tetrabromobisphenol A by aqueous permanganate: reaction kinetics, brominated products, and pathways. Environ Sci Technol 48:615–623. https://doi.org/10.1021/es4041094
doi: 10.1021/es4041094
Qu R, Li C, Liu J, Xiao R, Pan X, Zeng X, Wang Z, Wu J (2018) Hydroxyl radical based photocatalytic degradation of halogenated organic contaminants and paraffin on silica gel. Environ Sci Technol 120:7220–7229. https://doi.org/10.1021/acs.est.8b00499
doi: 10.1021/acs.est.8b00499
Rodil R, Moeder M, Altenburger R, Schmittjansen M (2009) Photostability and phytotoxicity of selected sunscreen agents and their degradation mixtures in water. Anal Bioanal Chem 395:1513–1524. https://doi.org/10.1007/s00216-009-3113-1
doi: 10.1007/s00216-009-3113-1
Rodil R, Quintana JB, Concha-Graña E, López-Mahía P, Muniategui-Lorenzo S, Prada-Rodríguez D (2012) Emerging pollutants in sewage, surface and drinking water in Galicia (NW Spain). Chemosphere 86:1040–1049. https://doi.org/10.1016/j.chemosphere.2011.11.053
doi: 10.1016/j.chemosphere.2011.11.053
Sanderson H, Johnson DJ, Wilson CJ, Brain RA, Solomon KR (2003) Probabilistic hazard assessment of environmentally occurring pharmaceuticals toxicity to fish, daphnids and algae by ECOSAR screening. Toxicol Lett 144:383–395. https://doi.org/10.1016/S0378-4274(03)00257-1
doi: 10.1016/S0378-4274(03)00257-1
Santos AJM, Miranda MS, Esteves da Silva JCG (2012) The degradation products of UV filters in aqueous and chlorinated aqueous solutions. Water Res 46:3167–3176. https://doi.org/10.1016/j.watres.2012.03.057
doi: 10.1016/j.watres.2012.03.057
Schlumpf M, Cotton B, Conscience M, Haller V, Steinmann B, Lichtensteiger W (2001) In vitro and in vivo estrogenicity of UV screens. Environ Health Perspect 109:239–244. https://doi.org/10.1289/ehp.01109239
doi: 10.1289/ehp.01109239
Schlumpf M, Kypke K, Wittassek M, Angerer J, Mascher H, Mascher D, Vökt C, Birchler M, Lichtensteiger W (2010) Exposure patterns of UV filters, fragrances, parabens, phthalates, organochlor pesticides, PBDEs, and PCBs in human milk: correlation of UV filters with use of cosmetics. Chemosphere 81:1171–1183. https://doi.org/10.1016/j.chemosphere.2010.09.079
doi: 10.1016/j.chemosphere.2010.09.079
Schreurs RH, Sonneveld E, Jansen JH, Seinen W, van der Burg B (2005) Interaction of polycyclic musks and UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone receptor (PR) in reporter gene bioassays. Toxicol Sci 83:264–272. https://doi.org/10.1093/toxsci/kfi035
doi: 10.1093/toxsci/kfi035
Suzuki T, Kitamura S, Khota R, Sugihara K, Fujimoto N, Ohta S (2005) Estrogenic and antiandrogenic activities of 17 benzophenone derivatives used as UV stabilizers and sunscreens. Toxicol Appl Pharmacol 203:9–17. https://doi.org/10.1016/j.taap.2004.07.005
doi: 10.1016/j.taap.2004.07.005
Tang R, Chen M, Ding G, Chen X, Han X, Zhou K, Chen L, Xia Y, Tian Y, Wang X (2013) Associations of prenatal exposure to phenols with birth outcomes. Environ Pollut 178:115–120. https://doi.org/10.1016/j.envpol.2013.03.023
doi: 10.1016/j.envpol.2013.03.023
Vione D, Caringella R, De Laurentiis E, Pazzi M, Minero C (2013) Phototransformation of the sunlight filter benzophenone-3 (2-hydroxy-4-methoxybenzophenone) under conditions relevant to surface waters. Sci Total Environ 463:243–251. https://doi.org/10.1016/j.scitotenv.2013.05.090
doi: 10.1016/j.scitotenv.2013.05.090
Waldemer R, Tratnyek PG (2006) Kinetics of contaminant degradation by permanganate. Environ Sci Technol 40:1055–1061. https://doi.org/10.1021/es051330s
doi: 10.1021/es051330s
Xiao R, Gao L, Wei Z, Spinney R, Luo S, Wang D, Dionysiou DD, Tang C-J, Yang W (2017) Mechanistic insight into degradation of endocrine disrupting chemical by hydroxyl radical: an experimental and theoretical approach. Environ Pollut 231:1446–1452. https://doi.org/10.1016/j.envpol.2017.09.006
doi: 10.1016/j.envpol.2017.09.006
Xu X, Chen J, Wang S, Ge J, Qu R, Feng M, Sharma VK, Wang Z (2018) Degradation kinetics and transformation products of chlorophene by aqueous permanganate. Water Res 138:293–300. https://doi.org/10.1016/j.watres.2018.03.057
doi: 10.1016/j.watres.2018.03.057
Yan YE, Schwartz FW (1999) Oxidative degradation and kinetics of chlorinated ethylenes by potassium permanganate. J Contam Hydrol 37:343–365. https://doi.org/10.1016/S0169-7722(98)00166-1
doi: 10.1016/S0169-7722(98)00166-1
Yang B, Ying G (2013) Oxidation of benzophenone-3 during water treatment with ferrate (VI). Water Res 47:2458–2466. https://doi.org/10.1016/j.watres.2013.02.018
doi: 10.1016/j.watres.2013.02.018
Ye X, Zhou X, Wong L, Calafat AM (2012) Concentrations of bisphenol A and seven other phenols in pooled sera from 3-11 year old children: 2001-2002 National Health and Nutrition Examination Survey. Environ Sci Technol 46:12664–12671. https://doi.org/10.1021/es303109c
doi: 10.1021/es303109c
Zhang T, Sun H, Qin X, Wu Q, Zhang Y, Ma J, Kannan K (2013) Benzophenone-type UV filters in urine and blood from children, adults, and pregnant women in China: partitioning between blood and urine as well as maternal and fetal cord blood. Sci Total Environ 461:49–55. https://doi.org/10.1016/j.scitotenv.2013.04.074
doi: 10.1016/j.scitotenv.2013.04.074
Zhuang J, Wang S, Tan Y, Xiao R, Chen J, Wang X, Jiang L, Wang Z (2019) Degradation of sulfadimethoxine by permanganate in aquatic environment: influence factors, intermediate products and theoretical study. Sci Total Environ 671:705–713. https://doi.org/10.1016/j.scitotenv.2019.03.277
doi: 10.1016/j.scitotenv.2019.03.277