Abstract
Iron species that occur in natural surface water could affect the photochemical behavior of pollutants. Complexation between iron species and polycarboxylate or heavy metals has been widely reported, where the ligands could be oxidized via ligand-to-metal charge transfer (LMCT) by light inducement. Such complexation and photochemical reactions might also occur for low valance metal-containing organic compounds, which is worthy of investigation. This work studied the phototransformation of p-arsanilic acid (ASA), an organic arsenic compound that is widely used as a feed additive in the poultry industry, by colloidal ferric hydroxide (CFH) using black light lamps (λ = 365 nm) as the light source. The results revealed the contribution to ASA transformation at circumneutral conditions by CFH through an LMCT process, which is the same as that for As(III). The complexation between ASA and CFH was investigated using UV–vis spectroscopy. The estimated equilibrium constant for the CFH–ASA complex was log Kf271 = 4.22. The analysis of the photoproducts found the generation of both inorganic and organic arsenic. Our findings confirmed the similarities in the photochemical mechanisms of ASA and As(III) in the presence of CFH. The results help in further understanding the fate of organoarsenicals in the surface water environment.
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References
Adamescu A, Gray H, Stewart KME, Hamilton IP, al-Abadleh HA (2010) Trends in the frequencies of ν (AsOxHx–1) [x=2–4] in selected As(V)-containing compounds investigated using quantum chemical calculations. Can J Chem 88:65–77. https://doi.org/10.1139/V09-147
Adamescu A, Hamilton IP, Al-Abadleh HA (2014) Density functional theory calculations on the complexation of p-arsanilic acid with hydrated iron oxide clusters: structures, reaction energies, and transition states. J Phys Chem A 118:5667–5679
Aschbacher PW, Feil VJ (1991) Fate of [14C]arsanilic acid in pigs and chickens. J Agric Food Chem 39:146–149. https://doi.org/10.1021/jf00001a028
Benesi H, Hildebrand JH (1949) A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc 71:2703–2707. https://doi.org/10.1021/ja01176a030
Bhandari N, Reeder RJ, Strongin DR (2012) Photoinduced oxidation of arsenite to arsenate in the presence of goethite. Environ Sci Technol 46:8044–8051. https://doi.org/10.1021/es300988p
Buxton GV, Greenstock CL, Helman WP, Ross AB (1988) Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (•OH/•O-) in aqueous solution. J Phys Chem Ref Data 17:513–886. https://doi.org/10.1063/1.555805
Catrouillet C, Davranche M, Dia A, Bouhnik-le Coz M, Demangeat E, Gruau G (2016) Does As(III) interact with Fe(II), Fe(III) and organic matter through ternary complexes? J Colloid Interface Sci 470:153–161. https://doi.org/10.1016/j.jcis.2016.02.047
Chabot M, Hoang T, Al-Abadleh HA (2009) ATR-FTIR studies on the nature of surface complexes and desorption efficiency of p-arsanilic acid on iron (oxyhydr)oxides. Environ Sci Technol 43:3142–3147. https://doi.org/10.1021/es803178f
Chen WR, Huang CH (2012) Surface adsorption of organoarsenic roxarsone and arsanilic acid on iron and aluminum oxides. J Hazard Mater 227–228:378–385. https://doi.org/10.1016/j.jhazmat.2012.05.078
Chen Y, Wu F, Lin Y, Deng N, Bazhin N, Glebov E (2007) Photodegradation of glyphosate in the ferrioxalate system. J Hazard Mater 148:360–365. https://doi.org/10.1016/j.jhazmat.2007.02.044
Cheng W, Xu J, Wang Y, Wu F, Xu X, Li J (2015) Dispersion-precipitation synthesis of nanosized magnetic iron oxide for efficient removal of arsenite in water. J Colloid Interface Sci 445:93–101. https://doi.org/10.1016/j.jcis.2014.12.082
Cortinas I, Field JA, Kopplin M, Garbarino JR, Gandolfi AJ, Sierra-Alvarez R (2006) Anaerobic biotransformation of roxarsone and related N-substituted phenylarsonic acids. Environ Sci Technol 40:2951–2957. https://doi.org/10.1021/es051981o
Czaplicka M, Jaworek K, Bąk M (2015) Study of photodegradation and photooxidation of p-arsanilic acid in water solutions at pH = 7: kinetics and by-products. Environ Sci Pollut Res 22:16927–16935. https://doi.org/10.1007/s11356-015-4890-z
Depalma S, Cowen S, Hoang T, Al-Abadleh HA (2008) Adsorption thermodynamics of p-arsanilic acid on iron (oxyhydr)oxides: in-situ ATR-FTIR studies. Environ Sci Technol 42:1922–1927. https://doi.org/10.1021/es071752x
Ding W, Xu J, Chen T, Liu C, Li J, Wu F (2018) Co-oxidation of As(III) and Fe(II) by oxygen through complexation between As(III) and Fe(II)/Fe(III) species. Water Res 143:599–607. https://doi.org/10.1016/j.watres.2018.06.072
Dixit S, Hering JG (2003) Comparison of arsenic(V) and arsenic(III) sorption onto iron oxide minerals: implications for arsenic mobility. Environ Sci Technol 37:4182–4189. https://doi.org/10.1021/es030309t
Hug SJ, Canonica L, Wegelin M, Gechter D, von Gunten U (2001) Solar oxidation and removal of arsenic at circumneutral pH in iron containing waters. Environ Sci Technol 35:2114–2121. https://doi.org/10.1021/es001551s
Jung BK, Jun JW, Hasan Z, Jhung SH (2015) Adsorptive removal of p-arsanilic acid from water using mesoporous zeolitic imidazolate framework-8. Chem Eng J 267:9–15. https://doi.org/10.1016/j.cej.2014.12.093
Kong L, He M, Hu X (2016) Rapid photooxidation of Sb(III) in the presence of different Fe(III) species. Geochim Cosmochim Acta 180:214–226. https://doi.org/10.1016/j.gca.2016.02.022
Li S, Xu J, Chen W, Yu Y, Liu Z, Li J, Wu F (2016) Multiple transformation pathways of p-arsanilic acid to inorganic arsenic species in water during UV disinfection. J Environ Sci (China) 47:39–48. https://doi.org/10.1016/j.jes.2016.01.017
Liu YS, Ying GG, Shareef A, Kookana RS (2013) Photodegradation of three benzotriazoles induced by four FeIII-carboxylate complexes in water under ultraviolet irradiation. Environ Chem 10:135–143. https://doi.org/10.1071/EN13054
Mitchell W, Goldberg S, Al-Abadleh HA (2011) In situ ATR-FTIR and surface complexation modeling studies on the adsorption of dimethylarsinic acid and p-arsanilic acid on iron-(oxyhydr)oxides. J Colloid Interface Sci 358:534–540. https://doi.org/10.1016/j.jcis.2011.02.040
Moody JP, Williams RT (1964) The fate of arsanilic acid and acetylarsanilic acid in hens. Food Cosmet Toxicol 2:687–693. https://doi.org/10.1016/S0015-6264(64)80420-X
Pozdnyakov IP, Glebov EM, Plyusnin VF, Grivin VP, Ivanov YV, Vorobyev DY, Bazhin NM (2000) Mechanism of Fe(OH)2+(aq) photolysis in aqueous solution. Pure Appl Chem 72:2187–2197
Silbergeld EK, Nachman K (2008) The environmental and public health risks associated with arsenical use in animal feeds. Ann N Y Acad Sci 1140:346–357. https://doi.org/10.1196/annals.1454.049
Tao Y, Brigante M, Zhang H, Mailhot G (2019) Phenanthrene degradation using Fe(III)-EDDS photoactivation under simulated solar light: a model for soil washing effluent treatment. Chemosphere 236:124366. https://doi.org/10.1016/j.chemosphere.2019.124366
Tian C, Zhao J, Ou X, Wan J, Cai Y, Lin Z, Dang Z, Xing B (2018) Enhanced adsorption of p-arsanilic acid from water by amine-modified UiO-67 as examined using extended x-ray absorption fine structure, x-ray photoelectron spectroscopy, and density functional theory calculations. Environ Sci Technol 52:3466–3475
Wan D, Zhang G, Chen Y, Lu X, Zuo Y (2019) Photogeneration of hydroxyl radical in Fe(III)-citrate-oxalate system for the degradation of fluconazole: mechanism and products. Environ Sci Pollut Res 26:8640–8649. https://doi.org/10.1007/s11356-019-04348-2
Wang HL, Hu ZH, Tong ZL, Xu Q, Wang W, Yuan S (2014) Effect of arsanilic acid on anaerobic methanogenic process: kinetics, inhibition and biotransformation analysis. Biochem Eng J 91:179–185. https://doi.org/10.1016/j.bej.2014.08.011
Wu F, Zhang L, Deng N, Zuo Y (2004) Quantitation for photoinduced formation of hydroxyl radicals in the water-containing Fe(III) and oxalate salts. Fresenius Environ Bull 13:748–752
Xie X, Hu Y, Cheng H (2016) Mechanism, kinetics, and pathways of self-sensitized sunlight photodegradation of phenylarsonic compounds. Water Res 96:136–147. https://doi.org/10.1016/j.watres.2016.03.053
Xu J, Li J, Wu F, Zhang Y (2014) Rapid photooxidation of As(III) through surface complexation with nascent colloidal ferric hydroxide. Environ Sci Technol 48:272–278. https://doi.org/10.1021/es403667b
Xu J, Ding W, Wu F, Mailhot G, Zhou D, Hanna K (2016) Rapid catalytic oxidation of arsenite to arsenate in an iron(III)/sulfite system under visible light. Appl Catal B Environ 186:56–61. https://doi.org/10.1016/j.apcatb.2015.12.033
Xu J, Shen X, Wang D, Zhao C, Liu Z, Pozdnyakov IP, Wu F, Xia J (2018a) Kinetics and mechanisms of pH-dependent direct photolysis of p-arsanilic acid under UV-C light. Chem Eng J 336:334–341. https://doi.org/10.1016/j.cej.2017.12.037
Xu J, Zhang H, Luo T, Liu Z, Xia J, Zhang X (2018b) Phototransformation of p-arsanilic acid in aqueous media containing nitrogen species. Chemosphere 212:777–783. https://doi.org/10.1016/j.chemosphere.2018.08.104
Yang Y, Tao S, Dong Z, Xu J, Zhang X, Pan G (2021) Adsorption of p-arsanilic acid on iron (Hydr)oxides and its implications for contamination in soils. Minerals 11:1–13. https://doi.org/10.3390/min11020105
Zeng H, Fisher B, Giammar DE (2008) Individual and competitive adsorption of arsenate and phosphate to a high-surface-area iron oxide-based sorbent. Environ Sci Technol 42:147–152. https://doi.org/10.1021/es071553d
Zhang JS, Stanforth R, Pehkonen SO (2008) Irreversible adsorption of methyl arsenic, arsenate, and phosphate onto goethite in arsenic and phosphate binary systems. J Colloid Interface Sci 317:35–43. https://doi.org/10.1016/j.jcis.2007.09.024
Zhu XD, Wang YJ, Liu C, Qin WX, Zhou DM (2014) Kinetics, intermediates and acute toxicity of arsanilic acid photolysis. Chemosphere 107:274–281. https://doi.org/10.1016/j.chemosphere.2013.12.060
Zuo Y, Holgné J (1992) Formation of hydrogen peroxide and depletion of oxalic acid in atmospheric water by photolysis of iron(III)-oxalato complexes. Environ Sci Technol 26:1014–1022
Zuo Y, Zhan J, Wu T (2005) Effects of monochromatic UV-visible light and sunlight on Fe(III)-catalyzed oxidation of dissolved sulfur dioxide. J Atmos Chem 50:195–210. https://doi.org/10.1007/s10874-005-2813-y
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Comments from the anonymous reviewers are appreciated.
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This work was supported by the National Natural Science Foundation of China (NSFC No. 21707106, 42077350), the Natural Science Foundation of Hubei Province (2017CFB156), and the China Postdoctoral Science Foundation (2016M602358).
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Jing Xu: Investigation, formal analysis, funding acquisition, and writing—original draft. Yi Wu: Investigation, formal analysis, and visualization. Mengling Ma: Investigation and formal analysis. Tao Luo: Formal analysis and methodology. Jun Xia: Conceptualization, resources, and writing—review and editing. Xiang Zhang: Resources, supervision, and writing—review and editing.
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Xu, ., Wu, Y., Ma, M. et al. A novel transformation pathway of p-arsanilic acid in water by colloid ferric hydroxide under UVA light. Environ Sci Pollut Res 29, 5043–5051 (2022). https://doi.org/10.1007/s11356-021-15975-z
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DOI: https://doi.org/10.1007/s11356-021-15975-z