Catalytic degradation of 2-phenylbenzimidazole-5-sulfonic acid by peroxymonosulfate activated with nitrogen and sulfur co-doped CNTs-COOH loaded CuFe2O4

Chemical Engineering Journal

Volumn 307, Issue , 2017, Pages 95-104

  Zhang, Xiaoling ^a   Feng, Mingbao ^a   Wang, Liansheng ^a   Qu, Ruijuan ^a   Wang, Zunyao ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

2 Phenylbenzimidazole 5 sulfonic acid; Degradation mechanism; Degradation pathways; Nitrogen and sulfur co doped CNTs COOH loaded CuFe2O4; Peroxymonosulfate

Indexed keywords

CARBON; CARBON NANOTUBES; CATALYST ACTIVITY; CATALYSTS; CHEMICAL ACTIVATION; DEGRADATION; ELECTRON SPIN RESONANCE SPECTROSCOPY; ENDOCRINE DISRUPTERS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; LIQUID CHROMATOGRAPHY; MAGNETIC RESONANCE; MASS SPECTROMETRY; MULTIWALLED CARBON NANOTUBES (MWCN); NITROGEN; PARAMAGNETIC RESONANCE; PRECIPITATION (CHEMICAL); REUSABILITY; SCANNING ELECTRON MICROSCOPY; SULFUR; SUN HOODS; TRANSMISSION ELECTRON MICROSCOPY; X RAY DIFFRACTION; YARN;

CO-DOPED; COPRECIPITATION METHOD; DEGRADATION INTERMEDIATES; DEGRADATION MECHANISM; DEGRADATION PATHWAYS; ELECTRON PARAMAGNETIC RESONANCES (EPR); LIQUID CHROMATOGRAPHY - MASS SPECTROMETRIES; PEROXYMONOSULFATE;

X RAY PHOTOELECTRON SPECTROSCOPY;

EID: 84989909366     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2016.08.078     Document Type: Article

References (63)

1. [1] Gasparro, F.P., Sunscreens, skin photobiology, and skin cancer: the need for UVA protection and evaluation of efficacy. Environ. Health Perspect. 108 (2000), 71–78.
2. [2] Kunz, P.Y., Fent, K., Estrogenic activity of UV filter mixtures. Toxicol. Appl. Pharmacol. 217 (2006), 86–99.
3. [3] Morohoshi, K., Yamamoto, H., Kamata, R., Shiraishi, F., Koda, T., Morita, M., Estrogenic activity of 37 components of commercial sunscreen lotions evaluated by in vitro assays. Toxicol. In Vitro 19 (2005), 457–469.
4. [4] Rodil, R., Moeder, M., Altenburger, R., Schmitt-Jansen, M., Photostability and phytotoxicity of selected sunscreen agents and their degradation mixtures in water. Anal. Bioanal. Chem. 395 (2009), 1513–1524.
5. [5] Schwarzenbach, R.P., Escher, B.I., Fenner, K., Hofstetter, T.B., Johnson, C.A., Von Gunten, U., Wehrli, B., The challenge of micropollutants in aquatic systems. Science 313 (2006), 1072–1077.
6. [6] Díaz-Cruz, M.S., Barceló, D., Chemical analysis and ecotoxicological effects of organic UV-absorbing compounds in aquatic ecosystems. Trends Anal. Chem. 28 (2009), 708–717.
7. [7] Díaz-Cruz, M.S., Llorca, M., Barceló, D., Organic UV filters and their photodegradates, metabolites and disinfection by-products in the aquatic environment. Trends Anal. Chem. 27 (2008), 873–887.
8. [8] Rodil, R., Quintana, J.B., López-Mahía, P., Muniategui-Lorenzo, S., Prada-Rodríguez, D., Multiclass determination of sunscreen chemicals in water samples by liquid chromatography–tandem mass spectrometry. Anal. Chem. 80 (2008), 1307–1315.
9. [9] Inbaraj, J.J., Bilski, P., Chignell, C.F., Photophysical and photochemical studies of 2-phenylbenzimidazole and UVB sunscreen 2-phenylbenzimidazole-5-sulfonic acid. Photochem. Photobiol. 75 (2002), 107–116.
10. [10] Ji, Y., Zhou, L., Zhang, Y., Ferronato, C., Brigante, M., Mailhot, G., Chovelon, J.M., Photochemical degradation of sunscreen agent 2-phenylbenzimidazole-5-sulfonic acid in different water matrices. Water Res. 47 (2013), 5865–5875.
11. [11] Bastien, N., Millau, J.F., Rouabhia, M., Davies, R.J.H., Drouin, R., The sunscreen agent 2-phenylbenzimidazole-5-sulfonic acid photosensitizes the formation of oxidized guanines in cellulo after UV-A or UV-B exposure. J. Invest. Dermatol. 130 (2010), 2463–2471.
12. 2 photocatalysis: kinetics, photoproducts and comparison to structurally related compounds. Appl. Catal. B Environ. 140 (2013), 457–467.
13. [13] Anipsitakis, G.P., Dionysiou, D.D., Radical generation by the interaction of transition metals with common oxidants. Environ. Sci. Technol. 38 (2004), 3705–3712.
14. [14] Guan, Y.H., Ma, J., Li, X.C., Fang, J.Y., Chen, L.W., Influence of pH on the formation of sulfate and hydroxyl radicals in the UV/peroxymonosulfate system. Environ. Sci. Technol. 45 (2011), 9308–9314.
15. [15] Hori, H., Nagaoka, Y., Murayama, M., Kutsuna, S., Efficient decomposition of perfluorocarboxylic acids and alternative fluorochemical surfactants in hot water. Environ. Sci. Technol. 42 (2008), 7438–7443.
16. [16] Rastogi, A., Al-Abed, S.R., Dionysiou, D.D., Sulfate radical-based ferrous–peroxymonosulfate oxidative system for PCBs degradation in aqueous and sediment systems. Appl. Catal. B Environ. 85 (2009), 171–179.
17. [17] Waldemer, R.H., Tratnyek, P.G., Johnson, R.L., Nurmi, J.T., Oxidation of chlorinated ethenes by heat-activated persulfate: kinetics and products. Environ. Sci. Technol. 41 (2007), 1010–1015.
18. [18] Neta, P., Huie, R.E., Ross, A.B., Rate constants for reactions of inorganic radicals in aqueous solution. J. Phys. Chem. Ref. Data 17 (1988), 1027–1284.
19. − in aqueous solution. J. Phys. Chem. Ref. Data 17 (1988), 513–886.
20. [20] Lee, Y.C., Lo, S.L., Chiueh, P.T., Chang, D.G., Efficient decomposition of perfluorocarboxylic acids in aqueous solution using microwave-induced persulfate. Water Res. 43 (2009), 2811–2816.
21. [21] Guan, Y.H., Ma, J., Ren, Y.M., Liu, Y.L., Xiao, J.Y., Lin, L.Q., Zhang, C., Efficient degradation of atrazine by magnetic porous copper ferrite catalyzed peroxymonosulfate oxidation via the formation of hydroxyl and sulfate radicals. Water Res. 47 (2013), 5431–5438.
22. 4 as a heterogeneous catalyst of peroxymonosulfate. Appl. Catal. B Environ. 129 (2013), 153–162.
23. 4/carbon sphere/cobalt composites for catalytic oxidation of phenol solutions with sulfate radicals. Chem. Eng. J. 245 (2014), 1–9.
24. 4 nanocrystals on graphene oxide as a synergistic catalyst for degradation of Orange II in water by advanced oxidation technology based on sulfate radicals. Appl. Catal. B Environ. 123–124 (2012), 265–272.
25. [25] Qu, R., Xu, B., Meng, L., Wang, L., Wang, Z., Ozonation of indigo enhanced by carboxylated carbon nanotubes: performance optimization, degradation products, reaction mechanism and toxicity evaluation. Water Res. 68 (2015), 316–327.
26. [26] Goncalves, A.G., Figueiredo, J.L., Orfao, J.J., Pereira, M.F., Influence of the surface chemistry of multi-walled carbon nanotubes on their activity as ozonation catalysts. Carbon 48 (2010), 4369–4381.
27. [27] Razmjooei, F., Singh, K.P., Song, M.Y., Yu, J.S., Enhanced electrocatalytic activity due to additional phosphorous doping in nitrogen and sulfur-doped graphene: a comprehensive study. Carbon 78 (2014), 257–267.
28. [28] Sun, D., Ban, R., Zhang, P.H., Wu, G.H., Zhang, J.R., Zhu, J.J., Hair fiber as a precursor for synthesizing of sulfur-and nitrogen-co-doped carbon dots with tunable luminescence properties. Carbon 64 (2013), 424–434.
29. [29] Liu, H., Sun, P., Feng, M., Liu, H., Yang, S., Wang, L., Wang, Z., Nitrogen and sulfur co-doped CNT-COOH as an efficient metal-free catalyst for the degradation of UV filter BP-4 based on sulfate radicals. Appl. Catal. B Environ. 187 (2016), 1–10.
30. [30] Su, Y., Zhang, Y., Zhuang, X., Li, S., Wu, D., Zhang, F., Feng, X., Low-temperature synthesis of nitrogen/sulfur co-doped three-dimensional graphene frameworks as efficient metal-free electrocatalyst for oxygen reduction reaction. Carbon 62 (2013), 296–301.
31. 4 nanocomposites. Nanotechnology 16 (2005), 1486–1489.
32. [32] Feng, M., Qu, R., Zhang, X., Sun, P., Sui, Y., Wang, L., Wang, Z., Degradation of flumequine in aqueous solution by persulfate activated with common methods and polyhydroquinone-coated magnetite/multi-walled carbon nanotubes catalysts. Water Res. 85 (2015), 1–10.
33. 4/MWCNTs in aqueous solution. Appl. Catal. B Environ. 107 (2011), 274–283.
34. 4. Appl. Surf. Sci. 253 (2006), 2589–2596.
35. 4-reduced graphene oxide. Ind. Eng. Chem. Res. 53 (2014), 12566–12574.
36. 4 nanoparticles: a magnetically recoverable catalyst for selective deacetylation of carbohydrate derivatives. Top. Catal. 53 (2010), 1087–1090.
37. 2 nanoparticles in heterogeneous activation of peroxymonosulfate for phenol degradation in aqueous solutions. Appl. Catal. B Environ. 127 (2012), 330–335.
38. 4 spinel in water: efficiency, stability, and mechanism. Environ. Sci. Technol., 47, 2013 2784–2491.
39. [39] Zhang, S., Chen, J., Qiao, X., Ge, L., Cai, X., Na, G., Quantum chemical investigation and experimental verification on the aquatic photochemistry of the sunscreen 2-phenylbenzimidazole-5-sulfonic acid. Environ. Sci. Technol. 44 (2010), 7484–7490.
40. [40] Wang, Y., Zhao, H., Li, M., Fan, J., Zhao, G., Magnetic ordered mesoporous copper ferrite as a heterogeneous Fenton catalyst for the degradation of imidacloprid. Appl. Catal. B Environ. 147 (2014), 534–545.
41. [41] Minisci, F., Citterio, A., Giordano, C., Electron-transfer processes: peroxydisulfate, a useful and versatile reagent in organic chemistry. Acc. Chem. Res. 16 (1983), 27–32.
42. 4 magnetic nanoparticles as heterogeneous activator of persulfate. J. Hazard. Mater. 186 (2011), 1398–1404.
43. [43] Lee, H., Lee, H.J., Jeong, J., Lee, J., Park, N.B., Lee, C., Activation of persulfates by carbon nanotubes: oxidation of organic compounds by nonradical mechanism. Chem. Eng. J. 266 (2015), 28–33.
44. [44] Floyd, R.A., Soong, L.M., Spin trapping in biological systems. Oxidation of the spin trap 5, 5-dimethyl-1-pyrroline-1-oxide by a hydroperoxide-hematin system. Biochem. Biophys. Res. Commun. 74 (1977), 79–84.
45. [45] Verstraeten, S.V., Lucangioli, S., Galleano, M., ESR characterization of thallium (III)-mediated nitrones oxidation. Inorg. Chim. Acta 362 (2009), 2305–2310.
46. [46] Lian, C., Su, H.W., Identification of sulfate and hydroxyl radicals in thermally activated persulfate. Ind. Eng. Chem. Res. 48 (2009), 5558–5562.
47. [47] Zhang, L., Xia, Z., Mechanisms of oxygen reduction reaction on nitrogen-doped graphene for fuel cells. J. Phys. Chem. C 115 (2011), 11170–11176.
48. [48] Duan, X., O'Donnell, K., Sun, H., Wang, Y., Wang, S., Sulfur and nitrogen co-doped graphene for metal-free catalytic oxidation reactions. Small 11 (2015), 3036–3044.
49. [49] Sun, H., Kwan, C., Suvorova, A., Ang, H.M., Tadé, M.O., Wang, S., Appl. Catal. B Environ. 154–155 (2014), 134–141.
50. [50] Liang, J., Jiao, Y., Jaroniec, M., Qiao, S.Z., Sulfur and nitrogen dual-doped mesoporous graphene electrocatalyst for oxygen reduction with synergistically enhanced performance. Angew. Chem. Int. Ed. 51 (2012), 11496–11500.
51. [51] Glenis, S., Nelson, A.J., Labes, M.M., Sulfur doped graphite prepared via arc discharge of carbon rods in the presence of thiophenes. J. Appl. Phys., 86, 1999, 4464.
52. [52] Yang, Z., Yao, Z., Li, G., Fang, G., Nie, H., Liu, Z., Huang, S., Sulfur-doped graphene as an efficient metal-free cathode catalyst for oxygen reduction. ACS Nano 6 (2012), 205–211.
53. [53] Paraknowitsch, J.P., Thomas, A., Doping carbons beyond nitrogen: an overview of advanced heteroatom doped carbons with boron, sulphur and phosphorus for energy applications. Energy Environ. Sci. 6 (2013), 2839–2855.
54. [54] Duan, X., Sun, H., Wang, Y., Kang, J., Wang, S., N-doping-induced nonradical reaction on single-walled carbon nanotubes for catalytic phenol oxidation. ACS Catal. 5 (2015), 553–559.
55. [55] Wohlgemuth, S.A., White, R.J., Willinger, M.G., Titirici, M.M., Antonietti, M.A., One-pot hydrothermal synthesis of sulfur and nitrogen doped carbon aerogels with enhanced electrocatalytic activity in the oxygen reduction reaction. Green Chem. 14 (2012), 1515–1523.
56. [56] Spiro, M., The standard potential of the peroxosulphate/sulphate couple. Electrochim. Acta 24 (1979), 313–314.
57. 2 at neutral pH. Appl. Catal. B Environ. 87 (2009), 30–36.
58. −1,−2). J. Phys. Chem. 79 (1975), 2693–2700.
59. [59] Fukui, K., Yonezawa, T., Shingu, H., A molecular orbital theory of reactivity in aromatic hydrocarbons. J. Phys. Chem. 20 (1952), 722–725.
60. [60] Shi, J., Qu, R., Feng, M., Wang, X., Wang, L., Yang, S., Wang, Z., Oxidative degradation of decabromodiphenyl ether (BDE 209) by potassium permanganate: reaction pathways, kinetics, and mechanisms assisted by density functional theory calculations. Environ. Sci. Technol. 49 (2015), 4209–4217.
61. [61] Xu, F., Wang, H., Zhang, Q., Zhang, R., Qu, X., Wang, W., Kinetic properties for the complete series reactions of chlorophenols with OH radicals relevance for dioxin formation. Environ. Sci. Technol. 44 (2010), 1399–1404.
62. [62] Wang, C., Liu, H.X., Fang, Z.Y., Wang, Z.Y., Density functional theory calculation on polychlorinated anthraquinones: their gas phase thermodynamic function and implication of the Cl substituted position. J. Chem. Eng. Data 55 (2009), 1077–1086.
63. [63] Han, J., Meng, S., Dong, Y., Hu, J., Gao, W., Capturing hormones and bisphenol A from water via sustained hydrogen bond driven sorption in polyamide microfiltration membranes. Water Res. 47 (2013), 197–208.