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Frontiers of Environmental Science & Engineering

Front. Environ. Sci. Eng.    2020, Vol. 14 Issue (4) : 64
Enhanced triallyl isocyanurate (TAIC) degradation through application of an O3/UV process: Performance optimization and degradation pathways
Yapeng Song1,2, Hui Gong1(), Jianbing Wang2, Fengmin Chang1, Kaijun Wang1()
1. State Key Joint Laboratory of Environment Simulation and Pollution Control, School of Environment, Tsinghua University, Beijing 100084, China
2. School of Chemical & Environmental Engineering, China University of Mining and Technology, Beijing 100083, China
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• UV/O3 process had higher TAIC mineralization rate than O3 process.

• Four possible degradation pathways were proposed during TAIC degradation.

• pH impacted oxidation processes with pH of 9 achieving maximum efficiency.

• CO32– negatively impacted TAIC degradation while HCO3 not.

• Cl can be radicals scavenger only at high concentration (over 500 mg/L Cl).

Triallyl isocyanurate (TAIC, C12H15N3O3) has featured in wastewater treatment as a refractory organic compound due to the significant production capability and negative environmental impact. TAIC degradation was enhanced when an ozone(O3)/ultraviolet(UV) process was applied compared with the application of an independent O3 process. Although 99% of TAIC could be degraded in 5 min during both processes, the O3/UV process had a 70%mineralization rate that was much higher than that of the independent O3 process (9%) in 30 min. Four possible degradation pathways were proposed based on the organic compounds of intermediate products identified during TAIC degradation through the application of independent O3 and O3/UV processes. pH impacted both the direct and indirect oxidation processes. Acidic and alkaline conditions preferred direct and indirect reactions respectively, with a pH of 9 achieving maximum Total Organic Carbon (TOC) removal. Both CO32– and HCO3 decreased TOC removal, however only CO32– negatively impacted TAIC degradation. Effects of Cl as a radical scavenger became more marked only at high concentrations (over 500 mg/L Cl). Particulate and suspended matter could hinder the transmission of ultraviolet light and reduce the production of HO· accordingly.

Keywords Triallyl isocyanurate      O3/UV      Advanced oxidation processes (AOP)      Degradation pathway     
Corresponding Author(s): Hui Gong,Kaijun Wang   
Issue Date: 14 April 2020
 Cite this article:   
Yapeng Song,Hui Gong,Jianbing Wang, et al. Enhanced triallyl isocyanurate (TAIC) degradation through application of an O3/UV process: Performance optimization and degradation pathways[J]. Front. Environ. Sci. Eng., 2020, 14(4): 64.
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Yapeng Song
Hui Gong
Jianbing Wang
Fengmin Chang
Kaijun Wang
Fig.1  Schematic representation of TAIC (left), UV/O3 reactor flowchart (center) and real ozone reactor facility (right) used in this study.
Fig.2  Comparison of TAIC removal (a) and mineralisation (b) through application of independent O3 and O3/UV processes; intermediate products obtained during TAIC degradation with the application of independent O3 (c) and O3/UV processes (d).
Reaction time (min) O3 O3/UV
2.5 18.35 2.25 26.75 2.89
5 0.055 1.02 0.23 1.26
Tab.1  EE/O values of independent O3 and O3/UV processes
Reaction time Molecular structure Product name
O3-5 min 1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-tri-2-propenyl P0
O3-20 min 1-Butyl-3-methyl-2,4,5-trioxoimidazolidine P3
O3-30 min 1-Butyl-3-methyl-2,4,5-trioxoimidazolidine P3
O3/UV-5 min 2,4,6-Triallyloxy-1,3,5-triazine P2
O3/UV-10 min 1-Butyl-3-methyl-2,4,5-trioxoimidazolidine P3
1,3-Dimethyl-2,4,5-trioxoimidazolidine P4
2-Propenal, 3,3-bis(dimethylamino)
O3/UV-20 min 1,3-Dimethyl-2,4,5-trioxoimidazolidine P4
Tab.2  Intermediate products formed during TAIC degradation through the application of independent O3 and O3 /UV processes
Fig.3  Proposed TAIC degradation pathway during application of independent O3 and O3/UV processes. Four possible pathways (1), (2), (3), (4) were proposed.
Fig.4  TAIC removal (left) and mineralization (right) during application of the O3/UV process at various pH levels.
Fig.5  TAIC removal (a, c) and mineralization (b, d) during application of the O3/UV process at various CO32– and HCO3 concentrations.
Fig.6  TAIC removal (a) and mineralization (b, c) during application of the O3/UV process at various Cl concentrations.
Fig.7  TAIC removal (a) and mineralization (b) during application of the O3/UV process at various concentrations of SS; UV intensity variation shown as distance (c).
1 J Altmann, A S Ruhl, F Zietzschmann, M Jekel (2014). Direct comparison of ozonation and adsorption onto powdered activated carbon for micropollutant removal in advanced wastewater treatment. Water Research, 55: 185–193
2 G Boczkaj, M GäGol , M Klein, A Przyjazny (2018). Effective method of treatment of effluents from production of bitumens under basic pH conditions using hydrodynamic cavitation aided by external oxidants. Ultrasonics Sonochemistry, 40(Pt A): 969–979
3 G Boczkaj, A Fernandes (2017). Wastewater treatment by means of advanced oxidation processes at basic pH conditions: A review. Chemical Engineering Journal, 320: 608–633
4 R E Buehler, J Staehelin, J Hoigne (1984). Ozone decomposition in water studied by pulse radiolysis. 1. Perhydroxyl(HO2)/hyperoxide(O2–) and HO3/O3– as intermediates. Journal of Physical Chemistry B, 88(12): 2560–2564
5 C Busset, P Mazellier, M Sarakha, J de Laat (2007). Photochemical generation of carbonate radicals and their reactivity with phenol. Journal of Photochemistry and Photobiology A Chemistry, 185(2-3): 127–132
6 Y Bustos-Terrones, J G Rangel-Peraza, A Sanhouse, E R Bandala, L G Torres (2016). Degradation of organic matter from wastewater using advanced primary treatment by O3 and O3/UV in a pilot plant. Physics and Chemistry of the Earth Parts A/B/C, 91: 61–67
7 G V Buxton, C L Greenstock, W P Helman, A B Ross (1988). Critical Review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (·OH/·O– in Aqueous Solution. Journal of Physical and Chemical Reference Data, 17(2): 513–886
8 P Caregnato, J A Rosso, J M Soler, A Arques, D O Martire, M C Gonzalez (2013). Chloride anion effect on the advanced oxidation processes of methidathion and dimethoate: Role of Cl2–· radical. Water Research, 47(1): 351–362
9 C Wu, K G Linden (2010). Phototransformation of selected organophosphorus pesticides: roles of hydroxyl and carbonate radicals. Water Research, 44(12): 3585–3594
10 Y Chen, J Ye, Y Chen, H Hu, H Zhang, H Ou (2019). Degradation kinetics, mechanism and toxicology of tris(2-chloroethyl) phosphate with 185 nm vacuum ultraviolet. Chemical Engineering Journal, 356: 98–106
11 W Chu, C W Ma (2000). Quantitative prediction of direct and indirect dye ozonation kinetics. Water Research, 34(12): 3153–3160
12 P Evgeny, M Muhamed, S Domenico, L Lorenzo, E Jussi (2010). Kinetics of UV-H2O2 advanced oxidation in the presence of alcohols: The role of carbon centered radicals. Environmental Science & Technology, 44(20): 7827–7832
13 A Fernandes, M Gągol, P Makoś, J A Khan, G Boczkaj (2019). Integrated photocatalytic advanced oxidation system (TiO2/UV/O3/H2O2) for degradation of volatile organic compounds. Separation and Purification Technology, 224: 1–14
14 A Fernandes, P Makoś, G Boczkaj (2018). Treatment of bitumen post oxidative effluents by sulfate radicals based advanced oxidation processes (S-AOPs) under alkaline pH conditions. Journal of Cleaner Production, 195: 374–384
15 M Gągol, A Przyjazny, G Boczkaj (2018). Effective method of treatment of industrial effluents under basic pH conditions using acoustic cavitation: A comprehensive comparison with hydrodynamic cavitation processes. Chemical Engineering and Processing- Process Intensification, 128: 103–113
16 W R Haag, C C D Yao (1992). Rate constants for reaction of hydroxyl radicals with several drinking water contaminants. Environmental Science & Technology, 26(5): 1005–1013
17 J W Lee, E J Won, S Raisuddin, J S Lee (2015). Significance of adverse outcome pathways in biomarker-based environmental risk assessment in aquatic organisms. Journal of Environmental Sciences, 35(9): 115–127
18 O N Legrini, E Oliveros, A M Braun (1993). Photochemical process for water treatment. Chemical Reviews, 93(2): 671–698
19 H Liu, P Sun, Q He, M Feng, H Liu, S Yang, L Wang, Z Wang (2016a). Ozonation of the UV filter benzophenone-4 in aquatic environments: Intermediates and pathways. Chemosphere, 149: 76–83
20 Y Liu, X He, X Duan, Y Fu, D Fatta-Kassinos, D D Dionysiou (2016b). Significant role of UV and carbonate radical on the degradation of oxytetracycline in UV-AOPs: Kinetics and mechanism. Water Research, 95: 195–204
21 H V Lutze, N Kerlin, T C Schmidt (2015). Sulfate radical-based water treatment in presence of chloride: Formation of chlorate, inter-conversion of sulfate radicals into hydroxyl radicals and influence of bicarbonate. Water Research, 72: 349–360
22 S J Masten, J Hoigné (1992). Comparison of ozone and hydroxyl radical-induced oxidation of chlorinated hydrocarbons in water. Ozone Science and Engineering, 14(3): 197–214
23 N Nagasawa, A Kaneda, S Kanazawa, T Yagi, H Mitomo, F Yoshii, M Tamada (2005). Application of poly(lactic acid) modified by radiation crosslinking. Nuclear Instruments & Methods in Physics Research. Section B, Beam Interactions with Materials and Atoms, 236(1–4): 611–616
24 P Mazellier, C Busset, A Delmont, J de Laat (2007). A comparison of fenuron degradation by hydroxyl and carbonate radicals in aqueous solution. Water Research, 41(20): 4585–4594
25 S Rong, Y Sun (2015). Degradation of TAIC by water falling film dielectric barrier discharge–influence of radical scavengers. Journal of Hazardous Materials, 287: 317–324
26 E J Rosenfeldt, K G Linden, S Canonica, U Von Gunten (2006). Comparison of the efficiency of ⋅OH radical formation during ozonation and the advanced oxidation processes O3/H2O2 and UV/ H2O2. Water Research, 40(20): 3695–3704
27 S A Snyder, E C Wert, D J Rexing, R E Zegers, D D Drury (2006). Ozone Oxidation of Endocrine Disruptors and Pharmaceuticals in Surface Water and Wastewater. Ozone Science and Engineering, 28(6): 445–460
28 J Staehelin, R E Buehler, J Hoigne (1984). Ozone decomposition in water studied by pulse radiolysis. 2. Hydroxyl and hydrogen tetroxide (HO4) as chain intermediates. The Journal of Physical Chemistry, 88(24): 5999–6004
29 J Staehelin, J Hoigne (1982). Decomposition of ozone in water: Rate of Initiation by hydroxide ions and hydrogen peroxide. Environmental Science & Technology, 16(10): 676–681
30 M Stapf, U Miehe, M Jekel (2016). Application of online UV absorption measurements for ozone process control in secondary effluent with variable nitrite concentration. Water Research, 104: 111–118
31 H Tomiyasu, H Fukutomi, G Gordon (1985). Kinetics and mechanism of ozone decomposition in basic aqueous solution. Inorganic Chemistry, 24(19): 2962–2966
32 G L Truong, J D Laat, B Legube. (2004). Effects of chloride and sulfate on the rate of oxidation of ferrous ion by H2O2. Water Research, 38(9): 2384–2393
33 L Vereecken, H Harder, A Novelli (2014). The reactions of Criegee intermediates with alkenes, ozone, and carbonyl oxides. Physical Chemistry Chemical Physics, 16(9): 4039–4049
34 G U Von (2007). The basics of oxidants in water treatment. Part B: Ozone reactions. Water Science & Technology, 55(12): 25–29
35 M Yamaura (2013). Triallyl isocyanurate, triallyl cyanurate and process for producing triallyl isocyanurate. Patent No. US8431697 B2
36 W Yao, S W Ur Rehman, H Wang, H Yang, G Yu, Y Wang (2018). Pilot-scale evaluation of micropollutant abatements by conventional ozonation, UV/O3, and an electro-peroxone process. Water Research, 138: 106–117
37 H Zhao, J Chen, H Zhang, Y Shang, X Wang, B Han, Z Li (2017). Theoretical study on the reaction of triallyl isocyanurate in the UV radiation cross-linking of polyethylene. RSC Advances, 7(59): 37095–37104
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