Enhanced triallyl isocyanurate (TAIC) degradation through application of an O₃/UV process: Performance optimization and degradation pathways

Abstract

• 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.

• CO₃^2– 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 CO₃^2– and HCO₃^– decreased TOC removal, however only CO₃^2– 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.

Graphical abstract

Keywords

Triallyl isocyanurate / O ₃/UV / Advanced oxidation processes (AOP) / Degradation pathway

References

[1] Altmann J, Ruhl A S, Zietzschmann F, Jekel M (2014). Direct comparison of ozonation and adsorption onto powdered activated carbon for micropollutant removal in advanced wastewater treatment. Water Research, 55: 185–193

[2] Boczkaj G, GäGol M, Klein M, Przyjazny A (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] Boczkaj G, Fernandes A (2017). Wastewater treatment by means of advanced oxidation processes at basic pH conditions: A review. Chemical Engineering Journal, 320: 608–633

[4] Buehler R E, Staehelin J, Hoigne J (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] Busset C, Mazellier P, Sarakha M, de Laat J (2007). Photochemical generation of carbonate radicals and their reactivity with phenol. Journal of Photochemistry and Photobiology A Chemistry, 185(2-3): 127–132

[6] Bustos-Terrones Y, Rangel-Peraza J G, Sanhouse A, Bandala E R, Torres L G (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] Buxton G V, Greenstock C L, Helman W P, Ross A B (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] Caregnato P, Rosso J A, Soler J M, Arques A, Martire D O, Gonzalez M C (2013). Chloride anion effect on the advanced oxidation processes of methidathion and dimethoate: Role of Cl₂^–· radical. Water Research, 47(1): 351–362

[9] Wu C, Linden K G (2010). Phototransformation of selected organophosphorus pesticides: roles of hydroxyl and carbonate radicals. Water Research, 44(12): 3585–3594

[10] Chen Y, Ye J, Chen Y, Hu H, Zhang H, Ou H (2019). Degradation kinetics, mechanism and toxicology of tris(2-chloroethyl) phosphate with 185 nm vacuum ultraviolet. Chemical Engineering Journal, 356: 98–106

[11] Chu W, Ma C W (2000). Quantitative prediction of direct and indirect dye ozonation kinetics. Water Research, 34(12): 3153–3160

[12] Evgeny P, Muhamed M, Domenico S, Lorenzo L, Jussi E (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] Fernandes A, Gągol M, Makoś P, Khan J A, Boczkaj G (2019). Integrated photocatalytic advanced oxidation system (TiO₂/UV/O₃/H₂O₂) for degradation of volatile organic compounds. Separation and Purification Technology, 224: 1–14

[14] Fernandes A, Makoś P, Boczkaj G (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] Gągol M, Przyjazny A, Boczkaj G (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] Haag W R, Yao C C D (1992). Rate constants for reaction of hydroxyl radicals with several drinking water contaminants. Environmental Science & Technology, 26(5): 1005–1013

[17] Lee J W, Won E J, Raisuddin S, Lee J S (2015). Significance of adverse outcome pathways in biomarker-based environmental risk assessment in aquatic organisms. Journal of Environmental Sciences, 35(9): 115–127

[18] Legrini O N, Oliveros E, Braun A M (1993). Photochemical process for water treatment. Chemical Reviews, 93(2): 671–698

[19] Liu H, Sun P, He Q, Feng M, Liu H, Yang S, Wang L, Wang Z (2016a). Ozonation of the UV filter benzophenone-4 in aquatic environments: Intermediates and pathways. Chemosphere, 149: 76–83

[20] Liu Y, He X, Duan X, Fu Y, Fatta-Kassinos D, Dionysiou D D (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] Lutze H V, Kerlin N, Schmidt T C (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] Masten S J, Hoigné J (1992). Comparison of ozone and hydroxyl radical-induced oxidation of chlorinated hydrocarbons in water. Ozone Science and Engineering, 14(3): 197–214

[23] Nagasawa N, Kaneda A, Kanazawa S, Yagi T, Mitomo H, Yoshii F, Tamada M (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] Mazellier P, Busset C, Delmont A, de Laat J (2007). A comparison of fenuron degradation by hydroxyl and carbonate radicals in aqueous solution. Water Research, 41(20): 4585–4594

[25] Rong S, Sun Y (2015). Degradation of TAIC by water falling film dielectric barrier discharge–influence of radical scavengers. Journal of Hazardous Materials, 287: 317–324

[26] Rosenfeldt E J, Linden K G, Canonica S, Von Gunten U (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] Snyder S A, Wert E C, Rexing D J, Zegers R E, Drury D D (2006). Ozone Oxidation of Endocrine Disruptors and Pharmaceuticals in Surface Water and Wastewater. Ozone Science and Engineering, 28(6): 445–460

[28] Staehelin J, Buehler R E, Hoigne J (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] Staehelin J, Hoigne J (1982). Decomposition of ozone in water: Rate of Initiation by hydroxide ions and hydrogen peroxide. Environmental Science & Technology, 16(10): 676–681

[30] Stapf M, Miehe U, Jekel M (2016). Application of online UV absorption measurements for ozone process control in secondary effluent with variable nitrite concentration. Water Research, 104: 111–118

[31] Tomiyasu H, Fukutomi H, Gordon G (1985). Kinetics and mechanism of ozone decomposition in basic aqueous solution. Inorganic Chemistry, 24(19): 2962–2966

[32] Truong G L, Laat J D, Legube B. (2004). Effects of chloride and sulfate on the rate of oxidation of ferrous ion by H₂O₂. Water Research, 38(9): 2384–2393

[33] Vereecken L, Harder H, Novelli A (2014). The reactions of Criegee intermediates with alkenes, ozone, and carbonyl oxides. Physical Chemistry Chemical Physics, 16(9): 4039–4049

[34] Von G U (2007). The basics of oxidants in water treatment. Part B: Ozone reactions. Water Science & Technology, 55(12): 25–29

[35] Yamaura M (2013). Triallyl isocyanurate, triallyl cyanurate and process for producing triallyl isocyanurate. Patent No. US8431697 B2

[36] Yao W, Ur Rehman S W, Wang H, Yang H, Yu G, Wang Y (2018). Pilot-scale evaluation of micropollutant abatements by conventional ozonation, UV/O₃, and an electro-peroxone process. Water Research, 138: 106–117

[37] Zhao H, Chen J, Zhang H, Shang Y, Wang X, Han B, Li Z (2017). Theoretical study on the reaction of triallyl isocyanurate in the UV radiation cross-linking of polyethylene. RSC Advances, 7(59): 37095–37104

RIGHTS & PERMISSIONS

Higher Education Press and Springer-Verlag GmbH Germany, part of Springer Nature