Cyanided Covalent Triazine Frameworks with Enhanced Adsorption Capability Toward Chloranil

Abstract

Porous polymer (pyrrolopyrrole) was successfully prepared via domino-ring-formation reaction. The chemical-physical properties of cyanided covalent triazine frameworks (CTF-CN) were characteriazed by fourier transform infrared spectra (FT-IR), scanning electron microscopy (SEM), nuclear magnetic resonance (NMR), specific surface area analyzer (BET) and thermogravimetric analysis (TGA), respectively. The experimental results of adsorption of chloranil (TCBQ) in aqueous solution indicated that CTF-CN exhibited distinctive adsorption capacity toward TCBQ owing to its large specific surface area. Specifically, the adsorption equilibrium of as-prepared polymer was executed within 5 h and the calculated adsorption capacity was 499.76 mg/g. Furthermore, the adsorption kinetics could be well defined with the linear pseudo-second-order model, which implies that the chemical interaction are relative important in the course of TCBQ removal. Finally, the current studies verify that CTF-CN has unique rigid and nano-porous framework structure, which can be employed for the treatment of a series of harmful aromatic substances.

Keywords

disinfection by-products (DBPs) / adsorbent / haloquinones / covalent triazine frameworks

References

[1] Ning H, Lipeng Z, Hong X, et al. Stable Covalent Organic Frameworks for Exceptional Mercury Removal from Aqueous Solutions[J]. J. Am. Chem. Soc., 2017, 139(6): 2 428-2 434.

[2] Liu Q, Miao L, Zhang F, et al. The Removal of Trimethoprim and Sulfamethoxazole by a High Infiltration Rate Artificial Composite Soil Treatment System[J]. Frontiers of Environmental Science & Engineering, 2017, 11(2): 12-12.

[3] Zhao X, Cai Y, Wang T, et al. Preparation of Alkanethiolate-Functionalized Core/Shell Fe₃O₄@ Au Nanoparticles and Its Interaction with Several Typical Target Molecules[J]. Analytical Chemistry, 2008, 80(23): 9 091-9 096.

[4] Tahir N, Krishnaraj C, Leus K, et al. Development of Covalent Triazine Frameworks as Heterogeneous Catalytic Supports[J]. Polymers (Basel)., 2019, 11: 1 326.

[5] Cao S, Zhang Y, He N, et al. Metal-free 2D/2D Heterojunction of Covalent Triazine-Based Frameworks/Graphitic Carbon Nitride with Enhanced Interfacial Charge Separation for Highly Efficient Photocatalytic Elimination of Antibiotic Pollutants[J]. J Hazard Mater., 2020, 391: 122 204.

[6] Aslani H, Nabizadeh R, Alimohammadi M, et al. Disinfection of Raw Wastewater and Activated Sludge Effluent using Fenton Like Reagent[J]. J. Environ. Health Sci. Eng., 2014, 12(1): 149

[7] Zhao Y, Anichina J, Lu X, et al. Occurrence and Formation of Chloroand Bromo-Benzoquinones During Drinking Water Disinfection[J]. Water Res., 2012, 46(14): 4 351-4 360.

[8] Bond T, Goslan EH, Parsons SA, et al. A Critical Review of Trihalo-methane and Haloacetic Acid Formation from Natural Organic Matter Surrogates[J]. Environmental Technology Reviews., 2012, 1(1): 93-113.

[9] Cortes C, Marcos R. Genotoxicity of Disinfection Byproducts and Disinfected Waters: A Review of Recent Literature[J]. Mutat. Res. Genet. Toxicol Environ. Mutagen., 2018, 831: 1-12.

[10] Qin F, Zhao YY, Zhao Y, et al. A Toxic Disinfection By-product, 2,6-Dichloro-1,4-Benzoquinone, Identified in Drinking Water[J]. Angew Chem. Int. Ed. Engl., 2010, 49(4): 790-792.

[11] Wang W, Moe B, Li J, et al. Analytical Characterization, Occurrence, Transformation, and Removal of the Emerging Disinfection Byproducts Halobenzoquinones in Water[J]. TrAC Trends in Analytical Chemistry, 2016, 85: 97-110.

[12] Kosaka K, Nakai T, Hishida Y, et al. Formation of 2,6-Dichloro-1, 4-Benzoquinone from Aromatic Compounds After Chlorination[J]. Water Res., 2017, 110: 48-55.

[13] Grellier J, Rushton L, Briggs DJ, et al. Assessing the Human Health Impacts of Exposure to Disinfection By-products—a Critical Review of Concepts and Methods[J]. Environ. Int., 2015, 78: 61-81.

[14] Zuo YT, Hu Y, Lu WW, et al. Toxicity of 2,6-Dichloro-1,4-Benzoquinone and Five Regulated Drinking Water Disinfection By-products for the Caenorhabditis Elegans Nematode[J]. J. Hazard Mater., 2017, 321: 456-63.

[15] Prochazka E, Escher BI, Plewa MJ, et al. In Vitro Cytotoxicity and Adaptive Stress Responses to Selected Haloacetic Acid and Halobenzoquinone Water Disinfection Byproducts[J]. Chem. Res. Toxicol., 2015, 28(10): 2 059-2 068.

[16] Diemert S, Wang W, Andrews RC, et al. Removal of Halo-benzoquinone (Emerging Disinfection By-product) Precursor Material from Three Surface Waters Using Coagulation[J]. Water Res., 2013, 47(5): 1773-1882.

[17] Sillanpaa M, Ncibi MC, Matilainen A, et al. Removal of Natural Organic Matter in Drinking Water Treatment by Coagulation: A Comprehensive Review[J]. Chemosphere., 2018, 190: 54-71.

[18] Jiang J, Li W, Zhang X, et al. A New Approach to Controlling Halogenated DBPs by GAC Adsorption of Aromatic Intermediates from Chlorine Disinfection: Effects of Bromide and Contact Time[J]. Separation and Purification Technology, 2018, 203: 260-267.

[19] Kourounioti E, Psillakis E, Vione D. UV-induced Transformation of 2,3-Dibromo-5,6-Dimethyl-1,4-Benzoquinone in Water and Treated Wastewater[J]. Environ. Res., 2019, 175: 343-350.

[20] Ding Q, Sui R, Liu X, et al. Adsorption of Pb(II) in Water by Niobate/Titanate Nanoflakes[J]. Journal of Wuhan University of Technology-Mater. Sci. Ed., 2020, 35(4): 726-732.

[21] Liu J, Zong E, Fu H, et al. Adsorption of Aromatic Compounds on Porous Covalent Triazine-Based Framework[J]. Journal of Colloid & Interface Science, 2012, 372(1): 99-107.