Environmental Chemistry

ISSN 0254-6108

CN 11-1844/X

Vol. 38 No. 5
May  2019
Article Contents

Citation:

Oxidative removal of triclosan with hydrogen peroxide catalyzed by a Schiff base Cu(Ⅱ)-complex

  • Received Date: 2018-07-10
    Fund Project:

    Supported by the China Postdoctoral Science Foundation (2018M632783), the Science Foundation of Henan Normal University (5101219170124, 5101219170307, 5101219470210), the National Natural Science Foundation of China (21577059, 41807129), the Central Public Welfare Scientific Research Institute of Basic Scientific Research Business Special (GYZX180210) and the Open Foundation of State Key Laboratory of Pollution Control and Resource Reuse(PCRRF18028).

  • A Schiff base from the condensation of 5-nitrosalicylaldehyde with N-phenyl-o-phenylenediamine and its Cu(Ⅱ)-complex were synthesized by solution method. The structure and chemical composition of the Schiff base and its Cu(Ⅱ)-complex were characterized with various techniques including elemental analysis (EA), UV-Vis absorption spectroscopy (UV), Fourier-transform infrared spectroscopy (FT-IR), and X-ray photoelectron spectroscopy (XPS). Catalytic degradation of triclosan (TCS) by hydrogen peroxide in the presence of the Cu(Ⅱ)-complex was evaluated under various conditions. The results revealed that the Cu(Ⅱ)-complex showed good catalytic performance on the degradation of TCS. The TCS removal efficiency increased with the increase of Cu(Ⅱ)-complex concentration, H2O2 concentration, and reaction temperature. At optimal reaction conditions of 0.05 mmol·L-1 Cu(Ⅱ)-complex0, 1.0 mmol·L-1 H2O2, 0.02 mmol·L-1 TCS, pH 7.6, and at temperature 50℃, TCS was removed by 80.5% within 30 min. The dominant reactive oxygen species (ROS) involved in the reaction was identified as ·OH radical using 2-propanol, sodium azide, and nitro blue tetrazolium as scavengers for ·OH, 1O2 and O2-, respectively. The results suggested that the Cu(Ⅱ)-complex is a promising catalyst for catalyzing oxidative degradation of TCS by H2O2 in aqueous solution under neutral condition.
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  • [1] DANN A B, HONTELA A. Triclosan:Environmental exposure, toxicity and mechanisms of action[J]. Journal of Applied Toxicology, 2011, 31(4):285-311.
    [2] RICHARDSON S D, TERNES T A. Water analysis:Emerging contaminants and current issues[J]. Analytical Chemistry, 2014, 86:2813-2848.
    [3] ZHAO J L, ZHANG Q Q, CHEN F, et al. Evaluation of triclosan and triclocarban at river basin scale using monitoring and modeling tools:Implications for controlling of urban domestic sewage discharge[J]. Water Research, 2013, 47(1):395-405.
    [4] COOGAN M A, EDZIVIE R E, LA POINT T W, et al. Algal bioaccumulation of triclocarban, triclosan, and methyl-triclosan in a North Texas wastewater treatment plant receiving stream[J]. Chemosphere, 2007, 67(10):1911-1918.
    [5] COOGAN M A, LA POINT T W. Snail bioaccumulation of triclocarban, triclosan, and methyltriclosan in a north texas, usa, stream affected by wastewater treatment plant runoff[J]. Environmental Toxicology and Chemistry, 2008, 27(8):1788-1793.
    [6] ADOLFSSON-ERICI M, PETTERSSON M, PARKKONEN J, et al. Triclosan, a commonly used bactericide found in human milk and in the aquatic environment in Sweden[J]. Chemosphere, 2002, 46(9-10):1485-1489.
    [7] HOUTMAN C J, VAN OOSTVEEN A M, BROUWER A, et al. Identification of Estrogenic Compounds in Fish Bile Using Bioassay-Directed Fractionation[J]. Environmental Science & Technology, 2004, 38(23):6415-6423.
    [8] RUDEL H, BOHMER W, MULLER M, et al. Retrospective study of triclosan and methyl-triclosan residues in fish and suspended particulate matter:Results from the German environmental specimen bank[J]. Chemosphere, 2013, 91(11):1517-1524.
    [9] VALTERS K, LI H, ALAEE M, et al. Polybrominated diphenyl ethers and hydroxylated and methoxylated brominated and chlorinated analogues in the plasma of fish from the detroit river[J]. Environmental Science & Technology, 2005, 39(15):5612-5619.
    [10] BENNETT E R, ROSS P S, HUFF D, et al. Chlorinated and brominated organic contaminants and metabolites in the plasma and diet of a captive killer whale (Orcinus orca)[J]. Marine Pollution Bulletin, 2009, 58(7):1078-1083.
    [11] ALLMYR M, ADOLFSSON-ERICI M, MCLACHLAN M S, et al. Triclosan in plasma and milk from Swedish nursing mothers and their exposure via personal care products[J]. Science of the Total Environment, 2006, 372(1):87-93.
    [12] DAYAN A D. Risk assessment of triclosan[Irgasan®] in human breast milk[J]. Food and Chemical Toxicology, 2007, 45(1):125-129.
    [13] 米丽娟. 三氯生消毒相关性能研究进展[J]. 中国消毒学杂志, 2016, 33(1):76-79. MI LJ. Research progress on the performances related to triclosan disinfection[J]. Chinese Journal of Disinfection, 2016, 33(1):76-79(in Chinese).
    [14] ORVOS D R, VERSTEEG D J, INAUEN J, et al. Aquatic toxicity of triclosan[J]. Environmental Toxicology and Chemistry, 2002, 21:1338-1349.
    [15] TATARAZAKO N, ISHIBASHI H, TESHIMA K, et al. Effects of triclosan on various aquatic organisms[J]. Environmental Sciences, 2004, 11(2):133-140.
    [16] WILSON B A, SMITH V H, DENOYELLES F, et al. Effects of three pharmaceutical and personal care products on natural freshwater algal assemblages[J]. Environmental Science & Technology, 2003, 37(9):1713-1719.
    [17] 董玉瑛,王翔,邹学军,等. 三氯生对东北林蛙蝌蚪的急慢性毒性分析[J]. 大连民族大学学报, 2016, 18(1):11-14. DONG Y Y, WANG X, ZOU X J, et al. Analysis on acute and sub-chronic toxicity of triclosan to the Northeast Frog Tadpoles[J]. Journal of Dalian Minzu University, 2016, 18(1):11-14(in Chinese).
    [18] DESALVA S J, KONG B M, LIN Y J. Triclosan:A safety profile[J]. American Journal of Dentistry, 1989, 2:185-196.
    [19] FRAKER S L, SMITH G R. Direct and interactive effects of ecologically relevant concentrations of organic wastewater contaminants on Rana pipiens tadpoles[J]. Environmental Toxicology, 2004, 19(3):250-256.
    [20] 王凤花,贾文,张庆泉,等. 三氯生对土壤酶活性的影响[J]. 环境科学与技术, 2014, 37(8):36-40. WANG F H, JIA W, ZHANG Q Q, et al. Effects of triclosan on soil enzyme activities[J]. Environmental Science & Technology, 2014, 37(8):36-40(in Chinese).
    [21] LYMAN F, FURIA T. Toxicology of 2,4,4'-trichloro-2'-hydroxydiphenyl ether[J]. Industrial Medicine and Surgery, 1969, 38(2):64-71.
    [22] 杨倩兰,王育. 三氯生对人早孕滋养细胞11-βHSD2和HLA-G表达的影响[J]. 上海交通大学学报(医学版), 2016, 36(6):787-792. YANG Q L, WANG Y. Effects of triclosan on expression of 11-βHSD2 and HLA-G in human first trimester trophoblasts[J]. Journal of Shanghai Jiao Tong University (Medical Science), 2016, 36(6):787-792(in Chinese).
    [23] 李林朋,马慧敏,胡俊杰,等.三氯生和三氯卡班对人体干细胞DNA损伤的研究[J]. 生态环境学报,2010, 19(12):2897-2901. LI L P, MA H M, HU J J, et al. The genotoxicity of triclosan and triclocarban in human hepatocyte L02 cell[J]. Ecology and Environmental Sciences, 2010, 19(12):2897-2901(in Chinese).
    [24] SANCHEZ PRADO L, BARRO R, GARCIA JARES C, et al. Sonochemical degradation of triclosan in water and wastewater[J]. Ultrasonics Sonochemistry, 2008, 15(5):689-694.
    [25] YU J C, KWONG T Y, LUO Q, et al. Photocatalytic oxidation of triclosan[J]. Chemosphere, 2006, 65(3):390-399.
    [26] CHEN X J, RICHARD J, LIU Y L, et al. Ozonation products of triclosan in advanced wastewater treatment[J]. Water Research, 2012, 46(7):2247-2256.
    [27] SIRES I, OTURAN N, OTURAN M A, et al. Electro-Fenton degradation of antimicrobials triclosan and triclocarban[J]. Electrochimica Acta, 2007, 52(17):5493-5503.
    [28] MELO CF, DEZOTTI M. Evaluation of a horseradish peroxidase-catalyzed process for triclosan removal and antibacterial activity reduction[J]. Journal of Chemical Technology & Biotechnology, 2013, 88(5):930-936.
    [29] 雷亮,熊国宣,王银柱,等. 席夫碱及其金属配合物性能研究进展[J]. 化工新型材料,2012,40(2):16-20. LEI L, XIONG G X, WANG Y Z, et al. Research progress of Schiff bases and their complexes[J]. New Chemical Materials, 2012, 40(2):16-20(in Chinese).
    [30] 向庆华,李建章,谢家庆,等. Schiff碱配合物催化过氧化氢氧化苯酚的动力学研究[J]. 化学研究与应用,2004,16(1):19-22. XIANG Q H, LI J Z, XIE J Q, et al. The kinetic study on the oxidative reaction between phenol and H2O2 catalyzed by the CoLa and FeLb[J]. Chemical Research and Application, 2004, 16(1):19-22(in Chinese).
    [31] 刘峥,金黎霞,雍舒. 3, 5-二溴水杨醛缩乙醇胺席夫碱铜配合物的制备及其仿酶催化活性研究[J]. 化学与生物工程, 2008, 25(5):31-34. LIU Z, JIN L X, YONG S. Study on synthesis of copper complex of ethanolamine-3,5-dibromosalicylaldehyde schiff base and its biological activity as mimic enzyme[J]. Chemistry & Bioengineering, 2008, 25(5):31-34(in Chinese).
    [32] 曹婷婷,罗光富,邹彩琼,等. 席夫碱铁-TiO2复合物光催化降解有毒有机污染物[J]. 化学学报, 2011, 69(12):1438-1444. CAO TT, LUO GF, ZOU CQ, et al. Degradation of toxic organic pollutants by iron(Ⅲ) schiff-base/TiO2 complex under visible irradiation[J]. Acta Chimica Sinca, 2011, 69(12):1438-1444(in Chinese).
    [33] 冯辉霞,高晓红,陈娜丽,等. 钴-席夫碱-壳聚糖/凹凸棒土对苯乙烯环氧化的催化性能[J]. 应用化学,2014,31(2):159-164. FENG H X, GAO X H, CHEN N L, et al. Catalytic performance of cobalt-schiff base-chitosan/attapulgite for epoxidation of styrene[J]. Chinese Journal of Applied Chemistry, 2014, 31(2):159-164(in Chinese).
    [34] 刘晓,王涛,张晨,等.Co(Ⅱ)-席夫碱配合物在水溶液中催化苯甲醇氧化制苯甲醛的研究[J]. 石油化工,2015,44(12):1467-1474. LIU X, WANG T, ZHANG C, et al. Aerobic oxidation of benzyl alcohol to benzaldehyde with Co(Ⅱ)-schiff base complex catalysts in aqueous solution[J]. Petrochemical Technology, 2015, 44(12):1467-1474(in Chinese).
    [35] ARND V, HORST K. Ligand-to-ligand and intraligand charge transfer and their relation to charge transfer interactions in organic zwitterions[J]. Coordination Chemistry Reviews, 2007, 251(3-4):577-583.
    [36] REFAT M S, EL-SAYED M Y, ADAM A M A. Cu(Ⅱ), Co(Ⅱ) and Ni(Ⅱ) complexes of new schiff base ligand:Synthesis, thermal and spectroscopic characterizations[J]. Journal of Molecular Structure, 2013, 1038:62-72.
    [37] ELSHERBINY AS, EL-GHAMRY HA. Synthesis, characterization, and catalytic activity of new Cu(Ⅱ) complexes of schiff base:Effective catalysts for decolorization of Acid Red 37 dye solution[J]. International Journal of Chemical Kinetics, 2015, 47(3):162-172.
    [38] DHANARAJ CJ, JOHNSON J. Synthesis, characterization, electrochemical and biological studies on some metal(Ⅱ) schiff base complexes containing quinoxaline moiety[J]. Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy, 2014, 118:624-631.
    [39] PIGNATELLO JJ, OLIVEROS E, MACKAY A, Advanced oxidation processes for organic contaminant destruction based on the Fenton reaction and related chemistry[J]. Critical Reviews in Environmental Science and Technology, 2006, 36(1):1-84.
    [40] KIM S, CHOI W. Kinetics and mechanisms of photocatalytic degradation of (CH3)nNH4-n+ (0≤ n ≤ 4) in TiO2 suspension:The role of OH radicals[J]. Environmental Science & Technology, 2002, 36(9):2019-2025.
    [41] XU AH, LI XX, XIONG H, et al. Efficient degradation of organic pollutants in aqueous solution with bicarbonate-activated hydrogen peroxide[J]. Chemosphere, 2011, 82(8):1190-1195.
    [42] PHAM AN, XING GW, MILLER CJ, et al. Fenton-like copper redox chemistry revisited:Hydrogen peroxide and superoxide mediation of copper-catalyzed oxidant production[J]. Journal of Catalysis, 2013, 301:54-64.
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Oxidative removal of triclosan with hydrogen peroxide catalyzed by a Schiff base Cu(Ⅱ)-complex

  • 1. Henan Key Laboratory for Environmental Pollution Control, Key Laboratory for Yellow River and Huai River Water Environment and Pollution Control, Ministry of Education, School of Environment, Henan Normal University, Xinxiang, 453007, China;
  • 2. State Key Laboratory of Pollution Control and Resource Reuse, School of the Environment, Nanjing University, Nanjing, 210023, China;
  • 3. Nanjing Institute of Environmental Sciences, Ministry of Ecology and Environment of the People's Republic of China, Nanjing, 210042, China
Fund Project:  Supported by the China Postdoctoral Science Foundation (2018M632783), the Science Foundation of Henan Normal University (5101219170124, 5101219170307, 5101219470210), the National Natural Science Foundation of China (21577059, 41807129), the Central Public Welfare Scientific Research Institute of Basic Scientific Research Business Special (GYZX180210) and the Open Foundation of State Key Laboratory of Pollution Control and Resource Reuse(PCRRF18028).

Abstract: A Schiff base from the condensation of 5-nitrosalicylaldehyde with N-phenyl-o-phenylenediamine and its Cu(Ⅱ)-complex were synthesized by solution method. The structure and chemical composition of the Schiff base and its Cu(Ⅱ)-complex were characterized with various techniques including elemental analysis (EA), UV-Vis absorption spectroscopy (UV), Fourier-transform infrared spectroscopy (FT-IR), and X-ray photoelectron spectroscopy (XPS). Catalytic degradation of triclosan (TCS) by hydrogen peroxide in the presence of the Cu(Ⅱ)-complex was evaluated under various conditions. The results revealed that the Cu(Ⅱ)-complex showed good catalytic performance on the degradation of TCS. The TCS removal efficiency increased with the increase of Cu(Ⅱ)-complex concentration, H2O2 concentration, and reaction temperature. At optimal reaction conditions of 0.05 mmol·L-1 Cu(Ⅱ)-complex0, 1.0 mmol·L-1 H2O2, 0.02 mmol·L-1 TCS, pH 7.6, and at temperature 50℃, TCS was removed by 80.5% within 30 min. The dominant reactive oxygen species (ROS) involved in the reaction was identified as ·OH radical using 2-propanol, sodium azide, and nitro blue tetrazolium as scavengers for ·OH, 1O2 and O2-, respectively. The results suggested that the Cu(Ⅱ)-complex is a promising catalyst for catalyzing oxidative degradation of TCS by H2O2 in aqueous solution under neutral condition.

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