一种席夫碱铜配合物催化过氧化氢氧化降解三氯生
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摘要
利用溶液法,合成了5-硝基水杨醛缩N-苯基邻苯二胺席夫碱及其铜配合物,通过元素分析、紫外可见吸收光谱、红外吸收光谱和X射线电子能谱等技术进行了结构表征和确认.考察了不同条件下该配合物催化过氧化氢氧化降解三氯生的反应,结果表明该配合物能迅速催化过氧化氢氧化降解三氯生.催化反应速度与配合物的用量、过氧化氢的用量和反应温度等因素有关,在起始三氯生浓度0.02 mmol·L~(-1),铜配合物0.05 mmol·L~(-1),过氧化氢1.0 mmol·L~(-1),pH=7.6,反应温度50℃,反应时间为30 min条件下,三氯生的去除率高达80.5%.通过反应过程中反应活性物质的测定,发现降解过程主要涉及羟基自由基的氧化机理.综上结果表明,席夫碱金属配合物可以作为催化剂催化过氧化氢在近中性条件下氧化降解水中三氯生.
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, H_2O_2 concentration, and reaction temperature. At optimal reaction conditions of 0.05 mmol·L~(-1) Cu(Ⅱ)-complex_0, 1.0 mmol·L~(-1) H_2O_2, 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, ~1O_2 and O_2~-, respectively. The results suggested that the Cu(Ⅱ)-complex is a promising catalyst for catalyzing oxidative degradation of TCS by H_2O_2 in aqueous solution under neutral condition.
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, H_2O_2 concentration, and reaction temperature. At optimal reaction conditions of 0.05 mmol·L~(-1) Cu(Ⅱ)-complex_0, 1.0 mmol·L~(-1) H_2O_2, 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, ~1O_2 and O_2~-, respectively. The results suggested that the Cu(Ⅱ)-complex is a promising catalyst for catalyzing oxidative degradation of TCS by H_2O_2 in aqueous solution under neutral condition.
引文
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[2]RICHARDSON S D,TERNES T A.Water analysis:Emerging contaminants and current issues[J].Analytical Chemistry,2014,86:2813-2848.
[3]YOUNG S.FDA examining antibacterial soaps,body washes[EB/CNN Health].[2013-12-17].http://edition.cnn.com/2013/12/16/health/fda-antibacterial/.
[4]Triclosan and Antibiotics Resistance[EB/Green Facts].[2011-10-17].http://copublications.greenfacts.org/en/triclosan/index.htm.
[5]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.
[6]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.
[7]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.
[8]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.
[9]HOUTMAN C J,VAN OOSTVEEN A M,BROUWER A,et al.Identification of Estrogenic Compounds in Fish Bile Using BioassayDirected Fractionation[J].Environmental Science&Technology,2004,38(23):6415-6423.
[10]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.
[11]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.
[12]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.
[13]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.
[14]DAYAN A D.Risk assessment of triclosan[Irgasan]in human breast milk[J].Food and Chemical Toxicology,2007,45(1):125-129.
[15]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).
[16]ORVOS D R,VERSTEEG D J,INAUEN J,et al.Aquatic toxicity of triclosan[J].Environmental Toxicology and Chemistry,2002,21:1338-1349.
[17]TATARAZAKO N,ISHIBASHI H,TESHIMA K,et al.Effects of triclosan on various aquatic organisms[J].Environmental Sciences,2004,11(2):133-140.
[18]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.
[19]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).
[20]DESALVA S J,KONG B M,LIN Y J.Triclosan:A safety profile[J].American Journal of Dentistry,1989,2:185-196.
[21]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.
[22]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).
[23]LYMAN F,FURIA T.Toxicology of 2,4,4'-trichloro-2'-hydroxydiphenyl ether[J].Industrial Medicine and Surgery,1969,38(2):64-71.
[24]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).
[25]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).
[26]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.
[27]YU J C,KWONG T Y,LUO Q,et al.Photocatalytic oxidation of triclosan[J].Chemosphere,2006,65(3):390-399.
[28]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.
[29]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.
[30]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.
[31]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).
[32]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 H2O2catalyzed by the CoLa and Fe Lb[J].Chemical Research and Application,2004,16(1):19-22(in Chinese).
[33]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).
[34]曹婷婷,罗光富,邹彩琼,等.席夫碱铁-Ti O2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/Ti O2complex under visible irradiation[J].Acta Chimica Sinca,2011,69(12):1438-1444(in Chinese).
[35]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).
[36]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).
[37]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.
[38]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.
[39]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.
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