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Solid Phase Extraction of Bisphenol A Using Cu2+ and 1-Hexadecylamine Immobilized ITO Electrode
|關鍵字:||路易士酸鹼引力;Lewis acid-base interaction;固相萃取;雙酚A;Solid phase extraction;Bisphenol A||出版社:||化學工程學系所||引用:||參考文獻  J. Sagiv, Organized Monolayers by Adsorption. 1. Formation and Structure of Oleophobic Mixed Monolayers on Solid Surfaces, Journal of the American Chemical Society 102 (1980) 92.  R.G. Nuzzo, D.L. Allara, Adsorption of Bifunctional Organic Disulfides on Gold Surfaces, Journal of the American Chemical Society 102 (1983) 4481.  E.B. Troughton, C.D. Bain, G.M. Whitesides, R.G. Nuzzo, D.L. Allara, And M.D. Poter, Monolayer Films Prepared by The Spontaneous Self-Assembly of Symmetrical Dialkyl Sulfides from Solution onto Gold Substrates: Structure, Properties, and Reactivity of Constituent Functional Group, Langmuir 4 (1988) 365.  R.G. Nuzzo, L.H. Dobois, D.L. Allara, Fundamental Studies of Microscopic Wetting on Organic Surfaces. 1. Formation and Structural Characterization of a Self-Consistent Series of Polyfunctional Organic Monolayers, Journal of the American Chemical Society 112 (1990) 558.  Z. Li, M. Lieberman, W. Hill, XPS and SERS Study of Silicon Phthalocyanine Monolayers: Umbrella Vs Octopus Design Strategies for Formation of Oriented Sams, Langmuir 17 (2001) 4887.  W. Wang, B. Gu, L. Liang, W.A. Hamilton, Fabrication of Near-Infrared Photonic Crystals Using Highly-Monodispersed Submicrometer SiO2 Spheres, Journal of Physical Chemistry B 107 (2003) 12113.  R. Tian, O. Seitz, M. Li, W. Hu, Y.J. Chabal, J. Gao, Infrared Characterization of Interfacial Si-O Bond Formation on Silanized Flat SiO2/Si Surfaces, Langmuir 26 (2010) 4563.  K. Eder, M.R. Buchmeiser, G.K. Bonn, New Cation-Exchange Resins With High Reversed-Phase Character for Solid-Phase Extraction of Phenols, Journal of Chromatography A 810 (1998) 43.  M.C. Hennion, Solid-Phase Extraction: Method Development, Sorbents, and Coupling with Liquid Chromatography, Journal of Chromatography A 856 (1999) 3.  H. Sabik, R. Jeannot, B. Rondeau, Multiresidue Methods Using Solid-Phase Extraction Techniques for Monitoring Priority Pesticides, Including Triazines and Degradation Products, in Ground and Surface Waters, Journal of Chromatography A 885 (2000) 217.  M.C. Bruzzoniti, C. Sarzanini, E. Mentasti, Preconcentration of Contaminants in Water Analysis, Journal of Chromatography A 902 (2000) 289.  L.A. Reitzel, A. Ledin, Determination of Phenols in Landfill Leachate-Contaminated Groundwaters by Solid-Phase Extraction, Journal of Chromatography A 972 (2002) 175.  R. Westbom, L. Thorneby, S. Zorita, L. Mathiasson, E. Bjorklund, Development of a Solid-Phase Extraction Method for the Determination of Polychlorinated Biphenyls in Water, Journal of Chromatography A 1033 (2004) 1.  A. Lindstrom, A.C. Albertsson, M. Hakkarainen, Development of a Solid-Phase Extraction Method for Simultaneous Extraction of Adipic Acid, Succinic Acid and 1,4-Butanediol Formed During Hydrolysis of Poly (Butylene Adipate) and Poly (Butylene Succinate), Journal of Chromatography A 1022 (2004) 171.  A.H. Elsheikh, A.M. Alzawahreh, J.A. Sweileh, Application of Porous Membrane-Protected Micro-Solid-Phase Extraction Combined With HPLC for the Analysis Of Acidic Drugs in Wastewater, Analytical Chemistry 79 (2007) 6845.  L. Yang, D.S. Jensen, M.A. Vail, A. Dadson, M.R. Linford, Direct Modification of Hydrogen/Deuterium-Terminated Diamond Particles With Polymers to Form Reversed And Strong Cation Exchange Solid Phase Extraction Sorbents, Journal of Chromatography A 1217 (2010) 7621.  K.R. Reid, L.J. Kennedy, E.W. Crick, E.D. Conte, Solid-Phase Extraction Sorbent Consisting of Alkyltrimethylammonium Surfactants Immobilized onto Strong Cation-Exchange Polystyrene Resin, Journal of Chromatography A 975 (2002) 135.  Q. Zhao, S.A. Huss, J.K. Autry, K.R. Reid, E.D. Conte, Investigation of Elutions From a Surfactant Immobilized Solid Phase Extraction Sorbent Based upon the Hydrophobicity of the Trapped Species, Microchemical Journal, 80 (2005) 45.  J.K. Autry, E.G. Vaught, E.D. Conte, Preconcentration of Benzalkonium Chloride Using Sodium Dodecyl Sulfate Attached To a Strong Anion Exchange Resin, Microchemical Journal, 80 (2005) 25.  Q. Zhao, R.T. Philpott, T.D. Oakes, E.D. Conte, Determination of Polyaromatic Hydrocarbons in River Water Using a Sorbent Consisting of Removable Octadecyltrimethylammonium Ions Attached to Cation Exchange Silica in Conjuction with Commercial C18 Silica, Analyst 130 (2005) 750.  T. Kondo, S. Aoshima, K. Honda, Y. Einaga, A. Fujishima, T. Kawai, Fabrication of Covalent SAM/Au Nanoparticle/Boron-Doped Diamond Configurations with a Sequential Self-Assembly Method, Journal Physics Chemistry C 111 (2007) 12650.  N.I. Kovtyukhova, T.E. Mallouk, Electrochemically Assisted Deposition As A New Route to Transparent Conductive Indium Tin Oxide Films, Chemical Materials 22 (2010) 4939.  S. Flink, D.N. Reinhoudt, Functionalization of Self-Assembled Monolayers on Glass and Oxidized Silicon Wafers by Surface Reactions, Journal Physical Organic Chemistry 14 (2001) 407.  M. Kambayashi, J. Zhang, M. Oyama, Crystal Growth of Gold Nanoparticles on Indium Tin Oxides in the Absence and Presence of 3-Mercaptopropyl-Trimethoxysilane, Crystal Growth and Design 5 (2005) 81.  R.M. Pasternack, Sandrine R. Amy, Y.J. Chabal, Attachment of 3-(Aminopropyl)Triethoxysilane on Silicon Oxide Surfaces: Dependence on Solution Temperature, Langmuir 24 ( 2008) 12963.  W.K. Han, G.H. Hwang, Fabrication and Characterization of a Cu Seed Layer on a 60-nm Trench-Patterned SiO2 Substrate By a Self-Assembled-Monolayer (SAM) Process, Applied Surface Science 255 (2009) 6082.  G. Iucci, M. Dettin, Novel Immobilizations of an Adhesion Peptide on the Tio2 Surface: an XPS Investigation, Materials Science and Engineering C 27 (2007) 1201.  P. Silberzan, L. Leger, Silanation of Silica Surfaces. a New Method of Constructing Pure or Mixed Monolayers, Langmuir 7 (1991) 1647.  A.A. Baski, W. Schrepp, Growth of Self-Assembled N-Alkyltrichlorosilane Films on Si ( 100) Investigated by Atomic Force Microscopy, Langmuir 11 (1995) 2143.  T. Vallant, H. Brunner, Formation of Self-Assembled Octadecylsiloxane Monolayers on Mica And Silicon Surfaces Studied by Atomic Force Microscopy and Infrared Spectroscopy, Journal of Physical Chemistry 102 (1998) 7190.  J. Sagiv, Organized Monolayers by Adsorption, I. Formation and Structure of Oleophobic Mixed Monolayers on Solid Surfaces, Journal of the American Chemical Society 102 (1980) 93.  T. Kang, S. Kang, Fabrication of Reusable Sensor for Detection of Cu2+ in an Aqueous Solution Using a Self-Assembled Monolayer with Surface Plasmon Resonance Spectroscopy, Chemistry Communication 27 (2005) 3723.  S. Oh, T. Kang, Preparation of Novel Ceramic Membranes Modified by Mesoporous Silica with 3-Aminopropyltriethoxysilane (APTES) and Its Application to Cu2+ Separation in the Aqueous Phase, Journal of Membrane Science 301 (2007) 118.  S. Liang, M. Chen, Deposition Behaviors and Patterning of TiO2 Thin Films on Different Sams Surfaces from Titanium Sulfate Aqueous Solution, Colloids and Surfaces A 324 (2008) 137.  D. Aiello, F. Testa, Absolute Emission Quantum Yield Determination of Self-Assembled Mesoporous Titania Films Grafted with a Luminescent Zinc Complex, Inorganic Chemistry Communications 12 (2009) 237.  Y.Y. Song, H. Hildebrand, P. Schmuki, Optimized Monolayer Grafting of 3-Aminopropyltriethoxysilane onto Amorphous, Anatase and Rutile TiO2, Surface Science 604 (2010) 346.  G.N. Lewis, The Atom and the Molecule, Journal of the American Chemical Society 34 (1916) 763.  B.C. Trammell, M.A. Hillmyer, P.W. Carr, A Study of the Lewis Acid-Base Interactions of Vinylphosphonic Acid-Modified Polybutadiene-Coated Zirconia, Analytical Chemistry 73 (2001) 3323.  C. Laurence, J. Graton, J.F. Gal, an Overview of Lewis Basicity and Affinity Scales, Journal of Chemical Education 88 (2011) 1651.  A.A. Fiorillo, J.M. Galbraith, A Valence Bond Description of Coordinate Covalent Bonding, Journal of Physical Chemistry A 108 (2004) 5126.  I. Adato, A.H. Bassat, S. Sarel, Metal-Ligand Bonding in Copper(II) Chelates-an Electron Paramagnetic Resonance Study, Journal of Physical Chemistry 26 (1971) 3828.  J.C. Schulz, G.G. Warr, Adsorbed Layer Structure of Cationic and Anionic Surfactants on Mineral Oxide Surfaces, Langmuir 18 ( 2002) 3191.  B. Vercelli, G. Zotti, G. Schiavon, S. Zecchin, Adsorption of Hexylferrocene Phosphonic Acid on Indium-Tin Oxide Electrodes. Evidence of Strong Interchain Interactions in Ferrocene Self-Assembled Monolayers, Langmuir 19 (2003) 9351.  F. Li, Y. Zu, Effect of Nonionic Fluorosurfactant on the Electrogenerated Chemiluminescence Tris (2,2’-Bipyridine) Ruthenium(II) / Tri-N-Propylamine System: Lower Oxidation Potential and Higher Emission Intensity, Analytical Chemistry 76 (2004) 1768.  L.L. Norman, A. Badia, Electrochemical Surface Plasmon Resonance Investigation of Dodecyl Sulfate Adsorption to Electroactive Self-Assembled Monolayers Via Ion-Pairing Interactions, Langmuir 23 (2007) 10198.  M. Brust, P.M. Blass, A.J. Bard, Self-Assembly of Photoluminescent Copper(I)-Dithiol Multilayer Thin Films and Bulk Materials, Langmuir 13 (1997) 5602.  T.L. Brower, M. Cook, A. Ulman, Mixed Self-Assembled Multilayer of 4,4’-Dimercaptobiphenyl and 1,8-Octanedithiol, Journal of Physical Chemistry B 107 (2003) 11721.  Z. Nagy, J.P. Blaudeau, N.C. Hung, Chloride Ion Catalysis of the Copper Deposition Reaction, Journal of The Electrochemical Society 142 (1995) 87.  W.P. Dow, H.S. Huang, M.Y. Yen, H.H. Chen, Roles of Chloride Ion in Microvia Filling by Copper Electrodeposition, Journal of the Electrochemical Society 152 (2005) 77.  G.B. Seetharam, B.A. Saville, Degradation of Phenol Using Tyrosinase Immobilized on Siliceous Supports, Water Research 37 (2003) 436.  曹功勳，改質黏土吸附酚類化合物之平衡與動力學，碩士論文，元智大學化學工程研究所，中壢，台灣，2002。  G.B. Seetharam, B.A. Saville, Degradation of Phenol Using Tyrosinase Immobilized on Siliceous Supports, Water Research 37 (2003) 436.  I.B. Toledo, M.A. Garcia, J.R. Utrilla, Bisphenol A Removal from Water by Activated Carbon. Effects of Carbon Characteristics and Solution Chemistry, Environmental Science Technology 39 (2005) 6246.  N. Li, H.K. Lee, Trace Enrichment of Phenolic Compounds from Aqueous Samples by Dynamic Ion-Exchange Solid-Phase Extraction, Analytical Chemistry 69 (1997) 5193.  黃壬瑰，環境荷爾蒙－雙酚A，環檢新知43期，行政院環保署環境檢驗所，桃園，台灣，2002。  賴麗瑩，談環境荷爾蒙，環檢新知22期，行政院環保署管考處，台北，台灣，1999。  H. Frommea, T. Kuchler, T. Otto, K. Pilz, J. Muller, A Wenzel, Occurrence of Phthalates and Bisphenol A and Fin the Environment, Water Research 36 (2002) 1429.  T. Kubo, K. Hosoya, Y. Watabe, T. Ikegami, N. Tanaka, T. Sano, K. Kaya, Polymer-Based Adsorption Medium Prepared Using a Fragment Imprinting Technique for Homologues of Chlorinated Bisphenol A Produced in the Environment, Journal of Chromatography A 1029 (2004) 37.  V. Granek, J. Rishpon, Detecting Endocrine-Disrupting Compounds by Fast Impedance Measurements Environmental, Science Technology 36 (2002) 1574.  K.C. Wang, Y.F. Lin, C.H. Qin, T.L. Chen, C.H. Chen, Bisphenol A Interferes with Estradiol-Mediated Protection in Osteoarthritic Chondrocytes, Toxicology Letters 198 (2010) 127.  N. Simpson, Solid Phase Extraction: Principles, Strategies, and Application, Marcel Dekker, New York, 1998.  D.L. Mayer, J.S. Fritz, Silicalite as a Sorbent for Solid Phase Extraction, Journal of Chromatography A 771 (1997) 45.  Y.Z. Luo, M. Adams, J. Pawliszyn, Kinetic Study of Membrane Extraction with A Sorbent Interface for Solution Analysis, Analytical Chemistry 70 (1998) 248.  J.F. Pankow, M.P. Ligocki, M.E. Rosen, Adsorption/Thermal Desorption with Small Cartridges for the Determination of Trace Aqueous Semivolatile Organic Compounds, Analytical Chemistry 60 (1988) 40.  S.S. Datwani, V.N. Truskett, C.A. Rosslee, Redox-Dependent Surface Tension and Surface Phase Transitions of a Ferrocenyl Surfactant: Equilibrium and Dynamic Analyses with Fluorescence Images, Langmuir 19 (2003) 8292.  Q. Li, H. Li, G.F. Du, Z.H. Xu, Electrochemical Detection of Bisphenol A Mediated by [Ru(Bpy)3] 2+ on an ITO Electrode, Journal of Hazardous Materials 180 (2010) 703.||摘要:||
本研究發展一透過氧化/還原以濃縮疏水分析物的固相萃取程序，吸附劑基材則選用ITO 導電玻璃。先於ITO 導電玻璃表面鍵結胺基矽烷APTES，使表面形成末端胺基。藉由此末端胺基進行路易士酸鹼反應，以固定銅離子於ITO 玻璃上。下一步同樣經由路易士酸鹼反應，使銅離子與烷基胺HDA (十六烷基胺) 反應。由此，烷基即暴露在玻璃表面，藉而完成具有疏水與導電性的固相萃取吸附劑之製備。此疏水固相萃取吸附劑應用於批次雙酚A吸附。當使用500 ml、1 ppm雙酚 A水溶液時，所得吸附率為85 %。將此疏水固相萃取吸附劑ITO 璃當作工作電極，放入10 ml、0.1 M KCl、5 % 甲醇水溶液中，利用循環伏安機進行脫附。此方式可讓固定於玻璃表面的銅離子還原成零價銅，從而打斷路易士酸鹼作用。同時，吸附於其上的雙酚A 與HDA 一起被脫附至KCl 溶液中。電化學還原快速，且僅需很少量有機溶劑，因此本研究提出的方法符合經濟效率與環保訴求。脫附後，雙酚A濃度為42 ppm，顯示本法可完全脫附雙酚A，且濃縮倍率為42倍。藉由電化學法將沉積在ITO 玻璃上的零價銅氧化回銅離子，並再次進行烷基胺反應，即可簡易地再製備得疏水固相萃取吸附劑。此烷基胺-銅離子-胺基矽烷層可移除，但也很容易再生。本研究連續重複整個循環 (包括：雙酚A吸附、脫附、吸附劑再生) 5次，結果顯示吸附劑的再使用效果一致。
In this study is a SPE process via oxidation/reduction for hydrophobic analyte enrichment. The base material of SPE sorbent is a conductive glass, ITO glass. First, the ITO glass was coupled with the amine terminals, copper ions weir immobilized onto the ITO glass. The next step was to react the immobilized copper ions on ITO glass with an alkylamine HDA (hexadecylamine), similarly through Lewis acid-base interaction, for exposing the alkyl chains on the glass surface. Accordingly, a hydrophobic and conductive SPE sorbent was produced. The hydrophobic SPE sorbent was applied in batch adsorption of Bisphenol A. The adsorption percentage was 85 % when 500 ml of 1 ppm Bisphenol A was introduced to an ITO glass with the HDA-Cu2+-APTES layer the desorption stage was carried out by applying an electrical potential to the ITO glass (as working electrode) in 10 ml of 0.1 M KCl with 5% methanol using cyclic voltammetry. In this way the immobilized copper ions were reduced to zero-valent copper. thus breaking the Lewis acid-base interaction. At the same time, the adsorbed Bisphenol A was eluted together with HDA into the KCl solution. Since electrochemical reduction is fast and very little quantity of organic solvent is required, this method is time-efficient and environmentally-friendly. The desorbed Bisphenol A had a concentration of 42 ppm, indicating that the desorption was nearly complete and a 42-fold enrichment of Bisphenol A was achieved. The SPE sorbent could be easily regenerated by oxidizing the zero-valent copper deposited on ITO glass back to copper ions in the electrochemical cell and then re-conducting the alkyl amine reaction. The HDA-Cu2+-APTES layer is removable but also simply redeveloped. The cycle consisting of Bisphenol A adsorption, desorption, and sorbent regeneration was repeated five times in sequence and the sorbent reuse efficiency was not deteriorated at all.
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