研究生: |
王星翰 Wang, Sing-Han |
---|---|
論文名稱: |
纖維電噴灑游離質譜法結合線上微萃取濃縮技術對嘉磷塞的分析與研究 Applications of an on-line microextraction method for use in the analysis of glyphosate based on fiber-spray/mass spectrometry |
指導教授: |
林震煌
Lin, Cheng-Huang |
學位類別: |
碩士 Master |
系所名稱: |
化學系 Department of Chemistry |
論文出版年: | 2018 |
畢業學年度: | 106 |
語文別: | 中文 |
論文頁數: | 72 |
中文關鍵詞: | 嘉磷塞 、中空纖維 、液-液微萃取 |
英文關鍵詞: | glyphosate, hollow fiber, liquid-liquid microextration |
DOI URL: | http://doi.org/10.6345/THE.NTNU.DC.005.2018.B05 |
論文種類: | 學術論文 |
相關次數: | 點閱:146 下載:6 |
分享至: |
查詢本校圖書館目錄 查詢臺灣博碩士論文知識加值系統 勘誤回報 |
為了分析嘉磷塞,本研究開發了結合線上微萃取濃縮技術及纖維電噴灑游離質譜法的方法,本研究利用2毫升樣品瓶(儲存樣品溶液)及一小段中空纖維管(用來進行萃取, 3.5公分長, 外徑/內徑, 1.0 mm/0.6 mm)製作裝置,此微萃取裝置可架設於電噴灑游離源與質譜口之間,分析物能利用中空纖維液相微萃取操作過程,從稀的溶液被提取出來,被提取出來的分析物會透過擴散移動到纖維外,濃縮的分析物被蒸發並通過多孔表面逸出,同時間,由電噴灑游離源產生帶電液珠,一旦來自中空纖維表面(大部分為中性)的蒸發物質遇到電噴霧,游離化便會發生。本實驗用於液相微萃取的液膜為體積比octanol:Aliquat 336:dodecane = 0.4:1:8.6,萃取溶液為0.1 M HCL,利用此方法最低偵測極限可以達到1 ng/mL。當使用攪拌子攪拌時,萃取時間可以從60分鐘減少至僅15分鐘。
For the analysis of glyphosate, a novel method based on the combination of on-line microextraction and fiber-spray/mass spectrometry was developed. A microextraction kit was designed for this purpose, in which a 2 mL sample vial (reservoir for the sample solution) and a piece of a porous polypropylene hollow fiber (for sample extraction; 3.5 cm in length; O.D./I.D., 1.0/0.6 mm, respectively) were used, respectively. The microextraction kit was located between the mass inlet and the ESI needle. Analytes can be extracted from a very dilute solution operating the so-called hollow fiber liquid phase microextraction process, and the resulting extract then moves to the outside portion of the fiber by diffusion. Following this, the concentrated analytes were evaporated and escape through the porous surface. Meanwhile, the electrosprayed/charged droplets are produced from a regular ESI stainless needle. Once the evaporated materials from the surface of the hollow fiber (mostly neutral) meet the electrospray plume, ionization occurs under ambient conditions. In order to process liquid-phase microextraction, the membrane solution (0.2 M Aliquat 336 in dodecane modified with 4% octanol) and an acceptor solution (0.1 M HCl) were used, respectively. Using the setup, it was possible to improve the limit of detection after microextraction by ∼1000-fold. The limit of detection achieved was 1 ng/mL. When a stir bar was used, the extraction time can be shortened from 60 min to only 15 min.
(1) Wang, H.; Liu, J.; Cooks, R. G.; Ouyang, Z. Paper Spray for Direct Analysis of Complex Mixtures Using Mass Spectrometry. Angewandte Chemie International Edition 2010, 49, 877-880.
(2) Liu, J.; Wang, H.; Manicke, N. E.; Lin, J.-M.; Cooks, G. R.; Ouyang, Z. Development, Characterization, and Application of Paper Spray Ionization. Analytical Chemistry 2010, 82, 2463-2471.
(3) Xu, W.; Manicke, N. E.; Cooks, G. R.; Ouyang, Z. Miniaturization of Mass Spectrometry Analysis Systems. Journal of the Association for Laboratory Automation 2010, 15, 433-439.
(4) Jain, S.; Heiser, A.; Venter, A. R. Spray desorption collection: an alternative to swabbing for pharmaceutical cleaning validation. Analyst 2011, 136, 1298-1301.
(5) Wang, H.; Manicke, N. E.; Yang, Q.; Zheng, L.; Shi, R.; Cooks, G. R.; Ouyang, Z. Direct Analysis of Biological Tissue by Paper Spray Mass Spectrometry. Analytical Chemistry 2011, 83, 1197-1201.
(6) Zhang, Z.; Xu, W.; Manicke, N. E.; Cooks, R. G.; Ouyang, Z. Silica coated paper substrate for paper-spray analysis of therapeutic drugs in dried blood spots. Analytical Chemistry 2012, 84, 931-938.
(7) Li, A.; Wang, H.; Ouyang, Z.; Cooks, G. R. Paper spray ionization of polar analytes using non-polar solvents. Chemical Communications 2011, 47, 2811-2813.
(8) Manicke, N.; Abu-Rabie, P.; Spooner, N.; Ouyang, Z.; Cooks, G. R. Quantitative Analysis of Therapeutic Drugs in Dried Blood Spot Samples by Paper Spray Mass Spectrometry: An Avenue to Therapeutic Drug Monitoring. Journal of The American Society for Mass Spectrometry 2011, 22, 1501-1507.
(9) Manicke, N. E.; Yang, Q.; Wang, H.; Oradu, S.; Ouyang, Z.; Cooks, G. R. Assessment of paper spray ionization for quantitation of pharmaceuticals in blood spots. International Journal of Mass Spectrometry 2011, 300, 123-129.
(10) Espy, R. D.; Manicke, N. E.; Ouyang, Z.; Cooks, G. R. Rapid analysis of whole blood by paper spray mass spectrometry for point-of-care therapeutic drug monitoring. Analyst 2012, 137, 2344-2349.
(11) Zhang, Z.; Cooks, G. R.; Ouyang, Z. Paper spray: a simple and efficient means of analysis of different contaminants in foodstuffs. Analyst 2012, 137, 2556-2558.
(12) Oradu, S. A.; Cooks, G. R. Multistep mass spectrometry methodology for direct characterization of polar lipids in green microalgae using paper spray ionization. Analytical chemistry 2012, 84, 10576-10585.
(13) Yang, Q.; Manicke, N. E.; Wang, H.; Petucci, C.; Cooks, G. R.; Ouyang, Z. Direct and quantitative analysis of underivatized acylcarnitines in serum and whole blood using paper spray mass spectrometry. Analytical and Bioanalytical Chemistry 2012, 404, 1389-1397.
(14) Espy, R. D.; Muliadi, A. R.; Ouyang, Z.; Cooks, G. R. Spray mechanism in paper spray ionization. International Journal of Mass Spectrometry 2012, 325, 167-171.
(15) Yang, Q.; Wang, H.; Maas, J. D.; Chappell, W. J.; Manicke, N. E.; Cooks, G. R.; Ouyang, Z. Paper spray ionization devices for direct, biomedical analysis using mass spectrometry. International Journal of Mass Spectrometry 2012, 312, 201-207.
(16) Li, A.; Wei, P.; Hsu, H.-C.; Cooks, G. R. Direct analysis of 4-methylimidazole in foods using paper spray mass spectrometry. Analyst 2013, 138, 4624-4630.
(17) Wang, H.; Ren, Y.; McLuckey, M. N.; Manicke, N. E.; Park, J.; Zheng, L.; Shi, R.; Cooks, G. R.; Ouyang, Z. Direct Quantitative Analysis of Nicotine Alkaloids from Biofluid Samples using Paper Spray Mass Spectrometry. Analytical Chemistry 2013, 85, 11540-11544.
(18) Hamid, A. M.; Jarmusch, A. K.; Pirro, V.; Pincus, D. H.; Clay, B. G.; Gervasi, G.; Cooks, G. R. Rapid discrimination of bacteria by paper spray mass spectrometry. Analytical chemistry 2014, 86, 7500-7507.
(19) Espy, R. D.; Teunissen, S.; Manicke, N. E.; Ren, Y.; Ouyang, Z.; van Asten, A.; Cooks, G. R. Paper Spray and Extraction Spray Mass Spectrometry for the Direct and Simultaneous Quantification of Eight Drugs of Abuse in Whole Blood. Analytical Chemistry 2014, 86, 7712-7718.
(20) Liou, Y.-W.; Wang, J.-S.; Chen, C.-C.; Lin, C.-H. Development of an on-line microextraction method for use in fiber-spray/mass spectrometry. International Journal of Mass Spectrometry 2017, 421, 178-183.
(21) Zhang, L.; Liu, S.; Cui, X.; Pan, C.; Zhang, A.; Chen, F. A review of sample preparation methods for the pesticide residue analysis in foods. Central European Journal of Chemistry 2012, 10, 900-925.
(22) Brito, N. M.; Navickiene, S.; Polese, L.; Jardim, E. F. G.; Abakerli, R. B.; Ribeiro, M. L. Determination of pesticide residues in coconut water by liquid–liquid extraction and gas chromatography with electron-capture plus thermionic specific detection and solid-phase extraction and high-performance liquid chromatography with ultraviolet detection. Journal of Chromatography A 2002, 957, 201-209.
(23) Tahboub, Y. R.; Zaater, M. F.; Barri, T. A. Simultaneous identification and quantitation of selected organochlorine pesticide residues in honey by full-scan gas chromatography–mass spectrometry. Analytica Chimica Acta 2006, 558, 62-68.
(24) Albero, B.; Sánchez-Brunete, C.; Tadeo, J. L. Multiresidue determination of pesticides in juice by solid-phase extraction and gas chromatography–mass spectrometry. Talanta 2005, 66, 917-924.
(25) Xu, X.-L.; Li, L.; Zhong, W.-K.; He, Y.-J. Multi-Residue Analysis of 205 Crop Pesticides Using Mini-Solid Phase Extraction–Large Volume Injection–GC–MS. Chromatographia 2009, 70, 173-183.
(26) Nardelli, V.; dell’Oro, D.; Palermo, C.; Centonze, D. Multi-residue method for the determination of organochlorine pesticides in fish feed based on a cleanup approach followed by gas chromatography–triple quadrupole tandem mass spectrometry. Journal of Chromatography A 2010, 1217, 4996-5003.
(27) Arthur, C. L.; Pawliszyn, J. Solid phase microextraction with thermal desorption using fused silica optical fibers. Analytical Chemistry 1990, 62, 2145-2148.
(28) Liu, H.; Dasgupta, P. K. Analytical chemistry in a drop. Solvent extraction in a microdrop. Analytical chemistry 1996, 68, 1817-1821.
(29) Xu, X.; Liang, F.; Shi, J.; Zhao, X.; Liu, Z.; Wu, L.; Song, Y.; Zhang, H.; Wang, Z. Determination of hormones in milk by hollow fiber-based stirring extraction bar liquid–liquid microextraction gas chromatography mass spectrometry. Analytica Chimica Acta 2013, 790, 39-46.
(30) Yamini, Y.; Seidi, S.; Feizbakhsh, R.; Baheri, T.; Rezazadeh, M. Liquid‐phase microextraction based on two immiscible organic solvents followed by gas chromatography with mass spectrometry as an efficient method for the preconcentration and determination of cocaine, ketamine, and lidocaine in human urine samples. Journal of Separation Science 2014, 37, 2364-2371.
(31) Praveen, P.; Loh, K.-C. Solventless extraction/stripping of phenol using trioctylphosphine oxide impregnated hollow fiber membranes – Experimental & modeling analysis. Chemical Engineering Journal 2014, 255, 641-649.
(32) Franz, J. E. US patent 3799758 "N-phosphonomethyl-glycine phytotoxicant compositions". 1974.
(33) Sprankle, P.; Meggitt, W. F.; Penner, D. Rapid Inactivation of Glyphosate in the Soil. Weed Science 1975, 23, 224-228.
(34) Henderson, A. M.; Gervais, J. A.; Luukinen, B.; Buhl, K.; Stone, D. "Glyphosate Technical Fact Sheet" National Pesticide Information Center. 2010(revised June 2015).
(35) Steinrücken, H. C.; Amrhein, N. The herbicide glyphosate is a potent inhibitor of 5-enolpyruvylshikimic acid-3-phosphate synthase. Biochemical and Biophysical Research Communications 1980, 94, 1207-1212.
(36) Borggaard, O. K.; Gimsing, A. Fate of glyphosate in soil and the possibility of leaching to ground and surface waters: a review. Pest Management Science 2008, 64, 441-456.
(37) 衛生福利部食品藥物管理署. 農藥殘留容許量標準.
(38) Xu, L.; Basheer, C.; Lee, H. Developments in single-drop microextraction. Journal of Chromatography A 2007, 1152, 184-192.
(39) Jeannot, M. A.; Cantwell, F. F. Solvent microextraction into a single drop. Analytical chemistry 1996, 68, 2236-2240.
(40) Jeannot, M. A.; Cantwell, F. F. Mass Transfer Characteristics of Solvent Extraction into a Single Drop at the Tip of a Syringe Needle. Analytical Chemistry 1997, 69, 235-239.
(41) Ahmadi, F.; Assadi, Y.; Hosseini, S. M. R.; Rezaee, M. Determination of organophosphorus pesticides in water samples by single drop microextraction and gas chromatography-flame photometric detector. Journal of Chromatography A 2006, 1101, 307-312.
(42) Pedersen-Bjergaard, S.; Rasmussen, K. E. Liquid-liquid-liquid microextraction for sample preparation of biological fluids prior to capillary electrophoresis. Analytical chemistry 1999, 71, 2650-2656.
(43) Shen, G.; Lee, H. Hollow fiber-protected liquid-phase microextraction of triazine herbicides. Analytical chemistry 2002, 74, 648-654.
(44) Jiang, X.; Lee, H. Solvent Bar Microextraction. Analytical Chemistry 2004, 76, 5591-5596.
(45) Rezaee, M.; Assadi, Y.; Hosseini, M.-R.; Aghaee, E.; Ahmadi, F.; Berijani, S. Determination of organic compounds in water using dispersive liquid–liquid microextraction. Journal of Chromatography A 2006, 1116, 1-9.
(46) Nagaraju, D.; Huang, S.-D. Determination of triazine herbicides in aqueous samples by dispersive liquid–liquid microextraction with gas chromatography–ion trap mass spectrometry. Journal of Chromatography A 2007, 1161, 89-97.
(47) Berijani, S.; Assadi, Y.; Anbia, M.; Hosseini, M.-R.; Aghaee, E. Dispersive liquid–liquid microextraction combined with gas chromatography-flame photometric detection Very simple, rapid and sensitive method for the determination of organophosphorus pesticides in water. Journal of Chromatography A 2006, 1123, 1-9.
(48) Zacharis, C. K.; Tzanavaras, P. D.; Roubos, K.; Dhima, K. Solvent-based de-emulsification dispersive liquid–liquid microextraction combined with gas chromatography–mass spectrometry for determination of trace organochlorine pesticides in environmental water samples. Journal of Chromatography A 2010, 1217, 5896-5900.
(49) Leong, M.-I.; Huang, S.-D. Dispersive liquid–liquid microextraction method based on solidification of floating organic drop combined with gas chromatography with electron-capture or mass spectrometry detection. Journal of Chromatography A 2008, 1211, 8-12.
(50) Regueiro, J.; Llompart, M.; Garcia-Jares, C.; Garcia-Monteagudo, J. C.; Cela, R. Ultrasound-assisted emulsification–microextraction of emergent contaminants and pesticides in environmental waters. Journal of Chromatography A 2008, 1190, 27-38.
(51) Pedersen-Bjergaard, S.; Rasmussen, K. E. Liquid-phase microextraction with porous hollow fibers, a miniaturized and highly flexible format for liquid-liquid extraction. Journal of chromatography. A 2008, 1184, 132-142.
(52) V. L. Tal’roze, G. V. K., I. G. Gordetskii, V. E. Skurat, . Russ. J. Phys. Chem. 1968, 42, 1658.
(53) Zeleny, J. Instability of Electrified Liquid Surfaces. Physical Review 1917, 10, 1-6.
(54) Dole, M.; Mack, L. L.; Hines, R. L.; Mobley, R. C.; Ferguson, L. D.; Alice, M. B. Molecular Beams of Macroions. The Journal of Chemical Physics 1968, 49, 2240-2249.
(55) Mack, L. L.; Kralik, P.; Rheude, A.; Dole, M. Molecular Beams of Macroions. II. The Journal of Chemical Physics 1970, 52, 4977-4986.
(56) Yamashita, M.; Fenn, J. B. Negative ion production with the electrospray ion source. The Journal of Physical Chemistry 1984, 88, 4671-4675.
(57) Fenn, J. B.; Mann, M.; Meng, C. K.; Wong, S. F.; Whitehouse, C. M. Electrospray ionization for mass spectrometry of large biomolecules. Science 1989, 246, 64-71.
(58) Wong, S. F.; Meng, C. K.; Fenn, J. B. Multiple charging in electrospray ionization of poly(ethylene glycols). The Journal of Physical Chemistry 1988, 92, 546-550.
(59) Aleksandrov, M. L., Gall, L. N., Shkurov, V. A., Pavlenko, V. A., Krasnov, N. V., Nikolaev, V. I. Mechanism of Ion Formation During the Electrohydrodynamic Sputtering of a Liquid into a Vacuum. J. Anal. Chem. USSR 1984, 39, 1268.
(60) Cech, N. B.; Enke, C. G. Practical implications of some recent studies in electrospray ionization fundamentals. Mass Spectrometry Reviews 2001, 20, 362-387.
(61) Loo, J. A.; Edmonds, C. G.; Udseth, H. R.; Smith, R. D. Effect of reducing disulfide-containing proteins on electrospray ionization mass spectra. Analytical chemistry 1990, 62, 693-698.
(62) Smith, R. D.; Loo, J. A.; Edmonds, C. G.; Barinaga, C. J.; Udseth, H. R. New developments in biochemical mass spectrometry: electrospray ionization. Analytical chemistry 1990, 62, 882-899.
(63) Bruins, A. P.; Covey, T. R.; Henion, J. D. Ion spray interface for combined liquid chromatography/atmospheric pressure ionization mass spectrometry. Analytical Chemistry 1987, 59, 2642-2646.
(64) Olivares, J. A.; Nguyen, N. T.; Yonker, C. R.; Smith, R. D. On-line mass spectrometric detection for capillary zone electrophoresis. Analytical Chemistry 1987, 59, 1230-1232.
(65) Wahl, J. H.; Goodlett, D. R.; Udseth, H. R.; Smith, R. D. Attomole level capillary electrophoresis-mass spectrometric protein analysis using 5 .mu.m i.d. capillaries. Analytical Chemistry 1992, 64, 3194-3196.
(66) Wilm, M.; Mann, M. Analytical Properties of the Nanoelectrospray Ion Source. Analytical Chemistry 1996, 68, 1-8.
(67) Wilm, M. S.; Mann, M. Electrospray and Taylor-Cone theory, Dole's beam of macromolecules at last? International Journal of Mass Spectrometry and Ion Processes 1994, 136, 167-180.
(68) Link, A. J.; Eng, J.; Schieltz, D. M.; Carmack, E.; Mize, G. J.; Morris, D. R.; Garvik, B. M.; Yates, J. R. Direct analysis of protein complexes using mass spectrometry. Nature Biotechnology 1999, 17, 676-682.
(69) Wu, C.; Siems, W. F.; Hill, H. H. Secondary electrospray ionization ion mobility spectrometry/mass spectrometry of illicit drugs. Analytical chemistry 2000, 72, 396-403.
(70) Chang, D.-Y.; Lee, C.-C.; Shiea, J. Detecting large biomolecules from high-salt solutions by fused-droplet electrospray ionization mass spectrometry. Analytical chemistry 2002, 74, 2465-2469.
(71) Chen, H.; Venter, A.; Cooks, G. R. Extractive electrospray ionization for direct analysis of undiluted urine, milk and other complex mixtures without sample preparation. Chemical Communications 2006, 0, 2042-2044.
(72) Huang, M.-Z.; Hsu, H.-J.; Lee, J.-Y.; Jeng, J.; Shiea, J. Direct Protein Detection from Biological Media through Electrospray-Assisted Laser Desorption Ionization/Mass Spectrometry. Journal of Proteome Research 2006, 5, 1107-1116.
(73) Vick, S. J.; Bovet, D.; Anderson, J. R. How do African grey parrots (Psittacus erithacus) perform on a delay of gratification task? Animal Cognition 2010, 13, 351-358.
(74) Hu, B.; So, P.-K.; Chen, H.; Yao, Z.-P. Electrospray ionization using wooden tips. Analytical chemistry 2011, 83, 8201-8207.
(75) Jhang, C. S.; Lee, H.; He, Y. S.; Liu, J. T.; Lin, C. H. Rapid screening and determination of 4‐chloroamphetamine in saliva by paper spray‐mass spectrometry and capillary electrophoresis‐mass spectrometry. ELECTROPHORESIS 2012, 33, 3073-3078.
(76) Lee, H.; Jhang, C. S.; Liu, J. T.; Lin, C. H. Rapid screening and determination of designer drugs in saliva by a nib‐assisted paper spray‐mass spectrometry and separation technique. Journal of Separation Science 2012, 35, 2822-2825.
(77) Chen, H.-K.; Lin, C.-H.; Liu, J.-T.; Lin, C.-H. Electrospray ionization using a bamboo pen nib. International Journal of Mass Spectrometry 2013, 356, 37-40.
(78) Salentijn, G. I. J.; Permentier, H. P.; Verpoorte, E. 3D-Printed Paper Spray Ionization Cartridge with Fast Wetting and Continuous Solvent Supply Features. Analytical Chemistry 2014, 86, 11657-11665.
(79) Jiang, J.; Zhang, H.; Li, M.; Dulay, M. T.; Ingram, A. J.; Li, N.; You, H.; Zare, R. N. Droplet Spray Ionization from a Glass Microscope Slide: Real-Time Monitoring of Ethylene Polymerization. Analytical Chemistry 2015, 87, 8057-8062.
(80) Liu, J.-Y.; Chen, P.-C.; Liou, Y.-W.; Chang, K.-Y.; Lin, C.-H. Development and Application of a Brush-Spray Derived from a Calligraphy-Brush-Style Synthetic Hair Pen for Use in ESI/MS. Mass Spectrometry 2017, 6.
(81) Blades, A. T.; Ikonomou, M. G.; Kebarle, P. Mechanism of electrospray mass spectrometry. Electrospray as an electrolysis cell. Analytical Chemistry 1991, 63, 2109-2114.
(82) Gomez, A.; Tang, K. Charge and fission of droplets in electrostatic sprays. Physics of Fluids 1994, 6, 404-414.
(83) Iribarne, J. V. On the evaporation of small ions from charged droplets. The Journal of Chemical Physics 1976, 64, 2287.
(84) Fenn, J. B. Ion formation from charged droplets: roles of geometry, energy, and time. Journal of the American Society for Mass Spectrometry 1993, 4, 524-535.
(85) Agnes, G. R.; Stewart, I. I.; Horlick, G. Elemental Speciation Measurements with Electrospray Mass Spectrometry: An Assessment. Applied Spectroscopy 1994, 48, 1347-1359.
(86) Rios, C.; Salvadó, V.; Hidalgo, M. Facilitated transport and preconcentration of the herbicide glyphosate and its metabolite AMPA through a solid supported liquid-membrane. Journal of Membrane Science 2002, 203, 201-208.
(87) Goodwin, L.; Startin, J. R.; Goodall, D. M.; Keely, B. J. Tandem mass spectrometric analysis of glyphosate, glufosinate, aminomethylphosphonic acid and methylphosphinicopropionic acid. Rapid Communications in Mass Spectrometry 2003, 17, 963-969.