Flow markers in microreactors: A generally applicable chromatographic method for monitoring flow rates during reactions

Open Chemical Engineering Journal

Volumn 4, Issue 1, 2010, Pages 61-67

  Nieuwland, Pieter J ^a   Koch, Kaspar ^a   van Hest, Jan C M ^a   Rutjes, Floris P J T ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

Flow chemistry; Flow markers; Flow rate; Micoreactors; Oxidation; Parametric optimization

Indexed keywords

CHROMATOGRAPHIC METHODS; CONTINUOUS FLOWS; CRITICAL FACTORS; DATA INTERPRETATION; FLOW CHEMISTRY; FLOW MARKERS; MICRO REACTOR; MICROLITERS; NANOLITERS; OXIDATION REACTIONS; PARAMETRIC OPTIMIZATION; REACTION OPTIMIZATION; REACTION TIME; STOICHIOMETRIC RATIO;

CHEMICAL REACTORS; CHROMATOGRAPHIC ANALYSIS; COMBUSTORS; ELECTRIC NETWORK PARAMETERS; ELECTRONICS PACKAGING; OPTIMIZATION; OXIDATION; SYNTHESIS (CHEMICAL);

REACTION RATES;

EID: 78651589152     PISSN: None     EISSN: 18741231     Source Type: Journal    
DOI: 10.2174/1874123101004010061     Document Type: Article

References (31)

1. W. Ehrfeld, V. Hessel, and H. Löwe, Microreactors - New Technology for Modern Chemistry, Weinheim, Wiley-VCH, pp. 5-12, 2000.
2. K. Jänisch, V. Hessel, H. Löwe, and M. Baerns, Chemistry in Microstructured Reactors, Angew. Chem. Int. Ed. Engl., vol. 43, pp. 406-446, 2004.
3. P. Watts, and C. Wiles, Recent advances in synthetic micro reac- tion technology, Chem. Commun., doi: 10.1039/b609428g, pp. 443-467, 2007.
4. K. Geyer, J. D. C. Codee, and P. H. Seeberger, Microreactors as tools for synthetic chemists - The chemists' round-bottomed flask of the 21st century?, Chem. Eur. J., vol. 12, pp. 8434-8442, 2006.
5. B. P. Mason, K. E. Price, J. L. Steinbacher, A. R. Bogdan, and D. T. McQuade, Greener approaches to organic synthesis using mi- croreactor technology, Chem. Rev., vol. 107, pp. 2300-2318, 2007.
6. H. Usutani, Y. Tomida, A. Nagaki, H. Okamoto, T. Nokami, and J. Yoshida, Generation and Reactions of o-Bromophenyllithium without Benzyne formation using a microreactor, J. Am. Chem. Soc., vol. 129, pp. 3046-3047, 2007.
7. M. S. Thomsen, P. Polt, and B. Nidetzky, Development of a mi- crofluidic immobilised enzyme reactor, Chem. Commun., vol. 24, pp. 2527-2529, 2007.
8. R. Fortt, R. C. R. Wootton, and A. J. de Mello, Continuous-flow generation of anhydrous diazonium species: Monolithic microflu- idic reactors for the chemistry of unstable intermediates, Org. Process Res. Dev., vol. 7, pp. 762-768, 2003.
9. C. Wiles, P. Watts, and S. J. Haswell, The use of electroosmotic flow as a pumping mechanism for semi-preparative scale continuous flow synthesis, Chem. Commun., vol. 9, pp. 966-968, 2007.
10. M. Fernandez-Suarez, S. Y. F. Wong, and B. H. Warrington, Syn- thesis of a three-member array of cycloadducts in a glass microchip under pressure driven flow, Lab Chip, vol. 2, pp. 170-174, 2002.
11. H. Hisamoto, T. Saito, M. Tokeshi, A. Hibara, and T. Kitamori, Fast and high conversion phase-transfer synthesis exploiting the liquid-liquid interface formed in a microchannel chip, Chem. Commun., doi: 10.1039/b106494k, pp. 2662-2663, 2001.
12. E. R. Murphy, J. R. Martinelli, N. Zaborenko, S. L. Buchwald, and K. F. Jensen, Accelerating reactions with microreactors at elevated temperatures and pressures: Profiling aminocarbonylation reactions, Angew. Chem. Int. Ed. Engl., vol. 46, pp. 1734-1737, 2007.
13. E. Garcia-Egido, V. Spikmans, S. Y. F. Wong, and B. H. Warrington, Synthesis and analysis of combinatorial libraries performed in an automated micro reactor system, Lab Chip, vol. 3, pp. 73-76, 2003.
14. K. Koch, R. F. J. van den Berg, P. J. Nieuwland, R. Wijtmans, M. G. Wubbolts, H. E. Schoemaker, F. P. J. T. Rutjes, and J. C. M. van Hest, Enzymatic synthesis of optically pure cyanohydrins in microchannels using a crude cell lysate, Chem. Eng. J., vol. 135S, pp. S89-S92, 2008.
15. K. Koch, R. F. J. van den Berg, P. J. Nieuwland, R. Wijtmans, H. E. Schoemaker, J. C. M. van Hest, and F. P. J. T. Rutjes, Enzy- matic enantioselective C-C-bond formation in microreactors, Biotechnol. Bioeng., vol. 99, pp. 1028-1033, 2008.
16. K. Koch, B. J. A. van Weerdenburg, J. M. M. Verkade, P. J. Nieuwland, F. P. J. T. Rutjes, and J. C. M. van Hest, Optimizing the deprotection of the amine protecting p-methoxyphenyl group in an automated microreactor platform, Org. Process Res. Dev., vol. 13, pp. 1003-1006, 2009.
17. S. Devasenathipathy, J. G. Santiago, S. T. Wereley, C. D. Meinhart, and K. Takehara, Particle imaging techniques for micro- fabricated fluidic systems, Exp. Fluids, vol. 34, pp. 504-514, 2003.
18. F. Benito-Lopez, W. Verboom, M. Kakuta, J. G. E. Gardeniers, R. J. M. Egberink, E. R. Oosterbroek, A. van den Berg, and D. N. Reinhoudt, Optical fiber-based on-line UV/Vis spectroscopic monitoring of chemical reaction kinetics under high pressure in a capillary microreactor, Chem. Commun., pp. 2857-2859, 2005.
19. H. Lu, M. A. Schmidt, and K. F. Jensen, Photochemical reactions and on-line UV detection in microfabricated reactors, Lab Chip, vol. 1, pp. 22-28, 2001.
20. R. J. Jackman, T. M. Floyd, R. Ghodssi, M. A. Schmidt, and K. F. Jensen, Microfluidic systems with on-line UV detection fabricated in photodefinable epoxy, J. Micromech. Microeng., vol. 11, pp. 263-269, 2001.
21. R. Herzig-Marx, K. T. Queeney, R. J. Jackman, M. A. Schmidt, and K. F. Jensen, Infrared spectroscopy for chemically specific sensing in silicon-based microreactors, Anal. Chem., vol. 76, pp. 6476-6483, 2004.
22. S. A. Leung, R. F. Winkle, R. C. R. Wootton, and A. J. deMello, A method for rapid reaction optimisation in continuous-flow mi- crofluidic reactors using online Raman spectroscopic detection, Analyst, vol. 130, pp. 46-51, 2005.
23. P. D. I. Fletcher, S. J. Haswell, and X. L. Zhang, Monitoring of chemical reactions within microreactors using an inverted Raman microscopic spectrometer, Electrophoresis, vol. 24, pp. 3239-3245, 2003.
24. M. Tokeshi, T. Minagawa, K. Uchiyama, A. Hibara, K. Sato, H. Hisamoto, and T. Kitamori, Continuous-flow chemical processing on a microchip by combining microunit operations and a multi- phase flow network, Anal. Chem., vol. 74, pp. 1565-1571, 2002.
25. A. Smirnova, K. Shimura, A. Hibara, M. A. Proskurnin, and T. Kitamori, Application of a micro multiphase laminar flow on a microchip for extraction and determination of derivatized carba- mate pesticides, Anal. Sci., vol. 23, pp. 103-107, 2007.
26. A. Smirnova, K. Mawatari, A. Hibara, M. A. Proskurnin, and T. Kitamori, Micro-multiphase laminar flows for the extraction and detection of carbaryl derivative, Anal. Chim. Acta, vol. 558, pp. 69-74, 2006.
27. P. J. Nieuwland, K. Koch, N. van Harskamp, R. Wehrens, J. C. M. van Hest, and F. P. J. T. Rutjes, Flash chemistry extensively opti- mized: high temperature Swern-Moffatt oxidation in an automated microreactor platform, Chem. Asian J., 2010, early view: DOI: 10.1002/asia.200900705.
28. T. Kawaguchi, H. Miyata, K. Ataka, K. Mae, and J. Yoshida, Room-temperature Swern oxidations by using a microscale flow system, Angew. Chem. Int. Ed. Engl., vol. 44, pp. 2413-2416, 2005.
29. K. Omura, A. K. Sharma, and D. Swern, Dimethylsulfoxide- trifluoroacetic anhydride - New reagent for oxidation of alcohols to carbonyls, J. Org. Chem., vol. 41, pp. 957-962, 1976.
30. A. J. Mancuso, and D. Swern, Activated dimethylsulfoxide - Use- ful reagents for synthesis, Synthesis, pp. 165-185, 1981.
31. J. J. M. van der Linden, P. W. Hilberink, C. M. P. Kronenburg, and G. J. Kemperman, Investigation of the Moffatt-Swern oxidation in a continuous flow micro reactor system, Org. Process Res. Dev., vol. 12, pp. 911-920, 2008.