Commenced in January 2007
Frequency: Monthly
Edition: International
Paper Count: 30526
Highly-Efficient Photoreaction Using Microfluidic Device

Authors: Shigenori Togashi, Yukako Asano

Abstract:

We developed an effective microfluidic device for photoreactions with low reflectance and good heat conductance. The performance of this microfluidic device was tested by carrying out a photoreactive synthesis of benzopinacol and acetone from benzophenone and 2-propanol. The yield reached 36% with an irradiation time of 469.2 s and was improved by more than 30% when compared to the values obtained by the batch method. Therefore, the microfluidic device was found to be effective for improving the yields of photoreactions.

Keywords: Detection, Yield Improvement, Microfluidic Device, photoreaction, black aluminum oxide, benzophenone

Digital Object Identifier (DOI): doi.org/10.5281/zenodo.1093988

Procedia APA BibTeX Chicago EndNote Harvard JSON MLA RIS XML ISO 690 PDF Downloads 1446

References:


[1] Roberts, J. D. and M. C. Caserio; Basic Principles of Organic Chemistry, 2nd ed., W. A. Benjamin, Inc., Menlo Park, CA, USA, 1977.
[2] Hessel, V., S. Hardt and H. Löwe eds.; Chemical Micro Process Engineering: Fundamentals, Modeling and Reactions, Wiley-VCH, Weinheim, Germany, 2004.
[3] Hessel, V., H. Löwe, A. Müller and G. Kolb eds.; Chemical Micro Process Engineering: Processing and Plants, Wiley-VCH, Weinheim, Germany, 2005.
[4] Benson, R. S. and J. W. Ponton; "Process MiniaturisationA Route to Total Environmental Acceptability?,” Chem.Eng.Res.Des., A71, 1993, pp.160-168.
[5] Schubert, K., W. Bier, W. Keller, G. Linder and D. Seidel; "Gas to Gas Heat Transfer in Micro Heat Exchangers,” Chem. Eng. Process., 32, 1993, pp.33-43.
[6] Suga, S., A. Nagaki and J. Yoshida; "Highly Selective FriedelCrafts Monoalkylation Using Micromixing,” Chem. Commun., 3, 2003, pp.354-355.
[7] Taghavi-Moghadam, S., A. Kleemann and K. G. Golbig; "Microreaction Technology as a Novel Approach to Drug Design, Process Development and Reliability,” Org. Process. Res. Dev., 5, 2001, pp.652-658.
[8] Fukuyama, T., M. Shinmen, S. Nishitani, M. Sato and I. Ryu; "A Copper-Free Sonogashira Coupling Reaction in Ionic Liquids and its Application to a Microflow System for Efficient Catalyst Recycling,” Org. Lett., 4, 2002, pp.1691-1694.
[9] Yoshida, J. ed.; Microreactors, Epoch-making Technology for Synthesis (Maikuroriakuta, Shinjidai no Gouseigijutsu), CMC Publishing Co., Ltd., Tokyo, Japan, 2003.
[10] Matsushita, Y., T. Ichimura, N. Ohba, S. Kumada, K. Sakeda, T. Suzuki, H. Tanibata and T. Murata; "Recent Progress on Photoreactions in Microreactors,” Pure Appl. Chem., 79, 2007, pp.1959-1968.
[11] Lu, H., M. A. Schmidt and K. F. Jensen; "Photochemical Reactions and On-Line UV Detection in Microfabricated Reactors,” Lab Chip, 1, 2001, pp.22-28.
[12] Ueno, K., F. Kitagawa and N. Kitamura; "Photocyanation of Pyrene across and Oil/Water Interface in a Polymer Microchannel Chip,” Lab Chip, 2, 2002, pp.231-234.
[13] Gorges, R., S. Meyer and G. Kerisel; "Photocatalysis in Microreactors,” J. Photochem. Photobiol. A, 167, 2004, pp.95-99.
[14] Fukuyama, T., Y. Hino, N. Kamata and I. Ryu; "Quick Execution of
[2+2] Type Photochemical Cycloaddition Reaction by Continuous Flow System Using a Glass-made Microreactor,” Chem. Lett., 33, 2004, pp.1430-1431.
[15] Fukuyama, T., Y. Kajihara, Y. Hino and I. Ryu; "Continuous Microflow
[2+2] Photocycloaddition Reactions Using Energy-Saving Compact Light Sources,” J. Flow Chem., 1, 2011, pp.40-45.
[16] Maeda, H., H. Mukae and K. Mizuno; "Enhanced Efficiency and Regioselectivity of Intramolecular
[2+2] Photocycloaddition of 1-Cyanonaphthalene Derivative Using Microreactors,” Chem. Lett., 34, 2005, pp.66-67.
[17] Sugimoto, A., T. Fukuyama, Y. Sumino, M. Takagi and I. Ryu;"Microflow Photo-Radical Reaction Using a Compact Light Source: Application to the Barton Reaction Leading to a Key Intermediate for Myriceric Acid A,” Tetrahedron, 65, 2009, pp.1593-1598.
[18] Pitts, J. N., Jr., R. L. Letsinger, R. P. Taylor, J. M. Patterson, G. Reckten wald and R. B. Martin; "Photochemical Reactions ofBenzophenone in Alcohols,” J. Am. Chem. Soc., 81, 1958, pp.1068-1077.
[19] Lu, H., M. A. Schmidt and K. F. Jensen; "Photochemical Reactions and On-Line UV Detection in Microfabricated Reactors,” Lab Chip, 1, 2001, pp.22-28.