Dual-channel microreactor for gas-liquid syntheses

Journal of the American Chemical Society

Volumn 132, Issue 29, 2010, Pages 10102-10106

  Park, Chan Pil ^a   Kim, Dong Pyo ^a  

^a Chungnam National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC REACTIONS; DUAL CHANNEL; GAS FLOWING; GAS LIQUIDS; GASEOUS OXYGEN; GASEOUS REAGENTS; HECK REACTIONS; INDEPENDENT CONTROL; LIQUID PHASIS; MICRO-REACTOR; MICROFLUIDIC CHANNEL; REACTION TIME; THIN MEMBRANE;

BATCH REACTORS; CATALYSIS; MICROCHANNELS; OXYGEN;

LIQUIDS;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DUAL CHANNEL MICROREACTOR; GAS; HECK REACTION; LIQUID; MICROFLUIDICS; ORGANIC CHEMISTRY; PHYSICAL PHASE; REACTOR; SYNTHESIS;

EID: 77955531542     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja102666y     Document Type: Article

References (45)

1. For reviews and books, see: (a) Yoshida, J. I.; Nagaki, A.; Yamada, T. Chem.-Eur. J. 2008, 14, 7450-7459.
2. (b) Wiles, C.; Watts, P. Eur. J. Org. Chem. 2008, 1655-1671.
3. (c) Fukuyama, T.; Rahman, M. T.; Sato, M.; Ryu, I. Synlett 2008, 151-163.
4. (d) Ahmed-Omer, B.; Brandt, J. C.; Wirth, T. Org. Biomol. Chem. 2007, 5, 733-740.
5. (e) Mason, B. P.; Price, K. E.; Steinbacher, J. L.; Bogdan, A. R.; McQuade, D. T. Chem. Rev. 2007, 107, 2300-2318.
6. (f) Microreactors in Organic Synthesis; Wirth, T., Ed.; Wiley-VCH: Weinheim, 2008.
7. (g) Handbook of Micro Reactors; Hessel, V., Schouten, J. C, Renken, A., Wang, Y., Yoshida, J. I., Eds.; Wiley-VCH: Weinheim, 2009.
8. For representative reports, see: (a) Wang, N.; Matsumoto, T.; Ueno, M.; Miyamura, H.; Kobayashi, S. Angew. Chem., Int. Ed. 2009, 48, 4744-4746.
9. (b) Miller, P. W.; Long, N. J.; de Mello, A. J.; Vilar, R.; Audrain, H.; Bender, D.; Passchier, J.; Gee, A. Angew. Chem., Int. Ed. 2007, 46, 2875-2878.
10. (c) Rahman, M. T.; Fukuyama, T.; Kamata, N.; Sato, M.; Ryu, I. Chem. Commun. 2006, 21, 2236-2238.
11. (d) Rebrov, E. V.; Klinger, E. A.; Berenguer-Murcia, A.; Sulman, E. M.; Schouten, J. C. Org. Process Res. Dev. 2009, 13, 991-998.
12. The parallel contacting between gas and liquid was tried in the chemical-and bio-engineering field. See: (a) Choudhary, V. R.; Gaikwad, A. G.; Sansare, S. D. Angew. Chem., Int. Ed 2001, 40, 1776-1779.
13. (b) de Jong, J.; Verheijden, P. W.; Lammertink, R. G. H.; Wessling, M. Anal. Chem. 2008, 80, 3190-3197.
14. (c) Lemke, E. A.; Gambin, Y.; Vandelinder, V.; Brustad, E. M.; Liu, H. W.; Schultz, P. G.; Groisman, A.; Deniz, A. A. J. Am. Chem. Soc. 2009, 131, 13610-13612.
15. (d) Timmer, B. H.; Olthuis, W.; Van den Berg, A. Lab Chip 2004, 4, 252-255.
16. (e) Ohira, S. I.; Toda, K. Lab Chip 2005, 5, 1374-1379.
17. (f) Vollmer, A. P.; Probstein, R. F.; Gilbert, R.; Thorsen, T. Lab Chip 2005, 5, 1059-1066.
18. (g) Walker, G. M.; Ozers, M. S.; Beebe, D. J. Biomed. Microdevices 2002, 4, 161-166.
19. (h) Lam, R. H. W.; Kim, M.-C.; Thorsen, T. Anal. Chem. 2009, 81, 5918-5924.
20. (i) Aota, A.; Nonaka, M.; Hibara, A.; Kitamori, T. Angew. Chem., Int. Ed. 2007, 46, 878-880.
21. Ahmed-Omer, B.; Barrow, D. A.; Wirth, T. Tetrahedron Lett. 2009, 50, 3352-3355.
22. The preparation procedure of the DC microreactor was described in the Supporting Information (Figure 1S).
23. The contact area to volume ratio depends on the shape and volume of the reactor. As the simulation for a reaction with narrow contacting area between gas and liquid, a reaction in the NMR tube was tried (Table 2).
24. For representative reports on microreactors using immobilized Pd catalysts, see: (a) Kobayashi, J.; Mori, Y.; Okamoto, K.; Akiyama, R.; Ueno, M.; Kitamori, T.; Kobayashi, S. Science 2004, 304, 1305-1308.
25. (b) Kirschning, A.; Solodenko, W.; Mennecke, K. Chem.-Eur. J. 2006, 12, 5972-5990.
26. (c) Baxendale, I. R.; Griffiths-Jones, C. M.; Ley, S. V.; Tranmer, G. K. Chem.-Eur. J. 2006, 12, 4407-4416.
27. (d) Kawanami, H.; Matsushima, K.; Sato, M.; Ikushima, Y. Angew. Chem., Int. Ed. 2007, 46, 5129-5132.
28. (e) Mennecke, K.; Cecilia, R.; Glasnov, T. N.; Gruhl, S.; Vogt, C.; Feldhoff, A.; Vargas, M. A. L.; Kappe, C. O.; Kunz, U.; Kirschning, A. Adv. Synth. Catal. 2008, 350, 717-730.
29. (f) Shore, G.; Morin, S.; Organ, M. G. Angew. Chem., Int. Ed. 2006, 45, 2761-2766.
30. (a) Uozumi, Y.; Yamada, Y. M. A.; Beppu, T.; Fukuyama, N.; Ueno, M.; Kitamori, T. J. Am. Chem. Soc. 2006, 128, 15994-15995.
31. (b) Yamada, Y. M. A.; Watanabe, T.; Torii, K.; Uozumi, Y. Chem. Commun. 2009, 5594-5596.
32. (a) Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400-3420.
33. (b) Yoo, K. S.; Yoon, C. H.; Jung, K. W. J. Am. Chem. Soc. 2006, 128, 16384-16393.
34. (c) Yoo, K. S.; Park, C. P.; Yoon, C. H.; Sakaguchi, S.; O'Neill, J.; Jung, K. W. Org. Lett. 2007, 9, 3933-3935.
35. (d) Gligorich, K. M.; Sigman, M. S. Chem. Commun. 2009, 3854-3867.
36. Punniyamurthy, T.; Velusamy, S.; Iqbal, J. Chem. Rev. 2005, 105, 2329-2363.
37. For the detailed reaction mechanism, see the Supporting Information.
38. XPS spectra for the channel surface of the used DC microreactor show that there is no significant deposition of Pd (0) species.
39. Lee, J. N.; Park, C.; Whitesides, G. M. Anal. Chem. 2003, 75, 6544-6554. PDMS has a good transparency in UV-visible regions, chemical inertness. A fabrication is easy and requires low cost, compared to that for microfluidic materials (e.g., glass and silicon). For solvent compatibility at elevated temperature (60 °C), see the Supporting Information (Table 1S).
40. In the Kobayashi device, gas over 20 equiv amount should be used to conduct an efficient result.
41. He, L.; Wang, L.; Sun, H.; Ni, J.; Cao, Y.; He, H.; Fan, K. Angew. Chem., Int. Ed. 2009, 48, 9538-9541.
42. (a) Liu, J.; Zhu, J.; Jiang, H.; Wang, W.; Li, J. Chem. Asian J. 2009, 4, 1712-1716.
43. (b) Liu, J.; Zhu, J.; Jiang, H.; Wang, W.; Li, J. Chem. Commun. 2010, 46, 415-417.
44. We developed novel polymer microfluidic devices with high solvent resistance: (a) Yoon, T. H.; Park, S. H.; Min, K. I.; Zhang, X.; Haswell, S. J.; Kim, D.-P. Lap Chip 2008, 8, 1454-1459.
45. (b) Kim, B.-Y.; Hong, L.-Y.; Chung, Y.-M.; Kim, D.-P.; Lee, C.-S. Adv. Funct. Mater. 2009, 19, 3796-3803.