Investigating the existence of nonthermal/specific microwave effects using silicon carbide heating elements as power modulators

Journal of Organic Chemistry

Volumn 73, Issue 16, 2008, Pages 6321-6329

  Razzaq, Tahseen ^a   Kremsner, Jennifer M ^a   Kappe, C Oliver ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ENGINEERING; CHEMICAL REACTIONS; ELECTRIC FIELDS; ELECTRIC HEATING ELEMENTS; ELECTROMAGNETIC FIELD THEORY; ELECTROMAGNETIC FIELDS; ELECTROMAGNETISM; GRAFTING (CHEMICAL); HEATING; MAGNETIC FIELDS; MICROWAVE GENERATION; MICROWAVE POWER TRANSMISSION; MICROWAVES; MIXTURES; NONMETALS; RATE CONSTANTS; REACTION RATES; SILICON; SILICON CARBIDE; SYNTHESIS (CHEMICAL);

CHEMICAL EQUATIONS; CHEMICAL PROCESSING; CHEMICAL TRANSFORMATIONS; FIELD STRENGTHS; MICROWAVE ABSORBING; MICROWAVE CONDITIONS; MICROWAVE EFFECTS; MICROWAVE ENERGIES; MICROWAVE POWER LEVELS; MICROWAVE POWERS; POWER MODULATORS; REACTION MIXTURES; REACTION TEMPERATURES; REACTION-RATE; SILICON CARBIDE (SIC);

CHEMICAL ELEMENTS;

SILICON CARBIDE;

ARTICLE; ELECTROMAGNETIC FIELD; ENERGY ABSORPTION; HEAT; MICROWAVE RADIATION; REDUCTION; TEMPERATURE;

EID: 50149112426     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8009402     Document Type: Article

References (58)

1. (a) Microwaves in Organic Synthesis, 2nd ed.; Loupy, A., Ed.; Wiley-VCH:Weinheim, Germany, 2006.
2. (b) Kappe, C. O.; Stadler, A. Microwaves in Organic and Medicinal Chemistry; Wiley-VCH: Weinheim, Germany, 2005.
3. (a) Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250, and references cited therein,
4. (b) Roberts, B. A.; Strauss, C. R. Acc. Chem. Res. 2005, 38, 653.
5. (c) Kappe, C. O.; Dallinger, D. Nature Rev. Drug Discov. 2006, 5, 51.
6. (d) Collins, J. M.; Leadbeater, N. E. Org. Biomol. Chem. 2007, 5, 1141.
7. (e) Dallinger, D.; Kappe, C. O. Chem. Rev. 2007, 107, 2563.
8. (f) Appukkuttan, P.; Van der Eycken, E. Eur. J. Org. Chem. 2008, 1133.
9. (a) Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199.
10. (b) Perreux, L.; Loupy, A. In Microwaves in Organic Synthesis, 2nd ed.; Loupy, A., Ed.; Wiley-VCH: Weinheim, Germany, 2006; Chapter 4, pp 134-218.
11. (c) De La Hoz, A.; Diaz-Ortiz, A.; Moreno, A. Chem. Soc Rev. 2005, 34, 164.
12. For some recent examples, see: (a) Dressen, M. H. C. L.; van de Kruijs, B. H. P.; Meuldijk, J.; Vekemans, J. A. J. M.; Hulshof, L. A. Org. Process Res. Dev. 2007, 11, 865.
13. (b) Holtze, C.; Tauer, K. Macromol Rapid Commun. 2007, 28, 428.
14. (c) Young, D. D.; Deiters, A. Angew. Chem., Int. Ed. 2007, 46, 5187.
15. (d) Conner, W. C.; Tompsett, G. A. J. Phys. Chem. B 2008, 112, 2110.
16. For a more detailed definition and examples for thermal, specific, and nonthermal microwave effects, see: (a) Kappe, C. O.; Stadler, A. Microwaves in Organic and Medicinal Chemistry; Wiley-VCH: Weinheim, Germany, 2005; Chapter 2, pp 9-28. See also refs 2a and 3.
17. (a) Hayes, B. L.; Collins, M. J., Jr. World Patent 2004, WO 04002617.
18. (b) Hayes, B. L. Aldrichim. Acta 2004, 37, 66.
19. (a) Singh, B. K.; Appukkuttan, P.; Claerhout, S.; Parmar, V. S.; Van der Eycken, E. Org. Lett. 2006, 8, 1863.
20. (b) Appukkuttan, P.; Husain, M.; Gupta, R. K.; Parmar, V. S.; Van der Eycken, E. Synlett 2006, 1491.
21. (c) Singh, B.; Mehta, V. P.; Parmar, V. S.; Van der Eycken, E. Org. Biomol Chem. 2007, 5, 2962.
22. (a) Vanier, G. S. Synlett 2007, 131.
23. (b) Baxendale, I. R.; Griffiths-Jones, C. M.; Ley, S. V.; Tranmer, G. T. Chem. Eur. J. 2006, 12, 4407.
24. (c) Arvela, R. K.; Leadbeater, N. E. Org. Lett. 2005, 7, 2101.
25. (a) Leadbeater, N. E.; Pillsbury, S. J.; Shanahan. E.; Williams, V. A. Tetrahedron 2005, 61, 3565.
26. (b) Leadbeater, N. E.; Stencel, L. M.; Wood, E. C. Org. Biomol. Chem. 2007, 1052.
27. (c) Massi, A.; Nuzzi, A.; Dondoni. A. J. Org. Chem. 2007, 72, 10279.
28. Hosseini, M.; Stiasni, N.; Barbieri, V.; Kappe, C. O. J. Org. Chem. 2007, 72, 1417.
29. Herrero, M. A.; Kremsner, J. M.; Kappe, C. O. J. Org. Chem. 2008, 73, 36.
30. Kremsner, J. M.; Kappe, C. O. J. Org. Chem. 2006, 71, 4651.
31. Kremsner, J. M.; Stadler, A.; Kappe, C. O. J. Comb. Chem. 2007, 9, 285.
32. Geuens, J.; Kremsner, J. M.; Nebel, B. A.; Schober, S.; Dommisse, R. A.; Mittelbach, M.; Tavernier, S.; Kappe, C. O.; Maes, B. U. W. Energy Fuels 2008, 22, 643.
33. Razzaq, T.; Kappe, C. O. ChemSusChem 2008, 1, 123.
34. The ability of a specific solvent to convert microwave energy into heat at a given frequency and temperature is determined by the so-called loss tangent (tan δ), expressed as the quotient, tan δ = ε″/ ε′. A reaction medium with a high tan δ at the standard operating frequency of a microwave synthesis reactor (2.45 GHz) is required for good absorption and, consequently, for efficient heating. Solvents used for microwave synthesis can be classified as high (tan δ > 0.5), medium (tan δ 0.1-0.5), and low microwave absorbing (tan δ < 0.1). See refs 1 and 2 for more details.
35. Moseley, J. D.; Lenden, P.; Thomson, A. D.; Gilday, J. P. Tetrahedron Lett. 2007, 48, 6084.
36. This is achieved by using the instrument setting "very high absorbing" or "high absorbing" on the Biotage Initiator 2.0 model. For other instruments, the microwave output power can be manually adjusted to the desired level. Using higher power settings in some cases led to temperature overshoots and to a deformation of the Teflon-coated stir bars at the SiC cylinder contact surface indicating temperatures >270°C at the SiC surface. SiC is known to be a very strong microwave absorbing material:(a) Meredith, R. Engineers' Handbook of Industrial Microwave Heating; The Institution of Electrical Engineers: Stevenege, U.K., 1998.
37. (b) Baeraky, T. A. Egypt. J. Sol. 2002, 25, 263.
38. Moore, G. G.; Foglia, T. A.; McGahan, T. J. J. Org. Chem. 1979, 44, 2425.
39. For microwave-assisted esterifications of 2,4,6-trimethylbenzoic acid, see: (a) Wilson, N. S.; Sarko, C. R.; Roth, G. P. Org. Process Res. Dev. 2004, 8, 535.
40. (b) Cablewski, T.; Faux, A. F.; Strauss, C. R. J. Org. Chem. 1994, 59, 3408.
41. (c) Raner, K. D.; Strauss, C. R. J. Org. Chem. 1992, 57, 6231.
42. Bagley, M. C.; Lubinu, M. C. Synthesis 2006, 1283.
43. (a) Mingos, D. M. P.; Baghurst, D. R. Chem. Soc. Rev. 1991, 20, 1.
44. (b) Gabriel, C.; Gabriel, S.; Grant, E. H.; Halstead, B. S.; Mingos, D. M. P. Chem. Soc. Rev. 1998, 27, 213.
45. (a) Bogdal, D.; Lukasiewicz, M.; Pielichowski, J.; Miciak, A.; Bednarz, S. Tetrahedron 2003, 59, 649.
46. (b) Lukasiewicz, M.; Bogdal, D.; Pielichowski, J. Adv. Synth. Catal. 2003, 345, 1269.
47. -4). (a) Bogdal, D.; Prociak, A. Microwave-Enhanced Polymer Chemistry and Technology; Blackwell Publishing: Oxford, UK, 2007.
48. Desai, B.; Kappe, C. O. Top. Curr. Chem. 2004, 242, 177, and references cited therein.
49. 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, and references therein.
50. Stadler, A.; Yousefi, B. H.; Dallinger, D.; Walla, P.; Van der Eycken, E.; Kaval, N.; Kappe, C. O. Org. Process Res. Dev. 2003, 7, 707.
51. Köhler, K.; Heidenreich, R. G.; Krauter, J. G.; Pietsch, J.Chem. Eur. J. 2002, 8, 622.
52. Prokopcová, H.; Kappe, C. O. J. Org. Chem. 2007, 72, 4440.
53. (a) Kaiser, N.-F. K.; Bremberg, U.; Larhed, M.; Moberg, C.; Hallberg, A. Angew. Chem., Int. Ed. 2000, 39, 3596.
54. (b) Garbacia, S.; Desai, B.; Lavastre, O.; Kappe, C. O. J. Org. Chem. 2003, 68, 9136.
55. Shore, G.; Organ, M. G. Chem. Commun. 2008, 838.
56. McNulty, J.; Nair, J. J.; Cheekoori, S.; Larichev, V.; Capretta, A.; Robertson, A. J. Chem. Eur. J. 2006, 12, 9314.
57. (a) Lensen, N.; Mouelhi, S.; Bellassoued, M. Synth. Commun. 2001, 31, 1007.
58. Kuno, A.; Sugiyama, Y.; Katsuta, K.; Kamitani, T.; Takasugi, H. Chem. Pharm. Bull. 1992, 40, 1452.