A microwave-based chemical factory in the lab: From milligram to multigram preparations

Journal of Chemistry

Volumn 2015, Issue , 2015, Pages

  Rinaldi, Laura ^a   Carnaroglio, Diego ^a   Rotolo, Laura ^a   Cravotto, Giancarlo ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84924529873     PISSN: 20909063     EISSN: 20909071     Source Type: Journal    
DOI: 10.1155/2015/879531     Document Type: Review

References (142)

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2. F. Chemat and G. Cravotto, Microwave-Assisted Extraction for Bioactive Compounds: Theory and Practice, Vol. 4 of Food Engineering Series, Springer, New York, NY, USA, 2013.
3. S. Horikoshi and N. Serpone, Nanoparticle Synthesis - Fundamentals and Applications, Wiley-VCH, Weinheim, Germany, 2013.
4. Z. Fang, R. L. Smith, and X. Qi, Production of Biofuels and Chemicals with Microwave, Vol. 3 of Biofuels and Biorefineries, Springer Science, New York, NY, USA, 2014.
5. L. Chen, D. Song, Y. Tian, L. Ding, A. Yu, and H. Zhang, "Application of on-line microwave sample-preparation techniques," Trends in Analytical Chemistry, Vol. 27, no. 2, pp. 151-159, 2008.
6. R. Gedye, F. Smith, K. Westaway et al., "The use of microwave ovens for rapid organic synthesis," Thetrahedron Letters, Vol. 27, no. 3, pp. 279-282, 1986.
7. R. J. Giguere, T. L. Bray, S. M. Duncan, and G. Majetich, "Application of commercial microwave ovens to organic synthesis," Thetrahedron Letters, Vol. 27, no. 41, pp. 4945-4948, 1986.
8. C. O. Kappe and D. Dallinger, "Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature," Molecular Diversity, Vol. 13, no. 2, pp. 71-193, 2009.
9. R. B. N. Baig and R. S. Varma, "Alternative energy input: mechanochemical, microwave and ultrasound-assisted organic synthesis," Chemical Society Reviews, Vol. 41, no. 4, pp. 1559-1584, 2012.
10. C. O. Kappe, "Controlled microwave heating in modern organic synthesis," Angewandte Chemie International Edition, Vol. 43, no. 46, pp. 6250-6284, 2004.
11. G. Cravotto and P. Cintas, "The combined use of microwaves and ultrasound: improved tools in process chemistry and organic synthesis," Chemistry, Vol. 13, no. 7, pp. 1902-1909, 2007.
12. G. Cravotto and P. Cintas, "The combined use of microwaves and ultrasound: methods and practice," in Microwaves in Organic Synthesis, A. De La Hoz and A. Loupy, Eds., Vol. 1, Springer, New York, NY, USA, 3rd edition, 2012.
13. D. Garella, E. Borretto, A. Di Stilo, K. Martina, G. Cravotto, and P. Cintas, "Microwave-assisted synthesis of N-heterocycles in medicinal chemistry," MedChemComm, Vol. 4, no. 10, pp. 1323-1343, 2013.
14. K. Kempe, C. R. Becer, and U. S. Schubert, "Microwave-assisted polymerizations: recent status and future perspectives," Macromolecules, Vol. 44, no. 15, pp. 5825-5842, 2011.
15. R. S. Varma, "Greener routes to organics and nanomaterials: sustainable applications of nanocatalysts," Pure and Applied Chemistry, Vol. 85, no. 8, pp. 1703-1710, 2013.
16. S. Tabasso, E. Montoneri, D. Carnaroglio, M. Caporaso, and G. Cravotto, "Microwave-assisted flash conversion of non-edible polysaccharides and post-harvest tomato plant waste to levulinic acid," Green Chemistry, Vol. 16, no. 1, pp. 73-76, 2014.
17. R. van Noorden, "Microwaving myths," Chemistry World, Vol. 5, pp. 40-46, 2008.
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19. P. Cintas, D. Carnaroglio, L. Rinaldi, and G. Cravotto, "Complementary and synergic effects of microwaves and ultrasound in metal-assisted synthesis," Chemistry Today, Vol. 30, no. 3, pp. 33-35, 2012.
20. V. Hessel, G. Cravotto, P. Fitzpatrick, B. S. Patil, J. Lang, and W. Bonrath, "Industrial applications of plasma, microwave and ultrasound techniques: nitrogen-fixation and hydrogenation reactions," Chemical Engineering and Processing, Vol. 71, pp. 19-30, 2013.
21. A. Loupy, P. Pigeon, and M. Ramdani, "Synthesis of long chain aromatic esters in a solvent-free procedure under microwaves," Thetrahedron, Vol. 52, no. 19, pp. 6705-6712, 1996.
22. D. Rossi, M. Urbano, A. C. Baraglia et al., "Polymer-assisted solution-phase synthesis under combined ultrasound and microwave irradiation: preparation of α,β-unsaturated esters and carboxylic acids, key intermediates of novel sigma ligands," Synthetic Communications, Vol. 39, no. 18, pp. 3254-3262, 2009.
23. M. A. Herrero, J. M. Kremsner, and C. O. Kappe, "Nonthermal microwave effects revisited: on the importance of internal temperature monitoring and agitation in microwave chemistry," Journal of Organic Chemistry, Vol. 73, no. 1, pp. 36-47, 2008.
24. L. Alexandru, L. Pizzale, L. Conte, A. Barge, and G. Cravotto, "Microwave-assisted extraction of edible Cicerbita alpina shoots and its LC-MS phenolic profile," Journal of the Science of Food and Agriculture, Vol. 93, no. 11, pp. 2676-2682, 2013.
25. L. Orio, G. Cravotto, A. Binello, G. Pignata, S. Nicola, and F. Chemat, "Hydrodistillation and in situ microwave-generated hydrodistillation of fresh and dried mint leaves: a comparison study," Journal of the Science of Food and Agriculture, Vol. 92, no. 15, pp. 3085-3090, 2012.
26. A. A. Craveiro, F. J. A. Matos, J. W. Alencar, and M. M. Plumel, "Microwave oven extraction of an essential oil," Flavour and Fragrance Journal, Vol. 4, no. 1, pp. 43-44, 1989.
27. F. Chemat, M. Vian, and F. Visinoni, "Microwave Hydrodiffusion for Isolation of Natural Products," US 20100062121 A1, 2008.
28. A. Sharma, D. Vacchani, and E. van der Eycken, "Developments in direct C-H arylation of (hetero)arenes under microwave irradiation," Chemistry, Vol. 19, no. 4, pp. 1158-1168, 2013.
29. C. O. Kappe, "Reply to the correspondence on microwave effects in organic synthesis," Angewandte Chemie - International Edition, Vol. 52, no. 31, pp. 7924-7928, 2013.
30. C. O. Kappe, B. Pieber, and D. Dallinger, "Microwave effects in organic synthesis: myth or reality?" Angewandte Chemie - International Edition, Vol. 52, no. 4, pp. 1088-1094, 2013.
31. K. C. Nicolaou and E. J. Sorensen, Classics in Total Synthesis, Wiley-VCH, Weinheim, Germany, 1996.
32. R. F. Heck and J. P. Nolley Jr., "Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides," Journal of Organic Chemistry, Vol. 37, no. 14, pp. 2320-2322, 1972.
33. N. Miyaura and A. Suzuki, "Palladium-catalyzed cross-coupling reactions of organoboron compounds," Chemical Reviews, Vol. 95, no. 7, pp. 2457-2483, 1995.
34. M. Larhed and A. Hallberg, "Microwave-promoted palladium-catalyzed coupling reactions," Journal of Organic Chemistry, Vol. 61, no. 26, pp. 9582-9584, 1996.
35. N. E. Leadbeater and M. Marco, "Ligand-free palladium catalysis of the suzuki reaction in water using microwave heating," Organic Letters, Vol. 4, no. 17, pp. 2973-2976, 2002.
36. N. E. Leadbeater and M. Marco, "Transition-metal-free Suzukitype coupling reactions: scope and limitations of the methodology," Journal of Organic Chemistry, Vol. 68, no. 14, pp. 5660-5667, 2003.
37. N. E. Leadbeater, V. A. Williams, T. M. Barnard, and M. J. Collins Jr., "Open-vessel microwave-promoted Suzuki reactions using low levels of palladium catalyst: optimization and scale-up," Organic Process Research and Development, Vol. 10, no. 4, pp. 833-837, 2006.
38. F. Bergamelli, M. Iannelli, J. A. Marafie, and J. D. Moseley, "A commercial continuous flow microwave reactor evaluated for scale-up," Organic Process Research and Development, Vol. 14, no. 4, pp. 926-930, 2010.
39. A. Barge, S. Tagliapietra, L. Tei, P. Cintas, and G. Cravotto, "Pd-catalyzed reactions promoted by ultrasound and/or microwave irradiation," Current Organic Chemistry, Vol. 12, no. 18, pp. 1588-1612, 2008.
40. S. E. S. Leonhardt, A. Stolle, B. Ondruschka et al., "Chitosan as a support for heterogeneous Pd catalysts in liquid phase catalysis," Applied Catalysis A: General, Vol. 379, no. 1-2, pp. 30-37, 2010.
41. K. Martina, S. E. S. Leonhardt, B. Ondruschka, M. Curini, A. Binello, and G. Cravotto, "In situ cross-linked chitosan Cu(I) or Pd(II) complexes as a versatile, eco-friendly recyclable solid catalyst," Journal of Molecular Catalysis A: Chemical, Vol. 334, no. 1-2, pp. 60-64, 2011.
42. G. Palmisano, W. Bonrath, L. Boffa, D. Garella, A. Barge, and G. Cravotto, "Heck reactions with very low ligandless catalyst loads accelerated by microwaves or simultaneous microwaves/ultrasound irradiation," Advanced Synthesis and Catalysis, Vol. 349, no. 14-15, pp. 2338-2344, 2007.
43. G. Cravotto, L. Orio, E. C. Gaudino, K. Martina, D. Tavor, and A. Wolfson, "Efficient synthetic protocols in glycerol under heterogeneous catalysis," ChemSusChem, Vol. 4, no. 8, pp. 1130-1134, 2011.
44. G. Cravotto, E. C. Gaudino, S. Tagliapietra, D. Carnaroglio, and A. Procopio, "A green approach to heterogeneous catalysis using ligand-free, metal-loaded cross-linked cyclodextrins," Green Processing and Synthesis, Vol. 1, no. 3, pp. 269-273, 2012.
45. A. Demirbaş, "Biodegradability of biodiesel and petrodiesel fuels," Energy Sources, Part A: Recovery, Utilization and Environmental Effects, Vol. 31, no. 2, pp. 169-174, 2009.
46. F. Motasemi and F. N. Ani, "A review on microwave-assisted production of biodiesel," Renewable and Sustainable Energy Reviews, Vol. 16, no. 7, pp. 4719-4733, 2012.
47. N. E. Leadbeater and L. M. Stencel, "Fast, easy preparation of biodiesel using microwave heating," Energy and Fuels, Vol. 20, no. 5, pp. 2281-2283, 2006.
48. T. M. Barnard, N. E. Leadbeater, M. B. Boucher, L. M. Stencel, and B. A. Wilhite, "Continuous-flow preparation of biodiesel using microwave heating," Energy and Fuels, Vol. 21, no. 3, pp. 1777-1781, 2007.
49. Y. Groisman and A. Gedanken, "Continuous flow, circulating microwave system and its application in nanoparticle fabrication and biodiesel synthesis," Journal of Physical Chemistry C, Vol. 112, no. 24, pp. 8802-8808, 2008.
50. M.-C. Hsiao, C.-C. Lin, Y.-H. Chang, and L.-C. Chen, "Ultrasonic mixing and closed microwave irradiation-assisted trans-esterification of soybean oil," Fuel, Vol. 89, no. 12, pp. 3618-3622, 2010.
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72. A. De La Hoz and A. Loupy, Microwaves in Organic Synthesis, Springer Science, New York, NY, USA, 3rd edition, 2012.
73. F. Chemat and G. Cravotto, Microwave-Assisted Extraction for Bioactive Compounds: Theory and Practice, Vol. 4 of Food Engineering Series, Springer, New York, NY, USA, 2013.
74. S. Horikoshi and N. Serpone, Nanoparticle Synthesis - Fundamentals and Applications, Wiley-VCH, Weinheim, Germany, 2013.
75. Z. Fang, R. L. Smith, and X. Qi, Production of Biofuels and Chemicals with Microwave, Vol. 3 of Biofuels and Biorefineries, Springer Science, New York, NY, USA, 2014.
76. L. Chen, D. Song, Y. Tian, L. Ding, A. Yu, and H. Zhang, "Application of on-line microwave sample-preparation techniques," Trends in Analytical Chemistry, Vol. 27, no. 2, pp. 151-159, 2008.
77. R. Gedye, F. Smith, K. Westaway et al., "The use of microwave ovens for rapid organic synthesis," Thetrahedron Letters, Vol. 27, no. 3, pp. 279-282, 1986.
78. R. J. Giguere, T. L. Bray, S. M. Duncan, and G. Majetich, "Application of commercial microwave ovens to organic synthesis," Thetrahedron Letters, Vol. 27, no. 41, pp. 4945-4948, 1986.
79. C. O. Kappe and D. Dallinger, "Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature," Molecular Diversity, Vol. 13, no. 2, pp. 71-193, 2009.
80. R. B. N. Baig and R. S. Varma, "Alternative energy input: mechanochemical, microwave and ultrasound-assisted organic synthesis," Chemical Society Reviews, Vol. 41, no. 4, pp. 1559-1584, 2012.
81. C. O. Kappe, "Controlled microwave heating in modern organic synthesis," Angewandte Chemie International Edition, Vol. 43, no. 46, pp. 6250-6284, 2004.
82. G. Cravotto and P. Cintas, "The combined use of microwaves and ultrasound: improved tools in process chemistry and organic synthesis," Chemistry, Vol. 13, no. 7, pp. 1902-1909, 2007.
83. G. Cravotto and P. Cintas, "The combined use of microwaves and ultrasound: methods and practice," in Microwaves in Organic Synthesis, A. De La Hoz and A. Loupy, Eds., Vol. 1, Springer, New York, NY, USA, 3rd edition, 2012.
84. D. Garella, E. Borretto, A. Di Stilo, K. Martina, G. Cravotto, and P. Cintas, "Microwave-assisted synthesis of N-heterocycles in medicinal chemistry," MedChemComm, Vol. 4, no. 10, pp. 1323-1343, 2013.
85. K. Kempe, C. R. Becer, and U. S. Schubert, "Microwave-assisted polymerizations: recent status and future perspectives," Macromolecules, Vol. 44, no. 15, pp. 5825-5842, 2011.
86. R. S. Varma, "Greener routes to organics and nanomaterials: sustainable applications of nanocatalysts," Pure and Applied Chemistry, Vol. 85, no. 8, pp. 1703-1710, 2013.
87. S. Tabasso, E. Montoneri, D. Carnaroglio, M. Caporaso, and G. Cravotto, "Microwave-assisted flash conversion of non-edible polysaccharides and post-harvest tomato plant waste to levulinic acid," Green Chemistry, Vol. 16, no. 1, pp. 73-76, 2014.
88. R. van Noorden, "Microwaving myths," Chemistry World, Vol. 5, pp. 40-46, 2008.
89. C. O. Kappe and A. Stadler, Microwaves in Organic and Medicinal Chemistry, Wiley-VCH, Weinheim, Germany, 2005.
90. P. Cintas, D. Carnaroglio, L. Rinaldi, and G. Cravotto, "Complementary and synergic effects of microwaves and ultrasound in metal-assisted synthesis," Chemistry Today, Vol. 30, no. 3, pp. 33-35, 2012.
91. V. Hessel, G. Cravotto, P. Fitzpatrick, B. S. Patil, J. Lang, and W. Bonrath, "Industrial applications of plasma, microwave and ultrasound techniques: nitrogen-fixation and hydrogenation reactions," Chemical Engineering and Processing, Vol. 71, pp. 19-30, 2013.
92. A. Loupy, P. Pigeon, and M. Ramdani, "Synthesis of long chain aromatic esters in a solvent-free procedure under microwaves," Thetrahedron, Vol. 52, no. 19, pp. 6705-6712, 1996.
93. D. Rossi, M. Urbano, A. C. Baraglia et al., "Polymer-assisted solution-phase synthesis under combined ultrasound and microwave irradiation: preparation of α,β-unsaturated esters and carboxylic acids, key intermediates of novel sigma ligands," Synthetic Communications, Vol. 39, no. 18, pp. 3254-3262, 2009.
94. M. A. Herrero, J. M. Kremsner, and C. O. Kappe, "Nonthermal microwave effects revisited: on the importance of internal temperature monitoring and agitation in microwave chemistry," Journal of Organic Chemistry, Vol. 73, no. 1, pp. 36-47, 2008.
95. L. Alexandru, L. Pizzale, L. Conte, A. Barge, and G. Cravotto, "Microwave-assisted extraction of edible Cicerbita alpina shoots and its LC-MS phenolic profile," Journal of the Science of Food and Agriculture, Vol. 93, no. 11, pp. 2676-2682, 2013.
96. L. Orio, G. Cravotto, A. Binello, G. Pignata, S. Nicola, and F. Chemat, "Hydrodistillation and in situ microwave-generated hydrodistillation of fresh and dried mint leaves: a comparison study," Journal of the Science of Food and Agriculture, Vol. 92, no. 15, pp. 3085-3090, 2012.
97. A. A. Craveiro, F. J. A. Matos, J. W. Alencar, and M. M. Plumel, "Microwave oven extraction of an essential oil," Flavour and Fragrance Journal, Vol. 4, no. 1, pp. 43-44, 1989.
98. F. Chemat, M. Vian, and F. Visinoni, "Microwave Hydrodiffusion for Isolation of Natural Products," US 20100062121 A1, 2008.
99. A. Sharma, D. Vacchani, and E. van der Eycken, "Developments in direct C-H arylation of (hetero)arenes under microwave irradiation," Chemistry, Vol. 19, no. 4, pp. 1158-1168, 2013.
100. C. O. Kappe, "Reply to the correspondence on microwave effects in organic synthesis," Angewandte Chemie - International Edition, Vol. 52, no. 31, pp. 7924-7928, 2013.
101. C. O. Kappe, B. Pieber, and D. Dallinger, "Microwave effects in organic synthesis: myth or reality?" Angewandte Chemie - International Edition, Vol. 52, no. 4, pp. 1088-1094, 2013.
102. K. C. Nicolaou and E. J. Sorensen, Classics in Total Synthesis, Wiley-VCH, Weinheim, Germany, 1996.
103. R. F. Heck and J. P. Nolley Jr., "Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides," Journal of Organic Chemistry, Vol. 37, no. 14, pp. 2320-2322, 1972.
104. N. Miyaura and A. Suzuki, "Palladium-catalyzed cross-coupling reactions of organoboron compounds," Chemical Reviews, Vol. 95, no. 7, pp. 2457-2483, 1995.
105. M. Larhed and A. Hallberg, "Microwave-promoted palladium-catalyzed coupling reactions," Journal of Organic Chemistry, Vol. 61, no. 26, pp. 9582-9584, 1996.
106. N. E. Leadbeater and M. Marco, "Ligand-free palladium catalysis of the suzuki reaction in water using microwave heating," Organic Letters, Vol. 4, no. 17, pp. 2973-2976, 2002.
107. N. E. Leadbeater and M. Marco, "Transition-metal-free Suzukitype coupling reactions: scope and limitations of the methodology," Journal of Organic Chemistry, Vol. 68, no. 14, pp. 5660-5667, 2003.
108. N. E. Leadbeater, V. A. Williams, T. M. Barnard, and M. J. Collins Jr., "Open-vessel microwave-promoted Suzuki reactions using low levels of palladium catalyst: optimization and scale-up," Organic Process Research and Development, Vol. 10, no. 4, pp. 833-837, 2006.
109. F. Bergamelli, M. Iannelli, J. A. Marafie, and J. D. Moseley, "A commercial continuous flow microwave reactor evaluated for scale-up," Organic Process Research and Development, Vol. 14, no. 4, pp. 926-930, 2010.
110. A. Barge, S. Tagliapietra, L. Tei, P. Cintas, and G. Cravotto, "Pd-catalyzed reactions promoted by ultrasound and/or microwave irradiation," Current Organic Chemistry, Vol. 12, no. 18, pp. 1588-1612, 2008.
111. S. E. S. Leonhardt, A. Stolle, B. Ondruschka et al., "Chitosan as a support for heterogeneous Pd catalysts in liquid phase catalysis," Applied Catalysis A: General, Vol. 379, no. 1-2, pp. 30-37, 2010.
112. K. Martina, S. E. S. Leonhardt, B. Ondruschka, M. Curini, A. Binello, and G. Cravotto, "In situ cross-linked chitosan Cu(I) or Pd(II) complexes as a versatile, eco-friendly recyclable solid catalyst," Journal of Molecular Catalysis A: Chemical, Vol. 334, no. 1-2, pp. 60-64, 2011.
113. G. Palmisano, W. Bonrath, L. Boffa, D. Garella, A. Barge, and G. Cravotto, "Heck reactions with very low ligandless catalyst loads accelerated by microwaves or simultaneous microwaves/ultrasound irradiation," Advanced Synthesis and Catalysis, Vol. 349, no. 14-15, pp. 2338-2344, 2007.
114. G. Cravotto, L. Orio, E. C. Gaudino, K. Martina, D. Tavor, and A. Wolfson, "Efficient synthetic protocols in glycerol under heterogeneous catalysis," ChemSusChem, Vol. 4, no. 8, pp. 1130-1134, 2011.
115. G. Cravotto, E. C. Gaudino, S. Tagliapietra, D. Carnaroglio, and A. Procopio, "A green approach to heterogeneous catalysis using ligand-free, metal-loaded cross-linked cyclodextrins," Green Processing and Synthesis, Vol. 1, no. 3, pp. 269-273, 2012.
116. A. Demirbaş, "Biodegradability of biodiesel and petrodiesel fuels," Energy Sources, Part A: Recovery, Utilization and Environmental Effects, Vol. 31, no. 2, pp. 169-174, 2009.
117. F. Motasemi and F. N. Ani, "A review on microwave-assisted production of biodiesel," Renewable and Sustainable Energy Reviews, Vol. 16, no. 7, pp. 4719-4733, 2012.
118. N. E. Leadbeater and L. M. Stencel, "Fast, easy preparation of biodiesel using microwave heating," Energy and Fuels, Vol. 20, no. 5, pp. 2281-2283, 2006.
119. T. M. Barnard, N. E. Leadbeater, M. B. Boucher, L. M. Stencel, and B. A. Wilhite, "Continuous-flow preparation of biodiesel using microwave heating," Energy and Fuels, Vol. 21, no. 3, pp. 1777-1781, 2007.
120. Y. Groisman and A. Gedanken, "Continuous flow, circulating microwave system and its application in nanoparticle fabrication and biodiesel synthesis," Journal of Physical Chemistry C, Vol. 112, no. 24, pp. 8802-8808, 2008.
121. M.-C. Hsiao, C.-C. Lin, Y.-H. Chang, and L.-C. Chen, "Ultrasonic mixing and closed microwave irradiation-assisted trans-esterification of soybean oil," Fuel, Vol. 89, no. 12, pp. 3618-3622, 2010.
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