Recent advances for serial processes of hazardous chemicals in fully integrated microfluidic systems

Korean Journal of Chemical Engineering

Volumn 33, Issue 8, 2016, Pages 2253-2267

  Singh, Rakhi ^a   Lee, Hyune Jea ^a   Singh, Ajay Kumar ^a   Kim, Dong Pyo ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

Azide; Carbon Monoxide; Chloro Methyl Methyl Ether; Diaze Compound; Dual Channel Microreactor; Extraction Unit; Micro total Envelopment System; Ozone; Separator; Silicon Nanowire Reactor; Total Process System; Toxic Chemicals; Tube in Tube System

Indexed keywords

EID: 84976631373     PISSN: 02561115     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11814-016-0114-6     Document Type: Review

References (101)

1. T. Wirth, Microreactors in Organic Synthesis and Catalysis, Wiley-VCH (2008).
2. G.M. Whitesides, Nature, 442, 368 (2006).
3. C. G. Frost and L. Mutton, Green. Chem., 12, 1687 (2010).
4. S. Marre and K. F. Jensen, Chem. Soc. Rev., 39, 1183 (2010).
5. N. Kockmann and D. M. Roberge, Chem. Eng. Technol., 32, 1682 (2009).
6. B. Gutmann, D. Cantillo and C.O. Kappe, Angew. Chem. Int. Ed., 54, 6688 (2015).
7. C.J. Mallia and I.R. Baxendale, Org. Process. Res. Dev., 20, 327 (2016).
8. R. Porta, M. Benaglia and A. Puglisi, Org. Process. Res. Dev., 20, 2 (2016).
9. D. Webb and T. F. Jamison, Chem. Sci., 1, 675 (2010).
10. C. Wiles and P. Watts, Green. Chem., 14, 38 (2012).
11. B. J. Deadman, S.G. Collins and A.R. Maguire, Chem. Eur. J., 21, 2298 (2015).
12. S.T.R. Müller and T. Wirth, ChemSusChem, 8, 245 (2015).
13. H. Amii, A. Nagaki and J.-i. Yoshida, Beilstein J. Org. Chem., 9, 2793 (2013).
14. M. Brzozowski, M. O’Brien, S.V. Ley and A. Polyzos, Acc. Chem. Res., 48, 349 (2015).
15. N. Oger, E. Le Grognec and F.-X. Felpin, Org. Chem. Front., 2, 590 (2015).
16. S.G. Newman and K. F. Jensen, Green. Chem., 15, 1456 (2013).
17. D.T. McQuade and P. H. Seeberger, J. Org. Chem., 78, 6384 (2013).
18. H. P. L. Gemoets, Y. Su, M. Shang, V. Hessel, R. Luque and T. Noel, Chem. Soc. Rev., 45, 83 (2016).
19. P. J. Cossar, L. Hizartzidis, M. I. Simone, A. McCluskey and C. P. Gordon, Org. Biomol. Chem., 13, 7119 (2015).
20. A.K. Singh, D.-H. Ko, N. K. Vishwakarma, S. Jang, K.-I. Min and D.-P. Kim, Nat. Commun., 7 (2016).
21. R.A. Maurya, C. P. Park, J. H. Lee and D.-P. Kim, Angew. Chem. Int. Ed., 50, 5952 (2011).
22. F. Mastronardi, B. Gutmann and C.O. Kappe, Org. Lett., 15, 5590 (2013).
23. M. O’Brien, I.R. Baxendale and S.V. Ley, Org. Lett., 12, 1596 (2010).
24. V.D. Pinho, B. Gutmann, L. S. M. Miranda, R.O. M. A. de Souza and C.O. Kappe, J. Org. Chem., 79, 1555 (2014).
25. V.D. Pinho, B. Gutmann and C.O. Kappe, RSC Adv., 4, 37419 (2014).
26. E. Rossi, P. Woehl and M. Maggini, Org. Process. Res. Dev., 16, 1146 (2012).
27. G. Maas, Angew. Chem. Int. Ed., 48, 8186 (2009).
28. R.A. Maurya, K.-I. Min and D.-P. Kim, Green Chem., 16, 116 (2014).
29. H.E. Bartrum, D.C. Blakemore, C. J. Moody and C. J. Hayes, J. Org. Chem., 75, 8674 (2010).
30. L. J. Martin, A. L. Marzinzik, S.V. Ley and I.R. Baxendale, Org. Lett., 13, 320 (2011).
31. P. S. Bailey, Chem. Rev., 58, 925 (1958).
32. P. S. Bailey, Ozonolysis in Organic Chemistry, Academic Press (1978).
33. W. H. Bunnelle, Chem. Rev., 91, 335 (1991).
34. T. I. Zvereva, V. G. Kasradze, O. B. Kazakova and O. S. Kukovinets, Russ. J. Org. Chem., 46, 1431 (2010).
35. th Ed., Oxford (1990).
36. S. Caron, R.W. Dugger, S. G. Ruggeri, J. A. Ragan and D. H.B. Ripin, Chem. Rev., 106, 2943 (2006).
37. Y. Wada, M. A. Schmidt and K. F. Jensen, Ind. Eng. Chem. Res., 45, 8036 (2006).
38. S. Hübner, U. Bentrup, U. Budde, K. Lovis, T. Dietrich, A. Freitag, L. Küpper and K. Jähnisch, Org. Process. Res. Dev., 13, 952 (2009).
39. M.D. Roydhouse, A. Ghaini, A. Constantinou, A. Cantu-Perez, W. B. Motherwell and A. Gavriilidis, Org. Process. Res. Dev., 15, 989 (2011).
40. M.D. Roydhouse, W.B. Motherwell, A. Constantinou, A. Gavriilidis, R. Wheeler, K. Down and I. Campbell, RSC Adv., 3, 5076 (2013).
41. M. Irfan, T. N. Glasnov and C.O. Kappe, Org. Lett., 13, 984 (2011).
42. C. Battilocchio, I.R. Baxendale, M. Biava, M.O. Kitching and S.V. Ley, Org. Process. Res. Dev., 16, 798 (2012).
43. J. Zak, D. Ron, E. Riva, H. P. Harding, B. C. S. Cross and I.R. Baxendale, Chem. Eur. J., 18, 9901 (2012).
44. F. Fischer and H. Tropsch, Brennstoff-chem., 97 (1926).
45. H. Adkins and G. Krsek, J. Am. Chem. Soc., 71, 3051 (1949).
46. th Ed., Van Nostrand Reinhold (1989).
47. P.W. Miller, N. J. Long, A. J. de Mello, R. Vilar, J. Passchier and A. Gee, Chem. Commun., 546 (2006).
48. M.T. Rahman, T. Fukuyama, N. Kamata, M. Sato and I. Ryu, Chem. Commun., 2236 (2006).
49. E.R. Murphy, J.R. Martinelli, N. Zaborenko, S. L. Buchwald and K. F. Jensen, Angew. Chem. Int. Ed., 46, 1734 (2007).
50. P.W. Miller, N. J. Long, A. J. de Mello, R. Vilar, H. Audrain, D. Bender, J. Passchier and A. Gee, Angew. Chem. Int. Ed., 46, 2875 (2007).
51. P.W. Miller, L.E. Jennings, A. J. de Mello, A.D. Gee, N. J. Long and R. Vilar, Adv. Synth. Catal., 351, 3260 (2009).
52. T. Fukuyama, M.T. Rahman, N. Kamata and I. Ryu, Beilstein J. Org. Chem., 5, 34 (2009).
53. X. Gong, P.W. Miller, A.D. Gee, N. J. Long, A. J. de Mello and R. Vilar, Chem. Eur. J., 18, 2768 (2012).
54. C. Csajági, B. Borcsek, K. Niesz, I. Kovács, Z. Székelyhidi, Z. Bajkó, L. Ürge and F. Darvas, Org. Lett., 10, 1589 (2008).
55. P. Koos, U. Gross, A. Polyzos, M. O'Brien, I. Baxendale and S.V. Ley, Org. Biomol. Chem., 9, 6903 (2011).
56. M.A. Mercadante and N. E. Leadbeater, Org. Biomol. Chem., 9, 6575 (2011).
57. C.B. Kelly, C. Lee, M.A. Mercadante and N.E. Leadbeater, Org. Process. Res. Dev., 15, 717 (2011).
58. M.A. Mercadante and N. E. Leadbeater, Green. Process. Synth., 1, 499 (2012).
59. C. Brancour, T. Fukuyama, Y. Mukai, T. Skrydstrup and I. Ryu, Org. Lett., 15, 2794 (2013).
60. T. Fukuyama, Y. Mukai and I. Ryu, Beilstein J. Org. Chem., 7, 1288 (2011).
61. M. Cartwright and J. Wilkinson, Propellants Explos. Pyrotech., 35, 326 (2010).
62. S. Bräse, C. Gil, K. Knepper and V. Zimmermann, Angew. Chem. Int. Ed., 44, 5188 (2005).
63. M. E. Kopach, M. M. Murray, T. M. Braden, M. E. Kobierski and O. L. Williams, Org. Process. Res. Dev., 13, 152 (2009).
64. M. Weber, G. Yilmaz and G. Wille, Chim. Oggi., 29, 8 (2011).
65. M.M. E. Delville, P. J. Nieuwland, P. Janssen, K. Koch, J. C. M. van Hest and F. P. J. T. Rutjes, Chem. Eng. J., 167, 556 (2011).
66. C.D. Smith, I.R. Baxendale, S. Lanners, J. J. Hayward, S.C. Smith and S.V. Ley, Org. Biomol. Chem., 5, 1559 (2007).
67. I.R. Baxendale, S.V. Ley, A. C. Mansfield and C.D. Smith, Angew. Chem. Int. Ed., 48, 4017 (2009).
68. C.O. Kappe and E. Van der Eycken, Chem. Soc. Rev., 39, 1280 (2010).
69. S. Ceylan, T. Klande, C. Vogt, C. Friese and A. Kirschning, Synlett., 2010, 2009 (2010).
70. A.C. Varas, T. Noël, Q. Wang and V. Hessel, ChemSusChem, 5, 1703 (2012).
71. M. Fuchs, W. Goessler, C. Pilger and C.O. Kappe, Adv. Synth. Catal., 352, 323 (2010).
72. A.R. Bogdan and K. James, Chem. Eur. J., 16, 14506 (2010).
73. A.R. Bogdan and K. James, Org. Lett., 13, 4060 (2011).
74. A.R. Bogdan and N.W. Sach, Adv. Synth. Catal., 351, 849 (2009).
75. P. Zhang, M. G. Russell and T. F. Jamison, Org. Process. Res. Dev., 18, 1567 (2014).
76. H.R. Sahoo, J.G. Kralj and K.F. Jensen, Angew. Chem. Int. Ed., 46, 5704 (2007).
77. B. Gutmann, J.-P. Roduit, D. Roberge and C.O. Kappe, Angew. Chem. Int. Ed., 49, 7101 (2010).
78. B. Gutmann, D. Obermayer, J. P. Roduit, D. M. Roberge and C.O. Kappe, J. Flow. Chem., 2, 8 (2012).
79. L.A. Flippin, Tetrahedron Lett., 32, 6857 (1991).
80. M.B. Talawar, A. P. Agrawal, M. Anniyappan, D. S. Wani, M. K. Bansode and G. M. Gore, J. Hazard. Mater., 137, 1074 (2006).
81. H. Singh, A. S. Chawla, V. K. Kapoor, D. Paul and R. K. Malhotra, Prog. Med. Chem., 17, 151 (1980).
82. R. J. Herr, Bioorganic & Medicinal Chemistry, 10, 3379 (2002).
83. B. Gutmann, J.-P. Roduit, D. Roberge and C.O. Kappe, Chem. Eur. J., 17, 13146 (2011).
84. J.C. Brandt and T. Wirth, Beilstein J. Org. Chem., 5, 30 (2009).
85. C. Viuf and M. Bols, Angew. Chem. Int. Ed., 40, 623 (2001).
86. C.M. Pedersen, L. G. Marinescu and M. Bols, Org. Biomol. Chem., 3, 816 (2005).
87. R. J. Linderman, M. Jaber and B.D. Griedel, J. Org. Chem., 59, 6499 (1994).
88. M.A. Berliner and K. Belecki, J. Org. Chem., 70, 9618 (2005).
89. D.M. Barnes, J. Barkalow and D. J. Plata, Org. Lett., 11, 273 (2009).
90. A. Jasti, S. Prakash and V.K. Shahi, J. Membr. Sci., 428, 470 (2013).
91. A. Mitic and K.V. Gernaey, Chem. Eng. Technol., 38, 1699 (2015).
92. L. Hosta-Rigau, M. J. York-Duran, T. S. Kang and B. Städler, Adv. Funct. Mater., 25, 3860 (2015).
93. A.R. Bogdan, S.L. Poe, D.C. Kubis, S. J. Broadwater and D.T. McQuade, Angew. Chem., 121, 8699 (2009).
94. S. Mascia, P. L. Heider, H. Zhang, R. Lakerveld, B. Benyahia, P. I. Barton, R.D. Braatz, C.L. Cooney, J.M.B. Evans, T. F. Jamison, K. F. Jensen, A. S. Myerson and B. L. Trout, Angew. Chem. Int. Ed., 52, 12359 (2013).
95. P. Zhang, M. G. Russell and T. F. Jamison, Org. Process. Res. Dev., 18, 1567 (2014).
96. K. Gilmore, D. Kopetzki, J.W. Lee, Z. Horvath, D.T. McQuade, A. Seidel-Morgenstern and P.H. Seeberger, Chem. Commun., 50, 12652 (2014).
97. P. L. Heider, S. C. Born, S. Basak, B. Benyahia, R. Lakerveld, H. Zhang, R. Hogan, L. Buchbinder, A. Wolfe, S. Mascia, J.M.B. Evans, T. F. Jamison and K.F. Jensen, Org. Process. Res. Dev., 18, 402 (2014).
98. T.P. Petersen, S. Mirsharghi, P.C. Rummel, S. Thiele, M.M. Rosenkilde, A. Ritzén and T. Ulven, Chem. Eur. J., 19, 9343 (2013).
99. M.D. Symes, P. J. Kitson, J. Yan, C. J. Richmond, G. J. T. Cooper, R.W. Bowman, T. Vilbrandt and L. Cronin, Nat. Chem., 4, 349 (2012).
100. D. E. Fitzpatrick, C. Battilocchio and S.V. Ley, ACS Cent. Sci., 2(3), 131 (2016).
101. A.K. Au, W. Huynh, L.F. Horowitz and A. Folch, Angew. Chem. Int. Ed., 55, 3862 (2016).