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

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Abstract

The development and enlargement of toxic and hazardous chemicals are severely limited by health and safety concerns. We summarize studies on fully integrated micro-chemical systems and total processes to reduce accidental exposure to various regents that are toxic, explosive, or carcinogenic, which significantly improved the safety of work involving risky compounds. This review covers the leak-free continuous-flow processes of hazardous chemicals in fully integrated microfluidic systems, specially denoted as micro-total envelope systems (μ-TESs), that are conducting a serial process of the generation of hazardous reagents, in-situ purification and separation, subsequent reaction, and product isolation with improved efficiencies. These attempts suggest safe and efficient tools and processes of useful but hazardous chemicals for researchers and manufacturing workers in the field of pharmaceutic discovery, natural products, biology as well as materials synthesis.

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References

  1. T. Wirth, Microreactors in Organic Synthesis and Catalysis, Wiley-VCH (2008).

    Book  Google Scholar 

  2. G.M. Whitesides, Nature, 442, 368 (2006).

    Article  CAS  Google Scholar 

  3. C. G. Frost and L. Mutton, Green. Chem., 12, 1687 (2010).

    Article  CAS  Google Scholar 

  4. S. Marre and K. F. Jensen, Chem. Soc. Rev., 39, 1183 (2010).

    Article  CAS  Google Scholar 

  5. N. Kockmann and D. M. Roberge, Chem. Eng. Technol., 32, 1682 (2009).

    Article  CAS  Google Scholar 

  6. B. Gutmann, D. Cantillo and C.O. Kappe, Angew. Chem. Int. Ed., 54, 6688 (2015).

    Article  CAS  Google Scholar 

  7. C.J. Mallia and I.R. Baxendale, Org. Process. Res. Dev., 20, 327 (2016).

    Article  CAS  Google Scholar 

  8. R. Porta, M. Benaglia and A. Puglisi, Org. Process. Res. Dev., 20, 2 (2016).

    Article  CAS  Google Scholar 

  9. D. Webb and T. F. Jamison, Chem. Sci., 1, 675 (2010).

    Article  CAS  Google Scholar 

  10. C. Wiles and P. Watts, Green. Chem., 14, 38 (2012).

    Article  CAS  Google Scholar 

  11. B. J. Deadman, S.G. Collins and A.R. Maguire, Chem. Eur. J., 21, 2298 (2015).

    Article  CAS  Google Scholar 

  12. S.T.R. Müller and T. Wirth, ChemSusChem, 8, 245 (2015).

    Article  CAS  Google Scholar 

  13. H. Amii, A. Nagaki and J.-i. Yoshida, Beilstein J. Org. Chem., 9, 2793 (2013).

    Article  CAS  Google Scholar 

  14. M. Brzozowski, M. O’Brien, S.V. Ley and A. Polyzos, Acc. Chem. Res., 48, 349 (2015).

    Article  CAS  Google Scholar 

  15. N. Oger, E. Le Grognec and F.-X. Felpin, Org. Chem. Front., 2, 590 (2015).

    Article  CAS  Google Scholar 

  16. S.G. Newman and K. F. Jensen, Green. Chem., 15, 1456 (2013).

    Article  CAS  Google Scholar 

  17. D.T. McQuade and P. H. Seeberger, J. Org. Chem., 78, 6384 (2013).

    Article  CAS  Google Scholar 

  18. H. P. L. Gemoets, Y. Su, M. Shang, V. Hessel, R. Luque and T. Noel, Chem. Soc. Rev., 45, 83 (2016).

    Article  CAS  Google Scholar 

  19. P. J. Cossar, L. Hizartzidis, M. I. Simone, A. McCluskey and C. P. Gordon, Org. Biomol. Chem., 13, 7119 (2015).

    Article  CAS  Google Scholar 

  20. A.K. Singh, D.-H. Ko, N. K. Vishwakarma, S. Jang, K.-I. Min and D.-P. Kim, Nat. Commun., 7 (2016).

    Google Scholar 

  21. R.A. Maurya, C. P. Park, J. H. Lee and D.-P. Kim, Angew. Chem. Int. Ed., 50, 5952 (2011).

    Article  CAS  Google Scholar 

  22. F. Mastronardi, B. Gutmann and C.O. Kappe, Org. Lett., 15, 5590 (2013).

    Article  CAS  Google Scholar 

  23. M. O’Brien, I.R. Baxendale and S.V. Ley, Org. Lett., 12, 1596 (2010).

    Article  CAS  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  25. V.D. Pinho, B. Gutmann and C.O. Kappe, RSC Adv., 4, 37419 (2014).

    Article  CAS  Google Scholar 

  26. E. Rossi, P. Woehl and M. Maggini, Org. Process. Res. Dev., 16, 1146 (2012).

    Article  CAS  Google Scholar 

  27. G. Maas, Angew. Chem. Int. Ed., 48, 8186 (2009).

    Article  CAS  Google Scholar 

  28. R.A. Maurya, K.-I. Min and D.-P. Kim, Green Chem., 16, 116 (2014).

    Article  CAS  Google Scholar 

  29. H.E. Bartrum, D.C. Blakemore, C. J. Moody and C. J. Hayes, J. Org. Chem., 75, 8674 (2010).

    Article  CAS  Google Scholar 

  30. L. J. Martin, A. L. Marzinzik, S.V. Ley and I.R. Baxendale, Org. Lett., 13, 320 (2011).

    Article  CAS  Google Scholar 

  31. P. S. Bailey, Chem. Rev., 58, 925 (1958).

    Article  CAS  Google Scholar 

  32. P. S. Bailey, Ozonolysis in Organic Chemistry, Academic Press (1978).

    Google Scholar 

  33. W. H. Bunnelle, Chem. Rev., 91, 335 (1991).

    Article  CAS  Google Scholar 

  34. T. I. Zvereva, V. G. Kasradze, O. B. Kazakova and O. S. Kukovinets, Russ. J. Org. Chem., 46, 1431 (2010).

    Article  CAS  Google Scholar 

  35. L. B. P.G. Urben, Bretherick’s Handbook of Reactive Chemical Hazards, 7th Ed., Oxford (1990).

    Google Scholar 

  36. S. Caron, R.W. Dugger, S. G. Ruggeri, J. A. Ragan and D. H.B. Ripin, Chem. Rev., 106, 2943 (2006).

    Article  CAS  Google Scholar 

  37. Y. Wada, M. A. Schmidt and K. F. Jensen, Ind. Eng. Chem. Res., 45, 8036 (2006).

    Article  CAS  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  39. M.D. Roydhouse, A. Ghaini, A. Constantinou, A. Cantu-Perez, W. B. Motherwell and A. Gavriilidis, Org. Process. Res. Dev., 15, 989 (2011).

    Article  CAS  Google Scholar 

  40. M.D. Roydhouse, W.B. Motherwell, A. Constantinou, A. Gavriilidis, R. Wheeler, K. Down and I. Campbell, RSC Adv., 3, 5076 (2013).

    Article  CAS  Google Scholar 

  41. M. Irfan, T. N. Glasnov and C.O. Kappe, Org. Lett., 13, 984 (2011).

    Article  CAS  Google Scholar 

  42. C. Battilocchio, I.R. Baxendale, M. Biava, M.O. Kitching and S.V. Ley, Org. Process. Res. Dev., 16, 798 (2012).

    Article  CAS  Google Scholar 

  43. J. Zak, D. Ron, E. Riva, H. P. Harding, B. C. S. Cross and I.R. Baxendale, Chem. Eur. J., 18, 9901 (2012).

    Article  CAS  Google Scholar 

  44. F. Fischer and H. Tropsch, Brennstoff-chem., 97 (1926).

    Google Scholar 

  45. H. Adkins and G. Krsek, J. Am. Chem. Soc., 71, 3051 (1949).

    Article  CAS  Google Scholar 

  46. N. I. Sax and R. J. Lewis, Dangerous properties of industrial materials, 7th Ed., Van Nostrand Reinhold (1989).

    Google Scholar 

  47. P.W. Miller, N. J. Long, A. J. de Mello, R. Vilar, J. Passchier and A. Gee, Chem. Commun., 546 (2006).

    Google Scholar 

  48. M.T. Rahman, T. Fukuyama, N. Kamata, M. Sato and I. Ryu, Chem. Commun., 2236 (2006).

    Google Scholar 

  49. E.R. Murphy, J.R. Martinelli, N. Zaborenko, S. L. Buchwald and K. F. Jensen, Angew. Chem. Int. Ed., 46, 1734 (2007).

    Article  CAS  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  52. T. Fukuyama, M.T. Rahman, N. Kamata and I. Ryu, Beilstein J. Org. Chem., 5, 34 (2009).

    Article  CAS  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  54. C. Csajági, B. Borcsek, K. Niesz, I. Kovács, Z. Székelyhidi, Z. Bajkó, L. Ürge and F. Darvas, Org. Lett., 10, 1589 (2008).

    Article  CAS  Google Scholar 

  55. P. Koos, U. Gross, A. Polyzos, M. O'Brien, I. Baxendale and S.V. Ley, Org. Biomol. Chem., 9, 6903 (2011).

    Article  CAS  Google Scholar 

  56. M.A. Mercadante and N. E. Leadbeater, Org. Biomol. Chem., 9, 6575 (2011).

    Article  CAS  Google Scholar 

  57. C.B. Kelly, C. Lee, M.A. Mercadante and N.E. Leadbeater, Org. Process. Res. Dev., 15, 717 (2011).

    Article  CAS  Google Scholar 

  58. M.A. Mercadante and N. E. Leadbeater, Green. Process. Synth., 1, 499 (2012).

    CAS  Google Scholar 

  59. C. Brancour, T. Fukuyama, Y. Mukai, T. Skrydstrup and I. Ryu, Org. Lett., 15, 2794 (2013).

    Article  CAS  Google Scholar 

  60. T. Fukuyama, Y. Mukai and I. Ryu, Beilstein J. Org. Chem., 7, 1288 (2011).

    Article  CAS  Google Scholar 

  61. M. Cartwright and J. Wilkinson, Propellants Explos. Pyrotech., 35, 326 (2010).

    Article  CAS  Google Scholar 

  62. S. Bräse, C. Gil, K. Knepper and V. Zimmermann, Angew. Chem. Int. Ed., 44, 5188 (2005).

    Article  CAS  Google Scholar 

  63. M. E. Kopach, M. M. Murray, T. M. Braden, M. E. Kobierski and O. L. Williams, Org. Process. Res. Dev., 13, 152 (2009).

    Article  CAS  Google Scholar 

  64. M. Weber, G. Yilmaz and G. Wille, Chim. Oggi., 29, 8 (2011).

    CAS  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  67. I.R. Baxendale, S.V. Ley, A. C. Mansfield and C.D. Smith, Angew. Chem. Int. Ed., 48, 4017 (2009).

    Article  CAS  Google Scholar 

  68. C.O. Kappe and E. Van der Eycken, Chem. Soc. Rev., 39, 1280 (2010).

    Article  CAS  Google Scholar 

  69. S. Ceylan, T. Klande, C. Vogt, C. Friese and A. Kirschning, Synlett., 2010, 2009 (2010).

    Article  CAS  Google Scholar 

  70. A.C. Varas, T. Noël, Q. Wang and V. Hessel, ChemSusChem, 5, 1703 (2012).

    Article  CAS  Google Scholar 

  71. M. Fuchs, W. Goessler, C. Pilger and C.O. Kappe, Adv. Synth. Catal., 352, 323 (2010).

    Article  CAS  Google Scholar 

  72. A.R. Bogdan and K. James, Chem. Eur. J., 16, 14506 (2010).

    Article  CAS  Google Scholar 

  73. A.R. Bogdan and K. James, Org. Lett., 13, 4060 (2011).

    Article  CAS  Google Scholar 

  74. A.R. Bogdan and N.W. Sach, Adv. Synth. Catal., 351, 849 (2009).

    Article  CAS  Google Scholar 

  75. P. Zhang, M. G. Russell and T. F. Jamison, Org. Process. Res. Dev., 18, 1567 (2014).

    Article  CAS  Google Scholar 

  76. H.R. Sahoo, J.G. Kralj and K.F. Jensen, Angew. Chem. Int. Ed., 46, 5704 (2007).

    Article  CAS  Google Scholar 

  77. B. Gutmann, J.-P. Roduit, D. Roberge and C.O. Kappe, Angew. Chem. Int. Ed., 49, 7101 (2010).

    Article  CAS  Google Scholar 

  78. B. Gutmann, D. Obermayer, J. P. Roduit, D. M. Roberge and C.O. Kappe, J. Flow. Chem., 2, 8 (2012).

    Article  CAS  Google Scholar 

  79. L.A. Flippin, Tetrahedron Lett., 32, 6857 (1991).

    Article  CAS  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  81. H. Singh, A. S. Chawla, V. K. Kapoor, D. Paul and R. K. Malhotra, Prog. Med. Chem., 17, 151 (1980).

    Article  CAS  Google Scholar 

  82. R. J. Herr, Bioorganic & Medicinal Chemistry, 10, 3379 (2002).

    Article  CAS  Google Scholar 

  83. B. Gutmann, J.-P. Roduit, D. Roberge and C.O. Kappe, Chem. Eur. J., 17, 13146 (2011).

    Article  CAS  Google Scholar 

  84. J.C. Brandt and T. Wirth, Beilstein J. Org. Chem., 5, 30 (2009).

    Article  CAS  Google Scholar 

  85. C. Viuf and M. Bols, Angew. Chem. Int. Ed., 40, 623 (2001).

    Article  CAS  Google Scholar 

  86. C.M. Pedersen, L. G. Marinescu and M. Bols, Org. Biomol. Chem., 3, 816 (2005).

    Article  CAS  Google Scholar 

  87. R. J. Linderman, M. Jaber and B.D. Griedel, J. Org. Chem., 59, 6499 (1994).

    Article  CAS  Google Scholar 

  88. M.A. Berliner and K. Belecki, J. Org. Chem., 70, 9618 (2005).

    Article  CAS  Google Scholar 

  89. D.M. Barnes, J. Barkalow and D. J. Plata, Org. Lett., 11, 273 (2009).

    Article  CAS  Google Scholar 

  90. A. Jasti, S. Prakash and V.K. Shahi, J. Membr. Sci., 428, 470 (2013).

    Article  CAS  Google Scholar 

  91. A. Mitic and K.V. Gernaey, Chem. Eng. Technol., 38, 1699 (2015).

    Article  CAS  Google Scholar 

  92. L. Hosta-Rigau, M. J. York-Duran, T. S. Kang and B. Städler, Adv. Funct. Mater., 25, 3860 (2015).

    Article  CAS  Google Scholar 

  93. A.R. Bogdan, S.L. Poe, D.C. Kubis, S. J. Broadwater and D.T. McQuade, Angew. Chem., 121, 8699 (2009).

    Article  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  95. P. Zhang, M. G. Russell and T. F. Jamison, Org. Process. Res. Dev., 18, 1567 (2014).

    Article  CAS  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  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).

    Article  CAS  Google Scholar 

  100. D. E. Fitzpatrick, C. Battilocchio and S.V. Ley, ACS Cent. Sci., 2(3), 131 (2016).

    Article  CAS  Google Scholar 

  101. A.K. Au, W. Huynh, L.F. Horowitz and A. Folch, Angew. Chem. Int. Ed., 55, 3862 (2016).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Center of Applied Microfluidic Chemistry, Department of Chemical Engineering, POSTECH (Pohang University of Science and Technology), Pohang, 37673, Korea

    Rakhi Singh, Hyune-Jea Lee, Ajay Kumar Singh & Dong-Pyo Kim

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  1. Rakhi Singh
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  2. Hyune-Jea Lee
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  3. Ajay Kumar Singh
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  4. Dong-Pyo Kim
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Correspondence to Dong-Pyo Kim.

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Dong-Pyo Kim is professor in the Department of Chemical Engineering at Pohang University of Science and Technology (POSTECH) in Korea. He received his B.S. degree (Sogang University, Korea), M.S. degree ((Sogang University, Korea), and Ph.D. degree (Temple University, U.S) all in Chemistry and was a postdoctoral fellow in Univ. of Illinois at Urbana-Champaign, Material Science and Engineering. He worked for several years at the Korea Research Institution of Chemical Technology as senior researcher and he was professor at Chungnam National University for 17 years before joining POSTECH in 2012.

His research interests include material synthesis (preceramic polymer), microfluidic device fabrication, organic/inorganic synthesis in microfluidic system and microbiomass process.

These authors contributed equally to this work.

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Singh, R., Lee, HJ., Singh, A.K. et al. Recent advances for serial processes of hazardous chemicals in fully integrated microfluidic systems. Korean J. Chem. Eng. 33, 2253–2267 (2016). https://doi.org/10.1007/s11814-016-0114-6

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