Skip to main content
Log in

Homogeneously-catalyzed syntheses in supercritical fluids

  • Published:
Topics in Catalysis Aims and scope Submit manuscript

Abstract

Supercritical fluids (SCFs) differ from liquid solvents in a number of important properties, any of which could potentially alter the performance of a chemical reaction performed in a supercritical medium. Although rate, yield and selectivity improvements as well as environmental, health and engineering benefits are all possible, little research has been reported on homogeneously-catalyzed syntheses in SCFs. Several notable successes plus new techniques for solubilizing hydrophilic reagents in SCFs are encouraging further research in this growing field.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. B. Subramaniam and M.A. McHugh, Ind. Eng. Chem., Proc. Des. Dev. 25 (1986) 1.

    Article  CAS  Google Scholar 

  2. J.F. Brennecke, in: Supercritical Fluid Engineering Science: Fundamentals and Applications, ACS Symposium Series, No. 514, eds. E. Kiran and J.F. Brennecke (American Chemical Society, Washington, DC, 1993) pp. 201–219.

    Google Scholar 

  3. P.G. Jessop, T. Ikariya and R. Noyori, Science 269 (1995) 1065.

    CAS  Google Scholar 

  4. G. Kaupp, Angew. Chem. Int. Ed. Engl. 33 (1994) 1452.

    Article  Google Scholar 

  5. M. Buback, Angew. Chem. Int. Ed. Engl. 30 (1991) 641.

    Article  Google Scholar 

  6. E. Kiran and J.M.H. Levelt Sengers, Supercritical Fluids, Fundamentals for Application, NATO ASI Series E, No. 273 (Kluwer Academic, Dordrecht, 1994).

    Google Scholar 

  7. M. Poliakoff, S.M. Howdle and S.G. Kazarian, Angew. Chem. Int. Ed. Engl. 34 (1995) 1275.

    Article  CAS  Google Scholar 

  8. P.E. Savage, S. Gopalan, T.I. Mizan, C.J. Martino and E.E. Brock, AIChE J. 41 (1995) 1723.

    Article  CAS  Google Scholar 

  9. G.M. Kramer and F. Leder, U.S. Patent 3,880,945 (1975).

  10. S.M. Howdle and M. Poliakoff, J. Chem. Soc., Chem. Commun. (1989) 1099.

  11. J.W. Rathke, R.J. Klingler and T.R. Krause, Organometallics 10 (1991) 1350.

    Article  CAS  Google Scholar 

  12. P.G. Jessop, T. Ikariya and R. Noyori, Nature 368 (1994) 231.

    Article  CAS  Google Scholar 

  13. P.G. Jessop, Y. Hsiao, T. Ikariya and R. Noyori, J. Am. Chem. Soc. 118 (1996) 344.

    Article  CAS  Google Scholar 

  14. C.-C. Lai and C.-S. Tan, Ind. Eng. Chem. Res. 32 (1993) 1717.

    Article  CAS  Google Scholar 

  15. M.F. Vincent, S.G. Kazarian and C.A. Eckert, AIChE J. 43 (1997) 1838.

    Article  CAS  Google Scholar 

  16. F. Patat, Monatsh. Chem. 77 (1945) 352.

    Google Scholar 

  17. M. McHugh and V. Krukonis, Supercritical Fluid Extraction (Butterworth-Heinemann, Boston, 1994).

    Google Scholar 

  18. J.E. Cottle, U.S. Patent 3,294,772 (1966).

  19. A. Ahvenainen, K. Sarantila and H. Andtsjo, Int. Patent Appl. WO 92/12181 (1992).

  20. H.C. Welborn and C.S. Speed, U.S. Patent 5,084,534 (1992).

  21. K.R. Beck and L.G. Moore, Textile Chemist and Colorist 29 (1997) 66.

    CAS  Google Scholar 

  22. C. Bergemann, R. Cropp and G. Luft, J. Mol. Catal. A 102 (1995) 1.

    Article  CAS  Google Scholar 

  23. C. Bergemann, R. Cropp and G. Luft, J. Mol. Catal. A 105 (1996) 87.

    Article  CAS  Google Scholar 

  24. B. Folie and M. Radosz, in: 3rd International Symposium on Supercritical Fluids, Strasbourg, 1994, pp. 281–286.

  25. E. Kiran and J.F. Brennecke, Supercritical Fluid Engineering Science: Fundamentals and Applications, ACS Symposium Series, No. 514 (American Chemical Society, Washington, DC, 1991).

    Google Scholar 

  26. G.D. Hayman and R.G. Derwent, Environ. Sci. Technol. 31 (1997) 327.

    Article  CAS  Google Scholar 

  27. B. Subramaniam, R.A. Rajewski and K. Snavely, J. Pharm. Sci. 86 (1997) 885.

    Article  CAS  Google Scholar 

  28. K. Zosel, Angew. Chem. Int. Ed. Engl. 17 (1978) 702.

    Article  Google Scholar 

  29. D.E. Raynie, Anal. Chem. 65 (1993) 3127.

    Article  CAS  Google Scholar 

  30. C.R. Yonker, T.S. Zemanian, S.L. Wallen, J.C. Linehan and J.A. Franz, J. Magn. Reson. Series A 113 (1995) 102.

    Article  CAS  Google Scholar 

  31. M.P. Waugh and G.A. Lawless, in: Advanced Applications of NMR to Organometallic Chemistry, eds. M. Gielen, R. Willem and B. Wrackmeyer (Wiley, Chichester, 1996) pp. 227–246.

    Google Scholar 

  32. U. Frey, L. Helm, A.E. Merbach and R. Roulet, in: Advanced Applications of NMR to Organometallic Chemistry, eds. M. Gielen, R. Willem and B. Wrackmeyer (Wiley, Chichester, 1996) pp. 193–226.

    Google Scholar 

  33. S.M. Howdle and M. Poliakoff, in: Supercritical Fluids Fundamentals for Application, NATO ASI Series E, No. 273, eds. E. Kiran and J.M.H.L. Levelt Sengers (Kluwer Academic, Dordrecht, 1994) pp. 527–537.

    Google Scholar 

  34. S.V. Olesik, S.B. French and M. Novotny, Anal. Chem. 58 (1986) 2256.

    Article  CAS  Google Scholar 

  35. Y. Ikushima, N. Saito and M. Arai, Bull. Chem. Soc. Jpn. 64 (1991) 282.

    Article  CAS  Google Scholar 

  36. D.A. Masten, B.R. Foy, D.M. Harradine and R.B. Dyer, J. Phys. Chem. 97 (1993) 8557.

    Article  CAS  Google Scholar 

  37. M.L. Myrick, J. Kolis, E. Parsons, K. Chike, M. Lovelace, W. Scrivens, R. Holliday and M. Williams, J. Raman Spectrosc. 25 (1994) 59.

    Article  CAS  Google Scholar 

  38. S.M. Howdle, K. Stanley, V.K. Popov and V.N. Bagratashvili, Appl. Spectrosc. 48 (1994) 214.

    Article  CAS  Google Scholar 

  39. A.R. Renslo, R.D. Weinstein, J.W. Tester and R.L. Danheiser, J. Org. Chem. 62 (1997) 4530.

    Article  CAS  Google Scholar 

  40. A.F. Lagalante, B.N. Hansen, T.J. Bruno and R.E. Sievers, Inorg. Chem. 34 (1995) 5781.

    Article  CAS  Google Scholar 

  41. N.G. Smart, T. Carleson, T. Kast, A.A. Clifford, M.D. Burford and C.M. Wai, Talanta 44 (1997) 137.

    Article  CAS  Google Scholar 

  42. R.P. Warzinski, C.-H. Lee and G.D. Holder, J. Supercrit. Fluids 5 (1992) 60.

    Article  CAS  Google Scholar 

  43. A.N. Fedotov, A.P. Simonov, V.K. Popov and V.N. Bagratashvili, J. Phys. Chem. B 101 (1997) 2929.

    CAS  Google Scholar 

  44. A.V. Yazdi and E.J. Beckman, J. Mater. Res. 10 (1995) 530.

    CAS  Google Scholar 

  45. A.V. Yazdi and E.J. Beckman, Ind. Eng. Chem. Res. 36 (1997) 2368.

    Article  CAS  Google Scholar 

  46. S. Kainz, D. Koch, W. Baumann and W. Leitner, Angew. Chem. Int. Ed. Engl. 36 (1997) 1628.

    Article  CAS  Google Scholar 

  47. Y.H. Lin, N.G. Smart and C.M. Wai, Trends Anal. Chem. 14 (1995) 123.

    CAS  Google Scholar 

  48. R.P. Hughes and H.A. Trujillo, Organometallics 15 (1996) 286.

    Article  CAS  Google Scholar 

  49. A. Studer, S. Hadida, R. Ferritto, S.-Y. Kim, P. Jeger, P. Wipf and D.P. Curran, Science 275 (1997) 823.

    Article  CAS  Google Scholar 

  50. J.M. Dobbs, J.M. Wong and K.P. Johnston, J. Chem. Eng. Data 31 (1986) 303.

    Article  CAS  Google Scholar 

  51. J.M. Dobbs, J.M. Wong, R.J. Lahiere and K.P. Johnston, Ind. Eng. Chem. Res. 26 (1987) 56.

    Article  CAS  Google Scholar 

  52. H. Nishida, N. Takada and M. Yoshimura, Bull. Chem. Soc. Jpn. 57 (1984) 2600.

    Article  CAS  Google Scholar 

  53. M. Brookhart, B. Grant and A.F. Volpe Jr., Organometallics 11 (1992) 3920.

    Article  CAS  Google Scholar 

  54. M.J. Burk, S. Feng, M.F. Gross and W. Tumas, J. Am. Chem. Soc. 117 (1995) 8277.

    Article  CAS  Google Scholar 

  55. A.K. Dillow, S.L.J. Yun, D. Suleiman, D.L. Boatright, C.L. Liotta and C.A. Eckert, Ind. Eng. Chem. Res. 35 (1996) 1801.

    Article  CAS  Google Scholar 

  56. K.A. Consani and R.D. Smith, J. Supercrit. Fluids 3 (1990) 51.

    Article  CAS  Google Scholar 

  57. G.J. McFann, K.P. Johnston and S.M. Howdle, AIChE J. 40 (1994) 543.

    Article  CAS  Google Scholar 

  58. K.A. Bartscherer, H. Renon and M. Minier, Fluid Phase Equilib. 107 (1995) 93.

    Article  CAS  Google Scholar 

  59. M.J. Clarke, K.L. Harrison, K.P. Johnston and S.M. Howdle, J. Am. Chem. Soc. 119 (1997) 6399.

    Article  CAS  Google Scholar 

  60. K.P. Johnston, K.L. Harrison, M.J. Clarke, S.M. Howdle, M.P. Heitz, F.V. Bright, C. Carlier and T.W. Randolph, Science 271 (1996) 624.

    CAS  Google Scholar 

  61. Y. Ikushima, N. Saito and M. Arai, J. Colloid Interface Sci. 186 (1997) 254.

    Article  CAS  Google Scholar 

  62. Y. Ikushima, Z. Shervani, N. Saito and M. Arai, J. Colloid Interface Sci. 191 (1997) 177.

    Article  CAS  Google Scholar 

  63. T.S. Zemanian, R.M. Bean, J.L. Fulton, J.C. Linehan and R.D. Smith, in: Proceedings 2nd International Symposium on Supercritical Fluids, Boston, MA, 1991, pp. 193–195.

  64. C.Y. Tsang and W.B. Streett, Chem. Eng. Sci. 36 (1981) 993.

    Article  CAS  Google Scholar 

  65. P.G. Jessop, T. Ikariya and R. Noyori, unpublished results (1995).

  66. H. Coenen, R. Hagen and E. Kriegel, U.S. Patent 4,485,003 (1984).

  67. P.G. Jessop, T. Ikariya and R. Noyori, Organometallics (1995) 1510.

  68. T.E. Nalesnik and J.H. Freudenberger, M. Orchin, J. Organomet. Chem. 236 (1982) 95.

    Article  CAS  Google Scholar 

  69. Y. Matsui and M. Orchin, J. Organomet. Chem. 244 (1983) 369.

    Article  CAS  Google Scholar 

  70. J.-L. Xiao, S.C.A. Nefkens, P.G. Jessop, T. Ikariya and R. Noyori, Tetrahedron Lett. 37 (1996) 2813.

    Article  CAS  Google Scholar 

  71. S. Kainz, D. Koch and W. Leitner, in: Selective Reactions of Metal Activated Molecules, eds. H. Werner and W. Schreier (Vieweg, Wiesbaden), in press.

  72. S.C. Stinson, Chem. Eng. News 75 (1997) 37.

    Google Scholar 

  73. Roche Magazin, issue 41 (May, 1992) 2.

  74. K.H. Pickel and K. Steiner, in: 3rd International Symposium on Supercritical Fluids (Strasbourg, 1994) pp. 25–29.

  75. B. Minder, T. Mallat, K.H. Pickel, K. Steiner and A. Baiker, Catal. Lett. 34 (1995) 1.

    Article  CAS  Google Scholar 

  76. M.G. Hitzler and M. Poliakoff, Chem. Commun. (1997) 1667.

  77. W. Leitner, E. Dinjus and F. Gaßner, J. Organomet. Chem. 475 (1994) 257.

    Article  CAS  Google Scholar 

  78. P.G. Jessop, T. Ikariya and R. Noyori, Chem. Rev. 95 (1995) 259.

    Article  CAS  Google Scholar 

  79. W. Leitner, Angew. Chem., Int. Ed. Engl. 34 (1995) 2207.

    Article  CAS  Google Scholar 

  80. T. Ikariya, P.G. Jessop and R. Noyori, Japan Tokkai 5–274721 (1993).

  81. T. Ikariya, Y. Hsiao, P.G. Jessop and R. Noyori, European Patent Appl. 0 652 202 A1 (1995).

  82. T. Ikariya, P.G. Jessop, R. Noyori, Japan Tokkai 6–125,401 (1994).

  83. P.G. Jessop, Y. Hsiao, T. Ikariya and R. Noyori, J. Chem. Soc., Chem. Commun. (1995) 707.

  84. P.G. Jessop, Y. Hsiao, T. Ikariya and R. Noyori, J. Am. Chem. Soc. 116 (1994) 8851.

    Article  CAS  Google Scholar 

  85. T. Ikariya, P.G. Jessop, Y. Hsiao and R. Noyori, Japan Tokkai 6–125,402 (1994).

  86. O. Kröcher, R.A. Köppel and A. Baiker, Chem. Commun. (1996) 1497.

  87. O. Kröcher, R.A. Köppel and A. Baiker, Chem. Commun. (1997) 453.

  88. H. Koinuma, F. Kawakami, H. Kato and H. Hirai, J. Chem. Soc., Chem. Commun. (1981) 213.

  89. G. Süss-Fink and J. Reiner, J. Organomet. Chem. 221 (1981) C36.

    Article  Google Scholar 

  90. J.W. Rathke, R.J. Klingler and T.R. Krause, Organometallics 11 (1992) 585.

    Article  CAS  Google Scholar 

  91. J.W. Rathke and R.J. Klingler, U.S. Patent 5,198,589 (1993).

  92. R.J. Klingler and J.W. Rathke, J. Am. Chem. Soc. 116 (1994) 4772.

    Article  CAS  Google Scholar 

  93. B.L. Knutson, A.K. Dillow, C.L. Liotta and C.A. Eckert, in: Innovations in Supercritical Fluids, ACS Symposium Series, No. 608, eds. K.W. Hutchenson and N.R. Foster (American Chemical Society, Washington, DC, 1995) pp. 166–178.

    Google Scholar 

  94. M.B. Korzenski and J.W. Kolis, Tetrahedron Letters 38 (1997) 5611.

    Article  CAS  Google Scholar 

  95. E. Dinjus and R. Fornika, in: Applied Homogeneous Catalysis with Organometallic Compounds, Vol. 2, eds. B. Cornils and W.A. Herrmann (VCH, Weinheim, 1996) pp. 1048–1072.

    Google Scholar 

  96. M.T. Reetz, W. Könen and T. Strack, Chimia 47 (1993) 493; (b) footnote 5 of J.A. Banister, P.D. Lee and M. Poliakoff, Organometallics 14 (1995) 3876.

    CAS  Google Scholar 

  97. K.S. Jerome and E.J. Parsons, Organometallics 12 (1993) 2991.

    Article  CAS  Google Scholar 

  98. P. Reardon, S. Metts, C. Crittendon, P. Daugherity and E.J. Parsons, Organometallics 14 (1995) 3810.

    Article  CAS  Google Scholar 

  99. N. Jeong, S.H. Hwang, Y.W. Lee and J.S. Lim, J. Am. Chem. Soc. 119 (1997) 10549.

    Article  CAS  Google Scholar 

  100. S. Angus, B. Armstrong and K.M. de Reuck, International Thermodynamic Tables of the Fluid State: Carbon Dioxide, Vol. 3 (IUPAC, Pergamon Press, Oxford, 1976).

    Google Scholar 

  101. A. Fürstner, D. Koch, K. Langemann, W. Leitner and C. Six, Angew. Chem., Int. Ed. Engl. 36 (1997) 2466.

    Article  Google Scholar 

  102. M. Modell, in: Standard Handbook of Hazardous Waste Treatment and Disposal, ed. H.M. Freeman (McGraw-Hill, New York, 1989) pp. 8.153–8.168.

    Google Scholar 

  103. R.W. Shaw, T.B. Brill, A.A. Clifford, C.A. Eckert and E.U. Franck, Chem. Eng. News (23 December, 1991) 26.

  104. K.B. Sharpless and R.C. Michaelson, J. Am. Chem. Soc. 95 (1973) 6136.

    Article  CAS  Google Scholar 

  105. M.N. Sheng and J.G. Zajacek, J. Org. Chem. 35 (1970) 1839.

    Article  CAS  Google Scholar 

  106. P.G. Jessop, T. Ikariya and R. Noyori, unpublished results (1995).

  107. V.S. Bhise, U.S. Patent 4,400,559 (1983).

  108. D.A. Morgenstern, R.M. LeLacheur, D.K. Morita, S.L. Borkowsky, S. Feng, G.H. Brown, L. Luan, M.F. Gross, M.J. Burk and W. Tumas, in: Green Chemistry: Designing Chemistry for the Environment, ACS Symposium Series, No. 626, eds. P.T. Anastas and T.C. Williamson (American Chemical Society, Washington, DC, 1996) pp. 132–151.

    Google Scholar 

  109. R. Narayan and M.J. Antal, Jr., J. Am. Chem. Soc. 112 (1990) 1927.

    Article  CAS  Google Scholar 

  110. R.C. Crittendon and E.J. Parsons, Organometallics 13 (1994) 2587.

    Article  CAS  Google Scholar 

  111. C. Vieville, Z. Mouloungui and A. Gaset, Ind. Eng. Chem. Res. 32 (1993) 2065.

    Article  CAS  Google Scholar 

  112. O. Aaltonen and M. Rantakylä, CHEMTECH April (1991) 240.

  113. M. Rantakylä and O. Aaltonen, Biotechnol. Lett. 16 (1994) 825.

    Article  Google Scholar 

  114. J.F. Martins, I.B. Decarvalho, T.C. Desampaio and S. Barreiros, Enzyme Microb. Technol. 16 (1994) 785.

    Article  CAS  Google Scholar 

  115. J. Yao and R.F. Evilia, J. Am. Chem. Soc. 116 (1994) 11229.

    Article  CAS  Google Scholar 

  116. V.V. Altunin, V.Z. Geller, E.K. Petrov, D.C. Rasskazov and G.A. Spiridinov, Thermophysical Properties of Freons. Methane Series, Part 1, National Standard Reference Data Service of the USSR (Hemisphere, Washington, 1987).

  117. T.A. Rhodes, K. O'Shea, G. Bennett, K.P. Johnston and M.A. Fox, J. Phys. Chem. 99 (1995) 9903.

    Article  CAS  Google Scholar 

  118. R.C. Reid, J.M. Prausnitz and B.E. Poling, The Properties of Gases and Liquids (McGraw-Hill, New York, 1987).

    Google Scholar 

  119. V.V. Sychev, A.A. Vasserman, A.D. Kozlov, V.A. Zagoruchenko, G.A. Spiridinov and V.A. Tsymarny, Thermodynamic Properties of Ethane, National Standard Reference Data Service of the USSR (Hemisphere, Washington, 1987).

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Jessop, P.G. Homogeneously-catalyzed syntheses in supercritical fluids. Topics in Catalysis 5, 95–103 (1998). https://doi.org/10.1023/A:1019189600768

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1019189600768

Navigation