Homogeneously-catalyzed syntheses in supercritical fluids

Topics in Catalysis

Volumn 5, Issue 1-4, 1998, Pages 95-103

  Jessop, Philip G ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Fine chemical synthesis; Homogeneous catalysis; Supercritical fluids

Indexed keywords

EID: 0032377432     PISSN: 10225528     EISSN: None     Source Type: Journal    
DOI: 10.1023/a:1019189600768     Document Type: Article

References (120)

1. B. Subramaniam and M.A. McHugh, Ind. Eng. Chem., Proc. Des. Dev. 25 (1986) 1.
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.
3. P.G. Jessop, T. Ikariya and R. Noyori, Science 269 (1995) 1065.
4. G. Kaupp, Angew. Chem. Int. Ed. Engl. 33 (1994) 1452.
5. M. Buback, Angew. Chem. Int. Ed. Engl. 30 (1991) 641.
6. E. Kiran and J.M.H. Levelt Sengers, Supercritical Fluids, Fundamentals for Application, NATO ASI Series E, No. 273 (Kluwer Academic, Dordrecht, 1994).
7. M. Poliakoff, S.M. Howdle and S.G. Kazarian, Angew. Chem. Int. Ed. Engl. 34 (1995) 1275.
8. P.E. Savage, S. Gopalan, T.I. Mizan, C.J. Martino and E.E. Brock, AIChE J. 41 (1995) 1723.
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.
12. P.G. Jessop, T. Ikariya and R. Noyori, Nature 368 (1994) 231.
13. P.G. Jessop, Y. Hsiao, T. Ikariya and R. Noyori, J. Am. Chem. Soc. 118 (1996) 344.
14. C.-C. Lai and C.-S. Tan, Ind. Eng. Chem. Res. 32 (1993) 1717.
15. M.F. Vincent, S.G. Kazarian and C.A. Eckert, AIChE J. 43 (1997) 1838.
16. F. Patat, Monatsh. Chem. 77 (1945) 352.
17. M. McHugh and V. Krukonis, Supercritical Fluid Extraction (Butterworth-Heinemann, Boston, 1994).
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.
22. C. Bergemann, R. Cropp and G. Luft, J. Mol. Catal. A 102 (1995) 1.
23. C. Bergemann, R. Cropp and G. Luft, J. Mol. Catal. A 105 (1996) 87.
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).
26. G.D. Hayman and R.G. Derwent, Environ. Sci. Technol. 31 (1997) 327.
27. B. Subramaniam, R.A. Rajewski and K. Snavely, J. Pharm. Sci. 86 (1997) 885.
28. K. Zosel, Angew. Chem. Int. Ed. Engl. 17 (1978) 702.
29. D.E. Raynie, Anal. Chem. 65 (1993) 3127.
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.
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.
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.
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.
34. S.V. Olesik, S.B. French and M. Novotny, Anal. Chem. 58 (1986) 2256.
35. Y. Ikushima, N. Saito and M. Arai, Bull. Chem. Soc. Jpn. 64 (1991) 282.
36. D.A. Masten, B.R. Foy, D.M. Harradine and R.B. Dyer, J. Phys. Chem. 97 (1993) 8557.
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.
38. S.M. Howdle, K. Stanley, V.K. Popov and V.N. Bagratashvili, Appl. Spectrosc. 48 (1994) 214.
39. A.R. Renslo, R.D. Weinstein, J.W. Tester and R.L. Danheiser, J. Org. Chem. 62 (1997) 4530.
40. A.F. Lagalante, B.N. Hansen, T.J. Bruno and R.E. Sievers, Inorg. Chem. 34 (1995) 5781.
41. N.G. Smart, T. Carleson, T. Kast, A.A. Clifford, M.D. Burford and C.M. Wai, Talanta 44 (1997) 137.
42. R.P. Warzinski, C.-H. Lee and G.D. Holder, J. Supercrit. Fluids 5 (1992) 60.
43. A.N. Fedotov, A.P. Simonov, V.K. Popov and V.N. Bagratashvili, J. Phys. Chem. B 101 (1997) 2929.
44. A.V. Yazdi and E.J. Beckman, J. Mater. Res. 10 (1995) 530.
45. A.V. Yazdi and E.J. Beckman, Ind. Eng. Chem. Res. 36 (1997) 2368.
46. S. Kainz, D. Koch, W. Baumann and W. Leitner, Angew. Chem. Int. Ed. Engl. 36 (1997) 1628.
47. Y.H. Lin, N.G. Smart and C.M. Wai, Trends Anal. Chem. 14 (1995) 123.
48. R.P. Hughes and H.A. Trujillo, Organometallics 15 (1996) 286.
49. A. Studer, S. Hadida, R. Ferritto, S.-Y. Kim, P. Jeger, P. Wipf and D.P. Curran, Science 275 (1997) 823.
50. J.M. Dobbs, J.M. Wong and K.P. Johnston, J. Chem. Eng. Data 31 (1986) 303.
51. J.M. Dobbs, J.M. Wong, R.J. Lahiere and K.P. Johnston, Ind. Eng. Chem. Res. 26 (1987) 56.
52. H. Nishida, N. Takada and M. Yoshimura, Bull. Chem. Soc. Jpn. 57 (1984) 2600.
53. M. Brookhart, B. Grant and A.F. Volpe Jr., Organometallics 11 (1992) 3920.
54. M.J. Burk, S. Feng, M.F. Gross and W. Tumas, J. Am. Chem. Soc. 117 (1995) 8277.
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.
56. K.A. Consani and R.D. Smith, J. Supercrit. Fluids 3 (1990) 51.
57. G.J. McFann, K.P. Johnston and S.M. Howdle, AIChE J. 40 (1994) 543.
58. K.A. Bartscherer, H. Renon and M. Minier, Fluid Phase Equilib. 107 (1995) 93.
59. M.J. Clarke, K.L. Harrison, K.P. Johnston and S.M. Howdle, J. Am. Chem. Soc. 119 (1997) 6399.
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.
61. Y. Ikushima, N. Saito and M. Arai, J. Colloid Interface Sci. 186 (1997) 254.
62. Y. Ikushima, Z. Shervani, N. Saito and M. Arai, J. Colloid Interface Sci. 191 (1997) 177.
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.
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.
69. Y. Matsui and M. Orchin, J. Organomet. Chem. 244 (1983) 369.
70. J.-L. Xiao, S.C.A. Nefkens, P.G. Jessop, T. Ikariya and R. Noyori, Tetrahedron Lett. 37 (1996) 2813.
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.
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.
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.
78. P.G. Jessop, T. Ikariya and R. Noyori, Chem. Rev. 95 (1995) 259.
79. W. Leitner, Angew. Chem., Int. Ed. Engl. 34 (1995) 2207.
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.
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.
90. J.W. Rathke, R.J. Klingler and T.R. Krause, Organometallics 11 (1992) 585.
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.
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.
94. M.B. Korzenski and J.W. Kolis, Tetrahedron Letters 38 (1997) 5611.
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.
96. (a) M.T. Reetz, W. Könen and T. Strack, Chimia 47 (1993) 493;
97. (b) footnote 5 of J.A. Banister, P.D. Lee and M. Poliakoff, Organometallics 14 (1995) 3876.
98. K.S. Jerome and E.J. Parsons, Organometallics 12 (1993) 2991.
99. P. Reardon, S. Metts, C. Crittendon, P. Daugherity and E.J. Parsons, Organometallics 14 (1995) 3810.
100. N. Jeong, S.H. Hwang, Y.W. Lee and J.S. Lim, J. Am. Chem. Soc. 119 (1997) 10549.
101. 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).
102. A. Fürstner, D. Koch, K. Langemann, W. Leitner and C. Six, Angew. Chem., Int. Ed. Engl. 36 (1997) 2466.
103. 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.
104. R.W. Shaw, T.B. Brill, A.A. Clifford, C.A. Eckert and E.U. Franck, Chem. Eng. News (23 December, 1991) 26.
105. K.B. Sharpless and R.C. Michaelson, J. Am. Chem. Soc. 95 (1973) 6136.
106. M.N. Sheng and J.G. Zajacek, J. Org. Chem. 35 (1970) 1839.
107. P.G. Jessop, T. Ikariya and R. Noyori, unpublished results (1995).
108. V.S. Bhise, U.S. Patent 4,400,559 (1983).
109. 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.
110. R. Narayan and M.J. Antal, Jr., J. Am. Chem. Soc. 112 (1990) 1927.
111. R.C. Crittendon and E.J. Parsons, Organometallics 13 (1994) 2587.
112. C. Vieville, Z. Mouloungui and A. Gaset, Ind. Eng. Chem. Res. 32 (1993) 2065.
113. O. Aaltonen and M. Rantakylä, CHEMTECH April (1991) 240.
114. M. Rantakylä and O. Aaltonen, Biotechnol. Lett. 16 (1994) 825.
115. J.F. Martins, I.B. Decarvalho, T.C. Desampaio and S. Barreiros, Enzyme Microb. Technol. 16 (1994) 785.
116. J. Yao and R.F. Evilia, J. Am. Chem. Soc. 116 (1994) 11229.
117. 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).
118. T.A. Rhodes, K. O'Shea, G. Bennett, K.P. Johnston and M.A. Fox, J. Phys. Chem. 99 (1995) 9903.
119. R.C. Reid, J.M. Prausnitz and B.E. Poling, The Properties of Gases and Liquids (McGraw-Hill, New York, 1987).
120. 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).