Sustainable reactions in tunable solvents

Journal of Physical Chemistry B

Volumn 108, Issue 47, 2004, Pages 18108-18118

  Eckert, Charles A ^a   Liotta, Charles L ^a   Bush, David ^a   Brown, James S ^a   Hallett, Jason P ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GAS-EXPANDED LIQUIDS; NEAR-CRITICAL FLUIDS; PRODUCT SEPARATION; TUNABLE SOLVENTS;

CATALYSTS; COOLING; DISSOLUTION; IONS; PRESSURE VESSELS; SUPERCRITICAL FLUIDS;

REACTION KINETICS;

EID: 10044270935     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0487612     Document Type: Article

References (102)

1. Marshall, W. L.; Franck, E. U. J. Phys. Chem. Ref. Data 1981, 10, 295.
2. Beckman, E. J. J. Supercrit. Fluids 2004, 28, 121.
3. Katritzky, A. R.; Allin, S. M.; Sisken, M. Acc. Chem. Res. 1996, 29, 399.
4. Izzo, B.; Harrell, C. L.; Klein, M. T. AIChE J. 1997, 43, 2048.
5. Savage, P. E. Chem. Rev. 1999, 99, 603.
6. Patrick, H. R.; Griffith, K.; Liotta, C. L.; Eckert, C. A.; Gläser, R. Ind. Eng. Chem. Res. 2001, 40, 6063.
7. Ekart, M. P.; Bennett, K. L.; Ecken, C. A. ACS Symp. Ser. 1993, 514, 228.
8. Knutson, B. L.; Sherman, S. R.; Bennett, K. L.; Liotta, C. L.; Eckert, C. A. Ind. Eng. Chem. Res. 1997, 36, 854.
9. Chang, C. J. J. Chem. Eng. Jpn. 1992, 25, 164.
10. Kordiowski, A.; Schenk, A. P.; Van Nielen, R. M.; Peters, C. J. J. Supercrit. Fluids 1995, 7995, 205.
11. de la Fuente Badilla, J. C.; Peters, C. J.; de Swaan Arons, J. J. Supercrit. Fluids 2000, 17, 13.
12. Winters, M. A.; Knutson, B. L.; Debenedetti, P. G.; Sparks, H. G.; Przybycien, T. M.; Stevenson, C. L.; Prestelski, S. J. J. Pharm. Sci. 1996, 85, 586.
13. Bertucco, A.; Lora, M.; Kikic, I. AICHE J. 1998, 44, 2149.
14. Bertucco, A. Precipitation and Crystallization Techniques. In Chemical Sythnesis Using Supercritical Fluids', Jessop, P. G., Leitner, W., Eds.; Wiley-VCH: Weinheim, Germany, 1999.
15. Bertucco, A.; Pallado, P.; Benedetti, L. Process. Technol. Proc. 1996, 12, 217.
16. Gallagher, P. M.; Coffey, M. P.; Krukonis, V. J.; Hillstrom, W. W. J. Supercrit. Fluids 1992, 5, 130.
17. Reverchon, E.; Delia, G. Powder Technol. 1999, 106, 23.
18. Shishikura, A.; Kanamori, K.; Takahashi, H.; Kinbara, H. J. Agric. Food Chem. 1994, 42, 1993.
19. Chang, C. J.; Randolph, A. D. Biotechnol. Prag. 1991, 7, 275.
20. Lee, S. T.; Olesik, S. V.; Fields, S. M. J. Microcolumn Sep. 1995, 7, 477.
21. Yun, H.; Olesik, S. V.; Marti, E. H. Anal. Chem. 1998, 70, 3298.
22. Sun, Q.; Olesik, S. V. Anal. Chem. 1999, 71, 2139.
23. Musie, G.; Wei, M.; Subramaniam, B.; Busch, D. H. Coord. Chem. Rev. 2001, 219-221, 789.
24. Wei, M.; Musie, G. T.; Busch, D. H.; Subramaniam, B. J. Am. Chem. Soc. 2002, 124, 2513.
25. West, K.; Gulp, C.; McCarney, J.; Griffith, K.; Bush, D.; Liotta, C.; Eckert, C. J. Phys. Chem. A 2001, 105, 3947.
26. West, K. N.; Bush, D.; Hallett, J. P.; Brown, J. S.; Liotta, C. L.; Eckert, C. A. Novel Fluorous-Organic Systems for Environmentally Benign Processing: Phase Equilibria for Systems Containing Fluorous and Organic Solvents with Carbon Dioxide. The 2nd International Meeting on HighPressure Chemical Engineering, Hamburg, Germany, 2001.
27. 2 as a Miscibility Switch. The 6th Conference on Supercritical Fluids and Their Applications, Maiori, Italy, 2001.
28. Xie, X.; Brown, J. S.; Joseph, P. J.; Liotta, C. L.; Eckert, C. A. Chem. Commun. 2002, 1156.
29. Jessop, P. G.; Olmstead, M. M.; Ablan, C.; Grabenauer, M.; Sheppard, D.; Eckert, C. A.; Liotta, C. L. Inorg. Chem. 2002, 41, 3463.
30. Blanchard, L. A.; Brennecke, J. F. Ind. Eng. Chem. Res. 2001, 40, 287.
31. da Rocha, S. R. P.; Harrison, K. L.; Johnston, K. P. Langmuir 1999, 15, 419.
32. Johnston, K. P.; Harrison, K. L.; Clarke, M. J.; Howdle, S. M.; Heitz, M. P.; Bright, F. V.; Carlier, C.; Randolph, T. W. Science 1996, 277, 624.
33. Lesutis, H. P. Chem. Commun. 1999, 2063.
34. Brown, J. S.; Gläser, R.; Liotta, C. L.; Eckert, C. A. Chem. Commun. 2000, 1295.
35. Nolen, S. A.; Lu, J.; Brown, J. S.; Pollet, P.; Eason, B. C.; Griffith, K. N.; Gläser, R.; Bush, D.; Lamb, D. R.; Liotta, C. L.; Eckert, C. A.; Thiele, G. F.; Bartels, K. A. Ind. Eng. Chem. Res. 2002, 41, 316.
36. Starks, C. M.; Liotta, C. Phase Transfer Catalysis: Principles and Techniques; Academic Press: New York, 1978.
37. Starks, C. M.; Liotta, C. L.; Halpern, M. Phase-Transfer Catalysis: Fundamentals, Applications, and Industrial Perspectives; Chapman & Hall: New York, 1994.
38. Dillow, A. K.; Yun, S. L. J.; Suleiman, D.; Boatright, D. L.; Liotta, C. L.; Eckert, C. A. Ind. Eng. Chem. Res. 1996, 35, 1801.
39. Chandler, K.; Gulp, C. W.; Lamb, D. R.; Liotta, C. L.; Eckert, C. A. Ind. Eng. Chem. Res. 1998, 37, 3252.
40. Wheeler, C.; Lamb, D. R.; Jayachandran, J. P.; Hallett, J. P.; Liotta, C. L.; Eckert, C. A. Ind. Eng. Chem. Res. 2002, 41, 1763.
41. Jayachandran, J. P.; Wheeler, C.; Eason, B. C.; Liotta, C. L.; Eckert, C. A. J. Supercrit. Fluids 2003, 27, 179.
42. Pradhan, N. C.; Sharma, M. M. Ind. Eng. Chem. Res. 1990, 29, 1103.
43. Brown, J. S.; Lesutis, H. P.; Lamb, D. R.; Bush, D.; Chandler, K.; West, B. L.; Liotta, C. L.; Eckert, C. A.; Schiraldi, D.; Hurley, J. S. Ind. Eng. Chem. Res. 1999, 38, 3622.
44. Diaf, A.; Enick, R. M.; Beckman, E. J. J. Appl. Polym. Sci. 1993, 50, 835.
45. George, M.; Weiss, R. G. Langmuir 2002, 18, 7124.
46. Caddick, S.; Haynes, A. K. D. K.; Judd, D. B.; Williams, M. R. V. Tetrahedron Lett. 2000, 41, 3513.
47. Ablan, C. D.; Ballett, J. P.; West, K. N.; Jones, R. S.; Eckert, C. A.; Liotta, C. L.; Jessop, P. G. Chem. Commun. 2003, 2972.
48. West, K. N.; Hallett, J. P.; Jones, R. S.; Bush, D.; Liotta, C. L.; Eckert, C. A. Ind. Eng. Chem. Res. 2004, 43, 4827.
49. Horváth, I. T.; Rábai, J. Science 1994, 266, 72.
50. Cornus, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 2057.
51. Horváth, I. T. Ace. Chem. Res. 1998, 31, 641.
52. Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1174.
53. Barthel-Rosa, L. P.; Gladysz, J. A. Caord. Chem. Rev. 1999, 190-192, 587.
54. Haszeldine, R. N.; Smith, F. Chem. Soc. 1951, 603.
55. Reed, T. M. J. Phys. Chem. 1955, 59, 428.
56. Scott, R. L. J. Phys. Chem. 1958, 62, 136.
57. Reed, T. M. J. Phys. Chem. 1959, 63, 1798.
58. Munson, M. S. B. J. Phys. Chem. 1964, 68, 796.
59. Skripov, V. P.; Faizullin, M. Z. J. Chem. Themodyn. 1989, 21, 687.
60. Hildebrand, J. H.; Cochran, D. R. F. J. Am. Chem. Soc. 1949, 71, 22.
61. Hildebrand, J. H. J. Am. Chem. Soc. 1950, 72, 4348.
62. Ogawa, A.; Curran, D. P. J. Org. Chem. 1997, 62, 450.
63. Wende, M.; Meier, R.; Gladysz, J. A. J. Am. Chem. Soc. 2001, 123, 11490.
64. Wende, M.; Gladysz, J. A. J. Am. Chem. Soc. 2003, 125, 5861.
65. Heidebrandt, D. J.; Jessop, P. G. J. Am. Chem. Soc. 2002, 125, 5600.
66. Herrman, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524.
67. Jacobsen, G. B.; Lee, C. T.; Johnston, K. P.; Tumas, W. J. Am. Chem. Soc. 1999, 121, 11902.
68. Lu, J.; Lazzaroni, M. J.; Ballett, J. P.; Bommarius, A. S.; Liotta, C. L.; Eckert, C. A. Ind. Eng. Chem. Res. 2004, 43, 1586.
69. Kohlpaintner, C. W.; Fischer, R. W.; Cornus, B. Appl. Catal., A 2001, 227, 219.
70. Lazzaroni, M. J.; Bush, D.; Hallett, J. P.; Brown, J. S.; Liotta, C. L.; Eckert, C. A.; Gläser, R. High-Pressure Vapor + Liquid + Liquid Equilibria of Some Carbon Dioxide + Organic + Water Ternary Systems. Proceedings of the 6th International Symposium on Supercritical Fluids, Versailles, France, 2003.
71. Chandler, K.; Deng, F.; Dillow, A. K.; Liotta, C. L.; Eckert, C. A. Ind. Eng. Chem. Res. 1997, 36, 5175.
72. Chandler, K.; Liotta, C. L.; Eckert, C. A.; Schiraldi, D. AIChE J. 1998, 44, 2080.
73. Nolen, S. A.; Liotta, C. L.; Eckert, C. A.; Glaeser, R. Green Chem. 2003, 5, 663.
74. Xie, X. Private communication, 2004.
75. Chamblee, T.; Weikel, R.; Liotta, C. L.; Eckert, C. A. Green Chem., submitted for publication, 2004.
76. Corma, A. Curr. Opin. Solid State Mater. Sci. 1997, 2.
77. Clark, J. H.; Macquarrie, D. J. Handbook of Green Chemistry and Technology; Blackwell Science: Oxford, England, 2002.
78. Kuhlmann, B.; Arnett, E.; Sisken, M. J. Org. Chem. 1994, 59, 3098.
79. Akerlof, G. C.; Oshry, H. I. J. Am. Chem. Soc. 1950, 72, 2844.
80. Connolly, J. F. J. Chem. Eng. Data 1966, 11, 13.
81. Brown, J. S.; Hallett, J. P.; Bush, D. M.; Eckert, C. A. J. Chem. Eng. Data 2000, 45, 846.
82. Anderson, F. E.; Prausnitz, J. M. Fluid Phase Equilib. 1986, 32, 63.
83. Broil, D.; Kaul, C.; Kramer, A.; Krammer, P.; Richter, T.; Jung, M.; Vogel, H.; Zehner, P. Angew. Chem., Int. Ed. 1999, 38, 2998.
84. Iyer, S. D.; Klein, M. T. J. Supercrit. Fluids 1997, 10, 191.
85. Gläser, R.; Brown, J. S.; Eckert, C. A.; Liotta, C. L. ACS Preprints - Div. Fuel Chem. 1999, 44, 385.
86. Towes, K. L.; Shroll, R.; Wai, c. M.; Smart, N. G. Anal. Chem. 1995, 67, 4040.
87. Wen, D.; Olesik, S. V. Anal. Chem. 2000, 72, 475.
88. Gattow, G.; Berhendt, W. Angew. Chem. 1972, 84, 549.
89. Hulme, C.; Ma, L.; Romano, J. J.; Morton, G.; S.-Y., T.; Cherrier, M.-P.; Choi, S.; Salvino, J.; Labaudiniere, R. Tetrahedron Lett. 2000, 41.
90. Keating, T. A.; Armstrong, R. W. J. Org. Chem. 1998, 63, 867.
91. Bedoukian, P. Z. Terpineol; Elsevier: New York, 1967; p 328.
92. Charwath. Private communication, 1981.
93. Williams, C. M.; Whitaker, D. J. Chem. Soc. B 1971, 668.
94. Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Kroschwitz, J. I., Howe-Grant, M., Eds.; Wiley and Sons: New York, 1991; Vol. 9, p 730.
95. Ullmann's Encylcopedia of Industrial Chemistry, 5th ed.; Elvers, B., Hawkins, S., Ravenscroft, M., Eds.; VCH: New York, 1991: Vol. A13, p 443.
96. Ullmann's Encylcopedia of Industrial Chemistry, 5th ed.; Elvers, B., Hawkins, S., Ravenscroft, M., Eds.; VCH: New York, 1991; Vol. A19, p 199.
97. Thiele, G.; Brown, J. S.; Nolen, S. A.; Eason, B. C.; Lu, J.; Eckert, C. A.; Liotta, C. L. Process for the Epoxidation of Olefinic Compounds US, 2000.
98. Hancu, D.; Green, J.; Beckman, E. J. Ind. Eng. Chem. Res. 2002, 41, 4466.
99. Rajagopalan, B.; Wei, M.; Musie, G. T.; Subramaniam, B.; Busch, D. H. Ind. Eng. Chem. Res. 2003, 42, 6505.
100. Richardson, D. E.; Yao, H. J. Am. Chem. Soc. 2000, 722, 3220.
101. Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Kroschwitz, J. I., Howe-Orant, M., Eds.; Wiley and Sons; New York, 1991; Vol. 5, p 35.
102. Khidirov, S.; Aliev, Z. Izobreteniya 1993, 18, 60.