Kinetics of a phase-transfer catalysis reaction in supercritical fluid carbon dioxide

Industrial and Engineering Chemistry Research

Volumn 35, Issue 6, 1996, Pages 1801-1806

  Dillow, Angela K ^a   Yun, S L Jimmy ^a   Suleiman, David ^a   Boatright, David L ^a   Liotta, Charles L ^a   Eckert, Charles A ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; AMMONIUM COMPOUNDS; CARBON DIOXIDE; CATALYSIS; REACTION KINETICS; SOLUBILITY; SOLVENTS;

FIRST ORDER REVERSIBLE KINETICS; PHASE TRANSFER CATALYSIS; TETRAHEPTYLAMMONIUM BROMIDE;

SUPERCRITICAL FLUID EXTRACTION;

EID: 0030166542     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie9600405     Document Type: Article

References (40)

1. Brandstrom, A. Principles in Phase-transfer Catalysis by Quaternary Ammonium Salts. In Advances in Physical Organic Chemistry; Academic Press: London, 1977.
2. Brennecke, J. F.; Eckert, C. A. Phase Equilibria for Supercritical Fluid Process Design. AIChE J. 1989, 35, 1409.
3. Cook, F. L.; Bowers, C. W.; Liotta, C. L. Preparation and Purification of 18-crown-6 [1,4,7,10,15,16-hexaoxacyclooctadecane]. J. Org. Chem. 1974, 39, 3416.
4. Dehmlow, E. V. New Synthetic Methods. 20. Advances in Phase-transfer Catalysis. Angew. Chem., Int. Ed. Engl. 1977, 16, 493.
5. Dehmlow, E. V.; Dehmlow, S. S. Phase-transfer Catalysis, 2nd ed.; Verlag Chemie: Weinheim, Germany, 1983.
6. Dillow, A. K.; Padgett, K. R.; Kazarian, S.; Liotta, C. L.; Eckert, C. A. Cosolvent Effects on Reaction Rates in Supercritical Fluids, AIChE Annual Meeting, Miami Beach, FL, Nov 1995; Paper 73 a.
7. Eckert, C. A. High-Pressure Kinetics in Solution. Annu. Rev. Phys. Chem. 1972, 23, 239.
8. Eckert, C A.; Knutson, B. L. Molecular Charisma in Supercritical Fluids. Fluid Phase Equilib. 1993, 83, 93.
9. Eckert, C. A.; Ziger, D. H.; Johnston, K. P.; Ellison, T. K. The Use of Partial Molal Volume Data to Evaluate Equation of State for Supercritical Fluid Mixtures. Fluid Phase Equilib. 1983, 14, 167.
10. Eckert, C. A.; Van Alsten, J. G.; Stoicos, T. Supercritical Fluid Processing. Environ. Sci Technol. 1986a, 20, 319.
11. Eckert, C. A.; Ziger, D. H.; Johnston, K. P.; Kim, S. Solute Partial Molal Volumes in Supercritical Fluids. J. Phys. Chem. 1986b, 90, 2738.
12. Ekart, M. P.; Brennecke, J. F.; Eckert, C. A. Molecular Analysis of Phase Equilibria in Supercritical Fluids. In Supercritical Fluid Technology; Ely, J., Bruno, T., Eds.; CRC Press: Boca Raton, FL, 1991; p 165.
13. Ekart, M. P.; Bennett, K. L.; Eckert, C. A. Effects of Specific Interactions in Supercritical Fluid Solutions. A Chromatographic Study. In ACS Symposium Series; Kiran, E., Brennecke, J. F., Eds; American Chemical Society: Washington, DC, 1993a; Vol. 514, p 228.
14. Ekart, M. P.; Bennett, K L.; Ekart, S. M.; Gurdial, G. S.; Liotta, C. L.; Eckert, C. A. Cosolvent Interactions in Supercritical Fluid Solutions. AIChE J. 1993b, 39, 235.
15. Eyring, H. The Activated Complex in Chemical Reactions. J. Chem. Phys. 1935, 3, 107.
16. Foster, N. R.; Singh, H.; Yun, S. L. J.; Macnaughton, S. J.; Tomasko, D. L. Polar and Nonpolar Cosolvent Effects on the Solubility of Cholesterol in Supercritical Fluids. Ind. Eng. Chem. Res. 1993, 32, 2849.
17. Freedman, H. H. Industrial Applications of Phase-transfer Catalysis (PTC): past, present, and future. Pure Appl. Chem. 1986, 58, 857.
18. Glugla, P. G.; Byon, J. H.; Eckert, C. A. High-Pressure Kinetics and Solvent Effects on a Halide Exchange Reaction. Ind. Eng. Chem. Fundam. 1985, 24, 379.
19. Gurdial, G. S.; Foster, N. R. Solubility of o-Hydroxybenzoic Acid in Supercritical Carbon Dioxide. Ind. Eng. Chem. Res. 1991, 30, 575.
20. Johnston, K. P.; Haynes, C. Clustering in Supercritical Fluid Mixtures. AIChE J. 1987, 33, 2017.
21. 3H. J. Phys. Chem. 1988, 92, 1347.
22. Kim, S.; Johnston, K. P. Effects of Supercritical Solvents on the Rate of Homogeneous Chemical Reactions. In ACS Symposium Series; Squires, T. G., Paulaitis, M. E., Eds.; American Chemical Society: Washington, DC, 1986; Vol. 329, p 42.
23. Knutson, B. L.; Tomasko, D. L.; Eckert, C. A.; Debenedetti, P. G.; Chialvo, A. A. Local Density augmentation in Supercritical Solutions: A Comparison Between Fluorescence Spectroscopy and Molecular Dynamic Results. In ACS Symposium Series; Bright, F. V., McNally, M. E., Eds.; American Chemical Society: Washington, DC, 1992; Vol. 488, p 60.
24. Knutson, B. L.; Dillow, A. K.; Liotta, C. L.; Eckert, C. A. Kinetics of a Diels-Alder Reaction in Supercritical Propane. In ACS Symposium Series; Hutchenson, K. W., Foster, N. R., Eds.; American Chemical Society: Washington, DC, 1995; Vol. 608, p 166.
25. Laidler, K. J. Chemical Kinetics; Harper & Row Publishers: New York, 1987.
26. Liotta, C. L. Decarbalkoxylations of Geminal Diesters, β-keto esters, and α-cyanoesters Affected by Sodium Chloride in Wet Dimethyl Sulfoxide. Tetrahedron Lett. 1974, 28, 2417.
27. Liotta, C. L.; Harris, H. P. Chemistry of naked ions. I. Reactions of the 18-crown-6 Complex of Potassium Fluoride with Organic Substrates in Aprotic Organic Solvents. J. Am. Chem. Soc. 1974, 96, 2250.
28. Liotta, C. L.; Burgess, E. M.; Ray, C. C.; Black, E. D.; Fair, B. E. Mechanism of Phase-transfer Catalysis: The Omega Phase. In ACS Symposium Series; Starks, C. M., Ed.; American Chemical Society: Washington, DC, 1987; Vol. 326, p 87.
29. McHugh, M. A.; Krukonis, V. J. Supercritical Fluid Extraction: Principles and Practice; Butterworth Publishers: Boston, MA, 1986.
30. Montanari, F.; Landini, D.; Rolla, F Phase-transfer-catalyzed Reactions. Top. Curr. Chem. 1982, 120, 147.
31. Starks, C. M. Phase-Transfer Catalysis. I. Heterogeneous Reactions Involving Anion Transfer by Quaternary Ammonium and Phosphonium Salts. J. Am. Chem. Soc. 1971, 93, 195.
32. Starks, C. M.; Liotta, C. L. Phase-transfer Catalysis: Principles and Techniques; Academic Press: New York, 1978.
33. Starks, C. M.; Liotta, C. L.; Halpern, M. Phase-Transfer Catalysis; Chapman & Hall: New York, 1994.
34. Subramaniam, B.; McHugh, M. A. Reactions in Supercritical Fluids - A Review. Ind. Eng. Chem. Process Des. Dev. 1986, 25, 1.
35. Van Alsten, J. G.; Eckert, C. A. Effect of Entrainers and of Solute Size and Polarity in Supercritical Fluid Solutions. J. Chem. Eng. Data 1993, 38, 605.
36. Van Wasen, U.; Swaid, I.; Schneider, G. M. New Analytical Methods. 19. Physicochemicai Principles and Applications of Supercritical Fluid Chromotagraphy (SCF). Angew. Chem., Int. Ed. Engl. 1980, 19, 575.
37. Wang, M. L.; Wu, H. S. Kinetic and Mass Transfer Studies of a Sequential Reaction by Phase-transfer Catalysis. Chem. Eng. Sci. 1991, 46, 509.
38. Wang, M. L.; Yang, H. M. Dynamic Model of the Triphase Catalytic Reaction. Ind. Eng. Chem. Res. 1992, 31, 1868.
39. Weale, K. W. Chemical Reactions at High Pressure; Spon: London, 1967.
40. Weber, W. P.; Gokel, G. W. Phase-transfer Catalysis in Organic Synthesis; Springer-Verlag: Berlin, 1977.