Mixing and the selectivity of chemical reactions

Organic Process Research and Development

Volumn 7, Issue 4, 2003, Pages 471-508

  Bourne, John R ^a,b  

^a ETH ZURICH   (Switzerland)

^b Vine House   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINATION; CATALYSIS; CHEMICAL ENGINEERING; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL WASTE; DIFFUSION; FLOW RATE; HYDROLYSIS; KINETICS; LITERATURE; NITRATION; ORGANIC CHEMISTRY; PH; PHYSICAL PHASE; REACTION ANALYSIS; REACTOR; REVIEW; SYNTHESIS; THEORY; TIME; TURBULENT FLOW; VISCOSITY;

EID: 0043246743     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op020074q     Document Type: Review

References (83)

1. Baldyga, J.; Bourne, J. R. Turbulent Mixing and Chemical Reactions; Wiley: New York, 1999.
2. Doraiswamy, L. K.; Sharma, M. M. Heterogeneous Reactions; Wiley: New York, 1984; Vol. 2.
3. Westerterp, K. R.; van Swaaij, W. P. M.; Beenackers, A. A. C. M. Chemical Reactor Design and Operation; Wiley: New York, 1984.
4. Atherton, J. H. Mechanism in two-Phase Reaction Systems: Coupled Mass Transfer and Chemical Reaction. In Research in Chemical Kinetics; Elsevier: Amsterdam, 1994; Vol. 2, p 193.
5. Hammett, L. P. Physical Organic Chemistry; McGraw-Hill: New York, 1970.
6. Levenspiel, O. Chemical Reaction Engineering; Wiley: New York, 1972.
7. Agre, C. L.; Dinga, G.; Pflaum, R. Reactions of Acids with Diamines. J. Org. Chem. 1956, 21, 561.
8. Stoutland, D.; Helgen, L.; Agre, C. L. Reactions of Diamines with Isocyanates and Isothiocyanates. J. Org. Chem. 1959, 24, 818.
9. Jacobson, A. R.; Makris, A. N.; Sayre, L. M. Monoacylation of Symmetrical Diamines. J. Org. Chem. 1987, 52, 2592.
10. Christy, P. F.; Ridd, J. H.; Steers, N. D. Nitration of Bibenzyl by Nitronium Tetrafluoroborate. J. Chem. Soc. (B) 1970, 797.
11. Gastaminza, A; Ridd, J. H. The Nitration of Bibenzyl. J. Chem. Soc., Perkin Trans. II 1972, 813.
12. de la Mare, P. B. D.; Vernon, C. A. The Influence of the Methoxyl Group in Aromatic Substitution. J. Chem. Soc. 1951, 1764.
13. Bourne, J. R.; Kozicki, F. Mixing Effects During the Bromination of 1,3,5-Trimethoxybenzene. Chem. Eng. Sci. 1977, 32, 1538.
14. Paul, E. L.; Treybal, R. E. Mixing and Product Distribution for a Liquid Phase, Second-Order, Competitive-Consecutive Reaction. AIChE. J. 1971, 17, 718.
15. Schofield, K. Aromatic Nitration; Cambridge University Press: New York, 1980.
16. Rys, P. The Mixing-Sensitive Product Distribution of Chemical Reactions. Chimia 1992, 46, 469.
17. Manglik, A. K.; Moodie, R. B.; Schofield, K.; Dedeoglu, E.; Dutly, A.; Rys, P. Electrophilic Aromatic Substitution. J. Chem. Soc., Perkin Trans. II 1981, 1358.
18. Hanna, S. B.; Hunziker, E.; Saito, T.; Zollinger, H. The Problem of the Mononitration of Durene (in German) Helv. Chim. Acta 1969, 52, 1537.
19. Pfister, F.; Rys, P.; Zollinger, H. Mixing Disguised Nitration of Aromatic Compounds with Nitronium Salts. Helv. Chim. Acta 1975, 58, 2093.
20. Bourne, J. R.; Ravindranath, K.; Thoma, S. Control of Product Distribution in Mixing-Controlled Reactions. J. Org. Chem. 1988, 53, 5166.
21. Bourne, J. R.; Gablinger, H. Local pH Gradients and the Selectivity of Fast Reactions. Pt.1 (with Ravindranath, K.) Chem. Eng. Sci. 1941, 43; Pt. 2 Chem. Eng. Sci. 1989, 44, 1347.
22. Bourne, J. R.; Gablinger, H. Local pH Gradients and the Selectivity of Fast Reactions. Pt.1 (with Ravindranath, K.) Chem. Eng. Sci. 1941, 43; Pt. 2 Chem. Eng. Sci. 1989, 44, 1347.
23. Francis, A. W. The Relative Rates of Certain Ionic Reactions. J. Am. Chem. Soc. 1926, 48, 655.
24. Zaldivar, J. M.; Molga, E.; Alos, M. A.; Hernandez, H.; Westerterp, K. R. Aromatic Nitrations by Mixed Acid: Slow Liquid-Liquid Reaction Regime. Chem. Eng. Proc. 1995, 34, 543.
25. Tolgyesi, W. S. Relative Reactivity of Toluene-Benzene in Nitronium Tetrafluoroborate Nitration. Can. J. Chem. 1965, 43, 343.
26. Baldyga, J.; Bourne, J. R.; Walker, B. Nonisothermal Micromixing in Turbulent Liquids-Theory and Experiment. Can. J Chem. Eng. 1998, 76, 641.
27. Bourne, J. R.; Yu, S. Investigation of Micromixing in Stirred Tank Reactors Using Parallel Reactions. Ind. Eng. Chem. Res. 1994, 33, 41.
28. Paul, E. L.; Mahadevan, H.; Foster, T.; Kennedy, M.; Midler, M. Effect of Mixing on Scale-Up of a Parallel Reaction System. Chem. Eng. Sci. 1992, 47, 2837.
29. Bourne, J. R.; Rys, P.; Suter, K. Mixing Effects in the Bromination of Resorcin. Chem. Eng. Sci. 1977, 32, 711.
30. Kaminski, R.; Lauk, U.; Skrabal, P.; Zollinger, H. pH-Dependence and Micromixing Effects on the Product Distribution of Couplings with 6-Amino-4-hydroxy-2-naphthalenesulphonic Acid. Helv. Chim. Acta 1983, 66, 2002.
31. Danckwerts, P. V. Gas - Liquid Reactions; McGraw-Hill: New York, 1970.
32. Hanna, G. J.; Noble, R. D. Measurement of Liquid-Liquid Interfacial Kinetics. Chem. Rev. 1985, 85, 583.
33. Riddiford, A. C. Adv. Electrochem. Electrochem. Eng. 1966, 4, 47.
34. Teramoto, M.; Nagayasu, T.; Matsui, T.; Hashimoto, K.; Nagata, S. Selectivity of Consecutive Gas-Liquid Reactions. J. Chem. Eng. Jpn. 1969, 2, 186.
35. Teramoto, M.; Fujita, S.; Kataoka, M.; Hashimoto, K.; Nagata, S. Effect of Bubble Size on the Selectivity of Consecutive Gas - Liquid Reactions. J. Chem. Eng. Japan 1970, 3, 79.
36. Pangarkar, V. G.; Sharma, M. M. Consecutive Reactions: Role of Mass Transfer Factors. Chem. Eng. Sci. 1974, 29, 561.
37. Kondelik, P.; Pasek, J. Effect of Mass Transfer on the Selectivity of Consecutive Reactions in a Gas-Liquid System. Collect. Czech. Chem. Commun. 1981, 46, 1635.
38. Hanson, C.; Marsland, J. G. Macrokinetics of Toluene Nitration. Chem. Eng. Sci. 1971, 26, 1513.
39. Hanson, C.; Marsland, J. G.; Naz, M. A. Macrokinetics of Chlorobenzene Nitration. Chem. Eng. Sci. 1974, 29, 297.
40. Hanson, C.; Ismail, H. A. M. Macrokinetics of Toluene and Benzene Nitration under Laminar Conditions. Chem. Eng. Sci. 1977, 32, 775.
41. Tomita, A.; Ebina, N.; Tamai, Y. Base-Catalysed Ester Hydrolysis in a Toluene-Water System. J. Am. Chem. Soc. 1977, 99, 5725.
42. Yamazaki, H.; Yazawa, H.; Miyanami, K. Effect of Mixing on Esterification of Cephalosporic Acid in a Solid-Liquid System. Chem. Eng. Sci. 1989, 44, 109.
43. Beenackers, A. A. C. M.; Van Swaaij, W. P. M. Selectivity of Benzene Sulphonation in Three Gas-Liquid Reactors with Different Mass Transfer Characteristics. Chem. Eng. J. 1978, 15, 25 and 39. See also Am. Chem. Soc. Symp. Ser. 1978, 65, 327.
44. Beenackers, A. A. C. M.; Van Swaaij, W. P. M. Selectivity of Benzene Sulphonation in Three Gas-Liquid Reactors with Different Mass Transfer Characteristics. Chem. Eng. J. 1978, 15, 25 and 39. See also Am. Chem. Soc. Symp. Ser. 1978, 65, 327.
45. Harnby, N.; Edwards, M. F.; Nienow, A. W. Mixing in the Process Industries; Butterworth-Heinemann: New York, 1992.
46. Nienow, A. W. On Impeller Circulation and Mixing Effectiveness in the Turbulent Flow Regime. Chem. Eng. Sci. 1997, 52, 2557.
47. Bourne, J. R.; Yu, S. Investigation of Micromixing in Stirred Tank Reactors Using Parallel Reactions. Ind. Eng. Chem. Res. 1994, 33, 41.
48. Bourne, J. R.; Gholap, R. V. An Approximate Method for Predicting the Product Distribution of Fast Reactions in Stirred Tank Reactors. Chem. Eng. J. 1995, 59, 293.
49. Hearn, S. J. Turbulent Mixing Mechanisms in Motionless Mixers. Ph.D. Thesis, University of Birmingham, U.K. 1995.
50. Special feature section: Process Intensification/Continuous Processing in the Fine Chemicals Arena. Org. Process Res. Dev. 2001, 5, 612-664.
51. Carpenter, K. J. Chemical Reaction Engineering Aspects of Fine Chemicals Manufacture. Chem. Eng. Sci. 2001, 56, 305.
52. Bourne, J. R.; Dell'Ava, P. Micro- and Macro-Mixing in Stirred Tank Reactors of Different Sizes. Chem. Eng. Res. Des. 1987, 65, 180.
53. Baldyga, J.; Bourne, J. R. Calculation of Micromixing in Inhomogeneous Stirred Tank Reactors. Chem. Eng. Res. Des. 1988, 66, 33.
54. Baldyga, J.; Bourne, J. R.; Dubuis, B.: Etchells, A. W.; Gholap, R. V.; Zimmermann, B. Jet Reactor Scale-Up for Mixing-Controlled Reactions. Chem. Eng. Res. Des. 1995, 73, 497.
55. Tipnis, S. K.; Penney, W. R.; Fasano, J. B. An Experimental Investigation To Determine a Scale-Up Method for Fast Competitive Reactions in Agitated Vessels. AIChE Symp. Ser. No. 299 1994, 90, 78.
56. Bourne, J. R.; Thoma, S. A. Some Factors Determining the Critical Feed Time of a Semibatch Reactor. Chem. Eng. Res. Des. 1991, 69, 321.
57. Prausnitz, J. M.; Lichtenthaler, R. N.; de Azevado, E. G. Molecular Thermodynamics of Fluid-Phase Equilibria; Prentice Hall: New York, 1986.
58. Schofield, K. Aromatic Nitration; Cambridge University Press: Cambridge, UK, 1980.
59. Cox, P. R.; Strachan, A. N. Two-Phase Nitration of Chlorobenzene. Chem. Eng. Sci. 1971, 26, 1013.
60. Cox, P. R.; Strachan, A. N. Two-Phase Nitration of Toluene: Part 2. Chem. Eng. J. 1972, 4, 253.
61. Sherwood, T. K.; Pigford, R. L.; Wilke, C. R. Mass Transfer; McGraw-Hill: New York, 1975.
62. Doraiswamy, L. K.; Sharma, M. M. Heterogeneous Reactions; Wiley: New York, 1984; Vol. 2.
63. Hanson, C.; Marsland, J. G.; Naz, M. A. Macrokinetics of Chlorobenzene Nitration. Chem. Eng. Sci. 1974, 29, 297.
64. Hanson, C.; Ismail, H. A. M. Diffusion of Benzene and Toluene into Aqueous Nitric Acid-Sulphuric Acid Mixtures. J. Appl. Chem. 1976, 26, 111.
65. Hanson, C.; Ismail, H. A. M. Solubility and Distribution Data for Benzene and Toluene between Aqueous and Organic Phases. J. Appl. Chem. 1975, 25, 319.
66. Danckwerts, P. V. Gas - Liquid Reactions; McGraw-Hill: New York, 1970.
67. Chapman, J. W.; Cox, P. R.; Strachan, A. N. Two-pchase Nitration of Toluene: Part 3. Chem. Eng. Sci. 1974, 29, 1247.
68. Sharma, M. M.; Nanda, A. K. Extraction with Second-Order Reaction. Trans. Inst. Chem. Eng. 1968, 46, 44.
69. Bamford, C. H.; Tipper, C. F. H. Comprehensive Chemical Kinetics; Elsevier: Amsterdam, 1972; Vol. 10.
70. Atherton, J. H. Methods for Study of Reaction Mechanisms in Liquid-Liquid and Liquid-Solid Reaction Systems and Their Relevance to the Development of Fine Chemical Processes. Trans. Inst. Chem. Eng. A 1993, 71, 111.
71. Atherton, J. H.; Carpenter, K. J. Process Development: Physicochemical Concepts; Oxford University Press: New York, 1999.
72. Sankholkar, D. S.; Sharma, M. M. A New System for the Measurement of Effective Interfacial Area in Agitated Liquid-Liquid Contactors by the Chemical Method. Chem. Eng. Sci. 1973, 28, 2089.
73. Zaldivar, J. M.; Molga, E.; Alos, M. A.; Hernandez, H.; Westerterp, K. R. Aromatic Nitrations by Mixed Acid: Fast Liquid-Liquid Reaction Regime. Chem. Eng. Prog. 1996, 35, 91.
74. Woezik, B. A. A.; Westerterp, K. R. Measurement of Interfacial Area with the Chemical Method for a System with Alternating Dispersed Phases. Chem. Eng. Prog. 2000, 39, 299.
75. Harnby, N., Edwards, M. F., Nienow, A. W., Eds. Mixing in the Process Industries; Butterworth-Heinemann: Woburn, MA, 1997.
76. Sharratt, P. N., Ed. Handbook of Batch Process Design; Blackie: London, 1997.
77. Asai, S.; Nakamura, H.; Furuichi, Y. Alkaline Hydrolysis of n-Butyl Acetate with Phase Transfer Catalyst Aliquat 336. AIChE J. 1992, 38, 397.
78. Asai, S.; Nakamura, H.; Sumita, T. Oxidation of Benzyl Alcohol Using Hypochlorite Ion via Phase Transfer Catalysis. AIChE J. 1994, 40, 2028.
79. Atherton, J. H. Chemical Aspects of Scale-Up. In Pilot Plants and Scale-up of Chemical Processes, 2nd ed.; Hoyle, W., Ed.; Royal Society of Chemistry: Cambridge, UK, 1999.
80. Gehlawat, J. K.; Sharma, M. M. Alkylation of Phenols with Isobutylene. J. Appl. Chem. 1970, 20, 93.
81. Compton, R. G.; Harding, M. S.; Atherton, J. H.; Brennan, C. M. Mechanism of a Solid/Liquid Interfacial Reaction: The Reaction of an Aqueous Solution of an Aromatic Amine with Cyanuric Chloride. J. Phys. Chem. 1993, 97, 4677.
82. Horrobin, S. The Hydrolysis of some Chloro-1,3,5-triazines: Mechanism, Structure and Reactivity. J. Chem. Soc. 1963, 4130.
83. King, J. F.; Rathore, R.; Lam, J. Y. L.; Guo, Z. R.; Klassen, D. F. pH Optimization of Nucleophilic Reactions in Water. J. Am. Chem. Soc. 1992, 114, 3028.