Kinetic and thermodynamic analysis of liquid-phase benzene hydrogenation

AIChE Journal

Volumn 45, Issue 5, 1999, Pages 1059-1071

  Singh, Utpal K ^a   Vannice, M Albert ^a  

^a The Pennsylvania State University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALUMINA; CATALYSTS; GAS ADSORPTION; HYDROGEN; HYDROGENATION; MATHEMATICAL MODELS; PALLADIUM; PARTIAL PRESSURE; REACTION KINETICS; SOLUBILITY; SOLVENTS; THERMODYNAMICS;

LIQUID PHASE HYDROGENATION;

BENZENE;

BENZENE; SOLVENT;

BENZENE; HYDROGENATION; KINETICS; THERMODYNAMICS;

ADSORPTION; ARTICLE; DISSOCIATION; HYDROGENATION; KINETICS; LIQUID; MODEL; REACTION ANALYSIS; SOLUBILITY; THERMODYNAMICS;

EID: 0032924311     PISSN: 00011541     EISSN: None     Source Type: Journal    
DOI: 10.1002/aic.690450514     Document Type: Article

References (60)

1. Aben, P. C., J. C. Platteeuw, and B. Stouthamer, "The Hydrogenation of Benzene over Supported Platinum, Palladium, and Nickel Catalysts," Recl. Trav. Chim. Pays-Bas. Belg., 89, 449 (1970).
2. Abon, M., J. C. Bertolini, and B. J. Massardier, "Adsorption States of Benzene and Toluene on Pt(111): A Vibrational EELS, Δφ, AES, and TDS Study," Surface Sci., 162, 395 (1985).
3. Augustine, R. L., "The Stereochemistry of Hydrogenation of α-β Unsaturated Ketones," Adv. Catal., 25, 56 (1976).
4. Augustine, R. L., and P. Techasauvapak, "Heterogeneous Catalysis in Organic Synthesis. Part 9: Specific Site Solvent Effects in Catalytic Hydrogenation," J. Mol. Catal., 87, 95 (1994).
5. 3 Catalysts," J. Catal., 37, 22 (1995).
6. Boudart, M., D. E. Mears, and M. A. Vannice, "Kinetics of Heterogeneous Catalytic Reactions," Ind. Chim. Belge, 32, 281 (1967).
7. Boudart, M., "Two-Step Catalytic Reactions," AIChE J., 18, 465 (1972).
8. Boudart, M., and G. Djega-Mariadassou, Kinetics of Heterogeneous Catalytic Reactions, Chap. 5, Princeton Univ. Press, Princeton, NJ (1984).
9. Boudart, M., and D. J. Sajkowski, "Catalytic Hydrogenation of Cyclohexene: Liquid-Phase Reaction on Rhodium," Faraday Discuss., 92, 57 (1991).
10. Chou, P., and M. A. Vannice, "Calorimetric Heat of Adsorption Measurements on Palladium: 1. Influence of Crystallite Size and Support on Hydrogen Adsorption," J. Catal., 104, 1 (1987a).
11. Chou, P., and M. A. Vannice, "Benzene Hydrogenation over Supported and Unsupported Palladium: 1. Kinetic Behavior," J. Catal., 107, 129 (1987b).
12. Chou, P., and M. A. Vannice, "Benzene Hydrogenation over Supported and Unsupported Palladium: 2. Reaction Model," J. Catal., 107, 140 (1987c).
13. Derbentsev, Y. I., Z. Paal, and P. Tetenyi, "Investigation on the Mechanism of Benzene Hydrogenation: A Radiotracer Study," Z. Phys. Chem. Neue Folge., 80, 51 (1972).
14. Eckert, C. A., C. K. Hsieh, and J. R. McCabe, "Molecular Thermodynamics for Chemical Reaction Design," AIChE J., 20, 20 (1974).
15. Fajarde, F., J.-F. Tempere, G. Djega-Mariadassou, and G. Blanchard, "Benzene Hydrogenation as a Tool for the Determination of the Percentage of Metal Exposed on Low Loaded Ceria Supported Rh Catalysts," J. Catal., 163, 77 (1996).
16. Hancock, E. G., Benzene and Its Derivatives, Wiley, New York (1975).
17. Konyukhov, V. Y., S. D. Tret'yakov, A. G. Zyyskin, V. V. Kul'kova, and M. I. Temkin, "Kinetics of Liquid-Phase Hydrogenation of Benzene on Palladium Catalyst and Hydrogenation of Toluene on Palladium and Platinum Catalysts," Kinet. Catal., 28, 360 (1987).
18. Lin, S. D., and M. A. Vannice, "Hydrogenation of Aromatic Hydrocarbons over Supported Pt Catalysts: 1. Benzene Hydrogenation," J. Catal., 143, 539 (1993a).
19. Lin, S. D., and M. A. Vannice, "Hydrogenation of Aromatic Hydrocarbons over Supported Pt Catalysts: 3. Reaction Models for Metal Surfaces and Acidic Sites on Oxide Supports," J. Catal., 143, 563 (1993b).
20. Madon, R. J., J. P. O'Connell, and M. Boudart, "Catalytic Hydrogenation of Cyclohexene. II: Liquid-Phase Reaction on Supported Platinum in a Gradientless Slurry Reactor," AIChE J., 24, 904 (1978).
21. Madon, R. J., and M. Boudart, "Experimental Criterion for the Absence of Artifacts in the Measurement of Rates of Heterogeneous Catalytic Reactions," Ind. Eng. Chem. Fundam., 21, 438 (1982).
22. Marecot, P. E., J. M. Paraiso, J. M. Dumas, and J. Barbier, "Benzene Hydrogenation on Nickel Catalysts. Role of Weakly-Bound Hydrogen," Appl. Catal., 74, 261 (1991).
23. Mears, D. E., and M. Boudart, "The Dehydrogenation of Isopropanol on Catalysts Prepared by Sodium Borohydride Reduction," AIChE J., 12, 313 (1966).
24. Mirodatos, C., "Benzene Hydrogenation: An Isotopic Transient Study," J. Phys. Chem., 90, 481 (1986).
25. Mirodatos, C., J. A. Dalmon, and G. A. Martin, "Steady-State and Isotopic Transient Kinetics of Benzene Hydrogenation on Ni Catalysts," J. Catal., 105, 405 (1987).
26. Moysan, J. M., M. J. Huron, H. Paradowski, and J. Vidal, "Prediction of the Solubility of Hydrogen in Hydrocarbon Solvents through Cubic Equations of State," Chem. Eng. Sci., 38, 1085 (1983).
27. Moyes, R. B., and P. B. Wells, "The Chemisorption of Benzene," Adv. Catal., 23, 121 (1973).
28. 2 on Pd(III)," Chem. Phys. Lett., 266, 437 (1997).
29. Myers, A. K., G. R. Schobs, and J. B. Benziger, "Comparison of Benzene Adsorption on Ni(111) and Ni(100)," J. Phys. Chem., 91, 2230 (1987).
30. Nagahara, H., M. Ono, M. Konishi, and P. Fukuoka, "Partial Hydrogenation of Benzene to Cyclohexene," Appl. Surf. Sci., 121/122, 448 (1997).
31. Odenbrand, C. U. I., and S. T. Lundin, "Hydrogenation of Benzene to Cyclohexene on a Ruthenium Catalyst: Influence of Some Reaction Parameters," J. Chem. Tech. Biotechnol., 30, 677 (1980).
32. Orozco, J. M., and G. Webb, "The Adsorption and Hydrogenation of Benzene and Toluene on Alumina- and Silica-Supported Palladium and Platinum Catalysts," Appl. Catal., 6, 67 (1983).
33. Palmer, M. B., and M. A. Vannice, "The Effect of Preparation Variables on the Dispersion of Supported Platinum Catalysts," J. Chem. Tech. Biotechnol., 30, 205 (1980).
34. Poondi, D. P., and M. A. Vannice, "Competitive Hydrogenation of Benzene and Toluene on Palladium and Platinum Catalysts," J. Catal., 161, 742 (1996).
35. Prasad, K. H. V., K. B. S. Prasad, M. M. Mallikarjunan, and R. Vaidyeswaran, "Self-Poisoning and Rate Multiplicity in Hydrogenation of Benzene," J. Catal., 84, 65 (1983).
36. Prausnitz, J. M., R. N. Lichtenthaler, and E. G. de Azevedo, Molecular Thermodynamics of Fluid-Phase Equilibria, Chap. 2, Prentice Hall, Englewood Cliffs, NJ (1986).
37. Rajadhyaksha, R. A., and S. L. Karwa, "Solvent Effects in Catalytic Hydrogenation," Chem. Eng. Sci., 41, 1765 (1986).
38. Shustrorovich, E., "The Bond-Order Conservation Approach to Chemisorption and Heterogeneous Catalysis: Applications and Implications," Adv. Catal., 37, 101 (1990).
39. 3," Appl. Catal., A: General, 125, 271 (1995).
40. Stair, P. C., and G. A. Somorjai, "The Adsorption of Benzene on the Pt(111) Surface Studied by Low-Energy Electron Diffraction Intensity Measurements and Quantitative Auger Electron Spectroscopy," J. Chem. Phys., 67, 4361 (1977).
41. Struijk, J., M. d'Angremond, W. J. M. Lucas-de-Regt, and J. J. F. Scholten, "Partial Liquid Phase Hydrogenation of Benzene to Cyclohexene over Ruthenium Catalysts in the Presence of an Aqueous Salt Solution: I. Preparation, Characterization of the Catalyst and Study of a Number of Process Variables," Appl. Catal., A: General, 83, 263 (1992a).
42. Struijk, J., R. Moene, T. van der Kamp, and J. J. F. Scholten, "Partial Liquid Phase Hydrogenation of Benzene to Cyclohexene over Ruthenium Catalysts in the Presence of an Aqueous Salt Solution: II. Influence of Various Salts on the Performance of the Catalyst," Appl. Catal., A: General, 89, 77 (1992b).
43. Struijk, J., and J. J. F. Scholten, "Selectivity to Cyclohexenes in the Liquid-Phase Hydrogenation of Benzene and Toluene over Ruthenium Catalysts, As Influenced by Reaction Modifiers," Appl. Catal., A: General, 82, 277 (1992).
44. Surman, M., S. R. Bare, P. Hofmann, and D. A. King, "Direct Characterization of a Catalytic Surface Reaction Step: Benzene-Deuterium Exchange on Pt(110)," Surface Sci., 126, 349 (1983).
45. Surman, M., S. R. Bare, P. Hofmann, and D. A. King, "The Influence of Orientation on the H-D Exchange Reactions in Chemisorbed Aromatics: Benzene and Pyridine Adsorbed on Pt(100)," Surface Sci., 179, 243 (1987).
46. 2," J. Mol. Struct., 174, 395 (1988).
47. Temkin, M. I., D. Y. Murzin, and V. V. Kul'kova, "Mechanism of the Liquid-Phase Hydrogenation of the Benzene Ring," Kinet. Catal., 30, 637 (1989).
48. Tetenyi, P., "Comments on Shawn D. Lin and M. Albert Vannice in Hydrogenation of Aromatic Hydrocarbons over Supported Pt Catalysts," J. Catal., 147, 601 (1994).
49. Tetenyi, P., and Z. Paal, "Investigation on the Mechanism of Benzene Hydrogenation: A Radiotracer Study. II. Discussion of the Reaction Mechanism," Z. Phys. Chem. Neue Folge., 80, 63 (1972).
50. Toppinen, S., T. K. Rantakula, T. Salmi, and J. Aittamaa, "Kinetics of Liquid-Phase Hydrogenation of Benzene and Some Monosubstituted Alkylbenzenes over a Nickel Catalyst," Ind. Eng. Chem. Res., 35, 1824 (1996).
51. Toppinen, S., T. K. Rantakyla, T. Salmi, and J. Aittamaa, "The Liquid-Phase Hydrogenation of Benzene and Substituted Alkylbenzenes over a Nickel Catalyst in a Semi-Batch Reactor," Catal. Today, 38, 23 (1997).
52. Tsai, M. C., C. M. Friend, and E. L. Muetterites, "Dehydrogenation Processes on Nickel and Platinum Surfaces. Conversion of Cyclohexane, Cyclohexene, and Cyclohexadiene to Benzene," J. Amer. Chem. Soc., 104, 2539 (1982).
53. van Meerten, R. Z. C., A. C. M. Verhaak, and J. W. E. Coenen, "Gas-Phase Benzene Hydrogenation on a Nickel-Silica Catalyst: 2. Gravimetric Experiments of Benzene, Cyclohexene, and Cyclohexane Adsorption and Benzene Hydrogenation," J. Catal., 44, 217 (1976).
54. van Meerten, R. Z. C., and J. W. E. Coenen, "Gas-Phase Benzene Hydrogenation on a Nickel-Silica Catalyst: 4. Rate Equations and Curve Fitting," J. Catal., 46, 13 (1977).
55. van Meerten, R. Z. C., T. F. M. de Graaf, and J. W. E. Coenen, "Gas-Phase Benzene Hydrogenation on a Nickel-Silica Catalyst: 3. Low-Field Magnetization Measurements on Hydrogen, Benzene, Cyclohexene, and Cyclohexane Adsorption, and Benzene Hydrogenation," J. Catal., 46, 1 (1977).
56. van Meerten, R. Z. C., A. Morales, J. Barbier, and R. Maurel, "Isotope Effects in the Hydrogenation and Exchange of Benzene on Platinum and Nickel," J. Catal., 58, 43 (1979).
57. van Meerten, R. Z. C., and J. W. E. Coenen, "Gas-Phase Benzene Hydrogenation on a Nickel-Silica Catalyst: 1. Experimental Data and Phenomenological Description," J. Catal., 37, 37 (1995).
58. Vannice, M. A., S. H. Hyun, B. Kalpakci, and W. C. Liauh, "Entropies of Adsorption in Heterogeneous Catalytic Reactions," J. Catal., 56, 358 (1979).
59. Wong, K. F., and C. A. Eckert, "Solvent Design for Chemical Reactions," Ind. Eng. Chem. Process Des. Develop., 8, 568 (1969).
60. Yu, Y. F., J. J. Chessick, and A. C. Zettlemoyer, "Adsorption Studies on Metals. VIII. Monofunctional Organic Molecules on Reduced and Oxide-Coated Nickel and Copper," J. Phys. Chem., 63, 1626 (1959).