Kinetic study of dowex 50 Wx8-catalyzed esterification and hydrolysis of benzyl acetate

Industrial and Engineering Chemistry Research

Volumn 48, Issue 5, 2009, Pages 2519-2532

  Ali, Sami H ^a   Merchant, Sabiha Q ^a  

^a KUWAIT UNIVERSITY   (Kuwait)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION BEHAVIORS; ADSORPTION DATUM; ADVERSE EFFECTS; BENZYL ACETATES; BENZYL ALCOHOLS; CATALYST LOADINGS; CATALYZED REACTIONS; COMPONENT ACTIVITIES; DOWEX-50; EQUILIBRIUM BEHAVIORS; ESTERIFICATION KINETICS; FEED COMPOSITIONS; HYDROLYSIS KINETICS; KINETIC STUDIES; LANGMUIR-HINSHELWOOD; NEW FORMS; PRESENCE OF WATERS; REACTION CONDITIONS; RESIN PHASE; THREE COMPONENTS;

ADSORPTION; ESTERS; HYDROLYSIS; RESINS;

ESTERIFICATION;

EID: 65349187613     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie8006787     Document Type: Article

References (79)

1. Saha, B.; Chopade, S. P.; Mahajani, S. M. Recovery of Dilute Acetic Acid through Esterification in a Reactive Distillation Column. Catal. Today 2000, 60, 147.
2. Schmitt, M.; Scala, C.; Moritz, P.; Hasse, H. n-Hexyl Acetate Pilot Plant Reactive Distillation with Modified Internals. Chem. Eng. Process 2005, 44, 677.
3. Doherty, M. F.; Buzad, G. Reactive Distillation by Design. Trans. IChemE. 1992, 70, 448.
4. Agreda, V. H.; Partin, L. R. Reactive Distillation Process for the Production of Methyl Acetate, US Patent 4.435.595, 1984.
5. Agreda, V. H.; Partin, L. R.; Heise, W. H. High-Purity Methyl Acetate via Reactive Distillation. Chem. Eng. Prog. 1990, 86, 40.
6. http://www.inchem.org/.
7. Sharma, O. N.; Nageshwar, G. D.; Mene, P. S. Esterification of Ethanol with Propionic Acid Catalysed by a Cation Exchange Resin. Indian J. Technol. 1973, 11, 360.
8. Liu, W. T.; Tan, C. S. Liquid-Phase Esterification of Propionic Acid with n-Butanol. Ind. Eng. Chem. Res. 2001, 40, 3281.
9. Bhatia, S.; Rajamani, K.; Rajkhowa, P.; Rao, M. G. Ion Exchange Resin Catalysis. Ion Exch. Membr. 1973, 1, 127.
10. Dakshinamurty, P.; Ramarao, M. V. S.; Ramachandramurty, Ch. V. Kinetics of Catalytic Esterification of Propan-1-ol with Propanoic Acid using Cation-Exchange Resin. J. Chem. Technol. Biotechnol. 1984, 34 A, 257.
11. Nagaraju, N.; Mehboob, P. A Comparison of Catalytic Activity of Zeolites with Some Lewis Acids in Esterification Reaction. Ind. J. Chem. Technol. 1996, 3, 253.
12. Roy, R.; Bhatia, S. Kinetics of Esterification of Benzyl Alcohol with Acetic Acid Catalysed by Cation-Exchange Resin (Amberlyst-15). J. Chem. Technol. Biotechnol. 1987, 37, 1.
13. Patel, D.; Saha, B. Heterogeneous Kinetics and Residue Curve Map (RCM) Determination for Synthesis of n-Hexyl Acetate Using Ion-Exchange Resins as Catalysts. Ind. Eng. Chem. Res. 2007, 46, 3157.
14. Schmitt, M.; Hasse, H. Chemical Equilibrium and Reaction Kinetics of Heterogeneously Catalyzed n-Hexyl Acetate Esterification. Ind. Eng. Chem. Res. 2006, 45, 4123.
15. Desai, S. B.; Krishnaswamy, N. Use of Cation Exchange Resins as Catalysts in the Hydrolysis of Esters in 70% Acetone Solution and in Esterification Reactions. Indian J. Technol. 1973, 11, 255.
16. Yadav, G. D.; Rahuman, M. S. M. M. Cation-Exchange Resin- Catalysed Acylations and Esterifications in Fine Chemical and Perfumery Industries. Org. Process Res. Dev. 2002, 6, 706.
17. Kirumakki, S. R.; Nagaraju, N.; Narayanan, S. A Comparative Esterification of Benzyl Alcohol with Acetic Acid over Zeolites Hβ, HY and HZSM5. Appl. Catal. A. Gen. 2004, 273, 1.
18. El-Noamany, H. M.; Shaheen, F. A.; El-Kenawy, O. S.; Zaher, F. A. Studies on Some Factors Affecting the Rate of Esterification of Acetic Acid with Monohydric Alcohols. Modelling Meas. Cont. C 1994, 43, 25.
19. Weidlich, U.; Gmehling, J. A Modified UNIFAC model. 1. Prediction of VLE, hE, and gamma. infin. Ind. Eng. Chem. Res. 1987, 26, 1372.
20. Gmehling, J.; Li, J.; Schiller, M. A Modified UNIFAC Model. 2. Present Parameter Matrix and Results for Different Thermodynamic Properties. Ind. Eng. Chem. Res. 1993, 32, 178.
21. Gmehling, J.; Lohmann, J.; Jakob, A.; Li, J.; Joh, R. A Modified UNIFAC (Dortmund) Model. 3. Revision and Extension. Ind. Eng. Chem. Res. 1998, 37, 4876.
22. Wittig, R.; Lohmann, J.; Joh, R.; Horstmann, S.; Gmehling, J. Vapor-Liquid Equilibria and Enthalpies of Mixing in a Temperature Range from 298.15 to 413.15 K for the Further Development of Modified UNIFAC (Dortmund). Ind. Eng. Chem. Res. 2001, 40, 5831.
23. Lohmann, J.; Joh, R.; Gmehling, J. From UNIFAC to Modified UNIFAC (Dortmund). Ind. Eng. Chem. Res. 2001, 40, 957.
24. Lohmann, J.; Gmehling, J. Modified UNIFAC (Dortmund): Reliable Model for the Development of Thermal Separation Processes. J. Chem. Eng. Jpn. 2001, 34, 43.
25. Gmehling, J.; Wittig, R.; Lohmann, J.; Joh, R. A Modified UNIFAC (Dortmund) Model. 4. Revision and Extension. Ind. Eng. Chem. Res. 2002, 41, 1678.
26. Wittig, R.; Lohmann, J.; Gmehling, J. Prediction of Phase Equilibria and Excess Properties for Systems with Sulfones. AIChE J. 2003, 49, 530.
27. Jakob, A.; Grensemann, H.; Lohmann, J.; Gmehling, J. Further Development of Modified UNIFAC (Dortmund): Revision and Extension 5. Ind. Eng. Chem. Res. 2006, 45, 7924.
28. Lilja, J.; Murzin, D. Y.; Salmi, T.; Aumo, T.; Maki-Arvel, P.; Sundell, M. Esterification of Different Acids over Heterogeneous and Homogeneous Catalysts and Correlation with the Taft Equation. J. Mol. Catal. A: Chem. 2002, 182, 555.
29. Ali, S. H.; Tarakmah, A.; Merchant, S. Q.; Al-Sahhaf, T. Synthesis of Esters: Development of the Rate expression for the Dowex 50 Wx8- 400 Catalyzed Esterification of Propionic Acid with 1-propanol. Chem. Eng. Sci. 2007, 62, 3197.
30. Froment, G. F.; Bischoff. K. B. Chemical Reactor Analysis and Design, 2nd ed.; Wiley: New York, 1990.
31. Smith, M. B.; March, J. Advanced Organic Chemistry; Wiley: Toronto, Canada, 2001.
32. Lane, C. A.; Cheung, M. F.; Dorsey, G. F. The Possibility of a Cyclic Mechanism for Acid-Catalyzed Ester Hydrolysis. J. Am. Chem. Soc. 1968, 90, 6492.
33. Martin, R. B. Mechanisms of Acid Hydrolysis of Carboxylic Acid Esters and Amides. J. Am. Chem. Soc. 1962, 84, 4130.
34. Yates, K. Kinetics of Ester Hydrolysis in Concentrated Acid. Acc. Chem. Res. 1971, 4, 136.
35. Huskey, W. P.; Warren, C. T.; Hogg, J. L. Substrate Hydrophobicity and its Influence on the Transition-State Structure for the Water-Catalyzed Hydrolysis of Acyl Esters. J. Org. Chem. 1981, 46, 59.
36. Hori, K.; Ikenaga, Y.; Arata, K.; Takahashi, T.; Kasai, K.; Noguchi, Y.; Sumimoto, M.; Yamamoto, H. Theoretical Study on the Reaction Mechanism for the Hydrolysis of Esters and Amides under Acidic Conditions. Tetrahedron 2007, 63, 1264.
37. Hicks, J. S.; Weisz, P. B. The Behaviour of Porous Catalyst Particles in View of Internal Mass and Heat Diffusion Effects. Chem. Eng. Sci. 1962, 17, 265.
38. Krishnaiah, D.; Rao, M. B. Kinetics of Esterification of n-Propyl Alcohol with Acetic Acid Catalyzed by Dowex-50W. Indian J. Technol. 1984, 22, 268.
39. Bart, H. I.; Kaltenbrunner, W.; Landschutzer, H. Kinetics of Esterification of Acetic Acid with Propyl Alcohol by Heterogeneous Catalysis. Int. J. Chem. Kinet. 1996, 28, 649.
40. Yadav, G. D.; Thathagar, M. B. Esterification of Maleic Acid with Ethanol over Cation-Exchange Resin Catalysts. React. Funct. Polym. 2002, 52, 99.
41. Ali, S. H.; Merchant, S. Q. Kinetics of the Esterification of Acetic Acid with 2-Propanol: Impact of Different Acidic Cation Exchange Resins on Reaction Mechanism. Int. J. Chem. Kinet. 2006, 38, 593.
42. Perkins, L. R.; Geankoplis, C. J. Molecular Diffusion in a Ternary Liquid System with the Diffusing Component Dilute. Chem. Eng. Sci. 1969, 24, 1035.
43. Fredenslund, A.; Jones, R. L.; Prausnitz, J. M. Group-Contribution Estimation of Activity Coefficients in Nonideal Liquid Mixtures. AIChE J. 1975, 21, 1086.
44. http://134.106.215.86/UNIFAC/Model-Comparison.htm.
45. Steinigeweg, S.; Gmehling, J. Esterification of a Fatty Acid by Reactive Distillation. Ind. Eng. Chem. Res. 2003, 42, 3612.
46. Rohm and Haas website: http://www.amberlyst.com/faq-general. htm#gel.
47. Sigma Aldrich website: http://www.sigmaaldrich.com/aldrich/ brochure/al-pp-ionx.pdf.
48. Pietrzyk, D. J. Ion Exchange Resins in Non-aqueous solvents-III Solvent-Uptake Properties of Ion-Exchange Resins and Related Adsorbents. Talanta 1966, 13, 209.
49. Kunin, R.; Meitzner, E. F.; Oline, J. A.; Fisher, S. A.; Frisch, N. Characterization of Amberlyst 15. Macroreticular Sulfonic Acid Cation Exchange Resin. Ind. Eng. Chem. Prod. Res. Dev. 1962, 1, 140.
50. Chakrabarti, A.; Sharma, M. M. Cationic Ion Exchange Resins as Catalyst. React. Polym. 1993, 20, 1.
51. Xu, Z. P.; Chuang, K. T. Kinetics of Acetic Acid Esterification over Ion Exchange Catalysts. Can. J. Chem. Eng. 1996, 74, 493.
52. Fogler, S. H.; Scott, H. Elements of Chemical Reaction Engineering, 3rd ed.; Prentice Hall: Englewood Cliffs, NJ, 1999.
53. Kirbaslar, S. I.; Terzioglu, H. Z.; Dramur, U. Catalytic Esterification of Methyl Alcohol with Acetic Acid. Chin. J. Chem. Eng. 2001, 9, 90.
54. Tsvetkova, O. N.; Kovemev, K. D. Alkylation of Phenols with Higher Olefins, Part I. Int. J. Chem. Eng. 1967, 7, 107.
55. Mazzotti, M.; Kruglov, A.; Neri, B.; Gelosa, D.; Morbidelli, M. A Continuous Chromatographic Reactor: SMBR. Chem. Eng. Sci. 1996, 51, 1827.
56. Mazzotti, M.; Neri, B.; Gelosa, D.; Kruglov, A.; Morbidelli, M. Kinetics of Liquid-Phase Esterification Catalyzed by Acidic Resins. Ind. Eng. Chem. Res. 1997, 36, 3.
57. Grob, S.; Hasse, H. Thermodynamics of Phase and Chemical Equilibrium in a Strongly Nonideal Esterification System. J. Chem. Eng. Data 2005, 50, 92.
58. Liu, Y.; Lotero, E.; Goodwin, J. G., Jr. A Comparison of the Esterification of Acetic Acid with Methanol Using Heterogeneous Versus Homogeneous Acid Catalysis. J. Catal. 2006, 242, 278.
59. Aafaaqi, R.; Mohamed, A. R.; Bhatia, S. Kinetics of Esterification of Palmitic Acid with Isopropanol Using P-Toluene Sulfonic Acid and Zinc Ethanoate Supported over Silica Gel as Catalysts. J. Chem. Technol. Biotechnol. 2004, 79, 1127.
60. Limbeck, U.; Altwicker, C.; Kunz, U.; Hoffmann, U. Rate Expression for THF Synthesis on Acidic Ion Exchange Resin. Chem. Eng. Sci. 2001, 56, 2171.
61. Kawase, M.; Inoue, Y.; Araki, T.; Hashimoto, K. The Simulated Moving-Bed Reactor for Production of Bisphenol A. Catal. Today 1999, 48, 199.
62. Yang, B.; Yang, S.; Yao, R. Synthesis of Ethyl Tert-Butyl Ether From Tert-Butyl Alcohol and Ethanol on Strong Acid Cation-Exchange Resins. React. Funct. Polym. 2000, 44, 167.
63. Du Toit, E. L. The Rate Inhibiting Effect of Water as a Product on Reactions Catalysed by Cation Exchange Resins Formation of Mesityl Oxide from Acetone as a Case Study, Thesis (M.Sc.) (Chem. Eng.) University of Pretoria, 2003.
64. Song, W.; Venimadhavan, G.; Manning, J. M.; Malone, M. F.; Doherty, M. F. Measurement of Residue Curve Maps and Heterogeneous Kinetics in Methyl Acetate Synthesis. Ind. Eng. Chem. Res. 1998, 37, 1917.
65. Pöpken, T.; Gotze, L.; Gmehling, J. Reaction Kinetics and Chemical Equilibrium of Homogeneously and Heterogeneously Catalyzed Acetic Acid Esterification with Methanol and Methyl Acetate Hydrolysis. Ind. Eng. Chem. Res. 2000, 39, 2601.
66. Ulusoy, E.; Gültekin, N. Investigation of vapor-liquid equilibrium of binary and ternary systems of acetic acid-water-solvents. Chim. Acta Turc. 1981, 9, 489.
67. Maki-Arvela, P.; Salmi, T.; Sundell, M.; Ekman, K.; Peltonen, R.; Lehtonen, J. Comparison of Polyvinylbenzene and Polyolefin Supported Sulphonic Acid Catalysts in the Esterification of Acetic Acid. Appl. Catal., A 1999, 184, 25.
68. Fité, C.; Tejero, J.; Iborra, M.; Cunill, F.; Izquierdo, J. F. The Effect of Ether on the Reaction Rate of MTBE Synthesis. Ind. Eng. Chem. Res. 2001, 40, 1348.
69. Lee, M.-J.; Chou, P.-L.; Lin, H.-M. Kinetics of Synthesis and Hydrolysis of Ethyl Benzoate over Amberlyst 39. Ind. Eng. Chem. Res. 2005, 44, 725.
70. Ali, S. H.; Merchant, S. Q. To be submitted for publication in Fluid Phase Equilib.
71. Petro, M.; Mravec, D.; Ilavsky, J. Kinetics of Esterification of 1-pentanol by Isobutyric Acid and Benzyl Alcohol by Acetic Acid J. Chem. Zvesti 1983, 37, 461.
72. Lee, M. J.; Wu, H. T.; Lin, H. M. Kinetics of Catalytic Esterification of Acetic Acid and Amyl Alcohol over Dowex. Ind. Eng. Chem. Res. 2000, 39, 4094.
73. Bonner, O. D.; Moorefield, J. C. Ion Exchange in Mixed Solvents. J. Phys. Chem. 1954, 58, 555.
74. Davies, C. W., III. Dioxan-Water Mixtures. J. Chem. Soc. 1964, 4169.
75. Gable, R. W.; Strobel, H. A. Non-Aqueous Ion Exchange. I. Some Cation Equilibrium Studies in Methanol. J. Phys. Chem. 1956, 60, 513.
76. Reichenberg, D.; Wall, W. F. The Absorption of Uncharged Molecules by Ion-Exchange Resins. J. Chem. Soc. 1956, 3364.
77. Bodamer, G. W.; Kunin, R. Behavior of Ion Exchange Resins in Solvents other than Water - Swelling and Exchange Characteristics. Ind. Eng. Chem. 1953, 45, 2577.
78. Arnold, R.; Churms, S. C. Swelling and Exchange Equilibria of Cation-Exchange Resins in Aqueous Monoethanolamine. J. Chem. Soc. 1965, 325.
79. Gregor, H. P.; Nobel, D.; Gottlieb, M. H. Studies on Ion Exchange Resins. XII Swelling in Mixed Solvents. J. Phys. Chem. 1955, 59, 10.