Cyclohexanol production via esterification of cyclohexene with formic acid and subsequent hydration of the ester - Reaction kinetics

Industrial and Engineering Chemistry Research

Volumn 46, Issue 4, 2007, Pages 1099-1104

  Steyer, Frank ^a   Sundmacher, Kai ^a,b  

^a MAX PLANCK INSTITUTE FOR DYNAMICS OF COMPLEX TECHNICAL SYSTEMS   (Germany)

^b OTTO VON GUERICKE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DISTILLATION COLUMNS; ESTERIFICATION; ESTERS; HYDRATION; PHASE SEPARATION; REACTION KINETICS;

PHASE SPLITTING BEHAVIOR; REACTIVE DISTILLATION COLUMNS;

OLEFINS;

DISTILLATION COLUMNS; ESTERIFICATION; ESTERS; HYDRATION; OLEFINS; PHASE SEPARATION; REACTION KINETICS;

EID: 33847639288     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie060781y     Document Type: Article

References (17)

1. Steyer, F.; Qi, Z. W.; Sundmacher, K. Synthesis of Cyclohexanol by Three-Phase Reactive Distillation: Influence of Kinetics on Phase Equilibria. Chem. Eng. Sci. 2002, 57, 1511.
2. Oudshoorn, O. L.; Janissen, M.; van Kooten, W. E. J.; Jansen, J. C; van Bekkum, H.; van den Bleek, C. M.; Calis, H. P. A. A Novel Structured Catalyst Packing for Catalytic Distillation of ETBE. Chem. Eng. Sci. 1999, 54, 1413.
3. Wang, E. Q.; Li, C. Y.; Wen, L. Y.; Min, E. Study on Suspension Catalytic Distillation for Synthesis of Linear Alkylbenzene. AIChE J. 2005, 51, 845.
4. Saha, B.; Sharma, M. M. Esterification of Formic Acid, Acrylic Acid and Methacrylic Acid with Cyclohexene in Batch and Distillation Column Reactors: Ion-Exchange Resins as Catalysts. React. Fund. Polym. 1996, 28, 263.
5. Steyer, F.; Sundmacher, K. VLE and LLE Data for the System Cyclohexane + Cyclohexene + Water + Cyclohexanol. J. Chem. Eng. Data 2004, 49, 1675.
6. Steyer, F.; Sundmacher, K. VLE and LLE Data Set for the System Cyclohexane + Cyclohexene + Water + Cyclohexanol + Formic Acid + Formic Acid Cyclohexyl Ester. J. Chem. Eng. Data 2005, 50, 1277.
7. Steele, W. V; Chirico, R. D.; Knipmeyer, S. E.; Nguyen, A.; Smith, N. K.; Tasker, I. R. Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for Cyclohexene, (2,5-dihydrobenzo-3,4-furan), Isoxazole, Octylamine, Dioctylamine, Trioctylamine, Phenyl Isocyanate, and 1,4,5,6- Tetrahydropyrimidine. J. Chem. Eng. Data 1996, 41, 1269.
8. Beckett, C. W.; Freeman, N. K.; Pitzer, K. S. The Thermodynamic Properties and Molecular Structure of Cyclopentene and Cyclohexene. J. Am. Chem. Soc. 1948, 70, 4227.
9. Wiberg, K. B.; Wassermann, D. J.; Martin, E. J.; Murcko, M. A Enthalpies of Hydration of Alkenes. 3. Cycloalkenes. J. Am Chem. Soc. 1985, 107, 6019.
10. Adachi, K.; Suga, H.; Seki, S. Phase Changes in Crystalline and Glassy-Crystalline Cyclohexanol. Bull. Chem. Soc. Jpn. 1968, 41, 1073.
11. Kozyro, A. A.; Blokhin, A. V.; Kabo, G. J.; Paulechka, Y. U. Thermodynamic Properties of some Cyclohexyl Esters in the Condensed State. J. Chem. Thermodyn. 2001, 33, 305.
12. Paulechka, Y. U.; Zaitsau, D. H.; Kabo, G. J. On the Difference between Isobaric and Isochoric Heat Capacities of Liquid Cyclohexyl Esters. J. Mol. Liq. 2004, 115, 105.
13. Guthrie, J. P. Hydration of Carboxamines. Evaluation of the Free Energy Change for Addition of Water to Acetamide and Formamide Derivatives. J. Am. Chem. Soc. 1974, 96, 3608.
14. Jakobsen, R. J.; Mikawa, Y., Brasch, J. W. Far Infrared Studies of Hydrogen Bonding in Carboxylic Acids. I. Formic and Acetic Acids. Spectrochim. Acta, Part A 1967, 23, 2199.
15. Cox, J. D.; Wagman, D. D.; Medvedev, V. A CODATA Key Values for Thermodynamics; Hemisphere Publishing Corp.: New York, 1989.
16. Chase, M. W. NIST-JANAF Themochemical Tables, fourth ed.; J. Phys. Chem. Ref. Data, Monograph 9; 1998.
17. Reutemann, W. Formic Acid. In Industrial Organic Chemicals: Starting Materials and Intermediates, an Ullmann's Encyclopedia; Wiley-VCH: Weinheim, Germany, 1999; pp 2711-2744.