Biphasic hydroformylation of 1,4-diacetoxy-2-butene: A kinetic study

Industrial and Engineering Chemistry Research

Volumn 46, Issue 25, 2007, Pages 8629-8637

  Chansarkar, Rashmi ^a   Kelkar, Ashutosh A ^a   Chaudhari, Raghunath V ^b  

^a NATIONAL CHEMICAL LABORATORY   (India)

^b University of Kansas   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHASIC HYDROFORMYLATION; CATALYST CONCENTRATION;

CATALYST ACTIVITY; COMPLEXATION; HYDROFORMYLATION; REACTION KINETICS;

OLEFINS;

CATALYST ACTIVITY; COMPLEXATION; HYDROFORMYLATION; OLEFINS; REACTION KINETICS;

EID: 37249030985     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie0700821     Document Type: Conference Paper

References (38)

1. Pino, P.; Piancenti, F.; Bianchini, M. Organic Synthesis via metal Carbonyls; Wender, I., Piero, P., Eds.; Wiley: New York, 1977; Vol. 2, p 43.
2. (a) Falbe, J. New Syntheses with Carbon Monoxide; Springer-Verlag: Berlin, Heidelberg, New York, 1980.
3. (b) Parshall, G. W. Homogeneous Catalysis; Wiley-Interscience: New York, 1980.
4. (c) Masters, C. Homogeneous Transition-Metal Catalysis; Chapman and Hall: London, 1981.
5. (a) Cornills, B., Herrmann, W. A., Eds. Applied Homogeneous Catalysis with Organometalllic Compounds; VCH: Weinheim, Germany, 1996; Vols. 1 and 2.
6. (b) Cornils, B., Herrmann, W. A., Eds. Aqueous Phase Organometallic Catalysis; VCH: Weinheim, Germany, 1998.
7. (c) Beller, M., BoIm, C., Eds. Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals; VCH: Weinheim, Germany, 1998; Vols. 1 and 2.
8. Fitton, P.; Moffet, H.; Fairlawn, Hoffmann-La Roche Inc., U.S. Patent 4,124,619, 1978.
9. (a) Himmele, W.; Walldorf, W.; Quila, R.; Prinz, BASF, Germany, U.S. Patent 3,661,890, 1972.
10. (b) Himmele, W.; Walldorf, W.; Quila, R.; BASF, Germany, U.S. Patent 3,732,287, 1973.
11. Chansarkar, R.; Mukhopadhyay, K.; Kelkar, A. A.; Chaudhari, R. V. Activity and Selectivity of Rh-Complex catalyst in hydroformylation of 1,4-diacetoxy-butene to Vitamin-A intermediate. Catal. Today 2003, 51, 79-80.
12. (a) Cornils, B.; Kuntz, E. G. Introducing TPPTS and related ligands for industrial biphasic processes. J. Organomet. Chem. 1995, 10, 177.
13. (b) Cornils, B.; Herrmann, W. A.; Eckl, R. W. Industrial aspects of aqueous catalysis. J. Mol. Catal., A 1997, 116 (1-2), 27.
14. (c) Joo, F.; Katho, A. Recent developments in aqueous organometallic chemistry and catalysis. J. Mol. Catal., A 1997, 116 (1-2), 2.
15. (d) Horvath, I. T. Water as solvent for catalysis. J. Mol. Catal., A 1997, 116 (1-2), 1.
16. Unveren, H. H. Y.; Schomacker, R. Hydroformylation with rhodium phosphine-modified catalyst in a microemulsion: Comparison of organic and aqueous systems for styrene, cyclohexene and 1,4-diacetoxy-2-butene. Catal Lett. 2005, 102, 83.
17. Bhanage, B. M. Studies in hydroformylation of olefins using transition metal complex catalysts. Ph.D. Thesis, University of Pune, India, 1995.
18. Chatt, J.; Venanzi, L. M. Olefin co-ordination compounds. Part VI. Diene complexes of Rhodium(I). J. Chem. Soc. A 1957, 4735.
19. Brevet, J. L.; Mori, K. Pheromone Synthesis; CXXXIX. Enzymatic Preparation of (2S,3R)-4-Acetoxy-2,3-epoxybutan-1-ol and Its Conversion to the Epoxy Pheromones of the Gypsy Moth and the Ruby Tiger Moth. Synthesis 1992, 1007.
20. (a) Deshpande, R. M.; Bhanage, B. M.; Divekar, S. S.; Kanagasabapathy, S.; Chaudhari, R. V. Kinetics of Hydroformylation of Ethylene in Homogeneous Medium: Comparison in Organic and Aqueous Systems. Ind. Eng. Chem. Res. 1998, 37, 2391.
21. (b) Purwanto, P.; Deshpande, R. M.; Chaudhari, R. V.; Delmas, H. Solubility of Hydrogen, Carbon Monoxide, and 1-Octene in Various Solvents and Solvent Mixtures. J. Chem. Eng. Data 1996, 47, 1414.
22. Purwanto, P.; Delmas, H. Gas-liquid-liquid reaction engineering: Hydroformylation of 1-octene using water soluble rhodium complex catalyst. Catal. Today 1995, 24, 135.
23. Wiebe, R.; Gaddy, V. L. The solubility of a mixture of hydrogen and nitrogen in water at 25 °C in the pressure range of 50 to 1000 atmospheres. J. Am. Chem. Soc. 1935, 57 (8), 1487.
24. Dean, J. A. Table 10-1 in Lange's Handbook of Chemistry, 13th ed.; McGraw-Hill Publications: New York, 1972.
25. 3 Catalyst. J. Mol. Catal., A 1997, 115, 247.
26. 3 complex catalyst. Ind. Eng. Chem. Res. 1988, 27 (11), 1996.
27. Chaudhari, R. V.; Gholap, R. V.; Emig, G.; Hoffmann, H. Gas-liquid mass transfer in "dead-end" autoclave reactors. Can. J. Chem. Eng. 1987, 65, 744.
28. Wilke, C. R.; Chang, P. Correlation of diffusion coefficients in dilute solutions. AIChE J. 1955, 1, 264.
29. Lagisetty, J. S.; Das, P. K.; Kumar, R.; Gandhi, K. S. Breakage of viscous and non-Newtonian drops in stirred dispersions. Chem. Eng. Sci. 1986, 41, 65.
30. 3 catalyst: A kinetic study. J. Mol. Catal., A 1989, 57 (2), 177.
31. 3 catalyst: A kinetic study. J. Catal. 1989, 115, 326.
32. Nair, V. S.; Mathew, S. P.; Chaudhari, R. V. Kinetics of hydroformylation of styrene using homogeneous rhodium complex catalyst. J. Mol. Catal., A 1998, 143, 99.
33. Kiss, G.; Mozeleski, E. J.; Nadler, K. C.; Van Driessche, E.; De Roover, C. Hydroformylation of ethene with triphenyl phosphine modified rhodium catalyst: Kinetic and mechanistic studies. J. Mol. Catal., A 1999, 138, 155.
34. 2-TPPTS complex catalyst in a two phase system in the presence of a cosolvent. Ind. Eng. Chem. Res. 1996, 35, 3927.
35. Herrmann, W. A.; Kellner, J.; Riepl, H.; Wasserlosliche Metallkomplexe und Katalyatoren III. Neue wasserlosliche Metallkomplexe des sulfonierten Triphenylphosphans (TPPTS): Mn, Fe, Ru, Co, Rh, Ir, Ni, Pd, Pt, Ag, Au. J. Organomet. Chem. 1990, 389, 103.
36. (a) Evans, D.; Osborn, J. A.; Wilkinson, G. Hydroformylation of alkenes by use of rhodium complex catalysts. J. Chem. Soc. A 1968, 3133.
37. (b) Yagupsky, G.; Brown, C. K.; Wilkinson, G.; Further studies on hydridocarbonyl tris (triphenylphosphine) rhodium (I): Intermediate species in hydroformylation; rhodium and iridium analogues. J. Chem. Soc. A 1970, 1392.
38. (c) Brown, C. K.; Mowat, W.; Yagupsky, G.; Wilkinson, G. J. Chem. Soc. A 1971, 850.