Hydroformylation of 1,4-Diacetoxy-2-butene using HRh(CO)(PPh 3)3 tethered on alumina as a catalyst: Kinetic study

Industrial and Engineering Chemistry Research

Volumn 48, Issue 21, 2009, Pages 9479-9489

  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

2-BUTENE; BEST MODEL; CATALYST LOADINGS; CATALYST STRUCTURES; COMPLEX CATALYSTS; CONCENTRATION-TIME; CPMASNMR; CROSS POLARIZATIONS; EXPERIMENTAL DATA; GAS MASS; HETEROGENEOUS CATALYST; INSTRUMENTAL TECHNIQUES; INTRINSIC KINETICS; KINETIC REGIME; KINETIC STUDY; MAGIC ANGLE SPINNING NUCLEAR MAGNETIC RESONANCE; MODEL DISCRIMINATION; MODEL PREDICTION; PHOSPHOTUNGSTIC ACID; PRODUCT DISTRIBUTIONS; SOLID-LIQUID; SPECTROSCOPIC EVIDENCE; TEMPERATURE RANGE;

ACTIVATION ENERGY; AVIATION; BATCH REACTORS; BUTENES; CATALYSIS; FLUORINE CONTAINING POLYMERS; HYDROCARBONS; HYDROFORMYLATION; HYDROXYLATION; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RESONANCE; SULFUR COMPOUNDS;

CATALYST SELECTIVITY;

EID: 72349092594     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie900269z     Document Type: Article

References (55)

1. Cornills, B., Herrman, W. A., Eds. Applied homogeneous Catalysis with Organometallic Compounds; VCH: Weinheim, 1996; Vol. 1 and 2.
2. Parshall, G. W. Homogeneous Catalysis; Wiley Interscience: New York, 1980.
3. Beller, M., Bolm, C., Eds. Transition Metals in Organic Synthesis; Wiley-VCH: Weinheim, 1998; Vol. 1.
4. Shimazu, S.; Ro, K.; Sento, T.; Ichikuni, N.; Uematsu, T. Asymmetric hydrogenation of R, αβunsaturated carboxylic acid esters by rhodium(I) s phosphine complexes supported on smectites. J. Mol. Catal. A. 1996, 107, 297.
5. 3. J. Oraganomet. Chem. 1981, 204, 249.
6. Allum, K. G.; Hancock, R. D.; Howell, I. V.; Lester, T. E.; Mckenzie, S.; Pitkenthly, R. C.; Robinson, P. J. Supported transition metal complexes: V. Liquid phase catalytic hydrogenation of hexene-1, cyclohexene and isoprene under continuous flow conditions. J. Catal. 1976, 43, 331.
7. (a) Collman, J. P.; Hegedus, L. S.; Cooke, M. P.; Norton, J. R.; Dolcetti, G.; Marquardt, D. N. Resin-bound transition metal complexes. J. Am. Chem. Soc. 1972, 94, 1789.
8. Dumont, W.; Poulin, J. C.; Daud, T. P.; Kagan, H. B. Asymmetric catalytic reduction with transition metal complexes. II. J. Am. Chem. Soc. 1973, 95, 8295.
9. (a) Weber, W. A.; Gates, B. C. Hexarhodium Clusters in NaY Zeolite: Characterization by Infrared and Extended X-ray Absorption Fine Structure Spectroscopies. J. Phys. Chem. B, 1997, 101, 10423.
10. Peng, Q.; Yang, Y.; Yuan, Y. Immobilization of rhodium complexes ligated with triphenyphosphine analogs on amino-functionalized MCM-41 and MCM-48 for 1-hexene hydroformylation. J. Mol. Catal. A: Chem. 2004, 219, 175.
11. Standfest-Hauser, C. M.; Lummerstorfer, T.; Schmid, R.; Hoffmann, H.; Kirchner, K.; Puchberger, M.; Trzeciak, A. M.; Mieczy'nska, E.; Tylus, W.; Zioḱowski, J. J. Rhodium phosphine complexes immobilized on silica as active catalysts for 1-hexene hydroformylation and arene hydrogenation. J. Mol. Catal. A: Chem. 2004, 210, 179.
12. Wrzyszcz, J.; Zawadzki, M.; Trzeciak, A. M.; Zioḱowski, J. J. Rhodium complexes supported on zinc aluminate spinel as catalysts for hydroformylation and hydrogenation: preparation and activity. J. Mol. Catal. A: Chem. 2002, 189, 203.
13. Sandee, A. J.; Reek, J. N. H.; Kamer, P. C. J.; Van Leeuwen, P. W. N. M. A Silica- Supported, Switchable, and Recyclable Hydroformylation-Hydrogenation Catalyst. J. Am. Chem. Soc. 2001, 123, 8468.
14. (a) Murrel, L. L. Advanced Materials in Catalysis; Academic Press: New York, 1977; Chapter 8.
15. Pu, L. 1, 1 -Binaphthyl Dimers, Oligomers, and Polymers: Molecular Recognition, Asymmetric Catalysis, and New Materials. Chem. Rev. 1998, 98, 2405.
16. (a) Schwab, E.; Mecking, S. Immobilization of a Catalytically Active Rhodium Complex by Electrostatic Interactions of Multiply Charged Phosphine Ligands with a Soluble Polyelectrolyte and Recovery by Ultrafiltration. Organometallics 2001, 20, 5504.
17. Bourque, S. C.; AlperLeo, H.; Arya, M. Hydroformylation Reactions Using Recyclable Rhodium-Complexed Dendrimers on Silica. J. Am. Chem. Soc. 2000, 122, 956.
18. Arya, P.; Panda, G.; Venugopal Rao, N.; Alper, H.; Bourque, S. C.; Manzer, L. E. Solid-Phase Catalysis: A Biomimetic Approach toward Ligands on Dendritic Arms to Explore Recyclable Hydroformylation Reactions. J. Am. Chem. Soc. 2001, 123, 2889.
19. (a) Yoon, T. J.; Kim, J. I.; Lee, J. K. Rh-based olefin hydroformylation catalysts and the change of their catalytic activity depending on the size of immobilizing supporters. Inorg. Chim. Acta 2003, 345, 228.
20. Fuerte, A.; Iglesias, M.; Sańchez, F. New chiral diphosphinites: synthesis of Rh complexes. Heterogenisation on zeolites. J. Organomet. Chem. 1999, 588, 186.
21. (a) Marks, T. J. Surface-bound metal hydrocarbyls. Organometallic connections between heterogeneous and homogeneous catalysis. Acc. Chem. Res. 1992, 25, 57.
22. Corma, A.; Garcia, H. Lewis Acids: From Conventional Homogeneous to Green Homogeneous and Heterogeneous Catalysis. Chem. Rev. 2003, 103, 4307.
23. Davies, W.; Matty, L.; Hughes, D. L.; Reider, P. J. Are Heterogeneous Catalysts Precursors to Homogeneous Catalysts. J. Am. Chem. Soc. 2001, 123, 10139.
24. Augustine, R.; Tanielyan, S.; Anderson, S.; Yang, H. A new technique for anchoring homogeneous catalysts. Chem. Commun. (Cambridge) 1999, 1257.
25. Tanielyan, S. K.; Augustine, R. Supported Catalysts, U.S. Patent, 6, 025, 295, 2000; to Seton Hall University.
26. (a) Augustine, R. L.; Tanielyan, S. K.; Mahata, N.; Gao, Y.; Zsigmond, A.; Yang, H. Anchored homogeneous catalysts: the role of the heteropoly acid anchoring agent. Appl. Catal.: A 2003, 256, 69.
27. Augustine, R. L.; Goel, P.; Mahata, N.; Reyes, C.; Tanielyan, S. K. Anchored homogeneous catalysts: high turnover number applications. J. Mol. Catal. A: Chem. 2004, 216, 189.
28. Augustine, R. L. Heterogeneous Catalysis for the Synthetic Chemist; Marcel Dekker: New York, 1995.
29. 3 on zeolite Y using phosphotungstic acid as tethering agent: a novel hydroformylation catalyst. J. Catal. 2003, 213, 73.
30. Chansarkar, R.; Mukhopadhyay, K.; Kelkar, A.; Chaudhari, R. V. Activity and selectivity of Rh-complex catalysts in hydroformylation of 1, 4-diacetoxy-butene to Vitamin A intermediate. Cat. Today 2003, 79-80, 51.
31. (a) Pequannock, P. F.; Fairlawn, H. M. Preparation of Esters of hydroxyl tiglic aldehyde (Hoffmann-La Roche Inc., NJ). U.S. Patent 4, 124, 619, 1978.
32. Himmele, W.; Quila, W.; Prinz, R. (BASF, Germany). Carboxylic Esters of 3-Formylbuten-(3)-ol-(1) and their production, U.S. Patent 3, 661, 980, 1972.
33. (a) Freyschlag, H.; Pommer, H.; Reif, W. (BASF, Germany). Production of Derivatives of Omega-Hydroxytiglaldehyde, U.S. Patent 3, 347, 930, 1967.
34. Freyschlag, H.; Stolp, F.; Reif, W. (BASF, Germany). Production of Derivatives of Omega-Hydroxytiglaldehyde, U.S. Patent 3, 760, 004, 1973.
35. Chansarkar, R.; Kelkar, A. A.; Chaudhari, R. V. Biphasic Hydroformylation of 1, 4-Diacetoxy-2-butene: A Kinetic Study. Ind. Eng. Chem. Res. 2007, 46 (25), 8629.
36. Unveren, H. H. Y.; Schomacker, R. Rhodium catalyzed hydroformylation of 1-octene in microemulsion: comparison with various catalytic systems. Catal. Lett. 2005, 102, 83.
37. 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.
38. Herron, N. Si-based life:zeolite as enzyme mimics. CHEMTECH 1989, 19, 542.
39. Mizuno, N.; Misono, M. Heterogeneous Catalysis. Chem. Rev. 1998, 98, 199.
40. Kozhevnikov, I. V. Catalysis by Heteropoly Acids and Multicomponent Polyoxometalates in Liquid-Phase Reactions. Chem. Rev. 1998, 98, 171.
41. Nakata, S.; Tanaka, Y.; Asaoka, S.; Nakamura, M. Recent advances in applications of multinuclear solid-state NMR to heterogeneous catalysis and inorganic materials. J. Mol. Struct. 1998, 441, 267.
42. Huang, L.; Kawi, S. Effects of supported donor ligands on the activity and stability of tethered rhodium complex catalysts for hydroformylation. J. Mol. Catal. A: Chem. 2004, 211, 23.
43. Shyu, S.; Cheng, S.; Tzou, D. Immobilization of Rh(PPh3)3Cl on phosphinated MCM-41 for catalytic hydrogenation of olefins. Chem. Commun. 1999, 2337.
44. 4. J. Am. Chem. Soc. 1963, 85, 3500.
45. Ramachandran, P. A.; Chaudhari, R. V. Three Phase Catalytic Reactors; Gordon and Breach: London, 1983.
46. 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.
47. Sano, Y.; Yamaguchi, N.; Adachi, T. Mass transfer coefficients for suspended particles in agitated vessels and bubble columns. J. Chem. Eng. Jpn. 1974, 7, 255.
48. Prasher, D.; Wills, G. B. Mass Transfer in an Agitated Vessel. Ind. Eng. Chem. Proc. Des. Dev. 1973, 13 (3), 351.
49. Wilke, C. R.; Chang, P. Correlation of diffusion coefficients in dilute solutions. AIChE. J. 1955, 1, 264.
50. Evans, D.; Osborn, J. A.; Wilkinson, G. Hydroformylation of alkenes by use of rhodium complex catalysts. J. Chem. Soc. A 1968, 3133.
51. 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.
52. Lazzaroni, R.; Pertici, P.; Bertozzi, S.; Fabrizi, G. 1-hexene rhodium catalyzed hydroformylation at partial substrate conversion: influence of reaction parameters on the chemo selectivity and regioselectivity. J. Mol. Catal. 1990, 58, 75.
53. 3 catalyst: A kinetic study. J. Mol. Catal. 1989, 57, 177.
54. 3 catalyst. J. Mol. Catal A: Chem. 1997, 115, 247.
55. 3 Catalyst in a Slurry Reactor: A Molecular Level Approach to Kinetic Modeling and Nonisothermal Effects. Ind. Eng. Chem. Res. 1997, 36, 592.