Regioselective hydroformylation of allylic alcohols using Rh/PPh 3 supported ionic liquid-phase catalyst, followed by hydrogenation to 1,4-butanediol using R11/PPh3 supported ionic liquid-phase catalyst

Industrial and Engineering Chemistry Research

Volumn 47, Issue 3, 2008, Pages 969-972

  Panda, Anil G ^a   Jagtap, Sachin R ^a   Nandurkar, Nitin S ^a   Bhanage, Bhalchandra M ^a  

^a UNIVERSITY OF MUMBAI   (India)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROFORMYLATION; HYDROGENATION; IONIC LIQUIDS; REGIOSELECTIVITY; SILICA;

ALLYLIC ALCOHOLS; PHASE CATALYST;

ALCOHOLS;

ALCOHOLS; HYDROFORMYLATION; HYDROGENATION; IONIC LIQUIDS; REGIOSELECTIVITY; SILICA;

EID: 39449105990     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie0706865     Document Type: Article

References (24)

1. Pittman, C. U., Jr.; Honnick, W. D. Rhodium Catalyzed Hydroformylation of Allyl Alcohol: A Potential Route to 1,4-Butanediol. J. Org, Chem. 1980, 45, 2132.
2. Weitz, H. M.; Reib, W. Ullmann's Encyclopaedia of Industrial Chemistry, Sixth Edition, Vol. 5; Wiley-VCH Verlag Gmbh and Co. KgaA: Weinheim, Germany, 2003; p 706.
3. Haas, T.; Jaeger, B.; Weber, R.; Mitchell, S. F.; King, C. F. New diol processes: 1,3-propanediol and 1,4-butanediol. Appl. Catal., A 2005, 280, 83.
4. Brownstein, M. A. 1,4-butanediol and tetrahydrofuran: exemplary small-volume commodities. CHEMTECH 1991, 21, 506.
5. Eilbracht, P.; Barfacker, L.; Buss, C.; Hollman, C.; Kitsos-Rzychon, B. E.; Kranemann, C. L.; Rische, T.; Roggenbuck, R.; Schmidt, A. Tandem reaction sequences under hydroformylation conditions: New synthetic applications of transition metal catalysis. Chem. Rev. 1999, 99, 3329.
6. Botteghi, C.; Ganzerla, R.; Lenarda, M.; Moreti, G. Advances in hydroformylation of olefins containing functional groups. J. Mol. Catal. 1987, 40, 129.
7. 3 catalyst in hydroformylation of allyl alcohol: effect of second immiscible liquid phase. J. Mol Catal. 1992, 75, L19.
8. Lindner, E.; Schneller, T.; Auer, F.; Mayer, H. A. Chemistry in interphases-A new approach to organometallic syntheses and catalysis. Angew. Chem., Int. Ed. Engl. 1999, 35, 2155.
9. Mehnert, C. P.; Cook, R. A.; Dispenziere, N. C.; Afeworki, M. Supported Ionic Liquid Catalysis-A New Concept for Homogeneous Hydroformylation Catalysis. J. Am. Chem. Soc. 2002, 124, 12932.
10. Cole-Hamilton, D. J. Homogeneous catalysis-new approaches to catalyst separation, recovery and recycling. Science 2003, 299, 1702.
11. Freixa, Z.; van Leeuwan, P. W. N. M. Bite angle effects in diphosphine metal catalysis: Steric or electronic? J. Chem. Soc. Dalton Trans. 2003, 1890.
12. Kranenberg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwan, P. W. N. M.; Goubitz, K.; Fraanje, J. New Diphosphine Ligands Based on Heterocyclic Aromatics Inducing Very High Regioselectivity in Rhodium-Catalyzed Hydroformylation: Effect of the Bite Angle. Organometallics 1995, 14, 3081.
13. Riisager, A.; Wasserscheid, P.; van Hal, R.; Fehrmann, R. Continuous fixed bed gas-phase hydroformylation using supported ionic liquid phase (SILP) Rh catalysts. J. Catal. 2003, 219, 252.
14. Chaudhari, R. V.; Bhanage, B. M.; Deshpande, R. M.; Delmas.,H. Enhancement of interfacial catalysis in a biphasic system using catalystbinding ligands. Nature 1995, 373 (6514), 501.
15. Wasserscheid, P.; Waffenschmidt, H.; Machnitzki, P.; Kottsieper, W. K.; Stelzer, O. Cationic phosphine ligands with phenylguanidinium modified xanthene moieties-a successful concept for highly regioselective, biphasic hydroformylation of oct-1-ene in hexafluorophosphate ionic liquids. Chem. Commun. 2001, 451.
16. Mehnert, C. P.; Mozeleski, E. J.; Cook, R. A. Supported ionic liquid catalysis investigated for hydrogenation reaction. Chem. Commun. 2002, 3010.
17. Breitenlechner, S.; Fleck, M.; Muller, T. E.; Suppan, A. Solid catalysts on the basis of supported ionic liquids and their use in hydroamination reactions. J. Mol. Catal., A: Chem. 2004, 214 175.
18. 2 in ionic liquid on silica: Application to Mizoroki-Heck reaction. Org. Lett. 2004, 6, 2325.
19. Riisager, A.; Fehrmann, R.; Flicker, S.; van Hall, R.; Haumann, M.; Wasserscheid, P. Very Stable and Highly Regioselective Supported Ionic-Liquid-Phase (SILP) Catalysis: Continuous Flow Fixed-Bed Hydroformylation of Propene. Angew. Chem., Int. Ed. 2005, 44, 815.
20. Carmichael, A. J., Deetlefs, M., Earle, M. J., Frohlich, U., Seddon, K. R., Rogers, R. D., Seddon, K. R., Eds. Ionic Liquids as Green Solvents, Progress and Prospects; ACS Symposium Series 856; American Chemical Society: Washington, DC, 2003.
21. Evans, D.; Yagupsky, G.; Wilkinson, G. The reaction of hydridocarbonyltris(triphenylphosphine)rhodium with carbon monoxide, and of the reaction products, Hydridodicarbonylbis(tripbenylphosphine)rhodium and dimeric species, with hydrogen. J. Chem. Soc. A 1968, 2660.
22. Stephenson, T. A.; Wilkinson, G. New complexes of ruthenium (II) and (III) with triphenylphosphine, triphenylarsine, trichlorostannate, pyridine and other ligands. J. Inorg. Nucl. Chim. 1966, 28, 945.
23. +/montmorrilonite: A kinetic study. J. Mol. Catal. 1994, 91, 187.
24. Deshpande, R. M.; Chaudhari, R. V. Hydroformylation of allyl alcohol using homogeneous HRhCO(PPh3)3 catalyst: A kinetic study J. Catal. 1989, 115, 326.