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Vol. 32 No. 8 (2020): Vol 32 Issue 8, 2020

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Hydroformylation of Higher Olefins in Aqueous Biphasic Medium Using Rhodium-Sulfoxantphos Catalyst: Activity and Selectivity Study

https://doi.org/10.14233/ajchem.2020.22735
Nitin S. Pagar
1 Homogeneous Catalysis Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, India 2 Post Graduate Department of Chemistry, Sir Parashurambhau College (Affiliated to Savitribai Phule Pune University), Pune-411030, India
https://orcid.org/0000-0002-3141-3356
Raj M. Deshpande
1 Homogeneous Catalysis Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, India 3 SABIC Technology Centre, Bangalore-562125, India

Asian Journal of Chemistry, Vol. 32 No. 8 (2020): Vol 32 Issue 8, 2020

Abstract

Hydroformylation of higher olefins such as 1-hexene, 1-octene, 1-decene and 1-dodecene has been studied in an aqueous biphasic medium using water-soluble Rh-sulfoxantphos complex  catalyst. The effect of temperature, presence of various co-solvents and concentration of co-solvent on the reaction rate and chemo and regioselectivity was investigated. N-Methyl  pyrrolidone (NMP) was found to be the best co-solvent, which enhances the rate dramatically (4-96 fold) as compared to the reactions in aqueous-organic biphasic medium for  hydroformylation of higher olefins. Catalyst recycle study was performed to check the leaching of metal in organic phase.

Keywords

Aqueous biphasic Hydroformylation Rh-Sulfoxantphos Co-solvent Recycle
Pagar, N. S. ., & Deshpande, R. M. . (2020). Hydroformylation of Higher Olefins in Aqueous Biphasic Medium Using Rhodium-Sulfoxantphos Catalyst: Activity and Selectivity Study. Asian Journal of Chemistry, 32(8), 2061–2066. https://doi.org/10.14233/ajchem.2020.22735
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References
  1. B. Cornils and W.A. Herrmann, Applied Homogeneous Catalysis with Organometallic Compounds, Wiley-VCH, Weinheim (2002).
  2. R. Franke, D. Selent and A. Börner, Chem. Rev., 112, 5675 (2012); https://doi.org/10.1021/cr3001803
  3. B. Cornils and W.A. Herrmann, Aqueous Phase Organometallic Catalysis: Concept and Application Viley-VCH, Weinheim (1998).
  4. L.C. Matsinha, S. Siangwata, G.S. Smith and B.C.E. Makhubela, Catal. Rev., 61, 111 (2019); https://doi.org/10.1080/01614940.2018.1541781
  5. G. Cravotto, E. Borretto, M. Oliverio, A. Procopio and A. Penoni, Catal. Commun., 63, 2 (2015);https://doi.org/10.1016/j.catcom.2014.12.014
  6. B. Cornils, Org. Process Res. Dev., 2, 121 (1998); https://doi.org/10.1021/op970057e
  7. E. Wiebus and B. Cornils, Chem. Ingen. Techn., 66, 916 (1994); https://doi.org/10.1002/cite.330660704
  8. B. Cornils and E. Wiebus, CHEMTECH, 25, 33 (1995).
  9. Y. Zhao, Y. Liu, J. Wei, H. Fu, X. Zheng, M. Yuan, R. Li and H. Chen, Catal. Lett., 148, 438 (2018); https://doi.org/10.1007/s10562-017-2247-6
  10. D.J. Cole-Hamilton, Science, 299, 1702 (2003); https://doi.org/10.1126/science.1081881
  11. M. Beller, B. Cornils, C.D. Frohning and C.W. Kohlpaintner, J. Mol. Catal., 104, 17 (1995); https://doi.org/10.1016/1381-1169(95)00130-1
  12. L. Obrecht, P.C.J. Kamer and W. Laan, Catal. Sci. Technol., 3, 541 (2013); https://doi.org/10.1039/C2CY20538F
  13. J.Z. Wei, J.W. Lang, H.Y. Fu, R.X. Li, X.L. Zheng, M.L. Yuan and H. Chen, Transition Met. Chem., 41, 599 (2016); https://doi.org/10.1007/s11243-016-0058-z
  14. R.M. Deshpande, P. Purwanto, H. Delmas and R.V. Chaudhari, Ind. Eng. Chem. Res., 35, 3927 (1996); https://doi.org/10.1021/ie960047m
  15. Y. Zhang, Z. Mao and J. Chen, Catal. Today, 74, 23 (2002); https://doi.org/10.1016/S0920-5861(01)00527-2
  16. R.M. Deshpande and H. Purwanto, J. Mol. Catal. Chem., 126, 133 (1997); https://doi.org/10.1016/S1381-1169(97)00103-9
  17. F. Monteil, R. Queau and P. Kalck, J. Organomet. Chem., 480, 177 (1994); https://doi.org/10.1016/0022-328X(94)87115-9
  18. I. Hablot, J. Jenck, G. Casamatta and H. Delmas, Chem. Eng. Sci., 47, 2689 (1992); https://doi.org/10.1016/0009-2509(92)87114-6
  19. P. Kalck, P. Escaffre, F. Serein-Spriau, A. Thorez, B. Besson, Y. Colleuille and R. Perron, New J. Chem., 12, 687 (1988).
  20. S.D. Christian and J.F. Scamehorn, Solubilization in Surfactant Aggregates, Marcel Dekker: New York (1995).
  21. A.A. Dabbawala, D.U. Parmar, H.C. Bajaj and R.V. Jasra, J. Mol. Catal. Chem., 282, 99 (2008); https://doi.org/10.1016/j.molcata.2007.11.026
  22. S. Tilloy, G. Crowyn, E. Monflier, P.W.N.M. van Leeuwen and J.N.H. Reek, New J. Chem., 30, 377 (2006); https://doi.org/10.1039/b515364f
  23. E. Monflier, G. Fremy, Y. Castanet and A. Mortreux, Angew. Chem. Int. Ed. Engl., 34, 2269 (1995); https://doi.org/10.1002/anie.199522691
  24. A. Cocq, H. Bricout, F. Djedaïni-Pilard, S. Tilloy and E. Monflier, Catalysts, 10, 56 (2020); https://doi.org/10.3390/catal10010056
  25. F. Hapiot, S. Menuel, H. Bricout, S. Tilloy and E. Monflier, Appl. Organomet. Chem., 29, 580 (2015); https://doi.org/10.1002/aoc.3340
  26. J.Z. Jiang, J.J. Yang and W.Y. Hua, Chin. Chem. Lett., 21, 515 (2010);https://doi.org/10.1016/j.cclet.2010.01.020
  27. R.V. Chaudhari, B.M. Bhanage, R.M. Deshpande and H. Delmas, Nature, 373, 501 (1995); https://doi.org/10.1038/373501a0
  28. H. Fu, M. Li, J. Chen, R. Zhang, W. Jiang, M. Yuan, H. Chen and X. Li, J. Mol. Catal. Chem., 292, 21 (2008); https://doi.org/10.1016/j.molcata.2008.06.005
  29. M. Schreuder Goedheijt, P.C.J. Kamer and P.W.N.M. van Leeuwen, J. Mol. Catal. Chem., 134, 243 (1998); https://doi.org/10.1016/S1381-1169(98)00042-9
  30. L. Leclercq, F. Hapiot, S. Tilloy, K. Ramkisoensing, J.N.H. Reek, P.W.N.M. van Leeuwen and E. Monflier, Organometallics, 24, 2070 (2005); https://doi.org/10.1021/om048994f
  31. Y.S. Varshavskii and T.G. Cherkasova, Russ. J. Inorg. Chem., 12, 899 (1967).
  32. R.M. Deshpande and R.V. Chaudhari, J. Catal., 115, 326 (1989); https://doi.org/10.1016/0021-9517(89)90037-7
  33. B. Cornils, Angew. Chem. Int. Ed. Engl., 34, 1575 (1995); https://doi.org/10.1002/anie.199515751
  34. H. Bahrmann and S. Bogdanovic, eds.: B. Cornils and W. A. Herrmann, Aqueous Phase Organometallic Catalysis: Concept and Application Viley-VCH: Weinheim, pp 306-321 (1998).
  35. O.R. Hughes and J.D. Unruh, J. Mol. Catal., 12, 71 (1981); https://doi.org/10.1016/0304-5102(81)80020-X
  36. O.R. Hughes and D.A. Young, J. Am. Chem. Soc., 103, 6636 (1981); https://doi.org/10.1021/ja00412a019
  37. T.J. Devon, G.W. Philips, T.A. Puckette, J.L. Stavinoha and J.J. Vanderbilt, Chelate Ligands for Low Pressure Hydroformylation Catalyst and Process Employing Same, U.S. Patent 4,694,109 (1989).
  38. C.P. Casey, G.T. Whiteker, M.G. Melville, L.M. Petrovich, J.A. Gavney and D.R. Powell, J. Am. Chem. Soc., 114, 5535 (1992); https://doi.org/10.1021/ja00040a008
  39. V.S. Nair, B.M. Bhanage, R.M. Deshpande and R.V. Chaudhari, Stud. Surf. Sci. Catal., 113, 529 (1998); https://doi.org/10.1016/S0167-2991(98)80328-5
  40. P. Purwanto and H. Delmas, Catal. Today, 24, 135 (1995); https://doi.org/10.1016/0920-5861(95)00013-6
  41. R.V. Chaudhari and B.M. Bhanage, ed.: B. Cornils and W.A. Herrmann Aqueous Phase Organometallic Catalysis: Concepts and Application Viley-VCH: Weinheim, pp 283-294 (1998).
  42. Z. Freixa and P.W.N.M. van Leeuwen, Dalton Trans., 1890 (2003);https://doi.org/10.1039/B300322C
  43. P. W.N.M. van Leeuwen and C. Claver, Rhodium Catalyzed Hydroformylation, Kluwer Academic Publishers: London (2002).
  44. M. Kranenburg, Y.E.M. van der Burgt, P.C.J. Kamer, P.W.N.M. van Leeuwen, K. Goubitz and J. Fraanje, Organometallics, 14, 3081 (1995); https://doi.org/10.1021/om00006a057
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