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Highly Efficient Rhodium-Phosphite Catalyzed Hydroformylation of Camphene and other Terpenes

https://doi.org/10.14233/ajchem.2019.21656
Nitin S. Pagar
Homogeneous Catalysis Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, India; Post Graduate Department of Chemistry, Sir Parshurambhau College (Affiliated to Savitribai Phule Pune University), Pune-411030, India
Raj M. Deshpande
Homogeneous Catalysis Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411008, India; SABIC Technology Centre, Bangalore-562125, India

Corresponding Author(s) : Nitin S. Pagar

nitin.pagar@spcollegepune.ac.in, nspagar@gmail.com

Asian Journal of Chemistry, Vol. 31 No. 1 (2019): Vol 31 Issue 1

Abstract

The hydroformylation of terpenes has been studied with homogeneous Rh, Co and Pt complexes. The rhodium complex, Rh(CO)2(acac) modified with triphenyl phosphite ligand has been found to be the best catalyst system for hydroformylation of camphene and other terpenes. The role of ligands, solvents, Rh:P ratio and reaction conditions on the activity and selectivity towards camphene hydroformylation have been investigated

Keywords

Homogeneous Hydroformylation Camphene Terpenes Rhodium phosphite
Pagar, N. S., & Deshpande, R. M. (2018). Highly Efficient Rhodium-Phosphite Catalyzed Hydroformylation of Camphene and other Terpenes. Asian Journal of Chemistry, 31(1), 213–219. https://doi.org/10.14233/ajchem.2019.21656
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References
  1. W.E. Erman, Chemistry of the Monoterpenes: An Encyclopedic Handbook, Marcel Dekker: New York (1985).
  2. A.J. Chalk, eds.: P.N. Rylander, H. Greenfield and R.L. Augustine, Catalysis of Organic Reactions, Marcel Dekker: New York, vol 22 (1988).
  3. K.A.D. Swift, Top. Catal., 27, 143 (2004); https://doi.org/10.1023/B:TOCA.0000013549.60930.da.
  4. N. Ravasio, F. Zaccheria, M. Guidotti and R. Psaro, Top. Catal., 27, 157 (2004); https://doi.org/10.1023/B:TOCA.0000013550.28170.6a.
  5. J.L.F. Monteiro and C.O. Veloso, Top. Catal., 27, 169 (2004); https://doi.org/10.1023/B:TOCA.0000013551.99872.8d.
  6. A. Behr and A.J. Vorholt, Top. Organomet. Chem., 39, 103 (2012); https://doi.org/10.1007/978-3-642-28288-1_3.
  7. J.C. Locicero and R.T. Johnson, J. Am. Chem. Soc., 74, 2094 (1952); https://doi.org/10.1021/ja01128a073.
  8. J. Hagen and K. Bruns, Verfahren zur herstellung von aldehyden und verwendung der verfahrensprodukte als riechstoffe, German Patent 2849742 (1980).
  9. S. Sirol and Ph. Kalck, New J. Chem., 21, 1129 (1997).
  10. K. Yuan and Y. Yuanqi, Fenzi Cuihua, 3, 262 (1989).
  11. L. Kollár and G. Bóadi, Chirality, 7, 121 (1995); https://doi.org/10.1002/chir.530070303.
  12. E.V. Gusevskaya, E.N. dos Santos, R. Augusti, A.O. Dias, P. RoblesDutenhefner, C.M. Foca and H.J.V. Barros, Stud. Surf. Sci. Catal., 130, 563 (2000); https://doi.org/10.1016/S0167-2991(00)81017-4.
  13. H.J.V. Barros, M.L. Ospina, E. Arguello, W.R. Rocha, E.V. Gusevskaya and E.N. dos Santos, J. Organomet. Chem., 671, 150 (2003); https://doi.org/10.1016/S0022-328X(03)00098-6.
  14. H.J.V. Barros, B.E. Hanson, E.V. Gusevskaya and E.N. dos Santos, Appl. Catal. A Gen., 278, 57 (2004); https://doi.org/10.1016/j.apcata.2004.09.025.
  15. C.K. Brown and G. Wilkinson, Tetrahedron Lett., 10, 1725 (1969); https://doi.org/10.1016/S0040-4039(01)87993-4.
  16. J. Hagen and K. Bruns, Mixture of Aldehydes Resulting from Hydroformylation of α-terpinene US Patent 4283561 (1981).
  17. A.O. Dias, R. Augusti, E.N. dos Santos and E.V. Gusevskaya, Tetrahedron Lett., 38, 41 (1997); https://doi.org/10.1016/S0040-4039(96)02251-4.
  18. P.W.N.M. van Leeuwen and C.F. Roobeek, J. Organomet. Chem., 258, 343 (1983); https://doi.org/10.1016/S0022-328X(00)99279-9.
  19. C.L. Kranemann and P. Eilbracht, Synthesis, 71 (1998); https://doi.org/10.1055/s-1998-4481.
  20. L. Kollar, J. Bakos, B. Heil, P. Sandor and G. Szalontai, J. Organomet. Chem., 385, 147 (1990); https://doi.org/10.1016/0022-328X(90)87153-5.
  21. J.C. Chalchat, R.P. Garry, E. Lecomte and A. Michet, Flav. Fragr. J., 6, 179 (1991); https://doi.org/10.1002/ffj.2730060303.
  22. P. Kalck, L. Miquel and M. Dessoudeix, Catal. Today, 42, 431 (1998); https://doi.org/10.1016/S0920-5861(98)00125-4.
  23. U.J. Jauregui-Haza, R. Nikolova, A.M. Wilhelm, H. Delmas and I. Nikov, Bulg. Chem. Commun., 34, 64 (2002).
  24. M. Marchetti, S. Paganelli and E. Viel, J. Mol. Catal. Chem., 222, 143 (2004); https://doi.org/10.1016/j.molcata.2004.07.022.
  25. R. Franke, D. Fridag, D. Hess and F. Klasovsky, WO 2014135413 (2014).
  26. S.B. Halligudi, K.N. Bhatt and K. Venkatasubramanian, React. Kinet. Catal. Lett., 51, 459 (1993); https://doi.org/10.1007/BF02069091.
  27. I. Ciprés, P. Kalck, D.-C. Park and F. Serein-Spirau, J. Mol. Catal., 66, 399 (1991); https://doi.org/10.1016/0304-5102(91)80031-W.
  28. E.N. dos Santos, C.U. Pittman Jr. and H. Toghiani, J. Mol. Catal., 83, 51 (1993); https://doi.org/10.1016/0304-5102(93)87006-T.
  29. K. Soulantica, S. Sirol, S. Koinis, G. Pneumatikakis and P. Kalck, J. Organomet. Chem., 498, 10 (1995); https://doi.org/10.1016/0022-328X(95)05594-F.
  30. F. Azzaroni, P. Biscarini, S. Bordoni, G. Longoni and E. Venturini, J. Organomet. Chem., 508, 59 (1996); https://doi.org/10.1016/0022-328X(95)05778-N.
  31. G. Klein, D. Arlt and R. Braden, Cyclic Keto-butyraldehydes a Process for their Preparation, and their use in the Preparation of Cyclic Diisocyanates, US Patent 4505860 (1985).
  32. A.J. Chalk, Dev. Food Sci., 18, 867 (1988).
  33. E.V. Gusevskaya, E.N. dos Santos, R. Augusti, A.O. Dias and C.M. Foca, J. Mol. Catal. Chem., 152, 15 (2000); https://doi.org/10.1016/S1381-1169(99)00264-2.
  34. C.M. Foca, E.N. dos Santos and E.V. Gusevskaya, J. Mol. Catal. Chem., 185, 17 (2002); https://doi.org/10.1016/S1381-1169(02)00056-0.
  35. P. W. N. M. van Leeuwen, C. F. Roobeek, Process for the Hydroformylation of Olefins, US Patent 4467116 (1984).
  36. D. Evans, J. Osborn and G. Wilkinson, J. Chem. Soc. A, 3133 (1968); https://doi.org/10.1039/j19680003133.
  37. J.G. da Silva, C.G. Vieira, E.N. dos Santos and E.V. Gusevskaya, Appl. Catal. A Gen., 365, 231 (2009); https://doi.org/10.1016/j.apcata.2009.06.019.
  38. C.G. Vieira, M.C. de Freitas, K.C.B. de Oliveira, A. de Camargo Faria, E.N. dos Santos and E.V. Gusevskaya, Catal. Sci. Technol., 5, 960 (2015); https://doi.org/10.1039/C4CY01020E.
  39. P.J. Baricelli, L.G. Melean, M. Rodriguez, M. dos Santos, M. Rosales and E. Escalante, J. Chem. Chem. Eng., 7, 299 (2013).
  40. Y.S. Varshavskii and T.G. Cherkasova, Russ. J. Inorg. Chem., 12, 899 (1967).
  41. J. Chatt and L.M. Venanzi, J. Chem. Soc. A, 4735 (1957); https://doi.org/10.1039/jr9570004735.
  42. R. Usan, Inorg. Synth., 23, 126 (1985).
  43. W.-C. Yang and D.L. Keairns, Ind. Eng. Prod. Res. Dev., 14, 259 (1975); https://doi.org/10.1021/i260055a011.
  44. G. Cavinato and L. Toniolo, Inorg. Chim. Acta, 52, 39 (1981); https://doi.org/10.1016/S0020-1693(00)88569-2.
  45. B.M. Bhanage, S.S. Divekar, R.M. Deshpande and R.V. Chaudhari, J. Mol. Catal. Chem., 115, 247 (1997); https://doi.org/10.1016/S1381-1169(96)00289-0.
  46. R.L. Pruett and J.A. Smith, J. Org. Chem., 34, 327 (1969); https://doi.org/10.1021/jo01254a015.
  47. R.L. Pruett and J.A. Smith, S. African Patent 6804937 (1968).
  48. P.W.N.M. van Leeuwen and C.F. Roobeek, British Patent 2068377 (1980).
  49. C.P. Casey, J.A. Tunge, T.Y. Lee and D.W. Carpenetti, Organometallics, 21, 389 (2002); https://doi.org/10.1021/om010817g.
  50. J. Falbe, eds.: B. Cornils and W.A. Hermann, New Synthesis with Carbon Monoxide, Springler Verlag: Berlien, Heidlberg, New York, pp 84-89 (1980).
  51. 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.
  52. P.W.N.M. van Leeuwen and C. Claver, Rhodium Catalyzed Hydroformylation, Kluwer Acadamic Publishers: Dordrecht, pp 35 (2001).
  53. O.R. Hughes and J.D. Unruh, J. Mol. Catal., 12, 71 (1981); https://doi.org/10.1016/0304-5102(81)80020-X.
  54. A.M. Trzeciak and J.J. Ziolkowski, J. Mol. Catal., 19, 41 (1983); https://doi.org/10.1016/0304-5102(83)80019-4.
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