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Catalysis Letters

, Volume 143, Issue 8, pp 839–843 | Cite as

Zwitterionic Phosphine Ligand with a Lysine Tag and its Application for Hydroformylation of 1-Octene in Ionic Liquid/MeOH System

  • Xin Jin
  • Kun Zhao
  • Fangfang Kong
  • Feifei Cui
  • Daoxing Yang
Article

Abstract

Here we report a highly active and selective hydroformylation of 1-octene in ionic liquid (IL)/MeOH system based on a zwitterionic phosphine ligand bearing a lysine moiety (L(NH2)COOH). The Rh-catalyst grafted lysine in the form of ammonium salt ([Rh-L(NH3 +)COOH]Tf2N) was successfully immobilized in the IL [bmim]Tf2N and recycled for seventeen times without significant loss of activity, selectivity and Rh catalysts. This study has provided a novel strategy for efficient separation and recycling of Rh catalysts.

Graphical Abstract

Keywords

Amino acid Catalyst recycling Hydroformylation Ionic liquid 

Notes

Acknowledgments

We gratefully thank the financial support from National Natural Science Foundation of China (No. 20606019, 20976086), Foundation of Key Laboratory of Oil & Gas Fine Chemicals, Ministry of Education, China (No. XJDX0908-2010 -01) and Qingdao Science and Technology Basic Research Foundation of China (No. 12-1-4-3-(6)-jch).

References

  1. 1.
    Frohning CD, Kohlpainter CW (1996) In: Cornils B, Herrmann WA (eds) Applied homogeneous catalysis with organometallic compounds, 1st edn. Wiley, Weinheim, p 29Google Scholar
  2. 2.
    Kuntz EG (1987) ChemTech 17:570–575Google Scholar
  3. 3.
    Haumann M, Riisager A (2008) Chem Rev 108:1474–1497CrossRefGoogle Scholar
  4. 4.
    Welton T (1999) Chem Rev 99:2071–2084CrossRefGoogle Scholar
  5. 5.
    Dupont J, de Souza RF, Suarez PAZ (2002) Chem Rev 102:3667–3692CrossRefGoogle Scholar
  6. 6.
    Pârvulescu VI, Hardacre C (2007) Chem Rev 107:2615–2665CrossRefGoogle Scholar
  7. 7.
    Chauvin Y, Mussmann L, Olivier H (1995) Angew Chem Int Ed 34:2698–2700Google Scholar
  8. 8.
    Wasserscheid P, Waffenschmidt H, Machnitzki P, Kottsieper KW, Stelzer O (2001) Chem Commun 451–452Google Scholar
  9. 9.
    Dupont J, Silva SM, de Souza RF (2001) Catal Lett 77:131–133CrossRefGoogle Scholar
  10. 10.
    Webb PB, Sellin MF, Kunene TE, Williamson S (2003) Slawin AMZ J Am Chem Soc 125(15577–1558):8Google Scholar
  11. 11.
    Silva SM, Bronger RPJ, Freixa Z, Dupont J, van Leeuwen PWNM (2003) New J Chem 27:1294–1296CrossRefGoogle Scholar
  12. 12.
    Mehner CP, Cook RA, Dispenziere NC, Mozeleski EJ (2004) Polyhedron 23:2679–2688CrossRefGoogle Scholar
  13. 13.
    Ni B, Headley AD (2010) Chem Eur J 16:4426–4436CrossRefGoogle Scholar
  14. 14.
    Lombardo M, Trombini C (2010) ChemCatChem 2:135–145CrossRefGoogle Scholar
  15. 15.
    Šebesta R, Kmentova I, Toma Š (2008) Green Chem 10:484–496CrossRefGoogle Scholar
  16. 16.
    Sirieix J, Ossberger M, Betzemeier B, Knochel P (2000) Synlett 11:1613–1615Google Scholar
  17. 17.
    Brasse CC, Englert U, Salzer A, Waffenschmidt H, Wasserscheid P (2000) Organometallics 19:3818–3823CrossRefGoogle Scholar
  18. 18.
    Favre F, Olivier-Bourbigou H, Commereuc D, Saussine L (2001) Chem Commun 1360–1361Google Scholar
  19. 19.
    Bronger RPJ, Silva SM, Kamer PCJ, van Leeuwen PWNM (2002) Chem Commun 3044–3045Google Scholar
  20. 20.
    Lee S, Zheng YJ, Piao JY, Yoon H, Song CE, Choi JH, Hong J (2003) Chem Commun 2624–2625Google Scholar
  21. 21.
    Yao Q, Zhang Y (2003) Angew Chem Int Ed 42:3395–3398CrossRefGoogle Scholar
  22. 22.
    Audic N, Clavier H, Mauduit M, Guillemin JC (2003) J Am Chem Soc 125:9248–9249CrossRefGoogle Scholar
  23. 23.
    Baleizão C, Gigante B, Garcia H, Corma A (2003) Tetrahedron Lett 44:6813–6816CrossRefGoogle Scholar
  24. 24.
    Gadenne B, Hesemann P, Moreau JJE (2005) Tetrahedron Asymmetry 16:2001–2006CrossRefGoogle Scholar
  25. 25.
    Doherty S, Goodrich P, Hardacre C, Knight JG, Nguyen MT, Pârvulescu VI (2007) Adv Synth Catal 349:951–963CrossRefGoogle Scholar
  26. 26.
    Gavrilov KN, Lyubimov SE, Bondarev OG, Maksimova MG, Zheglov SV (2007) Adv Synth Catal 349:609–616CrossRefGoogle Scholar
  27. 27.
    Feng X, Pugin B, Kűsters E, Sedelmeier G, Blaser HU (2007) Adv Synth Catal 349:1803–1807CrossRefGoogle Scholar
  28. 28.
    Doherty S, Goodrich P, Hardacre C, Pârvulescu V, Paun C (2008) Adv Synth Catal 350:295–302CrossRefGoogle Scholar
  29. 29.
    Šebesta R, Bilčīk F (2009) Tetrahedron Asymmetry 20:1892–1896CrossRefGoogle Scholar
  30. 30.
    Jin X, Xu X, Zhao K (2012) Tetrahedron Asymmetry 23:1058–1067CrossRefGoogle Scholar
  31. 31.
    Kuang SM, Fanwick PE, Walton RA (2002) Inorg Chim Acta 338:219–227CrossRefGoogle Scholar
  32. 32.
    Hoffman RV (1974) Tetrahedron Lett 28:2415–2416CrossRefGoogle Scholar
  33. 33.
    Krompieca S, Penkalaa M, Szczubiałkab K, Kowalska E (2012) Coord Chem Rev 256:2057–2095CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Xin Jin
    • 1
    • 2
  • Kun Zhao
    • 1
  • Fangfang Kong
    • 1
  • Feifei Cui
    • 1
  • Daoxing Yang
    • 1
  1. 1.College of Chemical Engineering, Qingdao University of Science and TechnologyQingdaoChina
  2. 2.Key Laboratory of Oil & Gas Fine Chemicals of Ministry of EducationXinjiang UniversityWulumuqiChina

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