Advertisement

We'd like to understand how you use our websites in order to improve them. Register your interest.

Effects of Alkali Halide Salts on Hydrocarboxylation of Styrene Catalyzed by Water-Soluble Palladium Phosphine Complexes

Abstract

Hydrocarboxylation of styrene catalyzed by water-soluble Pd-TPPTS complexes was investigated. The reaction conditions, including reaction pressure, temperature, time and etc. have a significant influence on the catalytic performance. It was found that the yield of total acids and the selectivity towards 3-phenylpropionic acid were enhanced by adding a suitable amount of alkali metal halide salts. In addition, the reaction mechanism and the role of alkali metal halide salts in the reaction were discussed on the basis of the characterization of 1H NMR and 31P NMR.

Graphical Abstract

This is a preview of subscription content, log in to check access.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Scheme 2
Fig. 4
Fig. 5
Fig. 6
Scheme 3

References

  1. 1.

    Lapidus A, Eliseev O, Bondarenko T, Stepin N (2006) J Mol Catal A: Chem 252:245

  2. 2.

    Williams DBG, Shaw ML, Hughes T (2011) Organometallics 30:4968

  3. 3.

    Tortosa-Estorach C, Ruiz N, Masdeu-Bulto AM (2006) Chem Commun 26:2789

  4. 4.

    del Río I, Claver C, van Leeuwen PWNM (2001) Eur J Inorg Chem 2001:2719

  5. 5.

    Seayad A, Kelkar AA, Chaudhari RV, Toniolo L (1998) Ind Eng Chem Res 37:2180

  6. 6.

    Zhou LM, Guo CH, Fu HY, Jiang XH, Chen H, Li RX, Li XJ (2012) Spectrochimica Acta Part A 93:198

  7. 7.

    Jayasree S, Seayad A, Chaudhari RV (2000) Chem Commun 2000:1239

  8. 8.

    Tilloy S, Monflier E, Bertoux F, Castanet Y, Mortreux A (1997) New J Chem 21:529

  9. 9.

    Bertoux F, Tilloy S, Monflier E, Castanet Y, Mortreux A (1999) J Mol Catal A: Chem 138:53

  10. 10.

    Bertoux F, Monflier E, Castanet Y, Mortreux A (1999) J Mol Catal A: Chem 143:11

  11. 11.

    Karlsson M, Ionescu A, Andersson C (2006) J Mol Catal A: Chem 259:231

  12. 12.

    Six N, Guerriero A, Landy D, Peruzzini M, Gonsalvi L, Hapiot F, Monflier E (2011) Catal Sci Technol 1:1347

  13. 13.

    Franke R, Selent D, Börner A (2012) Chem Rev 112:58

  14. 14.

    Aghmiz A, Giménez-Pedrós M, Masdeu-Bultó A, Schmidtchen FP (2005) Catal Lett 103:191

  15. 15.

    Duvenhage DJ, Coville NJ (2005) Catal Lett 104:129

  16. 16.

    Monflier E, Tilloy S, Bertoux F, Castanet Y, Mortreux A (1997) New J Chem 21:857

  17. 17.

    Tilloy S, Bertoux F, Mortreux A, Monflier E (1999) Catal Today 48:245

  18. 18.

    Li Z, Peng Q, Yuan Y (2003) Appl Catal A Gen 239:79

  19. 19.

    Bertoux F, Monflier E, Castanet Y, Mortreux A (1999) J Mol Catal A: Chem 143:23

  20. 20.

    Mukhopadhyay K, Sarkar BR, Chaudhari RV (2002) J Am Chem Soc 124:9692

  21. 21.

    Seayad A, Jayasree S, Damodaran K, Toniolo L, Chaudhari RV (2000) J Organomet Chem 601:100

  22. 22.

    Seayad A, Kelkar AA, Toniolo L, Chaudhari RV (2000) J Mol Catal A: Chem 151:47

  23. 23.

    Atla SB, Kelkar AA, Chaudhari RV (2009) J Mol Catal A: Chem 307:134

  24. 24.

    Seayad A, Jayasree S, Chaudhari RV (1999) Org Lett 1:459

  25. 25.

    Ding H, Hanson BE (1994) J Chem Soc, Chem Commun 13:2747

  26. 26.

    Ionescu A, Ruppel M, Wendt OF (2006) J Organomet Chem 691:3806

  27. 27.

    Papadogianakis G, Peters JA, Maat L, Sheldon RA (1995) J Chem Soc, Chem Commun 32:1105

  28. 28.

    Papadogianakis G, Verspui G, Maat L, Sheldon RA (1997) Catal Lett 47:43

  29. 29.

    Binkowski C, Cabou J, Bricout H, Hapiot F, Monflier E (2004) J Mol Catal A: Chem 215:23

  30. 30.

    Ali BE, Fettouhi M (2002) J Mol Catal A: Chem 182–183:195

  31. 31.

    Fontana G, Lubineau A, Scherrmann MC (2005) Org Biomol Chem 3:1375

  32. 32.

    Benedek C, Törös S, Heil B (1999) J Organomet Chem 586:85

  33. 33.

    Klingshirn MA, Rogers RD, Shaughnessy KH (2005) J Organomet Chem 690:3620

  34. 34.

    Kuntz EG, Vittori OM (1998) J Mol Catal A: Chem 129:159

  35. 35.

    del Río I, Ruiz N, Claver C, van der Veen LA, van Leeuwen PWNM (2000) J Mol Catal A Chem 161: 39

Download references

Acknowledgments

The authors are grateful for the support from the National Natural Science Foundation of China (U1179302) and One Hundred Person Project of the Chinese Academy of Sciences.

Author information

Affiliations

Authors

Corresponding author

Correspondence to Zhenshan Hou.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 3157 kb)

Rights and permissions

Reprints and Permissions

About this article

Cite this article

He, Z., Hou, Z., Luo, Y. et al. Effects of Alkali Halide Salts on Hydrocarboxylation of Styrene Catalyzed by Water-Soluble Palladium Phosphine Complexes. Catal Lett 143, 289–297 (2013). https://doi.org/10.1007/s10562-013-0961-2

Download citation

Keywords

  • Aqueous two-phase system
  • Hydrocarboxylation
  • Palladium-phosphine complexes
  • Alkali metal halide