Skip to main content
SpringerLink
Log in

Clean Carbonylations in Supercritical Carbon Dioxide. Part 1: Palladium-Catalyzed Alkoxycarbonylation of Allyl Bromide

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Palladium-catalyzed alkoxycarbonylation of allyl bromide to unsaturated esters in supercritical carbon dioxide (sc-CO2) was performed and compared with alkoxycarbonylation in organic solvents in this paper. Effects of the catalytic precursor, triphenyl phosphine ligand, base, pressure, and reaction temperature on the reaction yield and selectivity were mainly discussed. The results showed that sc-CO2 was a favorable reaction medium for the reaction under lower CO pressure. Small changes, both in the CO2 pressure as well as the amount of cosolvent ethanol, can cause drastic changes in both the reaction yield and selectivity. Moreover, FeCl2 was found to have a promoting effect as cocatalyst on the reaction. The synergic effect of cosolvent ethanol with FeCl2 can lead to an even better result than that in organic solvents.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. A. Baiker, Chem. Rev. 99 (1999) 453.

    Google Scholar 

  2. P.G. Jessop, T. Ikariya and R. Noyori, Chem. Rev. 99 (1999) 475.

    Google Scholar 

  3. R.Q. Song, J.Q. Zeng and B. Zhong, Chin. J. Environ. Sci. 22 (2001) 116.

    Google Scholar 

  4. B. Aikawa, R.C. Burk and B.B. Sitholé, Appl. Catal. A 32 (2001) 269.

    Google Scholar 

  5. J. Tsuji, J. Kiji and M. Morikawa, Tetrahedron Lett. 26 (1963) 1811.

    Google Scholar 

  6. J. Tsuji, J. Kiji, S. Imamura and M. Morikawa, J. Am. Chem. Soc. 86 (1964) 4350.

    Google Scholar 

  7. J. Kiji, T. Okano, Y. Higashimae and Y. Fukui, Bull. Chem. Soc. Jpn. 69 (1996) 1029.

    Google Scholar 

  8. H. M. Colquhoun, D. J. Thompson and M. V. Twigg, Carbonylation (Plenum, New York, 1991).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan, 030001, P.R. China. Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou 510650, P.R. China. School of Chemistry and Chemical Engineering, Zhongshan University, Guangzhou 510275, P.R. China

    Ruiqi Song

  2. Guangzhou Institute of Chemistry, Chinese Academy of Sciences, Guangzhou, 510650, P.R. China

    Jianqing Zeng

  3. School of Chemistry and Chemical Engineering, Zhongshan University, Guangzhou, 510275, P.R, China

    Bing Zhong

Authors
  1. Ruiqi Song
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jianqing Zeng
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Bing Zhong
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Song, R., Zeng, J. & Zhong, B. Clean Carbonylations in Supercritical Carbon Dioxide. Part 1: Palladium-Catalyzed Alkoxycarbonylation of Allyl Bromide. Catalysis Letters 82, 89–93 (2002). https://doi.org/10.1023/A:1020500410295

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1020500410295

Search

Navigation