Advertisement

Synthesis, Characterization and Transesterification Activity of Cross-Linked Styrenic Resins Containing the Triphenyltincarboxylate Moiety Spaced by a Dimethylene from the Aromatic Ring

  • Daniele Caretti
  • Luigi Angiolini
  • Elisa Cavicchi
  • Laura Mazzocchetti
  • Elisabetta Salatelli
  • Sara Ugolini
Article
  • 138 Downloads

Abstract

An organotin monomer, triphenyltin 3-(4-styryl)-propionate (TPTSPr) has been synthesized and copolymerized in different ratios with styrene and 1,4-divinylbenzene in order to obtain resins with catalytic activity in transesterification reactions. The resins and a low molecular weight model compound, triphenyltin 3-(4-ethylphenyl)-propionate (TPT-C2-Pr), mimicking the catalytic co-unit, have been characterized by FT-IR and NMR spectroscopy, with particular attention paid to the coordination at tin and how it correlates to the catalytic activity. The activity of both the resins and of the model compound have been tested in a transesterification model reaction between ethyl acetate and primary alcohol. All the resins show catalytic activity that decreases with increasing content of the active co-unit in the resins, owing to the interaction of the active sites among themselves.

Keywords

Styrenic resins Tin carboxylate Tin coordination Transesterification Catalytic activity 

Notes

Acknowledgments

The authors thank University of Bologna for the financial support of the research trough RFO founds.

References

  1. 1.
    M.A. Champ, P.F. Seligman, Organotin environmental fate and effects (Chapman and Hall, London, 1996)Google Scholar
  2. 2.
    M.C. Hermosin, P. Martin, J. Cornejo, Environ. Sci. Technol. 27, 2606 (1993)CrossRefGoogle Scholar
  3. 3.
    C.G. Arnold, A. Ciani, S.R. Muller, A. Amirbahman, R.P. Schwarzenbach, Environ. Sci. Techn. 32, 2976 (1998)CrossRefGoogle Scholar
  4. 4.
    O.A. Mascaretti, R.L.E. Furlan, Aldrichimica Acta 30, 55 (1997)Google Scholar
  5. 5.
    A.K. Kumar, T.K. Chattopadhyay, Tetrahedron Lett. 28, 3713 (1987)CrossRefGoogle Scholar
  6. 6.
    V. Pinoie, M. Biesemans, R. Willem, Appl. Organomet. Chem. 24, 135 (2010)Google Scholar
  7. 7.
    L. Angiolini, D. Caretti, L. Mazzocchetti, E. Salatelli, R. Willem, M. Biesemans, Appl. Organomet. Chem. 19, 841 (2005)CrossRefGoogle Scholar
  8. 8.
    L. Angiolini, D. Caretti, L. Mazzocchetti, E. Salatelli, R. Willem, M. Biesemans, J. Organomet. Chem. 691, 3043 (2006)CrossRefGoogle Scholar
  9. 9.
    D.D. Perrin, W.L.F. Amarego, D.R. Perrin, Purification of laboratory chemicals (Pergamon Press, Oxford, 1966)Google Scholar
  10. 10.
    L. Angiolini, M. Biesemans, D. Caretti, E. Salatelli, R. Willem, Polymer 41, 3913 (2000)CrossRefGoogle Scholar
  11. 11.
    L. Angiolini, D. Caretti, L. Mazzocchetti, E. Salatelli, R. Willem, M. Biesemans, J. Polym. Sci. A Polym. Chem. 42, 5372 (2004)CrossRefGoogle Scholar
  12. 12.
    L. Angiolini, D. Caretti, L. Mazzocchetti, E. Salatelli, R. Willem, M. Biesemans, J. Organomet. Chem. 691, 1965 (2006)CrossRefGoogle Scholar
  13. 13.
    A.G. Davies, Organotin chemistry, 2nd edn. (Wiley, Weinheim, 2004)CrossRefGoogle Scholar
  14. 14.
    R.A. Sheldon, M. Wallau, I.W.C.E. Arends, U. Schuchardt, Acc. Chem. Res. 31, 485 (1998)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Daniele Caretti
    • 1
  • Luigi Angiolini
    • 1
  • Elisa Cavicchi
    • 1
  • Laura Mazzocchetti
    • 1
  • Elisabetta Salatelli
    • 1
  • Sara Ugolini
    • 1
  1. 1.Dipartimento di Chimica Industriale “Toso Montanari”Università di BolognaBolognaItaly

Personalised recommendations