Computational and experimental investigations of the urethane formation mechanism in the presence of organotin(IV) carboxylate catalysts
DOI: 10.1016/j.molcata.2012.09.015
Title: Computational and experimental investigations of the urethane formation mechanism in the presence of organotin(IV) carboxylate catalysts
Journal Title: Journal of Molecular Catalysis A: Chemical
Volume: 366
Publication Date: January 2013
Start Page: 126
End Page: 139
Published online: online 24 September 2012
ISSN: 1381-1169
Author: Ransi Devendraa, Neil R. Edmondsa, Tilo Sö;hnelab
Affiliations:

  • a School of Chemical Sciences, The University of Auckland, New Zealand

  • b Centre for Theoretical Chemistry and Physics, The New Zealand Institute for Advanced Study, Massey University, Auckland, New Zealand
  • Abstract: organotin carboxylate compounds are widely used in the polyurethane industry as catalysts, their reactions mechanisms are not fully understood. The urethane formation between isocyanate and alcohol groups in the presence of organotin carboxylate catalysts is simulated with selected compounds using computational methods and the results are compared with experimental findings. The results reveal that organotin carboxylate catalysis of the reaction between these isocyanate and n-butanol in a non-polar medium follow two routes depending on the isocyanate structure. The reaction rate for aliphatic primary isocyanates the concentration of the carboxylate ligand in the catalyst has a significant effect while for aromatic isocyanates the effect is much less. Based on experimental and computational results a mechanism is proposed for organotin carboxylate catalysis of urethane formation for these isocyanates.
    Accepted: 14 September 2012
    Received: 9 November 2011
    Revised: 25 July 2012
    Tel: +64 9 373 923 9722
    Fax: +64 9 373 7422
    Email: t.soehnel@auckland.ac.nz

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