Understanding the Accelerating Effect of epsilon-Caprolactam on the Formation of Urethane Linkages (Articolo in rivista)

Type
Label
  • Understanding the Accelerating Effect of epsilon-Caprolactam on the Formation of Urethane Linkages (Articolo in rivista) (literal)
Anno
  • 2005-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1021/ma0480998 (literal)
Alternative label
  • Monica Bertoldo; Chiara Cappelli; Stefano Catanorchi; Vincenzo Liuzzo; Simona Bronco (2005)
    Understanding the Accelerating Effect of epsilon-Caprolactam on the Formation of Urethane Linkages
    in Macromolecules (Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Monica Bertoldo; Chiara Cappelli; Stefano Catanorchi; Vincenzo Liuzzo; Simona Bronco (literal)
Pagina inizio
  • 1385 (literal)
Pagina fine
  • 1394 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 38 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 10 (literal)
Note
  • ISI Web of Science (WOS) (literal)
  • Scopus (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • PolyLab-INFM, c/o Dipartimento di Chimica e Chimica Industriale, Universita` di Pisa, via Risorgimento 35, I-56126 Pisa, Italy Dipartimento di Chimica e Chimica Industriale, Universita` di Pisa, via Risorgimento 35, I-56126 Pisa, Italy (literal)
Titolo
  • Understanding the Accelerating Effect of epsilon-Caprolactam on the Formation of Urethane Linkages (literal)
Abstract
  • The accelerating role of ?-caprolactam on the formation of urethane linkages is studied in the case of the reaction between toluene 2,4-diisocyanate and n-propanol in carbon tetrachloride at room temperature. FT-IR spectroscopy is exploited to follow the consumption of the isocyanate groups. The comparison between the rate of the reactions carried out in the presence and absence of a catalytic amount of ?-caprolactam shows its accelerating effect. The acylurea-like derivative 1-methyl-2,4-[(2-oxoazepane- 1-carbonyl)amino]benzene has been prepared and identified as the real catalytic species formed in situ as a result of the reaction between toluene 2,4-diisocyanate and ?-caprolactam. A kinetic model is proposed to analyze the experimental data, and B3LYP/6-31+G* calculations are exploited to investigate the structure of 1-methyl-2,4-[(2-oxoazepane-1-carbonyl)amino]benzene and clarify the structural features leading the catalytic activity. (literal)
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