ArticlePolymers2019
Urethane Formation with an Excess of Isocyanate or Alcohol: Experimental and Ab Initio Study.
Article in Polymers, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Development of a triazine-pyrone Schiff base methacrylate adsorbent for the selective recovery of beryllium ions from hazardous industrial sludge.RSC advances · 2026Article
- Theoretical and Experimental Study on Carbodiimide Formation.International journal of molecular sciences · 2024Article
- Article
- Development of High-Performance Coconut Oil-Based Rigid Polyurethane-Urea Foam: A Novel Sequential Amidation and Prepolymerization Process.ACS omega · 2024Article
- An Ab Initio Investigation on Relevant Oligomerization Reactions of Toluene Diisocyanate (TDI).Polymers · 2022Article
- Article
- Current State and Perspectives of Simulation and Modeling of Aliphatic Isocyanates and Polyisocyanates.Polymers · 2022Review
- Chemorheological Monitoring of Cross-Linking in Slide-ring Gels Derived FromFrontiers in chemistry · 2022Article
- Computational Study of Catalytic Urethane Formation.Polymers · 2021Article
- Connecting Gas-Phase Computational Chemistry to Condensed Phase Kinetic Modeling: The State-of-the-Art.Polymers · 2021Review
- Reaction Mechanisms and Rate Constants of Auto-Catalytic Urethane Formation and Cleavage Reactions.ChemistryOpen · 2021Article
- Article
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Authors and funding
7 authors.
Funding
Abstract
A kinetic and mechanistic investigation of the alcoholysis of phenyl isocyanate using 1-propanol as the alcohol was undertaken. A molecular mechanism of urethane formation in both alcohol and isocyanate excess is explored using a combination of an accurate fourth generation Gaussian thermochemistry (G4MP2) with the Solvent Model Density (SMD) implicit solvent model. These mechanisms were analyzed from an energetic point of view. According to the newly proposed two-step mechanism for isocyanate excess, allophanate is an intermediate towards urethane formation via six-centered transition state (TS) with a reaction barrier of 62.6 kJ/mol in the THF model. In the next step, synchronous 1,3-H shift between the nitrogens of allophanate and the cleavage of the C-N bond resulted in the release of the isocyanate and the formation of a urethane bond via a low-lying TS with 49.0 kJ/mol energy relative to the reactants. Arrhenius activation energies of the stoichiometric, alcohol excess and the isocyanate excess reactions were experimentally determined by means of HPLC technique. The activation energies for both the alcohol (measured in our recent work) and the isocyanate excess reactions were lower compared to that of the stoichiometric ratio, in agreement with the theoretical calculations.
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