Exchange reactions of urethanes with proton-donating compounds: Kinetics of the reactions of phenyl-<Emphasis Type="Italic">N</Emphasis>-phenylurethane with butyl alcohols |
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Authors: | A S Dzhalmukhanova E R Badamshina V V Komratova V P Lodygina M P Garkushina Ya I Estrin |
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Institution: | (1) Shandong Provincial Key Laboratory of Fine Chemicals, Shandong Institute of Light Industry, Jinan, Shandong, 250353, China; |
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Abstract: | The exchange reactions of phenyl-N-phenylurethane with aliphatic alcohols, namely, n-butyl, sec-butyl, and tert-butyl alcohols, in ortho-dichlorobenzene and in the media of the corresponding alcohols were studied. In the absence of a catalyst and proton-donating compounds, the monomolecular cleavage of phenyl-N-phenylurethane to isocyanate and alcohol proceeds at a noticeable rate starting only at 250°C. Between 40 and 80°C, the exchange reactions take place via direct exchange between urethane and the photon-donating compound and are second-order up to high conversions (until the almost complete disappearance of the initial urethane). Activation energies and apparent rate constants have been determined for the exchange reactions of phenyl-N-phenylurethane with butyl alcohols. The rates of the exchange reactions in the alcohol medium are compared with those in ortho-dichlorobenzene. |
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