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The reaction of o-hydroxybenzyl alcohol with phenyl isocyanate in polar solvents

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Abstract

The reaction of o-hydroxybenzyl alcohol with phenyl isocyanate has been investigated in different polar solvents with in situ FT-IR. The rate constants for the reactions of the phenolic hydroxyl group and the aliphatic hydroxyl group were calculated as k 1 and k 2, respectively. It is found that the phenolic hydroxyl group reacts more easily than the aliphatic hydroxyl group. It is also found that k 1 increases with increasing solvent polarity, while the trend of k 2 is the opposite. Moreover, the reaction kinetics is second-order with respect to toluene, butyl acetate, cyclohexanone and pyridine, but is first-order with respect to NMP and DMF without distinction for the two kinds of hydroxyl groups.

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Acknowledgment

The work is supported by the National Natural Science Foundation Committee of China (Grant 20676074).

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Authors and Affiliations

  1. Shandong Provincial Key Laboratory of Fine Chemicals, Shandong Institute of Light Industry, Jinan, Shandong, 250353, China

    Yong De Han, Peng Fei Yang, Jun Ying Li, Cong De Qiao & Tian Duo Li

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  1. Yong De Han
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  2. Peng Fei Yang
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  3. Jun Ying Li
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  4. Cong De Qiao
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  5. Tian Duo Li
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Correspondence to Tian Duo Li.

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Han, Y.D., Yang, P.F., Li, J.Y. et al. The reaction of o-hydroxybenzyl alcohol with phenyl isocyanate in polar solvents. Reac Kinet Mech Cat 101, 41–48 (2010). https://doi.org/10.1007/s11144-010-0202-2

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  • DOI: https://doi.org/10.1007/s11144-010-0202-2

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