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Homogeneous pyrolysis kinetics of ethyl 3-hydroxy-3-methylbutanoate in the gas phase

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Abstract

The pyrolysis kinetics of ethyl 3-hydroxy-3-methylbutanoate have been examined over the temperature range of 286–330°C and pressure range of 29–108 Torr. In a seasoned vessel and in the presence of the free radical inhibitor cyclohexene or toluene the reaction is homogeneous, unimolecular and obeys a first-order rate law. The elimination products are mainly acetone and ethyl acetate, and very small amounts of ethyl 3-butenoate, acetic acid, ethylene and H2O. The rate coefficient is expressed by the following equation: log k1(s−1)=(12.39±0.46)−(174.5±5.2) kJ mol−1 (2.303RT)−1. The mechanism appears to proceed via a six-membered cyclic transition state, where polarization of the (CH3)C(OH)δ+...δ-CH2COOCH2CH3 bond is rate determining.

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Authors and Affiliations

  1. Centro de Química, Instituto Venezolano de Investigaciones Científicas (I.V.I.C.), Apartado 21827, 1020-A, Caracas, Venezuela

    Rosa M. Dominguez & Gabriel Chuchani

  2. Departamento de Química, Facultad de Ciencias, Universidad Nacional de Colombia, Apartado Aéreo 3840, Medellín, Colombia

    Jairo Quijano, Luz Janeth Orozco & Iliana Restrepo

Authors
  1. Rosa M. Dominguez
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  2. Gabriel Chuchani
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  3. Jairo Quijano
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  4. Luz Janeth Orozco
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  5. Iliana Restrepo
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Dominguez, R.M., Chuchani, G., Quijano, J. et al. Homogeneous pyrolysis kinetics of ethyl 3-hydroxy-3-methylbutanoate in the gas phase. React Kinet Catal Lett 57, 191–196 (1996). https://doi.org/10.1007/BF02076139

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  • DOI: https://doi.org/10.1007/BF02076139

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