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Acceleration of Disproportionation of Aromatic Alcohols through Self-Emulsification of Reactants in Water

Authors

  • Binbin Zhang,

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid and Interface and Thermodynamics, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 (PR China), Fax: (+86) 10-62559373
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  • Dr. Jinliang Song,

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid and Interface and Thermodynamics, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 (PR China), Fax: (+86) 10-62559373
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  • Dr. Huizhen Liu,

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid and Interface and Thermodynamics, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 (PR China), Fax: (+86) 10-62559373
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  • Prof. Buxing Han,

    Corresponding author
    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid and Interface and Thermodynamics, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 (PR China), Fax: (+86) 10-62559373
    • Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid and Interface and Thermodynamics, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 (PR China), Fax: (+86) 10-62559373
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  • Prof. Tao Jiang,

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid and Interface and Thermodynamics, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 (PR China), Fax: (+86) 10-62559373
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  • Dr. Honglei Fan,

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid and Interface and Thermodynamics, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 (PR China), Fax: (+86) 10-62559373
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  • Dr. Zhaofu Zhang,

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid and Interface and Thermodynamics, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 (PR China), Fax: (+86) 10-62559373
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  • Dr. Tianbin Wu

    1. Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Colloid and Interface and Thermodynamics, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190 (PR China), Fax: (+86) 10-62559373
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Abstract

Exploration of new and effective routes to conduct organic reactions in water using the special properties of water/organics is of great importance. In this work, we performed the disproportionation of various aromatic alcohols in water and in different organic solvents. It was demonstrated that the disproportionation reactions of the alcohols were accelerated more effectively in water than organic-solvent-based or solvent-free reactions. A series of control experiments were conducted to study the mechanism of the accelerated reaction rate in water. It was shown that the reactants could emulsify the reactant/water systems at the reaction conditions owing to their amphiphilic nature. The regularly orientated reactant molecules at the water/reactant droplet interface improved the contact probability of the reactive groups and the Pd nanocatalysts, which is one of the main reasons for the enhanced reaction rate in water. Controlling the self-emulsification of amphiphilic reactant/water systems has great application potential for optimizing the rate and/or selectivity of many organic reactions.

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