Replacing benzyl chloride with benzyl alcohol in heterogeneous catalytic benzylation of aromatic compounds

Author:

Candu Natalia1,Wuttke Stefan2,Kemnitz Erhard3,Coman Simona M.1,Pârvulescu Vasile I.1

Affiliation:

1. 1Department of Organic Chemistry, Biochemistry and Catalysis, Faculty of Chemistry, University of Bucharest, Bdul Regina Elisabeta, 4-12, Bucharest, 030016, Romania

2. 2Department of Chemistry, University of Munich (LMU), Butenandstr. 5-13 (E), D-81377 Munich, Germany

3. 3Institut für Chemie, Humboldt-Universität zu Berlin, Brook-Taylor-Straße 2, D-12489 Berlin, Germany

Abstract

Comparative catalytic liquid-phase benzylation of aromatic compouds (e.g., benzene and ethylbenzene) to diphenylmethane (DPM) derivatives with benzyl alcohol (BnOH) was investigated over various catalysts like zeolite (HSZ 600 mordenite, CBV 20A mordenite, H-beta zeolites with Si/Al ratios of 10.8 and 35.8, respectively) and nano-structured inorganic fluorides (MgF2) at 80–120 °C under atmospheric pressure. The reactions were carried out in batch reactors using two methodologies: (i) by introducing both the solution of substrate and BnOH at the beginning of the reaction, and (ii) by drop-wise addition of BnOH (1–2 drops/min for 4 h) to the reaction mixture. The analysis of the reaction products indicated that the conversion and product distribution depend on the experimental method and the nature of the catalyst. The reaction rate was found to correlate to the nucleophilicity of the substrates and their ability to delocalize the positive charge in the Wheland intermediate by inductive and resonance effects.

Publisher

Walter de Gruyter GmbH

Subject

General Chemical Engineering,General Chemistry

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