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Reductive Amination of 5-Hydroxymethylfurfural by the Hydrogenation of Intermediate Imines in the Presence of a Pt/Al2O3 Catalyst in a Flow Reactor

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Abstract

The catalytic properties of a platinum catalyst supported on γ-alumina in the hydrogenation of imines formed during the condensation of 5-hydroxymethylfurfural (HMF) with primary amines in methanol have been studied. The reaction has been run in a flow reactor at a hydrogen pressure of 5 bar and a temperature of 15–65ºC. It has been found that the reductive amination of HMF with n-hexylamine; aniline; ortho-, meta-, and para-toluidines; and aniline derivatives containing F, Cl, Br, and I substituents at the para- or meta-positions leads to the formation of N-substituted 5-hydroxymethyl-2-furfuryl amines with high yields (90–99%). At the same time, the reaction of HMF with aromatic amines exhibiting weak nucleophilic properties (o-chloroaniline, p-aminoacetophenone) provides a target product yield that does not exceed 52%.

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Funding

This work was supported by the Russian Science Foundation (project no. 20-43-05002).

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Correspondence to A. L. Nuzhdin.

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The authors declare that they have no conflicts of interest.

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Translated by M. Timoshinina

Abbreviations and designations: HMF, 5-hydroxymethylfurfural; AMHMF, aminomethylhydroxymethylfuran derivatives; HRTEM, high-resolution transmission electron microscopy.

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Nuzhdin, A.L., Simonov, P.A. & Bukhtiyarov, V.I. Reductive Amination of 5-Hydroxymethylfurfural by the Hydrogenation of Intermediate Imines in the Presence of a Pt/Al2O3 Catalyst in a Flow Reactor. Kinet Catal 62, 507–512 (2021). https://doi.org/10.1134/S0023158421040091

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  • DOI: https://doi.org/10.1134/S0023158421040091

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