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Low‐Temperature Reductive Aminolysis of Carbohydrates to Diamines and Aminoalcohols by Heterogeneous Catalysis

Abstract

Short amines, such as ethanolamines and ethylenediamines, are important compounds in today's bulk and fine chemicals industry. Unfortunately, current industrial manufacture of these chemicals relies on fossil resources and requires rigorous safety measures when handling explosive or toxic intermediates. Inspired by the elegant working mechanism of aldolase enzymes, a novel heterogeneously catalyzed process—reductive aminolysis—was developed for the efficient production of short amines from carbohydrates at low temperature. High‐value bio‐based amines containing a bio‐derived C2 carbon backbone were synthesized in one step with yields up to 87 C%, in the absence of a solvent and at a temperature below 405 K. A wide variety of available primary and secondary alkyl‐ and alkanolamines can be reacted with the carbohydrate to form the corresponding C2‐diamine. The presented reductive aminolysis is therefore a promising strategy for sustainable synthesis of short, acyclic, bio‐based amines.

Aminreagentien befördern die Spaltung von C‐C‐Bindungen in der reduktiven Aminolyse von Kohlenhydraten. Kurze Diamine und Aminoalkohole werden bei tiefen Temperature in der Gegenwart von heterogenen Metallkatalysatoren gebildet.

Authors:   Michiel Pelckmans, Walter Vermandel, Frederik Van Waes, Kristof Moonen, Bert F. Sels; Michiel Pelckmans, Walter Vermandel, Frederik Van Waes, Kristof Moonen, Bert F. Sels
Journal:   Angewandte Chemie
Volume:   129
edition:   46
Year:   2017
Pages:   14732
DOI:   10.1002/ange.201708216
Publication date:   13-Oct-2017
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