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.
A catalytic reductive aminolysis of reducing monosaccharides into short ethylene diamines (or C 2 diamines) was recently communicated by our group (Pelckmans et al.
Short amines,s uch as ethanolamines and ethylenediamines,a re important compounds in todaysb ulk and fine chemicals industry.U nfortunately,c urrent industrial manufacture of these chemicals relies on fossil resources and requires rigorous safety measures when handling explosive or toxici ntermediates.I nspired by the elegant working mechanism of aldolase enzymes,anovel heterogeneously catalyzed process-reductive aminolysis-was developed for the efficient production of short amines from carbohydrates at low temperature.H igh-value bio-based amines containing ab ioderived C2 carbon backbone were synthesized in one step with yields up to 87 C%, in the absence of as olvent and at at emperature below4 05 K. Aw ide variety of available primary and secondary alkyl-and alkanolamines can be reacted with the carbohydrate to form the corresponding C2diamine.T he presented reductive aminolysis is therefore apromising strategy for sustainable synthesis of short, acyclic, bio-based amines. Scheme 1. Twopossible bio-based routes to C2-amines from glucose.
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