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Pelckmans M, Vermandel W, Van Waes F, et al. Low-Temperature Reductive Aminolysis of Carbohydrates to Diamines and Aminoalcohols by Heterogeneous Catalysis. Angew Chem Int Ed Engl. 2017;56(46):14540-14544doi: 10.1002/anie.201708216.
Pelckmans, M., Vermandel, W., Van Waes, F., Moonen, K., & Sels, B. F. (2017). Low-Temperature Reductive Aminolysis of Carbohydrates to Diamines and Aminoalcohols by Heterogeneous Catalysis. Angewandte Chemie (International ed. in English), 56(46), 14540-14544. https://doi.org/10.1002/anie.201708216
Pelckmans, Michiel, et al. "Low-Temperature Reductive Aminolysis of Carbohydrates to Diamines and Aminoalcohols by Heterogeneous Catalysis." Angewandte Chemie (International ed. in English) vol. 56,46 (2017): 14540-14544. doi: https://doi.org/10.1002/anie.201708216
Pelckmans M, Vermandel W, Van Waes F, Moonen K, Sels BF. Low-Temperature Reductive Aminolysis of Carbohydrates to Diamines and Aminoalcohols by Heterogeneous Catalysis. Angew Chem Int Ed Engl. 2017 Nov 13;56(46):14540-14544. doi: 10.1002/anie.201708216. Epub 2017 Oct 13. PMID: 28892238.
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Angew Chem Int Ed Engl. 2017 Nov 13;56(46):14540-14544. doi: 10.1002/anie.201708216. Epub 2017 Oct 13.

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

Angewandte Chemie (International ed. in English)

Michiel Pelckmans, Walter Vermandel, Frederik Van Waes, Kristof Moonen, Bert F Sels

Affiliations

  1. Centre for Surface Chemistry and Catalysis, KU Leuven, Celestijnenlaan 200F, 3001, Leuven, Belgium.
  2. Eastman Chemical Company, Technologiepark 21, 9000, Ghent, Belgium.

PMID: 28892238 DOI: 10.1002/anie.201708216

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.

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: amines; biomass; heterogeneous catalysis; retro-aldol

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