Direct synthesis of partially ethoxylated branched polyethylenimine from ethanolamine

Claire N. Brodie, Alister S. Goodfellow, Matthew J. Andrews, Aniekan E. Owen, Michael Bühl () and Amit Kumar ()
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Claire N. Brodie: University of St Andrews
Alister S. Goodfellow: University of St Andrews
Matthew J. Andrews: University of St Andrews
Aniekan E. Owen: University of St Andrews
Michael Bühl: University of St Andrews
Amit Kumar: University of St Andrews

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract We report here a method to make a branched and partially ethoxylated polyethyleneimine derivative directly from ethanolamine. The polymerization reaction is catalysed by a pincer complex of Earth-abundant metal, manganese, and produces water as the only byproduct. Industrial processes to produce polyethyleneimines involve the transformation of ethanolamine to a highly toxic chemical, aziridine, by an energy-intensive/waste-generating process followed by the ring-opening polymerization of aziridine. The reported method bypasses the need to produce a highly toxic intermediate and presents advantages over the current state-of-the-art. We propose that the polymerization process follows a hydrogen borrowing pathway that involves (a) dehydrogenation of ethanolamine to form 2-aminoacetaldehyde, (b) dehydrative coupling of 2-aminoacetaldehyde with ethanolamine to form an imine derivative, and (c) subsequent hydrogenation of imine derivative to form alkylated amines.

Date: 2024
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DOI: 10.1038/s41467-024-50403-z

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