Issue 10, 2014

Lysinol: a renewably resourced alternative to petrochemical polyamines and aminoalcohols

Abstract

This paper reports the preparation of lysinol (2,6-diamino-1-hexanol) by the hydrogenation of lysine and an example of its use as a replacement for petrochemical-derived amines. Lysine is presently manufactured by fermentation of sugars and other carbon sources at scale exceeding 109 kg per year. Therefore, lysinol is potentially a renewable, platform aminoalcohol of previously unrecognized potential. Lysine hydrogenation proceeds under relatively modest conditions with Ru/C catalyst in water (100–150 °C, 48–70 bar, pH 1.5–2) to give lysinol in good yield (100% conversion, >90% selectivity; 50–70% isolated yield after purification by distillation). The impact of the various reaction parameters on conversion and selectivity are presented and discussed. Lysine hydrogenation at higher temperatures provides a pathway to piperidines and other products via further reduction and elimination of lysinol. The feasibility of lysinol synthesis from commodity, animal feed-grade lysine sources is presented as well. An example of the potential utility of lysinol is demonstrated by its use as a diamine curing agent with a standard epoxy resin. The properties of the resulting thermoset are contrasted with that obtained with a typical petrochemical amine used in this application (diethylenetriamine, DETA).

Graphical abstract: Lysinol: a renewably resourced alternative to petrochemical polyamines and aminoalcohols

Supplementary files

Article information

Article type
Paper
Submitted
22 Jun 2014
Accepted
28 Jul 2014
First published
06 Aug 2014

Green Chem., 2014,16, 4575-4586

Author version available

Lysinol: a renewably resourced alternative to petrochemical polyamines and aminoalcohols

P. S. Metkar, M. A. Scialdone and K. G. Moloy, Green Chem., 2014, 16, 4575 DOI: 10.1039/C4GC01167H

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