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ChemSusChem. 2011 Dec 16;4(12):1823-9. doi: 10.1002/cssc.201100398. Epub 2011 Nov 25.

Renewable rigid diamines: efficient, stereospecific synthesis of high purity isohexide diamines.

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1
Food & Biobased Research, Wageningen University & Research Centre, Wageningen, The Netherlands.

Abstract

We report an efficient three-step strategy for synthesizing rigid, chiral isohexide diamines derived from 1,4:3,6-dianhydrohexitols. These biobased chiral building blocks are presently the subject of several investigations (in our and several other groups) because of their application in high-performance biobased polymers, such as polyamides and polyurethanes. Among the three possible stereo-isomers, dideoxy-diamino isoidide and dideoxy-diamino isosorbide can be synthesized from isomannide and isosorbide respectively in high yield with absolute stereo control. Furthermore, by using this methodology dideoxy-amino isomannide-a tricyclic adduct-was obtained starting from isoidide in high yield. Our improved synthetic route is a valuable advance towards meeting scale and purity demands for evaluating the properties of new biobased performance materials, which will benefit the development of these plastics.

PMID:
22121062
DOI:
10.1002/cssc.201100398
[Indexed for MEDLINE]
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