Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 419502
Title Renewable Rigid Diamines: Efficient, Stereospecific Synthesis of High Purity Isohexide Diamines
Author(s) Thiyagarajan, S.; Gootjes, L.; Vogelzang, W.; Haveren, J. van; Lutz, M.; Es, D.S. van
Source ChemSusChem 4 (2011)12. - ISSN 1864-5631 - p. 1823 - 1829.
DOI http://dx.doi.org/10.1002/cssc.201100398
Department(s) FBR Sustainable Chemistry & Technology
Biobased Products
Publication type Refereed Article in a scientific journal
Publication year 2011
Keyword(s) chiral building-blocks - polyesters - polycondensation - derivatives - polyamides - resources
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.
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