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Renewable Rigid Diamines: Efficient, Stereospecific Synthesis of High Purity Isohexide Diamines

Authors

  • Dr. Shanmugam Thiyagarajan,

    1. Food & Biobased Research, Wageningen University & Research Centre, P.O. Box 17, 6700 AA Wageningen (The Netherlands), Fax: (+31) 317 483011
    2. Dutch Polymer Institute, P.O. Box 902, 5600 AX, Eindhoven (The Netherlands)
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  • Linda Gootjes,

    1. Food & Biobased Research, Wageningen University & Research Centre, P.O. Box 17, 6700 AA Wageningen (The Netherlands), Fax: (+31) 317 483011
    2. Dutch Polymer Institute, P.O. Box 902, 5600 AX, Eindhoven (The Netherlands)
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  • Willem Vogelzang,

    1. Food & Biobased Research, Wageningen University & Research Centre, P.O. Box 17, 6700 AA Wageningen (The Netherlands), Fax: (+31) 317 483011
    2. Dutch Polymer Institute, P.O. Box 902, 5600 AX, Eindhoven (The Netherlands)
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  • Dr. Jacco van Haveren,

    1. Food & Biobased Research, Wageningen University & Research Centre, P.O. Box 17, 6700 AA Wageningen (The Netherlands), Fax: (+31) 317 483011
    2. Dutch Polymer Institute, P.O. Box 902, 5600 AX, Eindhoven (The Netherlands)
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  • Dr. Martin Lutz,

    1. Bijvoet Center for Biomolecular Research, Crystal and Structural Chemistry, Utrecht University, Padualaan 8, 3584, Utrecht (The Netherlands)
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  • Dr. Daan S. van Es

    Corresponding author
    1. Food & Biobased Research, Wageningen University & Research Centre, P.O. Box 17, 6700 AA Wageningen (The Netherlands), Fax: (+31) 317 483011
    2. Dutch Polymer Institute, P.O. Box 902, 5600 AX, Eindhoven (The Netherlands)
    • Food & Biobased Research, Wageningen University & Research Centre, P.O. Box 17, 6700 AA Wageningen (The Netherlands), Fax: (+31) 317 483011
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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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