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

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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.
Original languageEnglish
Pages (from-to)1823-1829
JournalChemSusChem
Volume4
Issue number12
DOIs
Publication statusPublished - 2011

Keywords

  • chiral building-blocks
  • polyesters
  • polycondensation
  • derivatives
  • polyamides
  • resources

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