Renewable Rigid Diamines: Efficient, Stereospecific Synthesis of High Purity Isohexide Diamines
| Autor: | Thiyagarajan, S., Gootjes, L., Vogelzang, W., van Haveren, J., Lutz, M., van Es, D.S., Rontgen participation programme, Sub Crystal and Structural Chemistry |
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| Přispěvatelé: | Rontgen participation programme, Sub Crystal and Structural Chemistry |
| Jazyk: | angličtina |
| Rok vydání: | 2011 |
| Předmět: |
Conservation of Natural Resources
Magnetic Resonance Spectroscopy Materials science Isosorbide Condensation polymer Polymers General Chemical Engineering Diamines polyesters Stereospecificity X-Ray Diffraction Bridged Bicyclo Compounds BBP Sustainable Chemistry & Technology chiral building-blocks medicine Environmental Chemistry Organic chemistry General Materials Science Biobased Products polyamides chemistry.chemical_classification Stereoisomerism Polymer Bridged Bicyclo Compounds Heterocyclic Polyester General Energy chemistry Yield (chemistry) derivatives Chirality (chemistry) polycondensation resources medicine.drug |
| Zdroj: | ChemSusChem, 4(12), 1823-1829 Chemistry & sustainability, energy & materials, 4(12), 1823. Wiley-VCH Verlag ChemSusChem 4 (2011) 12 |
| ISSN: | 1823-1829 1864-5631 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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