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Sustainable Synthesis of Non‐Isocyanate Polyurethanes Based on Renewable 2,3‐Butanediol

Kirchberg, Anja 1; Khabazian Esfahani, Masood 2; Röpert, Marie-Christin 2; Wilhelm, Manfred 2; Meier, Michael A. R. 1,3
1 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)
2 Institut für Technische Chemie und Polymerchemie (ITCP), Karlsruher Institut für Technologie (KIT)
3 Institut für Biologische und Chemische Systeme (IBCS), Karlsruher Institut für Technologie (KIT)


In this work, three different cyclic carbonates are obtained from renewable diols and transformed into carbamates by reacting them with renewable 11-amino undecanoic acid methyl ester to synthesize non-isocyanate poly(ester urethane)s in a sustainable manner. A procedure using 2,3-butanediol (2,3-BDO) as a renewable starting material to synthesize a cyclic carbonate with dimethyl carbonate (DMC) is introduced, catalyzed by 1,5,7-triazabicylco[4.4.0]dec-5-ene (TBD). Three purification strategies, i.e., column chromatography, extraction, and distillation, are compared regarding their E-Factors. Propylene glycol (PG) and ethylene glycol (EG) are used as alternative starting materials to broaden the substrate scope and compare material properties, their cyclic carbonates likewise react to carbamates with 11-amino undecanoic acid methyl ester. All carbamates are then polymerized in a bulk polycondensation reaction, yielding non-isocyanate polyurethanes (NIPUs), specifically poly (ester urethane)s, with molecular weights (M$_n$) up to 10 kDa. Complete characterization is reported using differential scanning calorimetric (DSC), size exclusion chromatographic measurements (SEC), $^1$H-NMR as well as IR spectroscopy. ... mehr

Verlagsausgabe §
DOI: 10.5445/IR/1000146542
Veröffentlicht am 08.11.2022
DOI: 10.1002/macp.202200010
Zitationen: 2
Web of Science
Zitationen: 2
Zitationen: 2
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Biologische und Chemische Systeme (IBCS)
Institut für Organische Chemie (IOC)
Institut für Technische Chemie und Polymerchemie (ITCP)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2022
Sprache Englisch
Identifikator ISSN: 1022-1352, 0025-116X, 1521-3935
KITopen-ID: 1000146542
HGF-Programm 43.33.11 (POF IV, LK 01) Adaptive and Bioinstructive Materials Systems
Erschienen in Macromolecular Chemistry and Physics
Verlag Wiley-VCH Verlag
Band 223
Heft 13
Seiten Art.-Nr.: 2200010
Vorab online veröffentlicht am 07.05.2022
Nachgewiesen in Dimensions
Web of Science
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