Enzymatic polymerization of dimethyl 2,5-furandicarboxylate and heteroatom diamines

  • Previously, we have synthesized a diverse range of 2,5-furandicarboxylic acid (FDCA)-based semiaromatic polyamides via enzymatic polymerization. This novel class of polymers are biobased alternatives to polyphthalamides, which are petrol-based semiaromatic polyamides. From a commercial perspective, they have interesting properties as high-performance materials and engineering thermoplastics. It is even more appealing to explore novel FDCA-based polyamides with added functionality, for the development of sustainable functional materials. Here, a set of FDCA-based heteroatom polyamides have been successfully produced via Novozyme 435 (N435)-catalyzed polymerization of biobased dimethyl 2,5-furandicarboxylate with (potentially)heteroatom diamines, namely, 4,9-dioxa-1,12-dodecanediamine (DODA), diethylenetriamine, and 3,3-ethylenediiminopropylamine. We performed the enzymatic polymerization in solution and bulk. The latter approach is more sustainable and results in higher molecular weight products. Among the tested heteroatom diamines, N435 shows the highest catalytic activity toward DODA. Furthermore, we find that all obtained FDCA-based heteroatom polyamides are amorphous materials with a relatively high thermal stability. These heteroatom polyamides display a glass-transition temperature ranging from 41 to 107 °C.

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Author:Dina Maniar, Katharina F. Hohmann, Yi Jiang, Albert J. J. Woortman, Jur van Dijken, Katja Loos
Pubmed Id:https://pubmed.ncbi.nlm.nih.gov/30259005
Parent Title (English):ACS omega
Publisher:ACS Publications
Place of publication:Washington, DC
Document Type:Article
Year of Completion:2018
Date of first Publication:2018/06/28
Publishing Institution:Universitätsbibliothek Johann Christian Senckenberg
Release Date:2018/10/11
Tag:Polyamides; Polymerization (Polymers)
Page Number:9
First Page:7077
Last Page:7085
ACS AuthorChoice - This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License, which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
Institutes:Biochemie, Chemie und Pharmazie / Biochemie und Chemie
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Licence (German):License LogoCreative Commons - Namensnennung-Nicht kommerziell - Keine Bearbeitung 4.0