Enzymatic Polymerization of Dimethyl 2,5-Furandicarboxylate and Heteroatom Diamines

Dina Maniar, Katharina F. Hohmann, Yi Jiang, Albert J. J. Woortman, Jurjen van Dijken, Katja Loos*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

29 Citations (Scopus)
237 Downloads (Pure)

Abstract

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 degrees C.

Original languageEnglish
Pages (from-to)7077-7085
Number of pages9
JournalACS Omega
Volume3
Issue number6
DOIs
Publication statusPublished - Jun-2018

Keywords

  • UNSATURATED ALIPHATIC POLYESTERS
  • RENEWABLE RESOURCES
  • CATALYZED SYNTHESIS
  • BIOBASED POLYESTERS
  • POLYAMIDES
  • ACID
  • POLYMERS
  • MONOMERS
  • FUTURE
  • FURANS

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