Aarhus University Seal

Design of a green chemoenzymatic cascade for scalable synthesis of bio-based styrene alternatives

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaperJournal articleResearchpeer-review

  • Philipp Petermeier
  • Jan Philipp Bittner, Hamburg University of Technology
  • ,
  • Simon Müller, Hamburg University of Technology
  • ,
  • Emil Byström, SpinChem AB
  • ,
  • Selin Kara

As renewable lignin building blocks, hydroxystyrenes are particularly appealing as either a replacement or addition to styrene-based polymer chemistry. These monomers are obtained by decarboxylation of phenolic acids and often subjected to chemical modifications of their phenolic hydroxy groups to improve polymerization behaviour. Despite efforts, a simple, scalable, and purely (chemo)catalytic synthesis of acetylated hydroxystyrenes remains elusive. We thus propose a custom-made chemoenzymatic route that utilizes a phenolic acid decarboxylase (PAD). Our process development strategy encompasses a computational solvent assessment informing about solubilities and viable reactor operation modes, experimental solvent screening, cascade engineering, heterogenization of biocatalyst, tailoring of acetylation conditions, and reaction upscale in a rotating bed reactor. By this means, we established a clean one-pot two-step process that uses the renewable solvent CPME, bio-based phenolic acid educts and reusable immobilised PAD. The overall chemoenzymatic reaction cascade was demonstrated on a 1 L scale to yield 18.3 g 4-acetoxy-3-methoxystyrene in 96% isolated yield.

Original languageEnglish
JournalGreen Chemistry
Volume24
Issue18
Pages (from-to)6889-6899
Number of pages11
ISSN1463-9262
DOIs
Publication statusPublished - Sep 2022

    Research areas

  • CATECHOL, CHEMISTRY, CINNAMIC-ACIDS, DECARBOXYLATION, LIQUID-LIQUID EQUILIBRIA, PLUS WATER, POLYMERIZATION, POLYMERS, SOLUBILITY, SOLVENTS

See relations at Aarhus University Citationformats

ID: 279974840