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

Philipp Petermeier, Jan Philipp Bittner, Simon Müller, Emil Byström, Selin Kara*

*Corresponding author for this work

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

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Abstract

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 - Sept 2022

Keywords

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

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