Application L2204 Green Chemistry, Issue 18, 2022

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

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

Green Chemistry, 2022, 24(18), pp. 6889-6899.

“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.”




  • “To facilitate easy biocatalyst recovery after the first reaction step, we decided for a rotating bed reactor…”
  • “…the solvent was evaporated under reduced pressure to give 18.3 g of the product AMS (96% yield, 99% HPLC purity)…”
  • “… a heterogenized biocatalyst allows compartmentalization, recovery, and reuse, all potentially enhancing its practical applicability and productivity.”

Privacy Policy

This website uses cookies to ensure you get the best experience on our website. If you continue browsing, you agree to the privacy policy.