Application L2502

Intensified, Kilogram-Scaled, and Environment-Friendly: Chemoenzymatic Synthesis of Bio-Based Acylated Hydroxystyrenes

Philipp Petermeier, Pablo Domínguez de María, Emil Byström, Selin Kara

ACS Sustainable Chem. Eng. 2024, 12(34), 12869−12878

“… Herein, we demonstrate the production of 1 kg of 4-acetoxy-3-methoxy-styrene in a 10 L reactor and present practical adjustments to the up- and downstream processing that warrant a straightforward process and high isolated yields. Additionally, an environmental assessment is conducted, … the total CO2 production of the process is studied, including contributions from energy use and the treatment of generated wastes. … Overall, the holistic assessment of the process, its optimization, scale-up, product isolation, and environmental analysis indicate the feasibility of multistep chemoenzymatic reactions to deliver high-volume, low-value chemicals from biorefineries.”

A graph showing temperature and conversion data over a 12-hour reaction process, with three plotted lines: water jacket temperature, decarboxylation, and acetylation rates. Below are five photographs showing the reaction progression in a reactor vessel, from initial decarboxylation (white mixture) through to final phase separation, demonstrating visual changes in the mixture from clear to brown, followed by mixing, quenching, and final separation into distinct layers. — The image shows a graph with temperature and conversion data over time, accompanied by a series of five reactor photographs showing different stages of the process. The graph displays three lines: temperature (water jacket), decarboxylation, and acetylation, plotted against time over approximately 12 hours. Below the graph are five photographs of a reactor vessel showing the visual progression of the reaction from Decarboxylation start to Phase separation after quench.

A simple green line drawing showing a handshake between two hands, with a dollar sign on the left and a leaf symbol on the right. Below the handshake are process metrics including concentration (>100 g/L), productivity (>15 g/L/h), yield (>95%), waste factor (7 kg waste per kg product), and CO2 emissions (13 kg CO2 per kg product). — *Key performance metrics of the kilogram-scale chemoenzymatic synthesis, combining economic viability with environmental considerations*

Keywords: reaction cascade, styrene alternatives, carbon dioxide equivalents, green solvents, phenolic acids, polymer precursors

Highlights:

“The reaction cascade was conducted on a 120 mL lab scale using the SpinChem rotating bed reactor S2 in a 200 mL baffled glass reactor”
“Once the refined workup procedure was demonstrated on the lab scale, the reaction cascade was conducted on a 10 L scale to produce 1 kg AMS in a single batch.”
“Promising environmental metrics of the kilogram-scaled system, based on the E factor and the total CO2 released.”