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

verfasst von

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

Abstract

Lignin-derived styrene derivatives are versatile building blocks for the manufacture of biobased polymers. As shown previously, phenol-protected hydroxystyrenes are accessible under industrially sound conditions (>100 g L^-1, >95% yield) by subjecting biogenic phenolic acids to enzymatic decarboxylation and base-catalyzed acylation in nonaqueous media (wet cyclopentyl methyl ether, CPME). 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, starting with a thorough E factor analysis to identify the sources that contribute most to the environmental burden (solvent and downstream processing). Also, the total CO₂ production of the process is studied, including contributions from energy use and the treatment of generated wastes. The energy impact is evaluated through thermodynamic analysis, and the environmental footprint contributions by wastes-organic and aqueous fractions-are assessed based on CO₂ emissions from solvent incineration and wastewater treatment, respectively. 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.

Organisationseinheit(en)

Institut für Technische Chemie

Externe Organisation(en)

Aarhus University
SpinChem AB
Sustainable Momentum SL

Typ

Artikel

Journal

ACS Sustainable Chemistry and Engineering

Band

12

Seiten

12869-12878

Anzahl der Seiten

10

ISSN

2168-0485

Publikationsdatum

26.08.2024

Publikationsstatus

Veröffentlicht

Peer-reviewed

Ja

ASJC Scopus Sachgebiete

Chemie (insg.), Umweltchemie, Chemische Verfahrenstechnik (insg.), Erneuerbare Energien, Nachhaltigkeit und Umwelt

Ziele für nachhaltige Entwicklung

SDG 7 – Erschwingliche und saubere Energie, SDG 12 – Verantwortungsvoller Konsum und Produktion

Elektronische Version(en)

https://doi.org/10.1021/acssuschemeng.4c03648 (Zugang: Offen)