Acid-Catalyzed α-O-4 Aryl-Ether Cleavage Mechanisms in (Aqueous) γ-Valerolactone: Catalytic Depolymerization Reactions of Lignin Model Compound During Organosolv Pretreatment
| Autor: | Edita Jasiukaitytė-Grojzdek, Miha Grilc, Blaž Likozar, Matej Huš |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Lignin isolation
Reaction mechanism organosolv General Chemical Engineering Organosolv lignin ▫$gamma-valerolactone$▫ Ether 02 engineering and technology 010402 general chemistry 01 natural sciences γ-Valerolactone Hydrolysis chemistry.chemical_compound Ether bond Environmental Chemistry Organic chemistry lignin isolation Ether cleavage Bond cleavage ▫$alpha-O-4$▫ Renewable Energy Sustainability and the Environment Depolymerization Chemistry Aryl ether bond General Chemistry 021001 nanoscience & nanotechnology 0104 chemical sciences analizna kemija udc:544.3/.4 kataliza α-O-4 0210 nano-technology Research Article |
| Zdroj: | ACS Sustainable Chemistry & Engineering ACS sustainable chemistry & engineering, vol. 8, no. 47, pp. 17475-17486, 2020. |
| ISSN: | 2168-0485 |
| DOI: | 10.1021/acssuschemeng.0c06099 |
| Popis: | In this study, acidolysis of benzyl phenyl ether (BPE), being a representative lignin model compound with the α-O-4 linkage, was examined in γ-valerolactone (GVL) and a GVL/water mixture, each time acidified with sulfuric acid. The product distribution was strongly affected by water used as a cosolvent, which was found to be advantageous by inhibiting the formation of larger structures and introducing reactive OH groups instead. The experimental results indicate the GVL/water ratio as an important parameter to attain an optimal hydrolytic α-ether bond cleavage. Differences between the organosolv lignins (molecular weight distribution, OH group content, and structural features with reaction time), isolated under moderate reaction conditions, supported the findings obtained using BPE. A beneficial effect of the added water is reflected in the higher aliphatic OH group content and less intact structure. Analysis of the reaction mechanism represents an initial step toward kinetics and structure–activity correlation of biorefining industrial resources. A lignin model compound was found to accurately mimic lignin depolmerization/structural changes during the organosolv pulping in γ-valerolactone/water. |
| Databáze: | OpenAIRE |
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