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Acid-Catalyzed α-O-4 Aryl-Ether Cleavage Mechanisms in (Aqueous) γ-Valerolactone: Catalytic Depolymerization Reactions of Lignin Model Compound During Organosolv Pretreatment

[Image: see text] 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 wate...

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Detalles Bibliográficos
Autores principales: Jasiukaitytė-Grojzdek, Edita, Huš, Matej, Grilc, Miha, Likozar, Blaž
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7735783/
https://www.ncbi.nlm.nih.gov/pubmed/33335815
http://dx.doi.org/10.1021/acssuschemeng.0c06099
Descripción
Sumario:[Image: see text] 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.