化学
愈创木酚
氢解
茴香醚
加氢脱氧
有机化学
催化作用
键裂
醋酸
木质素
反应性(心理学)
溶剂
药物化学
选择性
替代医学
病理
医学
作者
Charles Vriamont,Tianyi Chen,Charles Romain,Paul J. Corbett,Phornphit Manageracharath,Janet Peet,Christopher M. Conifer,Jason P. Hallett,George J. P. Britovsek
标识
DOI:10.1021/acscatal.8b04714
摘要
The catalytic hydrogenation of a series of lignin model compounds, including anisole, guaiacol, 1,2-dimethoxybenzene, 4-propyl-2-methoxyphenol, and syringol, has been investigated in detail, using a Ru/C catalyst in acetic acid as the solvent. Both hydrogenation of the aromatic unit and C–O bond cleavage are observed, resulting in a mixture of cyclohexanes and cyclohexanols, together with cyclohexyl acetates due to esterification with the solvent. The effect on product composition of the reaction parameters temperature (80–140 °C), pressure (10–40 bar), and reaction time (0.5–4 h) has been evaluated in detail. The lignin model compound 4-propyl-2-methoxyphenol was converted to 4-propylcyclohexanol in 4 h at 140 °C and 30 bar of H2 pressure with 84% conversion and 63% selectivity. Mechanistic studies on the reactivity of reaction intermediates have shown that C–O bond cleavage under these relatively mild conditions does not involve a C–O bond hydrogenolysis reaction but is due to elimination and hydrolysis reactions (or acetolysis in acetic acid solvent) of highly reactive cyclohexadiene- and cyclohexene-based enols, enol ethers, and allyl ethers.
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