Alkylation of lignin-derived aromatic oxygenates with cyclic alcohols on acidic zeolites

Liu, Yuanshuai; Cheng, Guanhua; Baráth, Eszter; Shi, Hui; Lercher, Johannes A.

doi:10.1016/j.apcatb.2020.119424

Alkylation of lignin-derived aromatic oxygenates with cyclic alcohols on acidic zeolites

Journal Article · Thu Aug 13 00:00:00 EDT 2020 · Applied Catalysis B: Environmental

DOI:https://doi.org/10.1016/j.apcatb.2020.119424· OSTI ID:1671015

^[1]; Cheng, Guanhua ^[1]; Baráth, Eszter ^[1]; ^[2]; Lercher, Johannes A. ^[3]

Technische Univ. Munchen, Garching (Germany)
Yangzhou Univ. (China); Technische Univ. Munchen, Garching (Germany)
Technische Univ. Munchen, Garching (Germany); Pacific Northwest National Lab. (PNNL), Richland, WA (United States)

Moderately strong BAS and spacious microporous environments (i.e., large-pore acidic zeolites HBEA and HY) are important criteria for efficient alkylation of phenols with cyclic alcohols and alkenes, while very strong BAS appear to be responsible for catalyst deactivation. BAS confined in HBEA and HY pores show substantially higher turnover frequencies compared to solids without molecularly sized pore constraints. HBEA favors the formation of mono-alkylates, while enhanced formation of di-alkylates is observed on HY. Dehydration of alcohols always dominates over the alkylation at the onset of the reaction. Carbenium ions, the direct electrophile for aromatic oxygenates, are produced mainly from the adsorption and protonation of olefins. The present study shows that for the alkylation of phenols and cyclic alcohols in apolar liquids, the alcohol concentration should be kept low to avoid the formation of unreactive surface dimers and mitigate their inhibitory effects on olefin adsorption and protonation.

View Accepted Manuscript (DOE)

Research Organization:: Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)

Sponsoring Organization:: USDOE; USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division

Grant/Contract Number:: AC05-76RL01830

OSTI ID:: 1671015

Alternate ID(s):: OSTI ID: 1778306

Report Number(s):: PNNL-SA--155226

Journal Information:: Applied Catalysis B: Environmental, Journal Name: Applied Catalysis B: Environmental Vol. 281; ISSN 0926-3373

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
alkylation
aromatic oxygenates
phenol
reaction pathways
zeolites

Alkylation of lignin-derived aromatic oxygenates with cyclic alcohols on acidic zeolites

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