Probing direct carbon-carbon acylation of furans and long-chain acids over H-ZSM-5

Yichen Ji; Jie Pan; Paul Dauenhauer; Raymond J. Gorte

doi:10.1016/j.apcata.2019.03.012

Probing direct carbon-carbon acylation of furans and long-chain acids over H-ZSM-5

Yichen Ji, Jie Pan, Paul Dauenhauer, Raymond J. Gorte

Chemical Engineering and Materials Science

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

Abstract

The acylation of furan and 2-methylfuran (2-MF) with acetic acid (AA) and 1-hexanoic acid (HA) was studied over an H-ZSM-5 catalyst. Temperature-programmed desorption (TPD) measurements showed evidence that AA adsorbs strongly at Brønsted sites, with reaction to CO₂ and acetone beginning at 523 K, while both furan and 2-MF oligomerize upon adsorption at room temperature. Steady-state, flow-reactor measurements demonstrate that selectivities for the acylation reactions can approach 100% below 523 K when reactions are operated in excess organic acids, with maximum conversion limited by equilibrium. Coking becomes important when the reaction is operated in excess furan or 2-MF and at high reactant concentrations, while ketonization products are observed when the reaction is performed above 523 K. Potential uses for the reactions are discussed.

Original language	English (US)
Pages (from-to)	107-112
Number of pages	6
Journal	Applied Catalysis A: General
Volume	577
DOIs	https://doi.org/10.1016/j.apcata.2019.03.012
State	Published - May 5 2019

Bibliographical note

Funding Information:
We acknowledge support from the Catalysis Center for Energy Innovation, an Energy Frontier Research Center funded by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under Award no. DE-SC0001004.

Publisher Copyright:
© 2019 Elsevier B.V.

Keywords

1-Hexanoic acid
2-Methylfuran
Acetic acid
Acylation reaction
Furan
H-ZSM-5

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title = "Probing direct carbon-carbon acylation of furans and long-chain acids over H-ZSM-5",

abstract = "The acylation of furan and 2-methylfuran (2-MF) with acetic acid (AA) and 1-hexanoic acid (HA) was studied over an H-ZSM-5 catalyst. Temperature-programmed desorption (TPD) measurements showed evidence that AA adsorbs strongly at Br{\o}nsted sites, with reaction to CO2 and acetone beginning at 523 K, while both furan and 2-MF oligomerize upon adsorption at room temperature. Steady-state, flow-reactor measurements demonstrate that selectivities for the acylation reactions can approach 100% below 523 K when reactions are operated in excess organic acids, with maximum conversion limited by equilibrium. Coking becomes important when the reaction is operated in excess furan or 2-MF and at high reactant concentrations, while ketonization products are observed when the reaction is performed above 523 K. Potential uses for the reactions are discussed.",

keywords = "1-Hexanoic acid, 2-Methylfuran, Acetic acid, Acylation reaction, Furan, H-ZSM-5",

author = "Yichen Ji and Jie Pan and Paul Dauenhauer and Gorte, {Raymond J.}",

note = "Funding Information: We acknowledge support from the Catalysis Center for Energy Innovation, an Energy Frontier Research Center funded by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under Award no. DE-SC0001004. Publisher Copyright: {\textcopyright} 2019 Elsevier B.V.",

year = "2019",

month = may,

day = "5",

doi = "10.1016/j.apcata.2019.03.012",

language = "English (US)",

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journal = "Applied Catalysis A: General",

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T1 - Probing direct carbon-carbon acylation of furans and long-chain acids over H-ZSM-5

AU - Ji, Yichen

AU - Pan, Jie

AU - Dauenhauer, Paul

AU - Gorte, Raymond J.

N1 - Funding Information: We acknowledge support from the Catalysis Center for Energy Innovation, an Energy Frontier Research Center funded by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under Award no. DE-SC0001004. Publisher Copyright: © 2019 Elsevier B.V.

PY - 2019/5/5

Y1 - 2019/5/5

N2 - The acylation of furan and 2-methylfuran (2-MF) with acetic acid (AA) and 1-hexanoic acid (HA) was studied over an H-ZSM-5 catalyst. Temperature-programmed desorption (TPD) measurements showed evidence that AA adsorbs strongly at Brønsted sites, with reaction to CO2 and acetone beginning at 523 K, while both furan and 2-MF oligomerize upon adsorption at room temperature. Steady-state, flow-reactor measurements demonstrate that selectivities for the acylation reactions can approach 100% below 523 K when reactions are operated in excess organic acids, with maximum conversion limited by equilibrium. Coking becomes important when the reaction is operated in excess furan or 2-MF and at high reactant concentrations, while ketonization products are observed when the reaction is performed above 523 K. Potential uses for the reactions are discussed.

AB - The acylation of furan and 2-methylfuran (2-MF) with acetic acid (AA) and 1-hexanoic acid (HA) was studied over an H-ZSM-5 catalyst. Temperature-programmed desorption (TPD) measurements showed evidence that AA adsorbs strongly at Brønsted sites, with reaction to CO2 and acetone beginning at 523 K, while both furan and 2-MF oligomerize upon adsorption at room temperature. Steady-state, flow-reactor measurements demonstrate that selectivities for the acylation reactions can approach 100% below 523 K when reactions are operated in excess organic acids, with maximum conversion limited by equilibrium. Coking becomes important when the reaction is operated in excess furan or 2-MF and at high reactant concentrations, while ketonization products are observed when the reaction is performed above 523 K. Potential uses for the reactions are discussed.

KW - 1-Hexanoic acid

KW - 2-Methylfuran

KW - Acetic acid

KW - Acylation reaction

KW - Furan

KW - H-ZSM-5

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JO - Applied Catalysis A: General

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ER -

Probing direct carbon-carbon acylation of furans and long-chain acids over H-ZSM-5

Abstract

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