The effect of oxide acidity on HMF etherification

Jing Luo; Jingye Yu; Raymond J. Gorte; Eyas Mahmoud; Dionisios G. Vlachos; Michael A. Smith

doi:10.1039/c4cy00563e

The effect of oxide acidity on HMF etherification

Jing Luo
, Jingye Yu
, Raymond J. Gorte
, Eyas Mahmoud
, Dionisios G. Vlachos
, Michael A. Smith

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

91 Citations (Scopus)

Abstract

The liquid-phase (69 bar) reaction of 5-hydroxymethylfurfural (HMF) with 2-propanol for production of furanyl ethers was studied at 413 and 453 K over a series of oxide catalysts, including γ-Al₂O₃, ZrO₂, TiO₂, Al₂O₃/SBA-15, ZrO ₂/SBA-15, TiO₂/SBA-15, H-BEA, and Sn-BEA. The acidity of each of the catalysts was first characterized for Brønsted sites using TPD-TGA of 2-propanamine and for Lewis sites using TPD-TGA of 1-propanol. Catalysts with strong Brønsted acidity (H-BEA and Al₂O ₃/SBA-15) formed 5-[(1-methylethoxy)methyl]furfural with high selectivities, while materials with Lewis acidity (γ-Al₂O ₃, ZrO₂, TiO₂, and Sn-BEA) or weak Brønsted acidity (ZrO₂/SBA-15 and TiO₂/SBA-15) were active for transfer hydrogenation from the alcohol to HMF to produce 2,5-bis(hydroxymethyl)furan, with subsequent reactions to the mono- or di-ethers. Each of the catalysts was stable under the flow-reactor conditions but the selectivities varied with the particular oxide being investigated.

Original language	English
Pages (from-to)	3074-3081
Number of pages	8
Journal	Catalysis Science and Technology
Volume	4
Issue number	9
DOIs	https://doi.org/10.1039/c4cy00563e
Publication status	Published - Sept 2014
Externally published	Yes

ASJC Scopus subject areas

Catalysis

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title = "The effect of oxide acidity on HMF etherification",

abstract = "The liquid-phase (69 bar) reaction of 5-hydroxymethylfurfural (HMF) with 2-propanol for production of furanyl ethers was studied at 413 and 453 K over a series of oxide catalysts, including γ-Al2O3, ZrO2, TiO2, Al2O3/SBA-15, ZrO 2/SBA-15, TiO2/SBA-15, H-BEA, and Sn-BEA. The acidity of each of the catalysts was first characterized for Br{\o}nsted sites using TPD-TGA of 2-propanamine and for Lewis sites using TPD-TGA of 1-propanol. Catalysts with strong Br{\o}nsted acidity (H-BEA and Al2O 3/SBA-15) formed 5-[(1-methylethoxy)methyl]furfural with high selectivities, while materials with Lewis acidity (γ-Al2O 3, ZrO2, TiO2, and Sn-BEA) or weak Br{\o}nsted acidity (ZrO2/SBA-15 and TiO2/SBA-15) were active for transfer hydrogenation from the alcohol to HMF to produce 2,5-bis(hydroxymethyl)furan, with subsequent reactions to the mono- or di-ethers. Each of the catalysts was stable under the flow-reactor conditions but the selectivities varied with the particular oxide being investigated.",

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AU - Vlachos, Dionisios G.

AU - Smith, Michael A.

PY - 2014/9

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N2 - The liquid-phase (69 bar) reaction of 5-hydroxymethylfurfural (HMF) with 2-propanol for production of furanyl ethers was studied at 413 and 453 K over a series of oxide catalysts, including γ-Al2O3, ZrO2, TiO2, Al2O3/SBA-15, ZrO 2/SBA-15, TiO2/SBA-15, H-BEA, and Sn-BEA. The acidity of each of the catalysts was first characterized for Brønsted sites using TPD-TGA of 2-propanamine and for Lewis sites using TPD-TGA of 1-propanol. Catalysts with strong Brønsted acidity (H-BEA and Al2O 3/SBA-15) formed 5-[(1-methylethoxy)methyl]furfural with high selectivities, while materials with Lewis acidity (γ-Al2O 3, ZrO2, TiO2, and Sn-BEA) or weak Brønsted acidity (ZrO2/SBA-15 and TiO2/SBA-15) were active for transfer hydrogenation from the alcohol to HMF to produce 2,5-bis(hydroxymethyl)furan, with subsequent reactions to the mono- or di-ethers. Each of the catalysts was stable under the flow-reactor conditions but the selectivities varied with the particular oxide being investigated.

AB - The liquid-phase (69 bar) reaction of 5-hydroxymethylfurfural (HMF) with 2-propanol for production of furanyl ethers was studied at 413 and 453 K over a series of oxide catalysts, including γ-Al2O3, ZrO2, TiO2, Al2O3/SBA-15, ZrO 2/SBA-15, TiO2/SBA-15, H-BEA, and Sn-BEA. The acidity of each of the catalysts was first characterized for Brønsted sites using TPD-TGA of 2-propanamine and for Lewis sites using TPD-TGA of 1-propanol. Catalysts with strong Brønsted acidity (H-BEA and Al2O 3/SBA-15) formed 5-[(1-methylethoxy)methyl]furfural with high selectivities, while materials with Lewis acidity (γ-Al2O 3, ZrO2, TiO2, and Sn-BEA) or weak Brønsted acidity (ZrO2/SBA-15 and TiO2/SBA-15) were active for transfer hydrogenation from the alcohol to HMF to produce 2,5-bis(hydroxymethyl)furan, with subsequent reactions to the mono- or di-ethers. Each of the catalysts was stable under the flow-reactor conditions but the selectivities varied with the particular oxide being investigated.

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The effect of oxide acidity on HMF etherification

Abstract

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