Selective conversion of guaiacol to substituted alkylphenols in supercritical ethanol over MoO3

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Selective conversion of guaiacol to substituted alkylphenols in supercritical ethanol over MoO3. / Cui, Kai; Yang, Le; Ma, Zewei; Yan, Fei; Wu, Kai; Sang, Yushuai; Chen, Hong; Li, Yongdan.

In: Applied Catalysis B: Environmental, Vol. 219, 15.12.2017, p. 592-602.

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Cui, Kai ; Yang, Le ; Ma, Zewei ; Yan, Fei ; Wu, Kai ; Sang, Yushuai ; Chen, Hong ; Li, Yongdan. / Selective conversion of guaiacol to substituted alkylphenols in supercritical ethanol over MoO3. In: Applied Catalysis B: Environmental. 2017 ; Vol. 219. pp. 592-602.

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@article{162149b7c7eb4017aa8f1d24de9add16,
title = "Selective conversion of guaiacol to substituted alkylphenols in supercritical ethanol over MoO3",
abstract = "Selective conversion of guaiacol over MoO3 to produce various alkylphenols, including ethylphenols, isopropylphenols, butylphenols (tert-, sec-) and tert-amylphenol is investigated in ethanol without the addition of gaseous hydrogen. A high conversion of 99{\%} is achieved at 280 °C for 4 h and the total alkylphenols account for up to 94{\%} in the quantified products. Six molecules, i.e. 2,5-diethylphenol, 2,6-diisopropylphenol, 2,4-diisopropylphenol, 2,6-ditertbutylphenol, 2,4-ditertbutylphenol and 2,6-ditertbutyl-4-ethylphenol, are the main outcomes. The higher alkylphenols in the aforesaid products are verified to form via a novel reaction step in which hydrogen atom at the α-carbon of the lower alkylphenol is substituted consecutively with methyl or ethyl groups. Further examination reveals that catechol is formed as the intermediate via demethylation of guaiacol and followed by direct conversion to low alkylphenols without the formation of phenol. Post-catalytic analysis indicates that an oxycarbohydride phase (MoOxCyHz) with Mo5+ developed in the supercritical alcohol batch system played the role of active species. Ethanol is found to be the most effective solvent for the conversion. The MoO3 catalyst undergoes a gradual deactivation resulted from the consumption of Mo5+ and carbon deposition but can be regenerated with a simple calcination.",
keywords = "Alkylphenols, Deoxygenation, Guaiacol, Lignin, MoO",
author = "Kai Cui and Le Yang and Zewei Ma and Fei Yan and Kai Wu and Yushuai Sang and Hong Chen and Yongdan Li",
year = "2017",
month = "12",
day = "15",
doi = "10.1016/j.apcatb.2017.08.009",
language = "English",
volume = "219",
pages = "592--602",
journal = "APPLIED CATALYSIS B-ENVIRONMENTAL",
issn = "0926-3373",
publisher = "Elsevier BV",

}

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TY - JOUR

T1 - Selective conversion of guaiacol to substituted alkylphenols in supercritical ethanol over MoO3

AU - Cui, Kai

AU - Yang, Le

AU - Ma, Zewei

AU - Yan, Fei

AU - Wu, Kai

AU - Sang, Yushuai

AU - Chen, Hong

AU - Li, Yongdan

PY - 2017/12/15

Y1 - 2017/12/15

N2 - Selective conversion of guaiacol over MoO3 to produce various alkylphenols, including ethylphenols, isopropylphenols, butylphenols (tert-, sec-) and tert-amylphenol is investigated in ethanol without the addition of gaseous hydrogen. A high conversion of 99% is achieved at 280 °C for 4 h and the total alkylphenols account for up to 94% in the quantified products. Six molecules, i.e. 2,5-diethylphenol, 2,6-diisopropylphenol, 2,4-diisopropylphenol, 2,6-ditertbutylphenol, 2,4-ditertbutylphenol and 2,6-ditertbutyl-4-ethylphenol, are the main outcomes. The higher alkylphenols in the aforesaid products are verified to form via a novel reaction step in which hydrogen atom at the α-carbon of the lower alkylphenol is substituted consecutively with methyl or ethyl groups. Further examination reveals that catechol is formed as the intermediate via demethylation of guaiacol and followed by direct conversion to low alkylphenols without the formation of phenol. Post-catalytic analysis indicates that an oxycarbohydride phase (MoOxCyHz) with Mo5+ developed in the supercritical alcohol batch system played the role of active species. Ethanol is found to be the most effective solvent for the conversion. The MoO3 catalyst undergoes a gradual deactivation resulted from the consumption of Mo5+ and carbon deposition but can be regenerated with a simple calcination.

AB - Selective conversion of guaiacol over MoO3 to produce various alkylphenols, including ethylphenols, isopropylphenols, butylphenols (tert-, sec-) and tert-amylphenol is investigated in ethanol without the addition of gaseous hydrogen. A high conversion of 99% is achieved at 280 °C for 4 h and the total alkylphenols account for up to 94% in the quantified products. Six molecules, i.e. 2,5-diethylphenol, 2,6-diisopropylphenol, 2,4-diisopropylphenol, 2,6-ditertbutylphenol, 2,4-ditertbutylphenol and 2,6-ditertbutyl-4-ethylphenol, are the main outcomes. The higher alkylphenols in the aforesaid products are verified to form via a novel reaction step in which hydrogen atom at the α-carbon of the lower alkylphenol is substituted consecutively with methyl or ethyl groups. Further examination reveals that catechol is formed as the intermediate via demethylation of guaiacol and followed by direct conversion to low alkylphenols without the formation of phenol. Post-catalytic analysis indicates that an oxycarbohydride phase (MoOxCyHz) with Mo5+ developed in the supercritical alcohol batch system played the role of active species. Ethanol is found to be the most effective solvent for the conversion. The MoO3 catalyst undergoes a gradual deactivation resulted from the consumption of Mo5+ and carbon deposition but can be regenerated with a simple calcination.

KW - Alkylphenols

KW - Deoxygenation

KW - Guaiacol

KW - Lignin

KW - MoO

UR - http://www.scopus.com/inward/record.url?scp=85027889131&partnerID=8YFLogxK

U2 - 10.1016/j.apcatb.2017.08.009

DO - 10.1016/j.apcatb.2017.08.009

M3 - Article

VL - 219

SP - 592

EP - 602

JO - APPLIED CATALYSIS B-ENVIRONMENTAL

JF - APPLIED CATALYSIS B-ENVIRONMENTAL

SN - 0926-3373

ER -

ID: 16605952