Hydrogenation of benzoic acid to benzyl alcohol over Pt/SnO2

Xiaohan Chen; Ziyun Wang; Helen Daly; Richard Morgan; Haresh Manyar; Conor Byrne; Alex S. Walton; S.f. Rebecca Taylor; Matthew Smith; Robbie Burch; Peijun Hu; Christopher Hardacre

doi:10.1016/j.apcata.2020.117420

Hydrogenation of benzoic acid to benzyl alcohol over Pt/SnO2

Xiaohan Chen, Ziyun Wang, Helen Daly, Richard Morgan, Haresh Manyar, Conor Byrne, Alex S. Walton, S.f. Rebecca Taylor, Matthew Smith, Robbie Burch, Peijun Hu, Christopher Hardacre

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Abstract

Hydrogenation of benzoic acid in the liquid phase over Pt/SnO2 has afforded excellent selectivity to benzyl alcohol under mild reaction conditions (97% at 98% conversion of benzoic acid). DFT calculations have shown that the favoured mode of adsorption of benzoic acid switched from the aromatic ring to the acid carbonyl group with partial reduction of the SnO2 support. The switch in adsorption mode corroborates the experimentally observed selectivity with acid carbonyl group adsorption and hydrogenation occurring over Pt/SnO2. Reduction of Pt/SnO2 was observed by in-situ XPS forming a degree of metallic tin and complete reduction of Pt which could lead to Pt-Sn alloy phases and/or migration of SnOx onto Pt blocking sites for ring hydrogenation. No hydrogenation of benzene or the benzene ring of benzoic acid was observed over Pt/SnO2 with oxidic tin species at the interface of Pt particles proposed to activate the acid carbonyl group for hydrogenation.

Original language	English
Pages (from-to)	117420
Journal	Applied Catalysis A: General
Early online date	18 Jan 2020
DOIs	https://doi.org/10.1016/j.apcata.2020.117420
Publication status	Published - 2020

Keywords

Benzoic acid
benzyl alcohol
selective hydrogenation
DFT
ATR-IR

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10.1016/j.apcata.2020.117420

APCATA-D-19-01931_resubmissionAccepted author manuscript, 1.35 MB

https://linkinghub.elsevier.com/retrieve/pii/S0926860X20300132

Hydrogenation of benzoic acid to benzyl alchol over Pt/SnO2
Daly, H. (Creator), figshare , 31 Jan 2028
DOI: 10.6084/m9.figshare.11750730
Dataset

Near-Ambient Pressure X-ray Photoemission Spectroscopy (NAP-XPS)
Dwyer, L. (Technical Specialist) & Walton, A. (Academic lead)
Materials Engineering
Facility/equipment: Facility

Cite this

@article{3755dcf20fa44638b6c6e459f3cd5c0b,

title = "Hydrogenation of benzoic acid to benzyl alcohol over Pt/SnO2",

abstract = "Hydrogenation of benzoic acid in the liquid phase over Pt/SnO2 has afforded excellent selectivity to benzyl alcohol under mild reaction conditions (97% at 98% conversion of benzoic acid). DFT calculations have shown that the favoured mode of adsorption of benzoic acid switched from the aromatic ring to the acid carbonyl group with partial reduction of the SnO2 support. The switch in adsorption mode corroborates the experimentally observed selectivity with acid carbonyl group adsorption and hydrogenation occurring over Pt/SnO2. Reduction of Pt/SnO2 was observed by in-situ XPS forming a degree of metallic tin and complete reduction of Pt which could lead to Pt-Sn alloy phases and/or migration of SnOx onto Pt blocking sites for ring hydrogenation. No hydrogenation of benzene or the benzene ring of benzoic acid was observed over Pt/SnO2 with oxidic tin species at the interface of Pt particles proposed to activate the acid carbonyl group for hydrogenation.",

keywords = "Benzoic acid, benzyl alcohol, selective hydrogenation, DFT, ATR-IR",

author = "Xiaohan Chen and Ziyun Wang and Helen Daly and Richard Morgan and Haresh Manyar and Conor Byrne and Walton, {Alex S.} and Taylor, {S.f. Rebecca} and Matthew Smith and Robbie Burch and Peijun Hu and Christopher Hardacre",

year = "2020",

doi = "10.1016/j.apcata.2020.117420",

language = "English",

pages = "117420",

journal = "Applied Catalysis A: General",

issn = "0926-860X",

publisher = "Elsevier BV",

}

TY - JOUR

T1 - Hydrogenation of benzoic acid to benzyl alcohol over Pt/SnO2

AU - Chen, Xiaohan

AU - Wang, Ziyun

AU - Daly, Helen

AU - Morgan, Richard

AU - Manyar, Haresh

AU - Byrne, Conor

AU - Walton, Alex S.

AU - Taylor, S.f. Rebecca

AU - Smith, Matthew

AU - Burch, Robbie

AU - Hu, Peijun

AU - Hardacre, Christopher

PY - 2020

Y1 - 2020

N2 - Hydrogenation of benzoic acid in the liquid phase over Pt/SnO2 has afforded excellent selectivity to benzyl alcohol under mild reaction conditions (97% at 98% conversion of benzoic acid). DFT calculations have shown that the favoured mode of adsorption of benzoic acid switched from the aromatic ring to the acid carbonyl group with partial reduction of the SnO2 support. The switch in adsorption mode corroborates the experimentally observed selectivity with acid carbonyl group adsorption and hydrogenation occurring over Pt/SnO2. Reduction of Pt/SnO2 was observed by in-situ XPS forming a degree of metallic tin and complete reduction of Pt which could lead to Pt-Sn alloy phases and/or migration of SnOx onto Pt blocking sites for ring hydrogenation. No hydrogenation of benzene or the benzene ring of benzoic acid was observed over Pt/SnO2 with oxidic tin species at the interface of Pt particles proposed to activate the acid carbonyl group for hydrogenation.

AB - Hydrogenation of benzoic acid in the liquid phase over Pt/SnO2 has afforded excellent selectivity to benzyl alcohol under mild reaction conditions (97% at 98% conversion of benzoic acid). DFT calculations have shown that the favoured mode of adsorption of benzoic acid switched from the aromatic ring to the acid carbonyl group with partial reduction of the SnO2 support. The switch in adsorption mode corroborates the experimentally observed selectivity with acid carbonyl group adsorption and hydrogenation occurring over Pt/SnO2. Reduction of Pt/SnO2 was observed by in-situ XPS forming a degree of metallic tin and complete reduction of Pt which could lead to Pt-Sn alloy phases and/or migration of SnOx onto Pt blocking sites for ring hydrogenation. No hydrogenation of benzene or the benzene ring of benzoic acid was observed over Pt/SnO2 with oxidic tin species at the interface of Pt particles proposed to activate the acid carbonyl group for hydrogenation.

KW - Benzoic acid

KW - benzyl alcohol

KW - selective hydrogenation

KW - DFT

KW - ATR-IR

U2 - 10.1016/j.apcata.2020.117420

DO - 10.1016/j.apcata.2020.117420

M3 - Article

SN - 0926-860X

SP - 117420

JO - Applied Catalysis A: General

JF - Applied Catalysis A: General

ER -

Hydrogenation of benzoic acid to benzyl alcohol over Pt/SnO2

Abstract

Keywords

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Datasets

Hydrogenation of benzoic acid to benzyl alchol over Pt/SnO2

Equipment

Near-Ambient Pressure X-ray Photoemission Spectroscopy (NAP-XPS)

Cite this