Solvent controlled catalysis: Synthesis of aldehyde, acid or ester by selective oxidation of benzyl alcohol with gold nanoparticles on alumina

Sari Rautiainen; Olga Simakova; Hongfan Guo; Anne-Riikka Leino; Krisztián Kordás; Dmitry Murzin; Markku Leskelä; Timo Repo

doi:10.1016/j.apcata.2014.08.003

Solvent controlled catalysis: Synthesis of aldehyde, acid or ester by selective oxidation of benzyl alcohol with gold nanoparticles on alumina

Sari Rautiainen, Olga Simakova, Hongfan Guo, Anne-Riikka Leino, Krisztián Kordás, Dmitry Murzin, Markku Leskelä, Timo Repo

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

57 Citations (Scopus)

Abstract

As shown herein, selectivity of aerobic oxidation of benzyl alcohol with gold nanoparticles dispersed on Al₂O₃ support is solvent-controlled. Using different solvents, the reaction was directed toward a variety of products: benzaldehyde, benzoic acid or benzoic esters were selectively produced from benzyl alcohol depending on the conditions. In toluene, benzaldehyde was produced with high selectivity, while quantitative conversion to benzoic acid was achieved in alkaline water. In methanol, methyl benzoate was produced with very high yield. Moreover, activity of the catalyst was dramatically improved without loss of selectivity in biphasic media; with a toluene/alkaline water system the highest TOF for benzoic acid synthesis was close to 5200 h⁻¹, selectivity being 98%.

Original language	Undefined/Unknown
Pages (from-to)	202–206
Journal	Applied Catalysis A: General
Volume	485
DOIs	https://doi.org/10.1016/j.apcata.2014.08.003
Publication status	Published - 2014
MoE publication type	A1 Journal article-refereed

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10.1016/j.apcata.2014.08.003

Cite this

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title = "Solvent controlled catalysis: Synthesis of aldehyde, acid or ester by selective oxidation of benzyl alcohol with gold nanoparticles on alumina",

abstract = "As shown herein, selectivity of aerobic oxidation of benzyl alcohol with gold nanoparticles dispersed on Al2O3 support is solvent-controlled. Using different solvents, the reaction was directed toward a variety of products: benzaldehyde, benzoic acid or benzoic esters were selectively produced from benzyl alcohol depending on the conditions. In toluene, benzaldehyde was produced with high selectivity, while quantitative conversion to benzoic acid was achieved in alkaline water. In methanol, methyl benzoate was produced with very high yield. Moreover, activity of the catalyst was dramatically improved without loss of selectivity in biphasic media; with a toluene/alkaline water system the highest TOF for benzoic acid synthesis was close to 5200 h−1, selectivity being 98%.",

author = "Sari Rautiainen and Olga Simakova and Hongfan Guo and Anne-Riikka Leino and Kriszti{\'a}n Kord{\'a}s and Dmitry Murzin and Markku Leskel{\"a} and Timo Repo",

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doi = "10.1016/j.apcata.2014.08.003",

language = "Odefinierat/ok{\"a}nt",

volume = "485",

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journal = "Applied Catalysis A: General",

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TY - JOUR

T1 - Solvent controlled catalysis: Synthesis of aldehyde, acid or ester by selective oxidation of benzyl alcohol with gold nanoparticles on alumina

AU - Rautiainen, Sari

AU - Simakova, Olga

AU - Guo, Hongfan

AU - Leino, Anne-Riikka

AU - Kordás, Krisztián

AU - Murzin, Dmitry

AU - Leskelä, Markku

AU - Repo, Timo

PY - 2014

Y1 - 2014

N2 - As shown herein, selectivity of aerobic oxidation of benzyl alcohol with gold nanoparticles dispersed on Al2O3 support is solvent-controlled. Using different solvents, the reaction was directed toward a variety of products: benzaldehyde, benzoic acid or benzoic esters were selectively produced from benzyl alcohol depending on the conditions. In toluene, benzaldehyde was produced with high selectivity, while quantitative conversion to benzoic acid was achieved in alkaline water. In methanol, methyl benzoate was produced with very high yield. Moreover, activity of the catalyst was dramatically improved without loss of selectivity in biphasic media; with a toluene/alkaline water system the highest TOF for benzoic acid synthesis was close to 5200 h−1, selectivity being 98%.

AB - As shown herein, selectivity of aerobic oxidation of benzyl alcohol with gold nanoparticles dispersed on Al2O3 support is solvent-controlled. Using different solvents, the reaction was directed toward a variety of products: benzaldehyde, benzoic acid or benzoic esters were selectively produced from benzyl alcohol depending on the conditions. In toluene, benzaldehyde was produced with high selectivity, while quantitative conversion to benzoic acid was achieved in alkaline water. In methanol, methyl benzoate was produced with very high yield. Moreover, activity of the catalyst was dramatically improved without loss of selectivity in biphasic media; with a toluene/alkaline water system the highest TOF for benzoic acid synthesis was close to 5200 h−1, selectivity being 98%.

U2 - 10.1016/j.apcata.2014.08.003

DO - 10.1016/j.apcata.2014.08.003

M3 - Artikel

SN - 0926-860X

VL - 485

SP - 202

EP - 206

JO - Applied Catalysis A: General

JF - Applied Catalysis A: General

ER -