Clean preparation of methyl esters in one-step oxidative esterification of primary alcohols catalyzed by supported gold nanoparticles

Oliveira, Rafael de Lima; Kiyohara, Pedro Kunihiko; Rossi, Liane M.

doi:10.1039/b902499a

Cited by 126 publications

(65 citation statements)

References 28 publications

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“…However, the surfaces of acid or hydrophobic supports, such as SiO 2 , WO 3 , and active carbon, are not suitable for the deposition of anionic species and usually lead to large > 20 nm supported Au NPs. In such acid supports, other synthetic methods are required to produce small Au NPs, such as deposition of pre-synthesized colloidal gold, [40][41][42][43][44] chemical vapor deposition, [45] or atomic beam deposition. [46] In general, these methods involve many steps, the use of expensive sta-Abstract: The immobilization of gold nanoparticles (Au NPs) on silica is made possible by the functionalization of the silica surfaces with organosilanes.…”

Section: Introductionmentioning

confidence: 99%

On the Stabilization of Gold Nanoparticles over Silica‐Based Magnetic Supports Modified with Organosilanes

Oliveira

Zanchet²,

Kiyohara

et al. 2011

Chemistry A European J

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The immobilization of gold nanoparticles (Au NPs) on silica is made possible by the functionalization of the silica surfaces with organosilanes. Au NPs could only be stabilized and firmly attached to silica-support surfaces that were previously modified with amino groups. Au NPs could not be stabilized on bare silica surfaces and most of the NPs were then found in the solution. The metal-support interactions before and after the Au NP formation, observed by X-ray absorption fine structure spectroscopy (XAFS), indicate a stronger interaction of gold(III) ions with amino-modified silica surfaces than with the silanol groups in bare silica. An amino-modified, silica-based, magnetic support was used to prepare an active Au NP catalyst for the chemoselective oxidation of alcohols, a reaction of great interest for the fine chemical industry.

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Section: Introductionmentioning

confidence: 99%

On the Stabilization of Gold Nanoparticles over Silica‐Based Magnetic Supports Modified with Organosilanes

Oliveira

Zanchet²,

Kiyohara

et al. 2011

Chemistry A European J

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“…For this reason, the development of catalytic systems capable of producing FDMC directly from HMF (Scheme 3) received attention recently. Au-based catalysts have been successfully applied for the oxidative esterification of alcohols [71][72][73][74] and were also explored for the transformation of HMF. Wang et al [70] reported an Au-containing bimetallic catalyst for base-free oxidation of HMF consisting of a carbon nanotube-supported Au-Pd catalyst (Au-Pd/CNT) that reached 100% conversion within 12 h, with 94% selectivity for FDCA.…”

Section: Base-free 5-hydroxymethylfurfural Oxidationmentioning

confidence: 99%

“…For this reason, the development of catalytic systems capable of producing FDMC directly from HMF (Scheme 3) received attention recently. Au-based catalysts have been successfully applied for the oxidative esterification of alcohols [71][72][73][74] and were also explored for the transformation of HMF. The first example of esterification of HMF to produce dimethyl-2-furoate required the use of a base [75].…”

Section: Base-free 5-hydroxymethylfurfural Oxidationmentioning

confidence: 99%

Advances in Base-Free Oxidation of Bio-Based Compounds on Supported Gold Catalysts

et al. 2017

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Abstract:The oxidation of bio-based molecules in general, and of carbohydrates and furanics in particular, is a highly attractive process. The catalytic conversion of renewable compounds is of high importance. Acids and other chemical intermediates issued from oxidation processes have many applications related, especially, to food and detergents, as well as to pharmaceutics, cosmetics, and the chemical industry. Until now, the oxidation of sugars, furfural, or 5-hydroxymethylfurfural has been mainly conducted through biochemical processes or with strong inorganic oxidants. The use of these processes very often presents many disadvantages, especially regarding products separation and selectivity control. Generally, the oxidation is performed in batch conditions using an appropriate catalyst and a basic aqueous solution (pH 7-9), while bubbling oxygen or air through the slurry. However, there is a renewed interest in working in base-free conditions to avoid the production of salts. Actually, this gives direct access to different acids or diacids without laborious product purification steps. This review focuses on processes applying gold-based catalysts, and on the catalytic properties of these systems in the base-free oxidation of important compounds: C5-C6 sugars, furfural, and 5-hydroxymethylfurfural. A better understanding of the chemical and physical properties of the catalysts and of the operating conditions applied in the oxidation reactions is essential. For this reason, in this review we put emphasis on these most impacting factors.

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“…Gold on amino-modified fumed silica can efficiently catalyse primary alcohol selox to yield their esters in a single step. 41 Using nanocrystalline (5 nm) ceria, Corma and co-workers synthesised gold catalysts, which gave superior selectivity for cinnamyl alcohol oxidation to cinnamaldehyde over comparative mono-and bimetallic transition metal catalysts. 42,43 Gold nanoclusters on gallia polymorphs have also proven to be versatile green catalysts for the oxidative esterification of several alcohols.…”

Section: Metal Selox Catalystsmentioning

confidence: 99%

Recent advances in the heterogeneously catalysed aerobic selective oxidation of alcohols

Vinod

Wilson

Lee

2010

J. Chem. Technol. Biotechnol.

169

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The heterogeneously catalysed selective aerobic oxidation of alcohols is an important tool for the synthesis of valuable chemical intermediates and a hot topic within both academic and industrial arenas. In this mini-review, selected aspects of catalyst formulation, process operating conditions, and progress in identifying the active sites and surface reaction mechanisms notably through the application of synchrotron radiation, are highlighted.

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Clean preparation of methyl esters in one-step oxidative esterification of primary alcohols catalyzed by supported gold nanoparticles

Cited by 126 publications

References 28 publications

On the Stabilization of Gold Nanoparticles over Silica‐Based Magnetic Supports Modified with Organosilanes

On the Stabilization of Gold Nanoparticles over Silica‐Based Magnetic Supports Modified with Organosilanes

Advances in Base-Free Oxidation of Bio-Based Compounds on Supported Gold Catalysts

Recent advances in the heterogeneously catalysed aerobic selective oxidation of alcohols

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