Influence of Reaction Conditions on Diacid Formation During Au-Catalyzed Oxidation of Glycerol and Hydroxymethylfurfural

Zope, Bhushan N.; Davis, Sara E.; Davis, Robert J.

doi:10.1007/s11244-012-9777-3

Cited by 92 publications

(100 citation statements)

References 44 publications

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“…The Au/HT catalyst was recycled three times without a significant loss in activity (>99%, 92%, and 90%, respectively). However, further studies from Zope et al with Au/TiO 2 and hydrotalcite as a solid base for oxidation of HMF showed that leaching of Mg 2+ from HT occurred [69]. According to the authors, leaching resulted from an acid-base reaction occurring once the formed acid lowered the pH of the reaction medium and consumed the basic solid support.…”

Section: Base-free 5-hydroxymethylfurfural Oxidationmentioning

confidence: 99%

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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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Section: Base-free 5-hydroxymethylfurfural Oxidationmentioning

confidence: 99%

“…on [69]. According to the authors, leaching resulted from an acid-base reaction occurring once the formed acid lowered the pH of the reaction medium and consumed the basic solid support.…”

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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“…Hydroxypyruvic acid, glyceraldehydes and glyceric acid were also reported as by-products in the reaction. Monometallic supported Au nanoparticles on carbon and titania have also been recently reported in the continuous flow oxidation of glycerol [18]. Starting from a mixture containing a 2:1 NaOH/glycerol ratio (0. used under moderate temperature (60°C) and oxygen gas pressure (11 bar).…”

Section: Glycerol Oxidationmentioning

confidence: 99%

“…Glycerol oxidation afforded glyceric, glycolic, tartronic and oxalic acids as main compounds, with glyceric acid as main product (40-50% yields, depending on the type of catalyst, Scheme 7). Compared to semibatch processes, a good selectivity towards oxidation of the challenging secondary hydroxyl group to tartronic and oxalic acids was observed [18].…”

Section: Glycerol Oxidationmentioning

confidence: 99%

Continuous flow transformations of glycerol to valuable products: an overview

Len

Luque

2014

Sustain Chem Process

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Glycerol conversion to valuable products has been a research avenue that attracted a significant interest in recent years due to its large available volumes (as by-product of biodiesel production) and the different possibilities for chemical and biological conversion into high added value chemicals profiting from the unique presence of three hydroxyl groups in its structure. The utilization of continuous flow processes in combination with transformation of platform chemicals (e.g. glycerol) can offer several advantages to batch processes in view of their potential implementation in industry. This minireview has been aimed to highlight most recent key continuous flow systems for glycerol valorization to valuable products using different types of catalysts and processes.

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“…Ebitani et al [16] have shown that basic hydrotalcite (HT)-supported Au NP (3.2 nm) catalysts gave an excellent yield to FDCA without the addition of ahomogeneous base, and the Au/HT catalyst can be recycled three times. Subsequent study conducted by Zope et al [24] found that Mg 2 + ions leached from hydrotalcite during the oxidation reaction. On the other hand, increasing the HMF/base ratio can also improve the FDCA Abstract: Au nanoclusters with an average size of approximately 1 nm size supported on HY zeolite exhibit a superior catalytic performance for the selective oxidation of 5-hydroxymethyl-2-furfural (HMF) into 2,5-furandicarboxylic acid (FDCA).…”

Section: Introductionmentioning

confidence: 96%

Gold Nanoclusters Confined in a Supercage of Y Zeolite for Aerobic Oxidation of HMF under Mild Conditions

Cai

Zhang

et al. 2013

Chemistry A European J

192

104

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Au nanoclusters with an average size of approximately 1 nm size supported on HY zeolite exhibit a superior catalytic performance for the selective oxidation of 5‐hydroxymethyl‐2‐furfural (HMF) into 2,5‐furandicarboxylic acid (FDCA). It achieved >99 % yield of 2,5‐furandicarboxylic acid in water under mild conditions (60 °C, 0.3 MPa oxygen), which is much higher than that of Au supported on metal oxides/hydroxide (TiO2, CeO2, and Mg(OH)2) and channel‐type zeolites (ZSM‐5 and H‐MOR). Detailed characterizations, such as X‐ray diffraction, transmission electron microscopy, N2‐physisorption, and H2‐temperature‐programmed reduction (TPR), revealed that the Au nanoclusters are well encapsulated in the HY zeolite supercage, which is considered to restrict and avoid further growing of the Au nanoclusters into large particles. The acidic hydroxyl groups of the supercage were proven to be responsible for the formation and stabilization of the gold nanoclusters. Moreover, the interaction between the hydroxyl groups in the supercage and the Au nanoclusters leads to electronic modification of the Au nanoparticles, which is supposed to contribute to the high efficiency in the catalytic oxidation of HMF to FDCA.

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Influence of Reaction Conditions on Diacid Formation During Au-Catalyzed Oxidation of Glycerol and Hydroxymethylfurfural

Cited by 92 publications

References 44 publications

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

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

Continuous flow transformations of glycerol to valuable products: an overview

Gold Nanoclusters Confined in a Supercage of Y Zeolite for Aerobic Oxidation of HMF under Mild Conditions

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