Aqueous Oxidation of Sugars into Sugar Acids Using Hydrotalcite-supported Gold Nanoparticle Catalyst under Atmospheric Molecular Oxygen

Tomar, Radha; Sharma, Jatin; Nishimura, Shun; Ebitani, Kohki

doi:10.1246/cl.160364

Cited by 14 publications

(9 citation statements)

References 45 publications

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“…In particular, Au NPs/SiO 2 did not show any activity toward HMF conversion. The catalyst system was later applied to the aerobic oxidation of glucosamine derivatives 525 and monosaccharides, including xylose, ribose, galactose, and mannose, or disaccharides (Scheme 125), 526 in water. In contrast, Au NPs supported on polyoxometalate (Au/Cs x H 3−x PW 12 O 40 ) showed good activity for selective oxidative conversion into gluconic acid in water (Scheme 126).…”

Section: Metal Nanoparticle Catalystsmentioning

confidence: 99%

Catalytic Organic Reactions in Water toward Sustainable Society

et al. 2017

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Traditional organic synthesis relies heavily on organic solvents for a multitude of tasks, including dissolving the components and facilitating chemical reactions, because many reagents and reactive species are incompatible or immiscible with water. Given that they are used in vast quantities as compared to reactants, solvents have been the focus of environmental concerns. Along with reducing the environmental impact of organic synthesis, the use of water as a reaction medium also benefits chemical processes by simplifying operations, allowing mild reaction conditions, and sometimes delivering unforeseen reactivities and selectivities. After the "watershed" in organic synthesis revealed the importance of water, the development of water-compatible catalysts has flourished, triggering a quantum leap in water-centered organic synthesis. Given that organic compounds are typically practically insoluble in water, simple extractive workup can readily separate a water-soluble homogeneous catalyst as an aqueous solution from a product that is soluble in organic solvents. In contrast, the use of heterogeneous catalysts facilitates catalyst recycling by allowing simple centrifugation and filtration methods to be used. This Review addresses advances over the past decade in catalytic reactions using water as a reaction medium.

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Section: Metal Nanoparticle Catalystsmentioning

confidence: 99%

Catalytic Organic Reactions in Water toward Sustainable Society

et al. 2017

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“…Pd/Mg5Al-LDH yielded near quantitative 2,5-FDCA production from HMF, however catalysis was likely influenced by the presence of brucite, 76 while a bimetallic Pd0.2Pt0.8/MgAl-LDH achieved ~100 % 2,5-FDCA yield in the absence of aqueous base 77 (since extended to the aerobic oxidation of sugars to sugar acids 78 ). Calcined Mn0.70Cu0.05Al0.25-LDHs are also effective for HMF oxidation to 2,5-diformylfuran under 8 bar O2.…”

Section: Oxidation Of Carbohydrates and Platform Chemicalsmentioning

confidence: 99%

Catalytic applications of layered double hydroxides in biomass valorisation

Song

Beaumont

Zhang

et al. 2020

Current Opinion in Green and Sustainable Chemistry

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“…XANES revealed that calcination of Au/HT at temperatures higher than 373 K afforded reduced Au 0 species, which are catalytically active sites. Such bare Au/HT catalysts were applicable for the aerobic oxidation of glucosamine-HCl into a-amino acid 35) and sugars into sugar acids in water 36) . External base-free selective glycerol oxidation in water solvent with 0.1 MPa O2 was also demonstrated by using Pt/HT catalysts under mild conditions (333 K) 34) .…”

Section: Oxidative Transformations Of Glycerolmentioning

confidence: 99%

金属担持触媒を用いたバイオマス由来アルコールの選択的酸化反応

Nishimura

Ebitani

2017

J. Jpn. Petrol. Inst.

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Simple transformation of sustainable biomass-resources to value-added chemicals and fuels has become important to diminish our heavy reliance on decreasing petroleum resources. Biomass-derived materials with hydroxyl groups such as 5-hydroxymethylfurfural (HMF) and glycerol can be obtained from sugars directly and transesterification of triglycerides with methanol as by-products, respectively. These chemicals are versatile starting materials because hydroxyl groups can be easily converted to afford value-added chemicals and fuels under oxidative/reductive conditions using supported metal catalysts. This review overviews recent studies on supported metal catalyzed oxidation reactions of HMF, glycerol and biomass-derived aliphatic a,w-diols together with our research to develop highly efficient catalytic systems for bio-refining, based on petroleum conversion and nanotechnologies. Especially, role of external bases in the selective oxidation of biomass-derived alcohols will be discussed. We found that external base-free oxidation of HMF and glycerol is possible if basic supports are used. The activity of alloyed metal nanoparticles for selective oxidation of aliphatic a,w-diols to w-hydroxycarboxylic acids in basic aqueous media at high-pH value is also demonstrated. Keywords5-Hydroxymethylfurfural, Glycerol, Aliphatic a,w-diols, Selective oxidation, Supported metal catalyst, Bimetallic nanoparticle DOI: doi.org/10.1627/jpi.60.72 To whom correspondence should be addressed. E-mail: ebitani@jaist.ac.jp using molecular oxygen as the oxidant 18) . For example, Sahu and Dhepe compared the catalytic performance of various metal-oxide supported Pt catalysts with 0.1 MPa O2 in the presence of NaOH (1 equiv.) at 348 K for 12 h 19) . Under the same reaction conditions, Pt/ γ-A12O3, Pt/ZrO2, and Pt/C showed high catalytic activity with FDCA yields of 96, 94, and 89 %, respectively. In contrast, Pt supported on reducible TiO2 and CeO2 produced little FDCA (2 % and 8 % yields) even with ca. 100 % HMF conversion. Cai et al. reported superior catalytic performance of Au nanoparticles (1 nm size) encapsulated in the supercage of HY zeolite for selective HMF oxidation into FDCA with 99 % FDCA yield in water under 0.3 MPa O2 in the presence of NaOH at 333 K 20) . It has been reported the structures of Au nanoparticles and HY zeolite are stable under these conditions, and the Au/HY catalyst is reusable for several catalytic cycles. Negatively-charged Au nanoparticles may be responsible for this excellent catalytic performance.Pasini et al. reported AuCu bimetallic alloy catalyst (4.4 nm diameter) supported on TiO2 for HMF oxidation to FDCA under 1 MPa O2 in the presence of NaOH at 368 K to afford 99 % FDCA yield with complete HMF conversion 21) . A strong synergistic effect is evident with the addition of Cu to Au, especially for catalyst reusability without significant leaching of metal nanoparticles. However, stability test experiments showed the final product is mainly 5-hydroxymethyl-2-furancaoboxylic acid (HMFCA) instead...

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Aqueous Oxidation of Sugars into Sugar Acids Using Hydrotalcite-supported Gold Nanoparticle Catalyst under Atmospheric Molecular Oxygen

Cited by 14 publications

References 45 publications

Catalytic Organic Reactions in Water toward Sustainable Society

Catalytic Organic Reactions in Water toward Sustainable Society

Catalytic applications of layered double hydroxides in biomass valorisation

金属担持触媒を用いたバイオマス由来アルコールの選択的酸化反応

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