Selective oxidation of 5-hydroxymethyl-2-furaldehyde to furan-2,5-dicarboxaldehyde by catalytic systems based on vanadyl phosphate

Carlini, Carlo; Patrono, P.; Galletti, Anna Maria Raspolli; Sbrana, Glauco; Zima, Vı́tězslav

doi:10.1016/j.apcata.2005.05.006

Cited by 173 publications

(116 citation statements)

References 32 publications

Supporting

Mentioning

111

Contrasting

Unclassified

Order By: Relevance

“…Selective Oxidation Selective oxidation is conducted to form chemical intermediates that have specific functionality, and this reaction is carried out in the presence of aqueous or organic solvents at temperatures from 330 to 420 K and oxygen pressures of 2-10 bar in the presence of supported metals (Pt, Pd, Au, Ti, Zr, V) or metal oxides and metal derivatives such as vanadyl phosphate. [44] Catalytic oxidation reactions can lead to multiple products, and thus the challenge is to direct the reaction pathways to the desired products. Selective oxidation of HMF leads to the formation of diformylfuran (DFF), which has potential applications in the synthesis of drugs, fungicides, and in preparing new polymeric materials.…”

Section: Aldol Condensationmentioning

confidence: 99%

“…High temperatures and almost neutral pH in the presence of a Pt/C catalyst lead to oxidation of the hydroxymethyl group to give DFF, while low temperatures and basic conditions lead to oxidation of the formyl group of HMF to form 2,5-furandicarboxylic acid (FDCA). [44] Similarly, acidic conditions in the oxidation of glycerol favor the oxidation of the secondary alcoholic group to dihydroxyacetone (DHA), while under basic conditions the primary alcoholic groups are oxidized to form glyceric acid. Addition of Bi promotes the Pt/C catalyst in the presence of base to a mechanism that involves oxidation of the secondary alcoholic group to dihydroxyacetone.…”

Section: Aldol Condensationmentioning

confidence: 99%

See 1 more Smart Citation

Liquid‐Phase Catalytic Processing of Biomass‐Derived Oxygenated Hydrocarbons to Fuels and Chemicals

2007

View full text Add to dashboard Cite

Biomass has the potential to serve as a sustainable source of energy and organic carbon for our industrialized society. The focus of this Review is to present an overview of chemical catalytic transformations of biomass‐derived oxygenated feedstocks (primarily sugars and sugar‐alcohols) in the liquid phase to value‐added chemicals and fuels, with specific examples emphasizing the development of catalytic processes based on an understanding of the fundamental reaction chemistry. The key reactions involved in the processing of biomass are hydrolysis, dehydration, isomerization, aldol condensation, reforming, hydrogenation, and oxidation. Further, it is discussed how ideas based on fundamental chemical and catalytic concepts lead to strategies for the control of reaction pathways and process conditions to produce H2/CO2 or H2/CO gas mixtures by aqueous‐phase reforming, to produce furan compounds by selective dehydration of carbohydrates, and to produce liquid alkanes by the combination of aldol condensation and dehydration/hydrogenation processes.

show abstract

Section: Aldol Condensationmentioning

confidence: 99%

Section: Aldol Condensationmentioning

confidence: 99%

Liquid‐Phase Catalytic Processing of Biomass‐Derived Oxygenated Hydrocarbons to Fuels and Chemicals

2007

View full text Add to dashboard Cite

show abstract

“…[5] Moreover, due to its similar structure to terephthalic acid (PTA)-a monomer for the production of polyethyleneterephthalate (PET plastic)-renewable FDCA obtained from biomass has a great potential to replace PTA. [6][7][8][9][10] Therefore, the exploration of the efficient oxidation of HMF and production of FDCA is a significant and commercially viable alternative process to the petroleum approach.…”

Section: Introductionmentioning

confidence: 99%

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

111

View full text Add to dashboard Cite

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.

show abstract

“…This aldehyde group and the aldehyde group already present in HMF are further oxidized to the corresponding carboxylic acids, resulting in FDCA. The existing chemical methods for this reaction require the use of stoichiometric quantities of strong oxidants or involve metal salt catalysts in organic solvent and high temperature and pressure (4,5). Thus, a gentler and less expensive enzymatic procedure is desirable.…”

mentioning

confidence: 99%

Discovery and Characterization of a 5-Hydroxymethylfurfural Oxidase from Methylovorus sp. Strain MP688

Dijkman

Fraaije

2014

Appl Environ Microbiol

125

200

View full text Add to dashboard Cite

In the search for useful and renewable chemical building blocks, 5-hydroxymethylfurfural (HMF) has emerged as a very promising candidate, as it can be prepared from sugars. HMF can be oxidized to 2,5-furandicarboxylic acid (FDCA), which is used as a substitute for petroleum-based terephthalate in polymer production. On the basis of a recently identified bacterial degradation pathway for HMF, candidate genes responsible for selective HMF oxidation have been identified. Heterologous expression of a protein from Methylovorus sp. strain MP688 in Escherichia coli and subsequent enzyme characterization showed that the respective gene indeed encodes an efficient HMF oxidase (HMFO). HMFO is a flavin adenine dinucleotide-containing oxidase and belongs to the glucose-methanol-choline-type flavoprotein oxidase family. Intriguingly, the activity of HMFO is not restricted to HMF, as it is active with a wide range of aromatic primary alcohols and aldehydes. The enzyme was shown to be relatively thermostable and active over a broad pH range. This makes HMFO a promising oxidative biocatalyst that can be used for the production of FDCA from HMF, a reaction involving both alcohol and aldehyde oxidations.

show abstract

Selective oxidation of 5-hydroxymethyl-2-furaldehyde to furan-2,5-dicarboxaldehyde by catalytic systems based on vanadyl phosphate

Cited by 173 publications

References 32 publications

Liquid‐Phase Catalytic Processing of Biomass‐Derived Oxygenated Hydrocarbons to Fuels and Chemicals

Liquid‐Phase Catalytic Processing of Biomass‐Derived Oxygenated Hydrocarbons to Fuels and Chemicals

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

Discovery and Characterization of a 5-Hydroxymethylfurfural Oxidase from Methylovorus sp. Strain MP688

Contact Info

Product

Resources

About