Synthesis of phenols from hydroxymethylfurfural (HMF)

Tšupova, Svetlana; Röminger, Frank; Rudolph, Matthias; Hashmi, A. Stephen K.

doi:10.1039/c6gc01622g

Cited by 32 publications

(13 citation statements)

References 49 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Biomass‐derived furans such as 2‐furfuraldehyde (furfural) and 5‐hydroxymethyl‐2‐furfural (HMF) can be efficiently produced by the acid‐catalysed dehydration of pentose and hexose, respectively . As furans have highly reactive side chains, ‐CHO and/or ‐CH 2 OH with furan ring, these can be explored for the production of different C5, C6 or higher carbon containing valuable chemicals such as 2,5‐furandicarboxylic acid (FDCA), 2‐furoic acid, levulinic acid (LA), ketones/diketones, 1,6‐hexanediol (1,6‐HDO), 1‐hydroxyhexane‐2,5‐dione (1‐HHD), cyclopentanone (CPO), adipic acid, maleic anhydride (MA), caprolactam, caprolactone, γ‐valerolactone, 2,5‐dimethylfuran (DMF), alkanes and so on, having wide applications in various pharmaceutical and polymer industries as well as in the production of fuel components …”

Section: Introductionmentioning

confidence: 99%

Metal Catalysts for the Efficient Transformation of Biomass‐derived HMF and Furfural to Value Added Chemicals

2018

View full text Add to dashboard Cite

Catalytic transformation of biomass‐derived compounds to different platform chemicals and liquid fuel is a prominent way to reduce the global dependence on fossil resources. In past few decades, biomass‐derived furans such as 2‐furfuraldehyde (furfural) and 5‐hydroxymethyl‐2‐furfural (HMF) have received outstanding attention because of their wide applications in the production of various industrially important value‐added chemicals and fuel components. Various catalytic systems and methodologies have been extensively explored for the transformation of these furans to a wide range of products including open ring diketones, ketoacids, alcohols and long chain alkanes. This Review is aimed to provide an extensive overview of the recent developments of several high‐performing heterogeneous catalysts for the catalytic upgradation of the key biomass‐derived furans (furfural and HMF) to value‐added chemicals. Moreover, the role of these catalysts in the catalytic transformations including hydrogenation, decarbonylation, oxidation, hydrogenolysis and ring opening reactions, and the mechanistic pathways are also highlighted in this Review.

show abstract

Section: Introductionmentioning

confidence: 99%

Metal Catalysts for the Efficient Transformation of Biomass‐derived HMF and Furfural to Value Added Chemicals

2018

View full text Add to dashboard Cite

show abstract

“…In this regard, bio-based materials have attracted many attentions in the last two decades; therefore, a list of top value added chemicals from biomass has been drafted by the U.S. Department of Energy. Furfural, easily obtained from xylose, is considered in that list as a valuable chemical building block to synthesize other functionalized compounds [ 1 , 2 , 3 , 4 , 5 , 6 , 7 ]. One important class of new products derived from furfural are cyclopentenones, which are distinguished structural motifs present not only in notable natural molecules but also versatile as synthetic intermediates.…”

Section: Introductionmentioning

confidence: 99%

Biorenewable Deep Eutectic Solvent for Selective and Scalable Conversion of Furfural into Cyclopentenone Derivatives

et al. 2018

View full text Add to dashboard Cite

The development of novel synthetic routes to produce bioactive compounds starting from renewable sources has become an important research area in organic and medicinal chemistry. Here, we present a low-cost procedure for the tunable and selective conversion of biomass-produced furfural to cyclopentenone derivatives using a mixture of choline chloride and urea as a biorenewable deep eutectic solvent (DES). The proposed medium is a nontoxic, biodegradable, and could be reused up to four times without any unfavorable effect on the reaction yield. The process is tunable, clean, cheap, simple and scalable and meets most of the criteria; therefore, it can be considered as an environmental sustainable process in a natural reaction medium.

show abstract

“…For example, subjecting HMF to hydrothermolysis at high temperature and pressure led to 1,2,4benzenetriol 145 as the major product in yields up to 46% with 50% HMF conversion (Scheme 57). [167] The other example is the conversion of HMF to phenols which was reported by Hashmi et al [168] In this reaction, HMF first undergoes a O-propargylation and the resulting aldehyde 146 is converted into trifurylmethane under gold(III) catalysis. Finally, gold (I) catalysis promoted the conversion of 147 into the fused phenol 148 through ring rearrangement.…”

Section: Ring Opening/rearrangementmentioning

confidence: 98%

5-Hydroxymethylfurfural (HMF) in Organic Synthesis: A Review of its Recent Applications Towards Fine Chemicals

Fan

Verrier

Queneau

et al. 2019

COS

View full text Add to dashboard Cite

Background: 5-Hydroxymethylfurfural (5-HMF) is a biomass-derived platform chemical, which can be produced from carbohydrates. In the past decades, 5- HMF has received tremendous attention because of its wide applications in the production of various value-added chemicals, materials and biofuels. The manufacture and the catalytic conversion of 5-HMF to simple industrially-important bulk chemicals have been well reviewed. However, employing 5-HMF as a building block in organic synthesis has never been summarized exclusively, despite the rapid development in this area. Objective: The aim of this review is to bring a fresh perspective on the use of 5-HMF in organic synthesis, to the exclusion of already well documented conversion of 5-HMF towards relatively simple molecules such as 2,5-furandicarboxylic acid, 2,5-dimethylfuran and so on notably used as monomers or biofuels. Conclusion: As it has been shown throughout this review, 5-HMF has been the object of numerous studies on its use in fine chemical synthesis. Thanks to the presence of different functional groups on this platform chemical, it proved to be an excellent starting material for the preparation of various fine chemicals. The use of this C-6 synthon in novel synthetic routes is appealing, as it allows the incorporation of renewable carbonsources into the final targets.

show abstract

Synthesis of phenols from hydroxymethylfurfural (HMF)

Abstract: HMF-derived substrates were converted to highly substituted phenols by gold catalysis.

Cited by 32 publications

References 49 publications

Metal Catalysts for the Efficient Transformation of Biomass‐derived HMF and Furfural to Value Added Chemicals

Metal Catalysts for the Efficient Transformation of Biomass‐derived HMF and Furfural to Value Added Chemicals

Biorenewable Deep Eutectic Solvent for Selective and Scalable Conversion of Furfural into Cyclopentenone Derivatives

5-Hydroxymethylfurfural (HMF) in Organic Synthesis: A Review of its Recent Applications Towards Fine Chemicals

Contact Info

Product

Resources

About