4464-77-1

Usage

Type of compound

Synthetic organic compound

Derived from

Furan compound

Class

Diols

Use

Potent antibiotic agent

Target infections

Various bacterial infections, particularly staphylococci

Mechanism of action

Inhibits protein synthesis in bacteria

Effect on bacteria

Reduction in bacterial growth and elimination of infection

Additional potential uses

Treatment of skin infections, anti-inflammatory properties, and anti-cancer properties (under study)

Upstream product

• 98-01-1 furfural 
• 106-95-6 allyl bromide 
• 7732-18-5 water 

Downstream Products

• 98-01-1 furfural 
• 111944-35-5 Oxalic acid 2-ethoxyoxalyloxy-1,2-di-furan-2-yl-ethyl ester ethyl ester 
• 112-17-4 n-decyl acetate 
• 26118-61-6 1,10-decanediol diacetate 
• 492-94-4 furil 

Relevant academic research and scientific papers

A Divergent Paired Electrochemical Process for the Conversion of Furfural Using a Divided-Cell Flow Microreactor

Furfural is a prominent, non-petroleum-based chemical feedstock material, derived from abundantly available hemicellulose. Hence, its derivatization into other useful biobased chemicals is a subject of high interest in contemporary academic and industrial research activities. While most strategies to convert furfural require energy-intensive reaction routes, the use of electrochemical activation allows to provide a sustainable and green alternative. Herein, a disparate approach for the conversion of furfural is reported based on a divergent paired electrochemical conversion, enabling the simultaneous production of 2(5H)-furanone via an anodic oxidation, and the generation of furfuryl alcohol and/or hydrofuroin via a cathodic reduction. Using water as solvent and NaBr as supporting electrolyte and electron-mediator, a green and sustainable process was developed, which maximizes productive use of electricity and minimizes byproduct formation.

Electrocatalytic hydrogenation of furfural using non-noble-metal electrocatalysts in alkaline medium

The production of bio-oil from agricultural waste is a promising route to improve the agricultural value chain. Herein, furfural (FF), a model bio-oil compound, was subjected to electrocatalytic hydrogenation (ECH) in an alkaline medium to produce economically important furfuryl alcohol (FA) and hydrofuroin (HF). The selectivity of ECH products (FA and HF) on Cu, Pt, and Ni-foam electro-catalysts showed that their generation was dependent upon the availability of Hads, which in turn varied with the choice of electrocatalyst and applied potential. Cu-NPNi/NF was obtained through dealloying Cu from a co-electrodeposited Ni-Cu electrode on a Ni-foam substrate, followed by re-electrodeposition of Cu. A porous, high-surface-area bimetallic Ni-Cu catalyst (Cu-NPNi/NF) on Ni-foam yielded high rates of FA and HF generation from furfural, e.g. 118.7 ± 8 and 176.3 ± 3.4 μmol h-1 cm-2 at -1.45 V vs. Ag/AgCl/sat KCl after 1 h of electrolysis in an alkaline electrolyte. 100% conversion of furfural was observed after 2 h of electrolysis with the same catalyst. The high rate of FA and HF formation was ascribed to enhanced adsorbed FF because of the formation of Cu-nanoplates and bimetallic Ni-Cu. We have provided a rational, high-throughput design for preparing highly active nanoporous electrodes for producing industrially relevant chemicals (furfuryl alcohol and hydrofuroin).

Electrohydrodimerization of biomass-derived furfural generates a jet fuel precursor

Despite the increasing interest in upgrading biomass-derived molecules to value-added products, the electrochemical conversion of biomass platform chemicals to highly valuable biofuels, such as jet fuel, has not yet received wide attention. Herein, we report a catalyst-free electrochemical route for the production of a jet fuel precursor, hydrofuroin, from the electrohydrodimerization of furfural, which can be readily derived from lignocellulose and already has an industrial production of 300 000 tons per year. Detailed electrochemical studies using carbon and copper electrodes at various pH values enabled us to probe the reduction mechanism of furfural and obtain the kinetic details, such as the diffusion constant and electron transfer rate. Preparative electrolysis in a batch electrolyzer achieved a high yield of hydrofuroin (94%) with an excellent faradaic efficiency of 93%. Finally, a flow electrolyzer was employed to demonstrate the great promise of large-scale production of hydrofuroin from the electrohydrodimerization of furfural. This journal is

Mechanisms of Furfural Reduction on Metal Electrodes: Distinguishing Pathways for Selective Hydrogenation of Bioderived Oxygenates

Electrochemical reduction of biomass-derived platform molecules is an emerging route for the sustainable production of fuels and chemicals. However, understanding gaps between reaction conditions, underlying mechanisms, and product selectivity have limited the rational design of active, stable, and selective catalyst systems. In this work, the mechanisms of electrochemical reduction of furfural, an important biobased platform molecule and model for aldehyde reduction, are explored through a combination of voltammetry, preparative electrolysis, thiol-electrode modifications, and kinetic isotope studies. It is demonstrated that two distinct mechanisms are operable on metallic Cu electrodes in acidic electrolytes: (i) electrocatalytic hydrogenation (ECH) and (ii) direct electroreduction. The contributions of each mechanism to the observed product distribution are clarified by evaluating the requirement for direct chemical interactions with the electrode surface and the role of adsorbed hydrogen. Further analysis reveals that hydrogenation and hydrogenolysis products are generated by parallel ECH pathways. Understanding the underlying mechanisms enables the manipulation of furfural reduction by rationally tuning the electrode potential, electrolyte pH, and furfural concentration to promote selective formation of important biobased polymer precursors and fuels.

MeOH or H2O as efficient additive to switch the reactivity of allylSmBr towards carbonyl compounds

A variety of carbonyl compounds were treated by allylSmBr (allylSmBr) with MeOH as the cosolvent to have further insights on the previously reported reductive coupling of aryl ketones mediated by Sm/alkyl halide/MeOH. The results demonstrate that the real reducing species in Sm/alkyl halide/MeOH system should be allylSmBr, and MeOH has elegantly switched the reactivity of allylSmBr from being nucleophilic to being good reductive coupling reagent. Besides, H2O was also found to be a useful additive to realize the pinacol coupling of aliphatic aldehydes and ketones promoted by allylSmBr.

First pinacol coupling in emulsified water: Key role of surfactant and impact of alternative activation technologies

For the first time, the influence of surfactants on the radical pinacol coupling reaction is investigated. The rate and selectivity of this reductive C-C coupling are compared under three different activation technologies: thermal activation, microwave irradiation, and sonication. The use of IgepalCO520, a neutral surfactant, led to the successful conversion of aromatic or α,β-unsaturated aliphatic carbonyl compounds in moderate to excellent yield (55-90 %). An insight on the potential mechanism involved in the reaction is also proposed, based on microscopic observations and particle size measurement.

Simple and expeditious pinacol coupling of non usual α,β-unsaturated carbonyl compounds in water

Using zinc (0) in a 5% v AcOH aqueous solution allowed the efficient pinacol coupling of aliphatic or aromatic unusual, α,β-unsaturated carbonyl compounds such as citral A in good to excellent yields (56-99%). It can also be successfully applied to acetophenone.

The pinacol coupling of aromatic aldehydes in ethyl acetate mediated by TiCl4-Al

Titanium tetrachloride in ethyl acetate can be reduced by Al powder to the corresponding low valent titanium complexes, which can mediate the conversion of some aromatic aldehydes into the corresponding pinacols in 23-93% yields within 25-120 min under stirring at r.t. When N,N,N′,N′- tetramethylethylene diamine (TMEDA) is added, the diastereoselectivities of the reactions are improved.