85733-99-9

Upstream product

• 67-63-0 isopropyl alcohol 
• 57-50-1 Sucrose 
• 57-48-7 D-Fructose 
• 50-99-7 D-glucose 
• 470-23-5 D-fructose 
• 39131-44-7 5-bromomethyl-furan-2-carbaldehyde 
• 6347-01-9 fructopyranose 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 470-23-5 D-fructose 
• 57-48-7 fructose 
• 50-99-7 2,3,4,5,6-pentahydroxy-hexanal 

Downstream Products

• 3238-40-2 furan-2,5-dicarboxylic acid 
• 625-86-5 2,5-dimethylfuran 

Relevant academic research and scientific papers

Assembly of Zr-based coordination polymer over USY zeolite as a highly efficient and robust acid catalyst for one-pot transformation of fructose into 2,5-bis(isopropoxymethyl)furan

It is highly desirable but challenging to develop a one-pot process for the transformation of fructose into 2,5-bis(isopropoxymethyl)furan (BPMF), a promising biofuel component, because a cascade sequence involving dehydration, reduction, and etherification requires multifunctional acid catalysts. Herein, we propose a facile and firm assembly of Zr/2-methylimidazole (2-MeIM) coordination polymer over USY zeolite (USY?ZrCP) through N-Al bonds formed by the condensation of 2-MeIM and the hydroxyls on USY surface at room temperature. USY?ZrCP possesses an abundance of strong Lewis acid sites with suitable amount of Bronsted acid sites, which are mainly attributed to the highly dispersed Zr(IV) species and the hydroxyls over USY?ZrCP, respectively. Unexpectedly, USY?ZrCP could offer BPMF yield up to 82.6% from fructose in isopropanol by the integration of dehydration, Meerwein–Ponndorf–Verley reduction and etherification in a one-pot strategy. This work proposes a novel approach to prepare highly efficient and robust solid acid catalyst for the catalytic valorization of biomass-derived carbohydrates and their derivatives.

Importance of the synergistic effects between cobalt sulfate and tetrahydrofuran for selective production of 5-hydroxymethylfurfural from carbohydrates

In this study, an effective catalytic system (CoSO4·7H2O/THF) for selective conversion of fructose to 5-hydroxymethylfurfural (HMF; yield: 88%) was developed. The synergistic effects among Co2+, SO42-, crystal water and tetrahydrofuran (THF) were crucial for achieving selective dehydration of fructose to HMF. Co2+ worked as a Lewis acid for catalyzing mainly dehydration of fructose to HMF but not the further decomposition of HMF to levulinic acid. THF could help to retain HMF while CoSO4 could coordinate with HMF, enhancing the thermal stability of HMF in THF. The crystal water in cobalt sulfate could help to coordinate with fructose, which facilitated the conversion of fructose via dehydration reactions. The CoSO4·7H2O/THF catalytic system could also catalyze the conversion of inulin and cellulose into HMF. The main advantages of the CoSO4·7H2O/THF catalytic system are the low cost, the easy recycling of the CoSO4·7H2O catalyst and the easy separation of HMF from volatile THF.

HReO4 as highly efficient and selective catalyst for the conversion of carbohydrates into value added chemicals

This work describes the first catalyst (HReO4) that promotes the efficient and selective conversion of several carbohydrates into four compounds, ethyl levulinate (EL), 5-ethoxymethylfurfural (EMF), 5-hydroxymethylfurfural (HMF) and levulinic acid (LA), through a one-pot reaction strategy adjusting the reaction conditions. The reaction of fructose in ethanol at 160 °C gave EL in 80% yield after 16 h and in a mixture of ethanol/THF at 140 °C produced EMF in 73% yield after 1 h. HMF and LA can also be obtained selectively with 100% yield from fructose at 140 °C after 1 h, in DMSO or 1,4-dioxane, respectively. EL, HMF, LA and EMF were also produced in moderate to good yields from other carbohydrates such as inulin and sucrose. The catalyst HReO4 can be used in gram scale for the production of EL, EMF, HMF and LA with good yields and in at least 8 catalytic cycles on the conversion of fructose into EL with no significant reduction in its activity.

Role of lewis and Br?nsted acidity in metal chloride catalysis in organic media: Reductive etherification of furanics

Metal chlorides are demonstrated to behave as bifunctional acid catalysts in organic media in the one-pot reductive etherification of 5-hydroxymethylfurfural (HMF) in 2-propanol toward production of biodiesel. Two competing reaction pathways, direct etherification to 5-(isopropoxymethyl)furfural and reductive etherification to 2,5-bis-(isopropoxymethyl)furan, are proposed with the selectivity depending on the metal ion. Furfural and furfuryl alcohol are used as model compounds to investigate each pathway individually. The roles of Lewis/Br?nsted acidity of metal chlorides solution are elucidated by kinetic studies in conjunction with salt speciation using electrospray soft ionization mass spectrometer. Br?nsted acidic species, generated from alcoholysis of the metal chlorides, are the predominant catalytically active species in etherification. On the other hand, partially hydrolyzed metal cations produced by alcoholysis/hydrolysis are responsible Lewis acid centers for furfural reduction to furfuryl alcohol. Isotopic labeling experiments, in combination with GCMS and 1H NMR analysis, reveal an intermolecular hydrogen transfer from the a-C of 2-propanol to the a-C of furfural as the rate-limiting step of furfural hydrogenation.

A fructose-based biomass catalytic conversion systems furan derivatives

A method for preparing furan derivatives by catalytic conversion of fructose-based biomass is characterized by: taking biomass such as fructose, cane sugar, inulin and the like as raw materials, taking low-boiling-point alcohols comprising aliphatic alcohols or alicyclic alcohols all with six or less than six carbon atoms as a solvent, and under the effect of a catalyst, performing reactions comprising hydrolysis, dehydration, etherfication and the like for coupling so as to obtain furan derivatives such as 5-alkoxymethyl furfural, levulinate esters, 5-hydroxymethylfurfural and the like. The method has the advantages of high raw material utilization rate, high in-situ coupling efficiency in the dehydration and etherfication reactions, and easily separated and purified system.

METHOD FOR REDUCING HYDROXYMETHYLFURFURAL (HMF)

The invention relates to the conversion of renewable biomass resources into valuable compounds. More specifically, it relates to the selective valorisation of 5-(hydroxymethyl)furfural into useful chemicals and fuels. Provided is a method of reducing hydroxymethylfurfural (HMF), comprising the steps of: - providing a starting material comprising HMF in a solvent into a reactor; - providing H2 into the reactor; and - contacting the starting material with a catalyst, wherein said catalyst is copper-zinc alloy in a nanoparticulate form.

Copper-zinc alloy nanopowder: A robust precious-metal-free catalyst for the conversion of 5-hydroxymethylfurfural

Noble-metal-free copper-zinc nanoalloy (2. It is also possible to convert 10 wt % HMF solutions in CPME, with an excellent DMF yield of 90 %. Milder temperatures favor selective (95 %) formation of 2,5-furandimethanol (FDM). The one-pot conversion of fructose to valuable furan-ethers was also explored. Recycling experiments for DMF production show remarkable catalyst stability. Transmission electron microscopy (TEM) characterization provides more insight into morphological changes of this intriguing class of materials during catalysis.

Heterogeneous acidic TiO2 nanoparticles for efficient conversion of biomass derived carbohydrates

Selective conversion of biomass derived carbohydrates into fine chemicals is of great significance for the replacement of petroleum feedstocks and the reduction of environmental impacts. Levulinic acid, 5-hydroxymethyl furfural (HMF) and their derivatives are recognized as important precursor candidates in a variety of different areas. In this study, the synthesis, characterization, and catalytic activity of acidic TiO2 nanoparticles in the conversion of biomass derived carbohydrates were explored. This catalyst was found to be highly effective for selective conversion to value-added products. The nanoparticles exhibited superior activity and selectivity towards methyl levulinate from fructose in comparison to current commercial catalysts. The conversion of fructose to methyl levulinate was achieved with 80% yield and high selectivity (up to 80%). Additionally, conversions of disaccharides and polysaccharides were studied. Further, the production of versatile valuable products such as levulinic esters, HMF, and HMF-derived ethers was demonstrated using the TiO2 nano-sized catalysts in different solvent systems.

Preparation of potential biofuel 5-ethoxymethylfurfural and other 5-alkoxymethylfurfurals in the presence of oil shale ash

5-Ethoxymethylfurfural (EMF) can be prepared from the corresponding halomethylfurfural and absolute ethanol in good yield. The use of significantly more affordable 96% ethanol results in formation of levulinic acid or its ester in considerable amount (up to 16%), which is difficult to separate from the desired EMF. In the present study we report that the addition of oil shale ash prevents the hydrolysis of the furan ring and enables the use of 96% ethanol with great success. The developed procedure is applicable to a wide range of aqueous alcohols, is operationally simple and utilizes an inexpensive basic ash, which is deposited in millions of tons per year. Notably, the basicity of the ash is decreased during the process, making its deposits less hazardous to the environment.

Graphene oxide catalyzed dehydration of fructose into 5- hydroxymethylfurfural with isopropanol as cosolvent

The design of green heterogeneous catalysts for the efficient conversion of biomass into platform molecules is a key aim of sustainable chemistry. Graphene oxide prepared from Hummers oxidation of graphite was proven to be a green and efficient carbocatalyst for the dehydration of fructose into 5-hydroxymethylfurfural (HMF) in some three-carbon and four-carbon alcohol mediated solvent systems. HMF was obtained in up to 87 % yield in 90vol % isopropanol-mediated DMSO solvent. Some control experiments and analytical data showed that a small number of sulfonic groups and abundance of oxygen-containing groups (alcohols, epoxides, carboxylates) have an important synergic effect in maintaining the high performance of graphene oxide. GO-ing all the way: Graphene oxide is demonstrated to be a green heterogeneous catalyst for the selective dehydration of fructose into 5-hydroxymethylfurfural (HMF) in a cost efficient and environmentally benign isopropanol-mediated solvent system. A small number of sulfonic groups with the synergic effect of oxygen-containing groups (alcohols, epoxides, carboxylates) make graphene oxide an efficient acid catalyst.