113984-01-3

Basic information

• Product Name: Furan, 2-[(1-methylethoxy)methyl]-
• CAS NO: 113984-01-3
• Molecular Formula: C8H12O2
• Molecular Weight: 140.182
• Mol File: 113984-01-3.mol

Chemical Properties

• CAS DataBase Reference: Furan, 2-[(1-methylethoxy)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Furan, 2-[(1-methylethoxy)methyl]-(113984-01-3)
• EPA Substance Registry System: Furan, 2-[(1-methylethoxy)methyl]-(113984-01-3)

Safety Data

• Hazardous Substances Data: 113984-01-3(Hazardous Substances Data)

Upstream product

• 98-00-0 (2-furyl)methyl alcohol 
• 67-63-0 isopropyl alcohol 
• 98-01-1 furfural 

Downstream Products

• 21884-26-4 isopropyl levulinate 

Relevant articles and documents

Porous Zirconium–Furandicarboxylate Microspheres for Efficient Redox Conversion of Biofuranics

Biofuranic compounds, typically derived from C5 and C6 carbohydrates, have been extensively studied as promising alternatives to chemicals based on fossil resources. The present work reports the simple assembly of biobased 2,5-furandicarboxylic acid (FDCA) with different metal ions to prepare a range of metal–FDCA hybrids under hydrothermal conditions. The hybrid materials were demonstrated to have porous structure and acid–base bifunctionality. Zr-FDCA-T, in particular, showed a microspheric structure, high thermostability (ca. 400 °C), average pore diameters of approximately 4.7 nm, large density, moderate strength of Lewis-base/acid centers (ca. 1.4 mmol g?1), and a small number of Br?nsted-acid sites. This material afforded almost quantitative yields of biofuranic alcohols from the corresponding aldehydes under mild conditions through catalytic transfer hydrogenation (CTH). Isotopic 1H NMR spectroscopy and kinetic studies verified that direct hydride transfer was the dominant pathway and rate-determining step of the CTH. Importantly, the Zr-FDCA-T microspheres could be recycled with no decrease in catalytic performance and little leaching of active sites. Moreover, good yields of C5 (i.e., furfural) or C4 products [i.e., maleic acid and 2(5H)-furanone] could be obtained from furfuryl alcohol without oxidation of the furan ring over these metal–FDCA hybrids. The content and ratio of Lewis-acid/base sites were demonstrated to dominantly affect the catalytic performance of these redox reactions.

Catalytic Transfer Hydrogenation of Furfural to 2-Methylfuran and 2-Methyltetrahydrofuran over Bimetallic Copper–Palladium Catalysts

The catalytic transfer hydrogenation of furfural to the fuel additives 2-methylfuran (2-MF) and 2-methyltetrahydrofuran (2-MTHF) was investigated over various bimetallic catalysts in the presence of the hydrogen donor 2-propanol. Of all the as-prepared catalysts, bimetallic Cu-Pd catalysts showed the highest catalytic activities towards the formation of 2-MF and 2-MTHF with a total yield of up to 83.9 % yield at 220 °C in 4 h. By modifying the Pd ratios in the Cu-Pd catalyst, 2-MF or 2-MTHF could be obtained selectively as the prevailing product. The other reaction conditions also had a great influence on the product distribution. Mechanistic studies by reaction monitoring and intermediate conversion revealed that the reaction proceeded mainly through the hydrogenation of furfural to furfuryl alcohol, which was followed by deoxygenation to 2-MF in parallel to deoxygenation/ring hydrogenation to 2-MTHF. Finally, the catalyst showed a high reactivity and stability in five catalyst recycling runs, which represents a significant step forward toward the catalytic transfer hydrogenation of furfural.

Catalytic Transfer Hydrogenation of Furfural to Furfuryl Alcohol by using Ultrasmall Rh Nanoparticles Embedded on Diamine-Functionalized KIT-6

A Rh/ED-KIT-6 catalyst comprised of Rh nanoparticles embedded on mesoporous silica (KIT-6) functionalized with N1-[3-(trimethoxysilyl)propyl]ethane-1,2-diamine was synthesized by Rh3+ adsorption and chemical reduction in the liquid phase. The structure of ED-KIT-6 and textural properties of the pristine and supported Rh catalysts, as well as particle size and chemical state of the Rh species were examined by various analytical methods. The homogeneous dispersion of ultrasmall Rh nanoparticles, approximately 1.2 nm in size, stabilized by the grafted diamine (ED) species was confirmed. Rh/ED-KIT-6 was applied to the transfer hydrogenation of furfural (FFR) to furfuryl alcohol (FAL) by using formic acid (FA) as the hydrogen source. The effect of the solvent and reaction parameters, such as temperature, reaction time, and FA/FFR ratio, were investigated. The Rh-embedded catalyst exhibited a significantly high turnover frequency (TOF≈204 h?1) to that of Ru, Pd, or Ni-based catalysts on KIT-6. A plausible reaction mechanism was proposed after examining an independent FA decomposition reaction over the same Rh-ED-KIT-6 catalyst. The heterogeneity of the catalyst was verified by a hot filtration experiment. The Rh/ED-KIT-6 could be reused for up to three cycles without any decrease in catalytic activity and selectivity, but the slow oxidation of Rh species was detected.

Catalytic Activity of Ti-based MXenes for the Hydrogenation of Furfural

Herein we report on the catalytic activity of Ti-based MXenes (Ti3CNTz and Ti3C2Tz) for biomass transformation. MXenes were found to be active catalysts for the hydrogenation of furfural using either

Catalytic upgrading of furfuryl alcohol to bio-products: Catalysts screening and kinetic analysis

The conversion of furfuryl alcohol, a highly versatile biomass-derived platform molecule, into a large variety of bio-products, including ethers, lactones and levulinates, has been evaluated in alcohol media using different solid acid catalysts, such as commercial zeolites, sulfonic acid-functionalized materials, and sulfated zirconia. Reaction pathways and mechanisms have been correlated to the particular type of catalyst used, aiming to establish the influence of the main physico-chemical properties of the materials on the extent of furfuryl alcohol conversion, as well as on the predominant reaction pathway followed. Mechanistic and kinetics modelling studies for each type of catalyst have been developed and compared, providing an useful tool for the selection of the most suitable solid acid catalyst for the production of each of the reaction intermediates in the cascade from furfuryl alcohol to alkyl levulinate.

Synthesis of isopropyl levulinate from furfural: Insights on a cascade production perspective

The present work explores the production of isopropyl levulinate from furfural by a two-step microwave assisted cascade process. Furfural is a versatile biomass-derived industrial feedstock with high annual production volume. Alkyl levulinates are promising bio-based molecules with several applications in many sectors, in particular, as biofuels, blended with transportation fuels including biodiesel, these compounds can significantly reduce the formation of soot in engines. Thus, in the first step, the catalytic transfer hydrogenation of furfural to furfuryl alcohol was studied employing a simply “ad hoc” synthesized magnetically recoverable Cu catalyst and 2-propanol as H-donor. Subsequently, the alcoholysis of the previously obtained liquors rich in furfuryl alcohol or of neat furfuryl alcohol solutions to isopropyl levulinate was investigated using commercial solid acid catalysts such as niobium phosphate and Amberlyst sulfonic resins (A15 and A70). The cascade process resulted feasible leading to good furfuryl alcohol yields in the transfer hydrogenation process with Cu-Fe3O4 magnetic catalyst using much lower Cu to furfural molar ratios than commonly reported. The subsequent alcoholysis step of furfuryl alcohol-rich liquors was highly efficient with A70 resin even in presence of unreacted furfural from the first step.

Liquid phase catalytic transfer hydrogenation of furfural over a Ru/C catalyst

Methyl furan production through catalytic transfer hydrogenation of furfural in the liquid phase has been investigated over a Ru/C catalyst in the temperature range of 120-200 °C using 2-propanol as a solvent. It has been found that furfural hydrogenation produces furfuryl alcohol, which undergoes hydrogenolysis to methyl furan. Small amounts of furan and traces of tetrahydrofurfuryl alcohol are also produced via furfural decarbonylation and furfuryl alcohol ring hydrogenation, respectively. Furfuryl alcohol can dimerize or produce ether with 2-propanol. The yield of methyl furan is enhanced with increasing reaction temperature and/or reaction time. Optimum results are attained after 10 h of reaction at 180 °C, where furfural conversion and methyl furan yield reach 95% and 61%, respectively, which is the highest reported yield in the liquid phase at temperatures lower than 200 °C. The reaction network has been investigated by analysing the evolution of reaction intermediates and products and by starting from furfuryl alcohol, methyl furan, and furan hydrogenation. Intermediates, as well as methyl furan, are produced faster when starting with furfuryl alcohol as the reactant, rather than furfural, indicating that initial hydrogenation of furfural to furfuryl alcohol is slow. Catalyst recycling experiments over spent Ru/C catalyst show that, although furfural conversion does not decrease significantly, furfuryl alcohol yield increases at the expense of methyl furan. The initial catalytic activity and selectivity are regained completely after catalyst regeneration. We show evidence that the active phase of the catalyst involves Ru and RuOx.

Liquid-Phase Catalytic Transfer Hydrogenation of Furfural over Homogeneous Lewis Acid-Ru/C Catalysts

The catalytic performance of homogeneous Lewis acid catalysts and their interaction with Ru/C catalyst are studied in the catalytic transfer hydrogenation of furfural by using 2-propanol as a solvent and hydrogen donor. We find that Lewis acid catalysts hydrogenate the furfural to furfuryl alcohol, which is then etherified with 2-propanol. The catalytic activity is correlated with an empirical scale of Lewis acid strength and exhibits a volcano behavior. Lanthanides are the most active, with DyCl3 giving complete furfural conversion and a 97 % yield of furfuryl alcohol at 180 °C after 3 h. The combination of Lewis acid and Ru/C catalysts results in synergy for the stronger Lewis acid catalysts, with a significant increase in the furfural conversion and methyl furan yield. Optimum results are obtained by using Ru/C combined with VCl3, AlCl3, SnCl4, YbCl3, and RuCl3. Our results indicate that the combination of Lewis acid/metal catalysts is a general strategy for performing tandem reactions in the upgrade of furans.

Batch versus Continuous Flow Performance of Supported Mono- and Bimetallic Nickel Catalysts for Catalytic Transfer Hydrogenation of Furfural in Isopropanol

Furfural takes an important position in hemicelluloses biorefinery platforms. It can be converted into a wide range of chemicals. One important valorization route is the catalytic hydrogenation. Whereas molecular hydrogen is mostly used in industrial hydrogenation processes, recent studies also showed that alcohols can be used as reductants from which hydrides can be transferred catalytically to furfural. This process is often assisted by the formation of significant amounts of side products, in despite of high yields to the hydrogenolysis product 2-methylfuran. The present work explores the catalytic behavior in batch and continuous flow of mono- and bimetallic nickel catalysts supported on activated carbon for the catalytic transfer hydrogenation of furfural in isopropanol.

Alkali-metal-ions promoted Zr-Al-Beta zeolite with high selectivity and resistance to coking in the conversion of furfural toward furfural alcohol

Zirconium-substituted zeolites prepared by post-synthetic procedure have demonstrated excellent performance in the upgrading process of biomass platform compounds owing to the unique Lewis acid character. However, many pressing questions still surround these materials, especially relating to specific conversion, catalyst stability and substrate scalability. In the present study, a simple alkaline treatment to the Zr-Al-Beta zeolite in alcoholic solution of alkali metal hydroxide was conducted. The modification of alkali-metal ions on both Lewis acid sites and Br?nsted acid sites in Zr-Al-Beta was evidenced by XPS and FT-IR spectroscopy (CO and pyridine). The untreated materials displayed poor product selectivity and high coke deposit in the Meerwein-Ponndorf-Verley reduction of furfural and isopropanol; however, the treatment of alkali-metal ions promoted their catalytic performance with improved recalcitrance to deactivation and coking significantly. Both the type of alkali-metal ions and the concentration of alkaline solution influenced the catalytic performance, which were found to correlate to the acidity and textual properties. The optimum reaction result (97.3percent yield of furfuryl alcohol at 99.6percent conversion of furfural) can be obtained on 0.025 M-Na+-Zr-Al-Beta with high tolerance to the furfural concentration.