6126-49-4

Usage

Uses

Used in Flavoring Agents:
Tetrahydro-5-methylfuran-2-methanol is used as a flavoring agent in the food and beverage industry, providing a sweet, ethereal aroma to enhance the sensory experience of various products.
Used in Pharmaceutical Production:
In the pharmaceutical industry, tetrahydro-5-methylfuran-2-methanol serves as a solvent, aiding in the manufacturing process of various medications and ensuring the proper consistency and stability of the final products.
Used in Organic Compound Synthesis:
Tetrahydro-5-methylfuran-2-methanol is utilized in the synthesis of other organic compounds, contributing to the creation of a wide range of chemical products with diverse applications.
Used in Polymer and Resin Manufacturing:
This chemical compound also has potential applications in the manufacturing of polymers and resins, where it can be used to modify properties such as strength, flexibility, and durability.
It is important to handle tetrahydro-5-methylfuran-2-methanol with care due to its flammable and toxic nature, ensuring safety in all applications.

InChI:InChI=1/C19H21NO3/c1-3-15(14-10-6-5-7-11-14)18(21)20-17-13-9-8-12-16(17)19(22)23-4-2/h5-13,15H,3-4H2,1-2H3,(H,20,21)

Upstream product

• 72693-13-1 5,6-dihydroxy-hexan-2-one 
• 64-19-7 acetic acid 
• 10551-58-3 5-acetoxymethyl-2-furaldehyde 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 57-48-7 D-Fructose 
• 470-23-5 D-fructose 
• 620-02-0 5-Methylfurfural 
• 17397-24-9 hex-5-en-2-ol 
• 3857-25-8 2-hydroxymethyl-5-methylfuran 
• 625-86-5 2,5-dimethylfuran 
• 65313-46-4 1-hydroxyl-2,5-hexanedione 
• 10299-30-6 hexane-1,2,5-triol 
• 67-56-1 methanol 
• 1623-88-7 5-chloromethylfurfural 

Downstream Products

• 928-40-5 hexane-1,5-diol 
• 108-94-1 cyclohexanone 
• 21856-89-3 6-hydroxy-2-hexanone 

Relevant academic research and scientific papers

Selective aqueous-phase hydrogenation of furfural to cyclopentanol over Ni-based catalysts prepared from Ni-MOF composite

Metal-organic frameworks (MOFs) as an emerging class of porous materials exhibit some unique advantages, including controllable composition, a large surface area, high porosity, and so on. In this work, the spherical NiMo bimetal catalysts supported on porous carbon matrix were prepared using a simple wet impregnation method and studied for selective hydrogenation of furfural (FFA). Three different catalysts were investigated including Ni/C-Mo-BTC, Ni/C-Mo-DHTA and Ni/C-Mo-PTA. Of the catalysts studied the Ni/C-Mo-BTC catalyst could achieve the highest selectivity of CPL (up to 90%) under moderate reaction conditions (140 °C, 2 MPa, 2 h) in aqueous medium. In addition, other Ni-based catalysts (Ni/C-Fe, Ni/C-Zn, Ni/C-Cu, Ni/C-Ce) were also investigated to achieve yields of 20–70% under the same reaction conditions. The influence of temperature, H2 pressure, time and solvent were investigated for the best performing catalyst. Based on the optimal reaction condition, various of furfural derivatives could also be effectively transferred to produce corresponding products. The detailed physicochemical characterization was carried out by means of XRD, SEM, TEM, XPS, NH3-TPD and Raman analysis. In the end, the optimal Ni/C-Mo0.4 catalyst could be recycled magnetically and efficiently applied in the next run for five consecutive recycling tests in the FFA hydrogenation to CPL. The results suggested Ni/C-Mo0.4 catalyst occurred to increasingly favor the formation of Ni-Mo alloys and suggested a metallic active site in FFA hydrogenation with the addition of element Mo. Mechanism study indicated that water was a key factor contributing to the formation of different desired products, which was responsible for the arrangement of furan compound.

Formic Acid-Assisted Selective Hydrogenolysis of 5-Hydroxymethylfurfural to 2,5-Dimethylfuran over Bifunctional Pd Nanoparticles Supported on N-Doped Mesoporous Carbon

Biomass-derived 5-hydroxymethylfurfural (HMF) is regarded as one of the most promising platform chemicals to produce 2,5-dimethylfuran (DMF) as a potential liquid transportation fuel. Pd nanoparticles supported on N-containing and N-free mesoporous carbon materials were prepared, characterized, and applied in the hydrogenolysis of HMF to DMF under mild reaction conditions. Quantitative conversion of HMF to DMF was achieved in the presence of formic acid (FA) and H2 over Pd/NMC within 2 h. The reaction mechanism, especially the multiple roles of FA, was explored through a detailed comparative study by varying hydrogen source, additive, and substrate as well as by applying in situ ATR-IR spectroscopy. The major role of FA is to shift the dominant reaction pathway from the hydrogenation of the aldehyde group to the hydrogenolysis of the hydroxymethyl group via the protonation by FA at the C-OH group, lowering the activation barrier of the C?O bond cleavage and thus significantly enhancing the reaction rate. XPS results and DFT calculations revealed that Pd2+ species interacting with pyridine-like N atoms significantly enhance the selective hydrogenolysis of the C?OH bond in the presence of FA due to their high ability for the activation of FA and the stabilization of H?.

Insight into the hydrogenation of pure and crude HMF to furan diols using Ru/C as catalyst

5-hydroxymethylfurfural (HMF) is one of the most important renewable platform-chemicals, a very valuable precursor for the synthesis of bio-fuels and bio-products. In this work, the hydrogenation of HMF to two furan diols, 2,5-bis(hydroxymethyl)furan (BHMF) and 2,5-bis(hydroxymethyl)tetrahydrofuran (BHMTHF), both promising renewable monomers, was investigated. Three commercial catalysts, Ru/C, Pd/C and Pt/C, were tested in the hydrogenation of aqueous HMF solutions (2–3 wt%), using a metal loading of 1 wt% respect to HMF content. By appropriate tuning of the process conditions, either BHMF or BHMTHF were obtained in good yields, and Ru/C resulted the best catalyst for this purpose, allowing us to obtain BHMF or BHMTHF yields up to 93.0 and 95.3 mol%, respectively. This catalyst was also tested for in the hydrogenation of a crude HMF-rich hydrolyzate, obtained by one-pot the dehydration of fructose. The influence of each component of this hydrolyzate on the hydrogenation efficiency was investigated, including unconverted fructose, rehydration acids and humins, in order to improve the yields towards each furan diol. Moreover, ICP-OES and TEM analysis showed that the catalyst was not subjected to important leaching and sintering phenomena, as further confirmed by catalyst recycling study.

Catalytic selective hydrogenation and rearrangement of 5-hydroxymethylfurfural to 3-hydroxymethyl-cyclopentone over a bimetallic nickel-copper catalyst in water

The selective hydrogenation and rearrangement of 5-hydroxymethylfurfural (5-HMF) to 3-hydroxymethyl-cyclopentone (HCPN) were studied over a MOF-derived bimetallic nickel-copper catalyst in water. The combination of nickel and copper dramatically improved the efficiency in both the selective hydrogenation of the carbonyl group of 5-HMF and the hydrogenative ring-rearrangement of the C5 ring, affording 70.3% yield for HCPN and 99.8% yield for the rearrangement products. Moreover, it was indicated that water acted as a solvent, reactant, and proton donor by dissociation at an elevated temperature, which supplied slightly acidic conditions and promoted the rearrangement reaction.

Rhenium-catalyzed deoxydehydration of renewable triols derived from sugars

An efficient method for the catalytic deoxydehydration of renewable triols, including those obtained from 5-HMF, is described. The corresponding unsaturated alcohols were obtained in good yields using simple rhenium(vii)oxide under neat conditions and ambient atmosphere at 165 °C.

Tetrahydrofuran compound

The present invention is a method for producing a tetrahydrofuran compound represented by general formula (2), the method comprising a reaction step for bringing a furan compound represented by general formula (1) into contact with a palladium catalyst in the presence of a hydrogen source. (In formula (1), R is a formyl group or hydroxymethyl group, R1a is a hydrogen atom, C1-5 alkyl group, formyl group, or hydroxymethyl group, R2 and R3 are each independently a hydrogen atom or C1-5 alkyl group, and R1a and R2 or R2 and R3 may bond together to form a ring.) (In formula (2), R1b is a hydrogen atom, C1-5 alkyl group or hydroxymethyl group, R2 and R3 are the same as defined above, and R1b and R2 or R2 and R3 can bond together to form a ring.)

Application of apatite substance in catalytic hydrogenation and tetrahydrofurfuryl alcohol preparation method

The invention discloses application of an apatite substance in catalytic hydrogenation and a tetrahydrofurfuryl alcohol preparation method. The method can be used for an alcohol or alkane solvent system, furfural is completely hydrogenated in the hydrogen atmosphere of 0.1-6 MPa at the temperature of 0-200 DEG C under the effects of Pd-HAP prepared from hydroxyapatite and palladium metal by adopting an ion exchange method and other catalysts to generate the tetrahydrofurfuryl alcohol, and the method is provided for efficient utilization of biomass raw materials. The used catalysts can be used for high-conversion-rate and high-yield preparation of tetrahydrofurfuryl alcohol in the alcohol or alkane solvent system, and the conversion rate of the furfural and the yield of the furfural can be up to 100%. The tetrahydrofurfuryl alcohol preparation method is simple, reaction devices are simple, the operation is simple and convenient, a product and the catalysts are easy to separate, the catalysts are cheap and easy to obtain, and the catalysts have good hydrothermal stability and recycling performance, are suitable for industrial production and have a very broad application prospect.

Hydrogenation of levoglucosenone to renewable chemicals

We have studied the hydrogenation of levoglucosenone (LGO) to dihydrolevoglucosenone (Cyrene), levoglucosanol (Lgol), and tetrahydrofurandimethanol (THFDM) and elucidated the reaction network over supported palladium catalysts. At low temperature (40 °C) over a Pd/Al2O3 catalyst, LGO is selectively hydrogenated to Cyrene. At intermediate temperatures (100 °C) over a Pd/Al2O3 catalyst, Cyrene is selectively hydrogenated to Lgol, with an excess of the exo-Lgol isomer produced over the endo-Lgol isomer. At higher temperatures (150 °C) over a bifunctional Pd/SiO2-Al2O3 catalyst, Lgol is converted to THFDM in 58% selectivity, with 78% overall selectivity to 1,6-hexanediol precursors. The ratio of cis-THFDM relative to trans-THFDM is approximately 2.5, and this ratio is independent of the Lgol feed stereoisomer ratio. Tetrahydropyran-2-methanol-5-ketone (THP2M5one) and tetrahydropyran-2-methanol-5-hydroxyl (THP2M5H) are side-products of Lgol hydrogenolysis, but neither of these species are precursors to THFDM.

SYNTHESIS OF R-GLUCOSIDES, SUGAR ALCOHOLS, REDUCED SUGAR ALCOHOLS, AND FURAN DERIVATIVES OF REDUCED SUGAR ALCOHOLS

Disclosed herein are methods for synthesizing 1,2,5,6-hexanetetrol (HTO), 1,6 hexanediol (HDO) and other reduced polyols from C5 and C6 sugar alcohols or R glycosides. The methods include contacting the sugar alcohol or R-glycoside with a copper catalyst, most desirably a Raney copper catalyst with hydrogen for a time, temperature and pressure sufficient to form reduced polyols having 2 to 3 fewer hydoxy groups than the starting material. When the starting compound is a C6 sugar alcohol such as sorbitol or R-glycoside of a C6 sugar such as methyl glucoside, the predominant product is HTO. The same catalyst can be used to further reduce the HTO to HDO.

METHOD FOR PRODUCING TETRAHYDROFURAN COMPOUND

PROBLEM TO BE SOLVED: To provide a method for efficiently producing a tetrahydrofuran compound having a hydroxymethyl group by suppressing the hydrogenolysis of a hydroxymethyl group in a step of obtaining a tetrahydrofuran compound by reducing a furan compound. SOLUTION: There is obtained a corresponding tetrahydrofuran compound by reducing a furan compound represented by the following general formula (1) by bringing into contact with a palladium catalyst in a hydrogen atmosphere in the coexistence of a base. (wherein, Ra represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, a formyl group or a hydroxymethyl group; Rb represents a formyl group or a hydroxymethyl group; R1 and R2 each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group; and R1 and R2 may be bonded together to form a ring.) SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT