13679-46-4

Basic information

• Product Name: FURFURYL METHYL ETHER
• Synonyms: 2-(methoxymethyl)-fura;2-(Methoxymethyl)furan;Furan, 2-(methoxymethyl)-;FURFURYL METHYL ETHER
• CAS NO: 13679-46-4
• Molecular Formula: C₆H₈O₂
• Molecular Weight: 112.13
• EINECS: 237-176-5
• Mol File: 13679-46-4.mol

Chemical Properties

• Melting Point: 97 °C
• Boiling Point: 132°C (estimate)
• Flash Point: 22.1 °C
• Appearance: /
• Density: 1.0163
• Vapor Pressure: 11.1mmHg at 25°C
• Refractive Index: 1.4570 (estimate)
• CAS DataBase Reference: FURFURYL METHYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: FURFURYL METHYL ETHER(13679-46-4)
• EPA Substance Registry System: FURFURYL METHYL ETHER(13679-46-4)

Safety Data

• Hazardous Substances Data: 13679-46-4(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
Furfuryl methyl ether is used as a flavoring agent for its characteristic aroma, which is reminiscent of roasted coffee. It is particularly valued in the flavor and fragrance industry for enhancing the sensory experience of various products.
Used in Chemical Synthesis:
As a versatile chemical intermediate, furfuryl methyl ether is used in the synthesis of various compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows for a wide range of reactions, making it a valuable building block in the chemical industry.
Used in Solvent Applications:
Due to its polarity and solubility properties, furfuryl methyl ether can be employed as a solvent in various chemical processes. It is particularly useful in reactions involving other polar or heterocyclic compounds, where its solvation capabilities can facilitate the reaction and improve yields.
Used in Polymer Industry:
Furfuryl methyl ether can be utilized in the polymer industry as a monomer for the production of polymers with specific properties. Its incorporation into polymer chains can lead to materials with enhanced thermal stability, chemical resistance, and other desirable characteristics.

Preparation

From furfuryl chloride and potassium methoxide in ether solution.

InChI:InChI=1/C6H8O2/c1-7-5-6-3-2-4-8-6/h2-4H,5H2,1H3

Upstream product

• 617-88-9 2-Chloromethylfuran 
• 67-56-1 methanol 
• 117680-17-8 2-(Iodomethyl)tetrahydrofuran 
• 98-00-0 (2-furyl)methyl alcohol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 98-01-1 furfural 
• 1917-65-3 5-(ethoxymethyl)furfural 
• 611-13-2 2-furoic acid methyl ester 
• 167106-10-7 furfuryl alcohol α-(tributylstannyl)methyl ether 
• 623-17-6 furfurylacetate 
• 96-36-6 methyl phosphite 
• 76190-23-3 O-methyl furan-2-carbothiono ester 
• 503-30-0 trimethylene oxide 

Downstream Products

• 1255536-57-2 methyl 4-(5-(methoxymethyl)furan-2-yl)benzoate 
• 1569-98-8 2-(furan-2-yl)-1,3-benzothiazole 
• 6310-30-1 S-(4-chlorophenyl) furan-2-carbothioate 
• 1422191-56-7 (E)-2-(4-fluorostyryl)-5-(methoxymethyl)furan 
• 1422191-55-6 (E)-2-(3-chlorostyryl)-5-(methoxymethyl)furan 
• 1422191-53-4 (E)-2-(methoxymethyl)-5-styrylfuran 
• 109393-67-1 4-(2,4-dinitro-phenylhydrazono)-5-methoxy-valeraldehyde-(2,4-dinitro-phenylhydrazone) 
• 98560-91-9 2,4,5-Trimethoxy-2-methyl-tetrahydro-furan 
• 624-45-3 levulinic acid methyl ester 
• 686-21-5 4,5,5-trimethoxy-pentan-2-one 
• 3260-09-1 2-((phenylthio)methyl)furan 
• 586-84-5 2-(methoxymethyl)-5-nitrofuran 

Relevant articles and documents

Solid acid-catalyzed conversion of furfuryl alcohol to alkyl tetrahydrofurfuryl ether

The acidic zeolite HZSM-5 (Si/Al = 25) achieved 58.9% selectivity of methyl furfuryl ether (MFE) and 44.8% selectivity of ethyl furfuryl ether (EFE) from etherification of furfuryl alcohol with methanol and ethanol. MFE and EFE were quantitatively hydrogenated into methyl tetrahydrofurfuryl ether (MTE) and ethyl tetrahydrofurfuryl ether (ETE) using a Raney Ni catalyst.

New Conversion of Esters to Ethers and Its Application to the Preparation of Furano-18-crown-6

Thionoesters which are readily prepared from esters can be desulfurized with Raney nickel to form the corresponding ethers.This new synthetic pathway to convert esters to ethers avoids many of the steric and functional limitations of known methods and appears to be a general method for this conversion.

Utilization of renewable resources: Investigation on role of active sites in zeolite catalyst for transformation of furfuryl alcohol into alkyl levulinate

A bio-derived furfuryl alcohol transformation into various high-value chemicals is a growing field of interest among researchers. This study reports an exclusive investigation of the porosity and active sites responsible for the efficient alcoholysis of furfuryl alcohol to alkyl levulinate by the aid of zeolite catalyst. Alkyl levulinate is a promising platform chemical potentially used as a fuel additive and also for the production of chemicals. A detailed study using well-characterized HZSM-5 catalyst on the influence of acidity and post synthesis modification like desilication, dealumination, metal ion exchange and phosphate modification revealed the most desired type of acid sites required to catalyze this reaction. Among the HZSM-5 catalysts tested, HZSM-5 (SAR 95) showed the best performance of ≥ 99 % furfuryl alcohol conversion and 85 % butyl levulinate selectivity under optimum conditions. The catalyst exhibited good recyclability additionally addressing all the challenges reported in the previous literature fulfilling the green chemistry principles.

Synthesis of phenylthiomethyl substituted furans by Lewis acid catalysed substitution

Two routes to the differentially functionalised trisubstituted furan methyl 4-methyl-2-[(phenylthio)methyl]-3-furoate are presented. One is a direct palladium catalysed annulation which proceeds smoothly in the presence of a thioether and the other depends on a highly chemoselective displacement of a methoxy group by phenylthiotrimethylsilane. The scope and mechanism of the latter transformation was probed with simple model systems.

Conformational Analysis of Furyl- and Thienylhydroxymethyl Radicals

Low-temperature photolysis of ArCH2OH derivatives (Ar = 2- and 3-furyl and -thienyl) in the presence of ButOOBut yields the corresponding ArCHOH radicals which can be observed by means of EPR spectroscopy.Each radical displays E and Z rotational conformers due to restricted Ar-Cα rotation.The study of ArCHOMe radicals, as well as of 2-furyl- and 2-thienylhydroxymethyl radicals having a methyl group in position 3 of the ring, allowed us to identify the most stable of the two conformers.The temperature dependence of the αOH hfs constant (assigned by deuterium substitution) has been interpreted on the basis of an averaging of ab initio αOH hfs constant over the rotation about the Cα-O bond which also allowed us to obtain an estimate of the corresponding rotation barrier.

Microwave-assisted catalytic upgrading of bio-based furfuryl alcohol to alkyl levulinate over commercial non-metal activated carbon

A cheap and commercially available non-metal activated carbon (AC) as an efficient catalyst for the alcoholysis of furfuryl alcohol (FA) to alkyl levulinate (AL) under microwave assistance was firstly investigated. The catalyst gave an impressive methyl levulinate (ML) yield of 78% in only 5 min at 170 °C in the presence of FA (0.2 M, 3 mL) and AC (100 mg). Various reaction parameters in dependence of time such as temperature, catalyst and feedstock loadings as well as solvent types have been optimized. The re-utilization experiments of the catalyst showed that the activity related to the acidic groups of the catalysts, and the deactivation was due to the leaching of acidic specie, which was easily extracted by the solvent. Note that extremely low concentration of the active species extracted from AC (less than 1 wt %) could also give 62% ML yield. The present study provided a promising way for AL synthesis over cheap, commercially available and environmentally benign catalyst.

METAL-IODIDE CATALYTIC SYSTEM FOR DIRECT ETHERIFICATION FROM ALDEHYDES AND/OR KETONES

A process for etherification of aldehydes and/or ketones in the presence of a catalyst and an iodine source.

Facile synthesis of furfuryl ethyl ether in high yield: Via the reductive etherification of furfural in ethanol over Pd/C under mild conditions

The one-pot synthesis of furfuryl ethyl ether (FEE) over Pd nanoparticles supported on TiO2, Al2O3, SiO2, and active carbon via the catalytic reductive etherification of furfural in ethanol was systematically studied. The Pd nanoparticles supported on SiO2, TiO2 and active carbon are all active for this novel process under mild reaction conditions, with Pd/C showing the highest selectivity to FEE. The effects of palladium loading, reaction temperature, and hydrogen pressure on the activity and selectivity of Pd/C have been investigated in detail. The results demonstrate that suitable Pd amount, low reaction temperature of about 60 °C, and low H2 pressure of about 0.3 MPa are favorable for the formation of the desired ether product. Under the optimized conditions, an unprecedented high yield of up to 81% of FEE was firstly obtained with the major by-products being furfuryl alcohol and 2-methyltetrahydrofuran. Compared with the conventional hydrogenation-etherification route via furfural alcohol as a reaction intermediate, the reductive etherification shows significant advantage in product yield because of its much lower reaction temperature that is required.

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.

Preparation method for furfuryl alkyl ether

The invention discloses a preparation method for furfuryl alkyl ether through reaction of furfuryl alcohol and monohydric alcohol. The preparation method comprises the following steps: dissolving furfuryl alcohol in monohydric alcohol in a reaction kettle; then adding a catalyst; and next carrying out a reaction for 1-24 hours at the temperature of 150-260 DEG C, and thus obtaining the furfuryl alkyl ether. The preparation method is simple in process and easy to control, only adopts an inorganic metal oxide as the catalyst, has no addition of organic acids and alkalis, inorganic acids and alkalis or other co-catalysts, is convenient for separation of the catalyst and other operations, and is conducive to large-scale industrialized production.