96-47-9 Usage
Description
2-Methyltetrahydrofuran (MeTHF or 2-MTHF) is a bio-based solvent that is recognized as the most favorable of ether solvents. It has a relatively high boiling point (80°C) and low melting point (-137°C), providing a broad temperature range for various processing conditions. With its intermediate polarity and Lewis base strength between tetrahydrofuran (THF) and diethyl ether, 2-Methyltetrahydrofuran is a potential greener solvent alternative for organic synthesis. Its resistance to reduction by lithium makes it a promising candidate as electrolytes in lithium batteries.
Uses
Used in Organic Synthesis:
2-Methyltetrahydrofuran is used as a solvent in organic synthesis, serving as a replacement for tetrahydrofuran due to its higher reaction temperature and easy separation after the reaction.
Used in Electrolyte Formulation for Secondary Lithium Electrodes:
2-Methyltetrahydrofuran is used in the electrolyte formulation for secondary lithium electrodes, taking advantage of its resistance to reduction by lithium.
Used in Alternative Fuels:
2-Methyltetrahydrofuran is used as a component in alternative fuels, contributing to the development of greener energy sources.
Used in Spectroscopic Studies:
2-Methyltetrahydrofuran acts as a solvent for spectroscopic studies at -196°C, enabling precise analysis in various research applications.
Used in Organometallic Reactions:
2-Methyltetrahydrofuran serves as a solvent for Grignard reagent in organometallic reactions, facilitating important chemical processes.
Used in Motor Fuel:
2-Methyltetrahydrofuran plays an important role as a motor fuel, offering a potential alternative to traditional fossil fuels.
Used in Phosphatidylserine Synthesis:
2-Methyltetrahydrofuran may be used as a solvent for phosphatidylserine synthesis, contributing to the production of essential phospholipids.
Used as an Alternative Solvent in C-C Bond Forming Reactions:
2-Methyltetrahydrofuran may be used as an alternative solvent to DMSO (dimethyl sulfoxide) or MTBE (methyl tertiary butyl ether) in the C-C bond forming reactions catalyzed by lyase enzyme.
Used as an Alternative Solvent in Reactions Between Grignard Reagents and Carbonyl Compounds:
2-Methyltetrahydrofuran can replace THF in the reaction between Grignard reagents and carbonyl compounds, providing a greener and more efficient approach.
Used as an Alternative Solvent in Biphase Reactions:
2-Methyltetrahydrofuran can replace methylene chloride in some biphase reactions, offering a safer and more environmentally friendly option.
Used in ZerO2 Product Degassing:
ZerO2 products are rigorously degassed with highly pure inert gas, providing solvents and solutions (anhydrous if specified) with very low residual oxygen content, which can involve the use of 2-Methyltetrahydrofuran.
Hazard
Flammable, dangerous fire risk.
Flammability and Explosibility
Highlyflammable
Purification Methods
Likely impurities are 2-methylfuran, methyldihydrofurans and hydroquinone (stabiliser, which is removed by distillation under reduced pressures). It is washed with 10% aqueous NaOH, dried, vacuum distilled from CaH2, passed through freshly activated alumina under nitrogen, and refluxed over sodium metal under vacuum. Store it over sodium. [Ling & Kevan J Phys Chem 80 592 1976.] Distil it from sodium under vacuum, and store it with sodium-potassium alloy (this treatment removes water and prevents the formation of peroxides). Alternatively, it can be freed from peroxides by treatment with ferrous sulfate and sodium bisulfate, then solid KOH, followed by drying with, and distilling from, sodium, or type 4A molecular sieves under argon. It may be difficult to remove *benzene if it is present as an impurity (can be readily detected by its ultraviolet absorption in the 249-268nm region). [Ichikawa & Yoshida J Phys Chem 88 3199 1984.] It has also been purifed by percolating through Al2O3 and fractionated collecting fraction b 79.5-80o. After degassing, the material is distilled onto degassed molecular sieves, then distilled onto anthracene and a sodium mirror. The solvent is then distilled from the green solution onto potassium mirror or sodium-potassium alloy, from which it is distilled again. [Mohammad & Kosower J Am Chem Soc 93 2713 1971.] It should be stored in the presence of 0.1% of hydroquinone or 2,6-di-tert-butyl –p-cresol as stabiliser. The R(+)-enantiomer has b 78-80o/atm and []D +27.5o (neat), and the S(-)-enantiomer has b 86o/atm and [] D -27.0o (neat) [Iffland & Davis J Org Chem 42 4150 1977, Gagnaire & Butt Bull Soc Chim Fr 312 1961, Beilstein 17 III/IV 60, 17/1 V 78.] HARMFUL VAPOURS.
Check Digit Verification of cas no
The CAS Registry Mumber 96-47-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 6 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 96-47:
(4*9)+(3*6)+(2*4)+(1*7)=69
69 % 10 = 9
So 96-47-9 is a valid CAS Registry Number.
InChI:InChI=1/C5H10O/c1-5-3-2-4-6-5/h5H,2-4H2,1H3/t5-/m1/s1
96-47-9Relevant articles and documents
Organic modifiers promote furfuryl alcohol ring hydrogenation via surface hydrogen-bonding interactions
Coan, Patrick D.,Farberow, Carrie A.,Griffin, Michael B.,Medlin, J. Will
, p. 3730 - 3739 (2021)
Interactions between surface adsorbed species can affect catalyst reactivity, and thus, the ability to tune these interactions is of considerable importance. Deposition of organic modifiers provides one method of intentionally introducing controllable surface interactions onto catalyst surfaces. In this study, Pd/Al2O3 catalysts were modified with either thiol or phosphonic acid (PA) ligands and tested in the hydrogenation of furanic species. The thiol modifiers were found to inhibit ring hydrogenation (RH) activity, with the degree of inhibition trending with the thiol surface coverage. This suggests that thiols do not strongly interact with the reactants and simply serve to block active sites on the Pd surface. PAs, on the other hand, were found to enhance RH when furfuryl alcohol (FA) was used as the reactant. Density functional theory calculations suggested that this enhancement was due to hydrogen-bonding interactions between FA-derived surface intermediates and PA modifiers. Here, installation of hydrogen-bonding groups on the Pd surface served to preferentially stabilize RH product states. Furthermore, the promotional effect on the RH of FA was observed to be greater when a higher-coverage PA was used, providing a rate more than twice that of the unmodified Pd/Al2O3. The results of this work suggest that organic ligands can be designed to impart tunable surface interactions on heterogeneous catalysts, providing an additional method of controlling catalytic performance.
Platinum Single Atoms on Carbon Nanotubes as Efficient Catalyst for Hydroalkoxylation
Woo, Hyunje,Lee, Eun-Kyung,Yun, Su-Won,Park, Shin-Ae,Park, Kang Hyun,Kim, Yong-Tae
, p. 1221 - 1225 (2017)
We report a facile synthesis of Pt single atoms on thiolated carbon nanotubes. To obtain Pt single atoms, it is crucial to treat thiol groups on carbon nanotubes. Pt single atoms on carbon nanotubes were used efficient catalyst for hydroalkoxylation of 3-buten-1-ol or 4-penten-1-ol. Hydroalkoxylation represents an atom-economic route to construct four or five- membered cyclic ethers through intramolecular addition of hydroxyl group. This catalyst exhibited higher catalytic activity than Pt complex and Pt nanoparticles on carbon nanotubes.
Solvent effect on the rate and direction of furfural transformations during hydrogenation over the Pd/C catalyst
Belskaya, O. B.,Likholobov, V. A.,Mironenko, R. M.
, p. 64 - 69 (2022/02/25)
The rate and directions of transformations during the liquid-phase hydrogenation of furfural with molecular hydrogen in the presence of the 5%Pd/C catalyst (at 423 K, 3 MPa) depend substantially on the chemical nature of the solvent. The main products of
The relevance of Lewis acid sites on the gas phase reaction of levulinic acid into ethyl valerate using CoSBA-xAl bifunctional catalysts
Cecilia, J. A.,Dumesic, J. A.,Jiménez-Gómez, C. P.,López Granados, M.,Maireles-Torres, P.,Mariscal, R.,Mu?oz-Olasagasti, M.
, p. 4280 - 4293 (2021/06/30)
A series of Co supported on Al-modified SBA-15 catalysts has been studied in the gas phase direct transformation of levulinic acid (LA) into ethyl valerate (EV) using a continuous fixed-bed reactor and ethanol as solvent. It was observed that once the intermediate product gamma-valerolactone (GVL) has been formed, the presence of aluminum is required for the selective transformation to EV. Three Lewis acid sites (LAS) are identified (from highest to lowest acid strength): aluminum ions in tetrahedral and octahedral coordination and Co2+sites. The intrinsic activity of these LAS for the key reaction, the GVL ring opening, decreases with the strength of these acid sites, but so does the undesirable formation of coke, also catalyzed by these centers. The best catalyst was that with the highest Al content, CoSBA-2.5Al, that reached an EV yield of up to 70%. This result is associated with the presence of LAS attributed to the presence of Co2+surface species that, although having low intrinsic activity in the selective GVL ring-opening reaction, are highly concentrated in this sample and also possess less activity in the undesirable and deactivating formation of coke. These Co2+LAS have been stabilized by incorporation of aluminum into the support, modifying the reducibility and dispersion of cobalt species. Additionally, the lower proportion of metallic Co species decreases the hydrogenating capacity of this catalyst. This decrease is a positive result because it prevents GVL hydrogenation to undesired products. This catalyst also showed promising stability in a 140 h on-stream run.