Hazard
Flammable, dangerous fire risk.
Description
2-Methyltetrahydrofuran (MeTHF or 2-MTHF) is a bio-based solvent that is recognized as the most favorable of ether solvents. The relatively high boiling point (80?C) and low melting point (-137?C) provide a broad temperature range for a myriad of processing conditions. It is a potential greener solvent alternative for organic synthesis. It shows resistance to reduction by lithium making it a promising candidate as electrolytes in lithium batteries. Its polarity and Lewis base strength is intermediate between tetrahydrofuran (THF) and diethyl ether. The ring opening reaction of 2-MTHF has been studied using acid chloride and iodide.
Chemical Properties
Colorless liquid; ether-like odor. Solubility in waterincreases with a decrease in temperature. Freelysoluble in most organic solvents.
General Description
We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product is a biorenewable and thus aligns with "Safer Solvents and Auxiliaries" and "Use of Renewable Feedstocks". Click here for more information.
2-Methyltetrahydrofuran (2-MTHF), a 2-methyl substituted tetrahdrofuran, is a biomass derived solvent. It is a potential greener solvent alternative for organic synthesis. It shows resistance to reduction by lithium making it a promising candidate as electrolytes in lithium batteries. Its polarity and Lewis base strength is intermediate between tetrahydrofuran (THF) and diethyl ether. The ring opening reaction of 2-MTHF has been studied using acid chloride and iodide to form secondary chlorides and primary iodides respectively. On long term storage, tetrahydrofuran forms organic peroxides. This process can be suppressed by adding butylated hydroxytoluene (BHT) as a stabilizer. BHT removes the free radicals required for the peroxide formation.
Flammability and Explosibility
Highlyflammable
reaction suitability
reaction type: Grignard Reaction
Potential Exposure
Used as a chemical intermediate and asolvent.
First aid
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.
storage
Color Code—Red: Flammability Hazard: Store ina flammable liquid storage area or approved cabinet awayfrom ignition sources and corrosive and reactive materials.Prior to working with methyltetrahydrofuran you should betrained on its proper handling and storage. Store in tightlyclosed containers in a cool, well-ventilated area. Where possible, automatically pump liquid from drums or other storage containers to process containers. Drums must beequipped with self-closing valves, pressure vacuum bungs,and flame arresters. Use only nonsparking tools and equipment, especially when opening and closing containers ofthis chemical. Wherever this chemical is used, handled,manufactured, or stored, use explosion-proof electricalequipment and fittings.
Shipping
Methyltetrahydrofuran requires a shipping labelof “FLAMMABLE LIQUID.” It falls in Hazard Class 3 andPacking Group II.
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.
Incompatibilities
Strong oxidizers may cause fire andexplosion
Toxics Screening Level
The initial threshold screening level (ITSL) for 2-methyltetrahydrofuran (CAS # 96-47-9) is 420 μg/m3 with an annual averaging time.
