2-Methyltetrahydrofuran

changed 477214694 Methyltetrahydrofuran.svg 150px 2-Methyloxolane 2-Methyltetrahydrofuran, 2-Methyl-THF (Racemic) (R) (S) correct chemspider 7028 1/C5H10O/c1-5-3-2-4-6-5/h5H,2-4H2,1H3 JWUJQDFVADABEY-UHFFFAOYAM correct chemspider 1S/C5H10O/c1-5-3-2-4-6-5/h5H,2-4H2,1H3 correct chemspider JWUJQDFVADABEY-UHFFFAOYSA-N correct CAS 96-47-9 63798-13-0 63798-12-9 correct FDA FCD0VD8ALF 7301 202-507-4 2536 1580503 DTXSID9030258 O1C(C)CCC1 5 10 1 0.854 g/mL -136 80.2 21.0 wt% (0.0 °C)17.8 wt% (9.5 °C)14.4 wt% (19.3 °C)11.4 wt% (29.5 °C)9.2 wt% (39.6 °C)7.8 wt% (50.1 °C)6.6 wt%(60.7 °C)6.0 wt% (70.6 °C)Sicaire, Anne-Gaëlle; Vian, Maryline Abert; Filly, Aurore; Li, Ying; Bily, Antoine; Chemat, Farid (2014), Chemat, Farid; Vian, Maryline Abert (eds.), "2-Methyltetrahydrofuran: Main Properties, Production Processes, and Application in Extraction of Natural Products", Alternative Solvents for Natural Products Extraction, Berlin, Heidelberg: Springer Berlin Heidelberg, pp. 253–268, doi:10.1007/978-3-662-43628-8_12, ISBN 978-3-662-43627-1 External MSDS 02 05 07 Warning 225 302 315 318 319 335 336 210 233 240 241 242 243 261 264 270 271 280 301+312 302+352 303+361+353 304+340 305+351+338 310 312 321 330 332+313 337+313 362 370+378 403+233 403+235 405 501 2-Methyltetrahydrofuran (2-MeTHF) is an organic compound with the molecular formula C5H10O. It is a highly flammable, mobile liquid. It is mainly used as a replacement for tetrahydrofuran (THF) in specialized applications for its better performance, such as to obtain higher reaction temperatures, or easier separations (as, unlike THF, it is not miscible with water). It is derived from sugars via furfural and is occasionally touted as a biofuel.Leal Silva Jean Felipe Mariano Adriano Pinto Maciel Filho Rubens Economic potential of 2-methyltetrahydrofuran (MTHF) and ethyl levulinate (EL) produced from hemicelluloses-derived furfural Biomass and Bioenergy 119 December 2018 492–502 10.1016/j.biombioe.2018.10.008 2018 2018BmBe..119..492L 104836889 Structures and properties 2-Methyltetrahydrofuran is "inversely soluble" in water. That is, its solubility decreases with increasing temperature, which is a rare property.Sicaire Anne-Gaëlle 2-Methyltetrahydrofuran: Main Properties, Production Processes, and Application in Extraction of Natural Products 2014 Alternative Solvents for Natural Products Extraction 253–268 Chemat Farid Berlin, Heidelberg Springer Berlin Heidelberg en 10.1007/978-3-662-43628-8_12 978-3-662-43627-1 Vian Maryline Abert Filly Aurore Li Ying Bily Antoine Chemat Farid Vian Maryline Abert The solubility of water in 2-methyltetrahydrofuran is reported to be 14.4 g/ 100 g at 23 °C.Zeon Corporation https://www.zeon.co.jp/business_e/enterprise/spechemi/cpme_tec_sup_e_200906.pdf https://web.archive.org/web/20110722102229/http://www.zeon.co.jp/business_e/enterprise/spechemi/cpme_tec_sup_e_200906.pdf 2011-07-22 2024-08-05 Much like tetrahydrofuran, 2-methyltetrahydrofuran can act as a Lewis base in organometallic reactions. Aycock, David F. Solvent Applications of 2-Methyltetrahydrofuran in Organometallic and Biphasic Reactions Org. Process Res. Dev. 2007 11 156–159 10.1021/op060155c 2-Methyltetrahydrofuran is usually produced as a racemic mixture. Preparation 2-Methyltetrahydrofuran is usually synthesized by catalytic hydrogenation of furfural.10.1021/cr068360d 16967928 106 Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering September 2006 Chem. Rev. 4044–98 Huber GW Iborra S Corma A 9 https://works.bepress.com/cgi/viewcontent.cgi?article=1058&context=george_huber ref 306 OC4H3CHO + 4 H2 → OC4H7CH3 + H2O Furfural is produced by the acid-catalyzed digestion of pentosan sugars, C5 polysaccharides, in biomass. Thus, the raw materials of 2-methyltetrahydrofuran are renewable biomass rich with cellulose, hemicelluloses, and lignin, such as corncobs or bagasse and other plant and agricultural waste. Hoydonckx, H. E. Van Rhijn, W. M. Van Rhijn, W. De Vos, D. E. Jacobs, P. A. Furfural and Derivatives 10.1002/14356007.a12_119.pub2 2-Methyltetrahydrofuran can also be produced starting from levulinic acid. Cyclization and reduction gives γ-valerolactone: File:Cyclization of levulinic acid.svg γ-Valerolactone can be hydrogenated to 1,4-pentanediol, which can then be dehydrated to give 2-methyltetrahydrofuran: File:Reaction of Valerolactone to 2Me-THF.svg Applications 2-Methyltetrahydrofuran is mainly used as a higher boiling substitute for tetrahydrofuran as a specialty solvent. It also is used in the electrolyte formulation for secondary lithium electrodes and as a component in alternative fuels. It is a valued solvent for low-temperature reactions. 2-Methyltetrahydrofuran forms a glass, which does not crystallize, and is frequently used as a solvent for spectroscopic studies at −196 °C. Other common uses of 2-methyltetrahydrofuran is as a solvent for Grignard reagents used in organometallic and biphasic chemical processes, because of the oxygen atom's ability to coordinate to the magnesium ion component of the Grignard reagent, or to azeotropically dry products. The use of 2-methyltetrahydrofuran provides very clean organic water phase separations. It is a popular, but costlier substitute for tetrahydrofuran. 2-Methyltetrahydrofuran is approved by the United States Department of Energy as an additive to gasoline. Furfural and other furyl compounds (furfuryl alcohol, methylfuran, tetrahydrofufuryl alcohol) have a tendency to polymerize and are quite volatile. 2-Methyltetrahydrofuran itself, however, is more stable and less volatile, and thus is suitable for use as a motor fuel. 2-Methyltetrahydrofuran has been promoted as an ecologically-friendly alternative to THF.https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/115/677/greener_solvent_alternatives.pdf Greener Solvent Alternatives – Brochure Sigmaaldrich.com 2010-02-15 Whereas 2-MeTHF is more expensive, it may provide for greater overall process economy. 2-MeTHF has solvating properties that are intermediate between diethyl ether and THF, has limited water miscibility, and forms an azeotrope with water on distillation. Its lower melting point makes it useful for lower temperature reactions, and its higher boiling point allows procedures under reflux at higher temperatures (relative to THF). References Huber George W. Iborra Sara Corma Avelino 2006 Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering https://works.bepress.com/cgi/viewcontent.cgi?article=1058&context=george_huber Chemical Reviews 106 9 4044–4098 10.1021/cr068360d 16967928 Further reading Zheng, Hong-Yan Towards understanding the reaction pathway in vapour phase hydrogenation of furfural to 2-methylfuran Journal of Molecular Catalysis A: Chemical 10.1016/j.molcata.2005.10.003 2006 Zhu Yu-Lei Teng Bo-Tao Bai Zong-Qing Zhang Cheng-Hua Xiang Hong-Wei Li Yong-Wang 246 1–2 18–23 https://cms.chempoint.com/ChemPoint/media/ChemPointSiteMedia/Emails/MeTHF-System-Advantages-in-Organometallic-Chemistry-and-Biphasic-Reactions.pdf Category:Tetrahydrofurans Category:Ether solvents