2-Methyltetrahydrofuran
chemical compound
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.
Structures and properties
2-Methyltetrahydrofuran is "inversely soluble" in water. That is, its solubility decreases with increasing temperature, which is a rare property. The solubility of water in 2-methyltetrahydrofuran is reported to be 14.4 g/ 100 g at 23 °C. Much like tetrahydrofuran, 2-methyltetrahydrofuran can act as a Lewis base in organometallic reactions. 2-Methyltetrahydrofuran is usually produced as a racemic mixture.
Preparation
2-Methyltetrahydrofuran is usually synthesized by catalytic hydrogenation of furfural.
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.
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