Biobased 2,5-Dimethyltetrahydrofuran as a Green Aprotic Ether Solvent

Abstract

Aprotic ether solvents, such as tetrahydrofuran, diethyl ether, cyclopentyl methyl ether, 2-methyltetrahydrofuran, dioxane, etc., are widely used in the field of organic synthesis due to their good solvent properties and utility for organometallic reactions. However, most of the traditional polar aprotic solvents from petroleum have disadvantages such as toxicity and environmental unfriendliness. Consequently, 2-methyltetrahydrofuran, a green solvent derived from the hemicellulose component of biomass, has recently been of great interest due to its excellent performance synthesis. In this paper, 2,5-dimethyltetrahydrofuran, derived from the cellulose component of biomass, has been studied in detail as a potential greener solvent due to its higher boiling point, lower water solubility, and better stability as compared to 2-methyltetrahydrofuran or tetrahydrofuran. These results showed that 2,5-dimethyltetrahydrofuran offers excellent performance in the fields of organometallic reactions, biphasic reactions, and extraction.

Efficient Chemical Prelithiation with Modificatory Li+ Solvation Structure Enabling Spatially Homogeneous SEI toward High Performance SiOx Anode†

“…Among these ether solvents, CPME has low viscosity and wide temperature range, [ 32‐35 ] making it suitable for practical application in chemical prelithiation, and it as an environmentally friendly solvent partially addresses concerns surrounding environmental pollution caused by the extensive use of organic solvents. [ 36‐39 ] Therefore, CPME is predicted to be a more ideal solvent for the construction of weakly solvated LAC reagents with more efficient prelithiation process. However, considering the poor solubility of CPME for lithium metal, we introduced CPME in the original solvent tetrahydrofuran as a mixed solvent to prepare LAC reagents with two different solvent systems (marked as 0.5 T and 0.5 TC55) and systematically explored their correlation with the prelithiation efficiency.…”

“…[ 48,51‐52 ] Li 1s XPS spectra of the prelithiated electrode shows the appearance of the prelithiation product Li x SiO y (Figure 5b). [ 24‐47 ] It is noteworthy that the appearance of a new peak at 54.33 eV can be attributed to the pre‐decomposition of the organic components derived from the ether solvents in the LAC reagent, and that the higher content of organic component in the SEI of the 0.5 TC55‐5min electrode can be attributed to the greater involvement of the more readily desolvable CPME. The Si 2p XPS spectrum of pristine SiO x electrode exhibits continuous distribution of broad characteristic peaks from 99.58 eV to 103.39 eV, corresponding to the typical valence states 0, +2, and +4 of SiO x , respectively (Figure 5c).…”

Selective C(aryl)–O bond cleavage in biorenewable phenolics

“…212 Exploration of other THF derivatives such as 2,5-dimethyltetrahydrofuran is being made to further improve the properties. 213 Other more niche biorenewable solvents worth mentioning are monoterpenoid eucalyptol and cellulose derived dimethyl isosorbide (DMI). 214 Clearly, a range of less toxic, renewable solvents are available, though their use in C–O bond activation reactions is still uncommon.…”

Catalytic production of tetrahydropyran (THP): a biomass-derived, economically competitive solvent with demonstrated use in plastic dissolution

“…Table 7 lists the 10 most similar solvents to THP and their corresponding similarity scores, with 2-methyltetrahydrofuran (MeTHF), diethyl ether, tetrahydropthiopyran, and THF in the top 4. We have also added 2,5-dimethyltetrahydrofuran 48 and 2,2,5,5-tetramethyltetrahydrofuran 10 to the list as they are homologous compounds of THF and can be biomass-derived. However, their chemical properties are not as similar to THP, as evidenced by their higher similarity scores.…”