Cyclopentyl Methyl Ether (CPME): A Versatile Eco‐Friendly Solvent for Applications in Biotechnology and Biorefineries

Abstract

The quest for sustainable solvents is currently a matter of intense research and development, as solvents significantly contribute heavily to the waste generated by chemical industries. Cyclopentyl methyl ether (CPME) is a promising eco‐friendly solvent with valuable properties such as low peroxide formation rate, stability under basic and acidic conditions, and relatively high boiling point. This Review discusses the potential use of CPME for applications in biotechnology (e.g., biotransformations, as solvent or cosolvent), biorefineries, and bioeconomy (e.g., for furan synthesis or as an extractive agent in liquid–liquid separations), as well as for other purposes, such as chromatography or peptide synthesis. Although CPME is currently produced by petrochemical means with a remarkably high atom economy, its biogenic production can be envisaged from substrates such as cyclopentanol or cyclopentanone, which can be derived from furfural or from (bio‐based) adipic acid, respectively. The combination of the promising properties of CPME as a (co)solvent with a future (economic) biogenic origin would be advantageous for setting strategies aligned with the sustainable chemistry principles.

4‐Methyltetrahydropyran (4‐MeTHP): Application as an Organic Reaction Solvent

“…[3][4][5][6][7] The traditional ethereal solvents, such as diethyl ether (Et 2 O), tetrahydrofuran (THF) and 1,4-dioxane, which are still used in many laboratory experiments today,a re highly recommended to be replaced by safer and greener solvents in pilot-scale synthesis, in order to avoid the risks of inflammability,e xplosion from peroxideb uild-up, and toxic exposure. In this regard, less risky, recyclable ethereals olvents such as 2-methyltetrahydrofuran (2-MeTHF) [8][9][10] and cyclopentyl methyl ether (CPME) [11][12][13] have been developed as alternatives to conventional ethers, which are nowadays widely used in process chemistry. [14] tertButyl methyle ther (TBME), developed as an antiknock agent for gas-oline, is alsou sed occasionally;h owever,i ts flammable nature and volatile organic compound emissions are matters of concern.…”

“…MHz, CDCl 3 ): d = 0.44 (d, J = 0.6 Hz, 1H), 6.60 (dd, J = 2.4, 0.6 Hz, 1H), 6.40 (d, J = 2.4 Hz), 5.51 (s, 2H), 3.89 (s, 3H), 3.87 (s, 3H), 2.41 (t, J = 7.5 Hz, 2H), 1.68 (qui, J = 7.5 Hz, 2H), 1.31-1.18 (m, 24 H), 0.87 ppm (t, J = 6.7 Hz, 3H);13 CNMR (75 MHz, CDCl 3 ): d = 189.9, 173.3, 165.4, 165.3, 142.7, 115.9, 104.5, 96.6, 64.5, 56.0, 55.6, 34.5, 32.0, 29.82, 29.80, 29.78, 29.73, 29.6, 29.5, 29.4, 29.3, 25.2, 22.8, 14.2 ppm;I R( film on ZnSe): ñ = 2999, 2924, 2853, 1738, 1599, 1464, 1429, 1350, 1321, 1298 cm À1 ;H RMS (ESI +): m/z:c alcd for C 26 H 43 O 5 :435.3105 [M+ +H] + ;f ound 435.3089.2-Formyl-3-hydroxy-5-methoxybenzyl palmitate (27). BBr 3 (1.0 M solution in CH 2 Cl 2 ,2 .6 mL, 2.6 mmol) was added to as olution of aldehyde 26 (1.00 g, 2.30 mmol) in 4-MeTHP (40 mL) at 0 8C.…”

Sustainable Chemicals: A Brief Survey of the Furans

“…Although, lots of exhaustive discourses abound on furan series of chemical compounds and their derivatives [28][29][30][31][32][33]. Notwithstanding, a literature search using the search phrase "Sustainable + chemicals + furans" demonstrates that there Fig.…”

Natural flavor ester synthesis catalyzed by lipases

“…In a first screening, lipases were tested through acetylation reactions of natural alcohols ( cis ‐3‐hexen‐1‐ol and 2‐phenylethanol). In particular, the selected lipases were compared with different acetylating agents (triacetin and ethyl acetate for transesterification or acetic acid for esterification), in two more eco‐friendly and sustainable solvents (CPME and MeTHF) and, in the case of Novozym 435, also in toluene for comparison with an organic solvent non‐considered “green.” The reaction conversions, measured after 48 h, of the natural alcohols to form the corresponding acetyl esters are shown in Tables and .…”