Bio‐available Solvent Cyrene: Synthesis, Derivatization, and Applications

Abstract

The development of green solvents is one of the key tenets of Green Chemistry as solvents account for the majority of waste stemming from the production of the chemicals on which we have all come to rely. An important class of solvents is the dipolar aprotics, which include N,N-dimethylformamide (DMF) and N-methyl-2-pyrrolidone (NMP). In addition to being derived from non-renewable resources, these solvents are also under increased regulatory pressures that will limit their industrial applications. This Concept concerns the bio-available solvent Cyrene (dihydrolevoglucosenone) as a potential replacement for toxic dipolar aprotic solvents. An emphasis is placed on examining the strengths and weaknesses of Cyrene as a solvent and is accomplished by looking at the synthesis, derivatization, and application in synthetic protocols of Cyrene. With respect to the Twelve Principles of Green Chemistry, this Concept describes a bio-available solvent that should have a disruptive effect on the use of traditional industrial dipolar aprotic solvents.

Bio-Solvents: Synthesis, Industrial Production and Applications

“…Cyrene (dihydrolevoglucosenone or 6,8-dioxabicyclo[3.2.1]octanone) is a ketone functionality containing solvent that can be prepared in a two-step process from cellulose [66]. The common starting point in its synthesis is from levoglucosenone (LGO), which can be obtained from a variety of cellulosic starting feedstocks such as Bilberry presscake [67], corn cob [68], poplar wood [69] or bagasse [70].…”

Challenges and Directions for Green Chemical Engineering—Role of Nanoscale Materials

“…low volatility or obtained from renewable feedstock, but do not score as "green" in solvents guides when considered holistically. 62,63 Progress is being made to identify alternative, primarily bio-derived, solvents for the most problematic solvent classes such as polar aprotic solvents: propylene carbonate, 64 cyrene, 65 Nbutylpyrrolidinone, 66 polarclean. 67 and hydrocarbons.…”

Cycloamination strategies for renewable N-heterocycles

“…Renewable biomass is a future replacement for fossil resources being used to produce energy and chemicals. [1][2][3][4][5][6] Due to the presence of abundant oxygen species, biomass derivatives have been considered as consummate intermediates or platform molecules for the synthesis of oxygen-containing chemicals such as esters, acids, aldehydes, ketones, phenolics, and alcohols, [7][8][9][10][11][12] that contain unsaturated hydrocarbon moieties (e.g., alkenyl, alkynyl, aryl groups), [13][14][15][16][17][18] as shown in Fig. 1.…”