Dihydrolevoglucosenone

March is MOTW Solvent Month! This is the last of four articles about key solvents—Ed.

Unlike the previous three solvents in this series, dihydrolevoglucosenone will not be familiar to many chemists. It is a recently developed, “green” alternative to existing dipolar aprotic solvents.

Formally named (1S,5R)-6,8-dioxabicyclo[3.2.1]octan-4-one, dihydrolevoglucosenone is derived from cellulose and is therefore chiral. It was developed by the Circa Group (Parkville, Australia), which is promoting it under the trade name Cyrene. In February, Circa, in a joint venture with Norske Skogindustrier ASA (Halden, Norway), opened a 50 t/year demonstration plant at Norske Skog’s papermill in southern Tasmania.

Dihydrolevoglucosenone is advertised as a biobased, biodegradable alternative to traditional polar aprotic solvents such as N,N-dimethylformamide and N-methyl-2-pyrrolidone, both of which pose toxicological and environmental hazards. Its low toxicity and high flash point (108 ºC) promise to make it a “safer” solvent if the price is right. In the past 5 years, several publications and patents illustrated the usefulness of dihydrolevoglucosenone as a solvent for the synthesis of organic compounds and polymers.