Dihydrolevoglucosenone

March 25, 2019
I’m a next-generation solvent.
What molecule am I?

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.

Dihydrolevoglucosenone hazard information

GHS classification*: Serious eye irritation, category 2A
H319—Causes serious eye irritation Chemical Safety Warning

 

*Globally Harmonized System of Classification and Labeling of Chemicals. Explanation of pictograms.

Dihydrolevoglucosenone fast facts

CAS Reg. No. 53716-82-8
Empirical formula C6H8O3
Molar mass 128.13 g/mol
Appearance Colorless to pale yellow liquid
Boiling point 232 ºC
Water solubility Miscible
Chemical Abstract Service - a division of ACS

Learn more about this molecule from CAS, the most authoritative and comprehensive source for chemical information.

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