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RESEARCH ARTICLE
Contents Vol 75(5)

Simple and modestly scalable synthesis of iso-Cyrene from levoglucosenone and its comparison to the bio-derived and polar aprotic solvent Cyrene®

Xin Liu A # , Brett Pollard A # , Martin G. Banwell https://orcid.org/0000-0002-0582-475X A B * , Li-Juan Yu A , Michelle L. Coote A , Michael G. Gardiner A , Barbara M. A. van Vugt-Lussenburg C , Bart van der Burg C , Fabien L. Grasset D , Elisabeth Campillo D , James Sherwood E , Fergal P. Byrne E and Thomas J. Farmer E
+ Author Affiliations
- Author Affiliations

A Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 2601, Australia.

B Institute for Advanced and Applied Chemical Synthesis, Jinan University, Guangzhou, 510632, China.

C BioDetection Systems bv, Science Park 406, 1098XH Amsterdam, The Netherlands.

D V. Mane Fils, 620 route de Grasse, 06620 Le-Bar-sur-Loup, France.

E Green Chemistry Centre of Excellence, Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.

* Correspondence to: mgbanwell@jnu.edu.cn

Handling Editor: Craig Hutton

Australian Journal of Chemistry 75(5) 331-344 https://doi.org/10.1071/CH22046
Submitted: 28 February 2022  Accepted: 29 March 2022   Published: 7 July 2022

© 2022 The Author(s) (or their employer(s)). Published by CSIRO Publishing.

Abstract

The bio-derived platform molecule levoglucosenone (LGO, 1), which is the precursor to the green solvent Cyrene® (2), has been converted, at multi-gram scale, into its pseudo-enantiomer (iso-LGO, 2) and then reduced to iso-Cyrene (4). A less effective synthesis of this last compound from D-glucose is also described. Various physicochemical as well as certain toxicological properties of compound 4 are reported and compared to those established for the now commercially available Cyrene® (2). Such studies reveal that there are significant enough differences in the properties of the sustainably-derived Cyrene® (2) and isomer 4 (iso-Cyrene) to suggest they will exert complementary effects as solvents in a range of settings.

Keywords: bio-derived, Cyrene®, green solvent, iso-Cyrene, iso-levoglucosenone, levoglucosenone, physiochemical properties, toxicity.


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