Liu, Xin, Pollard, Brett, Banwell, Martin et al. (10 more authors) (2022) Simple and modestly scalable synthesis of iso-Cyrene from levoglucosenone and its comparison to the bio-derived and polar aprotic solvent Cyrene®. Australian Journal of Chemistry. ISSN 0004-9425
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.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2022 The Author(s) (or their employer(s))This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Funding Information: | Funder Grant number EUROPEAN COMMISSION 745450 |
Depositing User: | Pure (York) |
Date Deposited: | 15 Jul 2022 10:30 |
Last Modified: | 02 Apr 2025 23:24 |
Published Version: | https://doi.org/10.1071/CH22046 |
Status: | Published online |
Refereed: | Yes |
Identification Number: | 10.1071/CH22046 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:189126 |
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