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

Xin Liu; Brett Pollard; Martin Banwell; Li-Juan Yu; Michelle Coote; Michael Gardiner; Barbara M A van Vugt-Lussenburg; Bart van der Burg; Fabien Grasset; Elizabeth Campillo; James Richard Sherwood; Fergal Byrne; Thomas James Farmer

doi:10.1071/CH22046

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

Xin Liu, Brett Pollard, Martin Banwell, Li-Juan Yu, Michelle Coote, Michael Gardiner, Barbara M A van Vugt-Lussenburg, Bart van der Burg, Fabien Grasset, Elizabeth Campillo, James Richard Sherwood, Fergal Byrne, Thomas James Farmer

Chemistry

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Number of pages	14
Journal	Australian Journal of Chemistry
Early online date	7 Jul 2022
DOIs	https://doi.org/10.1071/CH22046
Publication status	E-pub ahead of print - 7 Jul 2022

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© 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

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10.1071/CH22046

iso-Cyrene_AuthorAccepted_BANWELL_2022
© 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
Accepted author manuscript, 1.48 MB

ReSolve: Renewable Solvents with high Performance in application and improved toxicity profile
Clark, J. H., Farmer, T. J. & Hunt, A. J.
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Liu, X., Pollard, B., Banwell, M., Yu, L.-J., Coote, M., Gardiner, M., van Vugt-Lussenburg, B. M. A., van der Burg, B., Grasset, F., Campillo, E., Sherwood, J. R., Byrne, F., & Farmer, T. J. (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. Advance online publication. https://doi.org/10.1071/CH22046

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title = "Simple and modestly scalable synthesis of iso-Cyrene from levoglucosenone and its comparison to the bio-derived and polar aprotic solvent Cyrene{\textregistered}",

abstract = "The bio-derived platform molecule levoglucosenone (LGO, 1), which is the precursor to the green solvent Cyrene{\textregistered} (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{\textregistered} (2). Such studies reveal that there are significant enough differences in the properties of the sustainably-derived Cyrene{\textregistered} (2) and isomer 4 (iso-Cyrene) to suggest they will exert complementary effects as solvents in a range of settings.",

author = "Xin Liu and Brett Pollard and Martin Banwell and Li-Juan Yu and Michelle Coote and Michael Gardiner and {van Vugt-Lussenburg}, {Barbara M A} and {van der Burg}, Bart and Fabien Grasset and Elizabeth Campillo and Sherwood, {James Richard} and Fergal Byrne and Farmer, {Thomas James}",

note = "{\textcopyright} 2022 The Author(s) (or their employer(s))This is an author-produced version of the published paper. Uploaded in accordance with the publisher{\textquoteright}s self-archiving policy. Further copying may not be permitted; contact the publisher for details ",

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Liu, X, Pollard, B, Banwell, M, Yu, L-J, Coote, M, Gardiner, M, van Vugt-Lussenburg, BMA, van der Burg, B, Grasset, F, Campillo, E, Sherwood, JR , Byrne, F & Farmer, TJ 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. https://doi.org/10.1071/CH22046

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T1 - Simple and modestly scalable synthesis of iso-Cyrene from levoglucosenone and its comparison to the bio-derived and polar aprotic solvent Cyrene®

AU - Liu, Xin

AU - Pollard, Brett

AU - Banwell, Martin

AU - Yu, Li-Juan

AU - Coote, Michelle

AU - Gardiner, Michael

AU - van Vugt-Lussenburg, Barbara M A

AU - van der Burg, Bart

AU - Grasset, Fabien

AU - Campillo, Elizabeth

AU - Sherwood, James Richard

AU - Byrne, Fergal

AU - Farmer, Thomas James

N1 - © 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

PY - 2022/7/7

Y1 - 2022/7/7

N2 - 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.

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U2 - 10.1071/CH22046

DO - 10.1071/CH22046

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SN - 0004-9425

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JF - Australian Journal of Chemistry

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

Abstract

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ReSolve: Renewable Solvents with high Performance in application and improved toxicity profile

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