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 G. Banwell; Li Juan Yu; Michelle L. Coote; Michael G. Gardiner; Barbara M.A. Van Vugt-Lussenburg; Bart Van Der Burg; Fabien L. Grasset; Elisabeth Campillo; James Sherwood; Fergal P. Byrne; Thomas J. 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 G. Banwell, Li Juan Yu, Michelle L. Coote, Michael G. Gardiner, Barbara M.A. Van Vugt-Lussenburg, Bart Van Der Burg, Fabien L. Grasset, Elisabeth Campillo, James Sherwood, Fergal P. Byrne, Thomas J. Farmer

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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
Pages (from-to)	331-344
Number of pages	14
Journal	Australian Journal of Chemistry
Volume	75
Issue number	5
DOIs	https://doi.org/10.1071/CH22046
Publication status	Published - 7 Jul 2022
Externally published	Yes

Keywords

bio-derived
Cyrene
green solvent
iso -Cyrene
iso -levoglucosenone
levoglucosenone
physiochemical properties
toxicity

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Liu, X., Pollard, B., Banwell, M. G., Yu, L. J., Coote, M. L., Gardiner, M. G., Van Vugt-Lussenburg, B. M. A., Van Der Burg, B., Grasset, F. L., Campillo, E., Sherwood, J., Byrne, F. P., & 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, 75(5), 331-344. https://doi.org/10.1071/CH22046

@article{de703ba72ad44af096dafa940676127b,

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.",

keywords = "bio-derived, Cyrene, green solvent, iso -Cyrene, iso -levoglucosenone, levoglucosenone, physiochemical properties, toxicity",

author = "Xin Liu and Brett Pollard and Banwell, {Martin G.} and Yu, {Li Juan} and Coote, {Michelle L.} and Gardiner, {Michael G.} and {Van Vugt-Lussenburg}, {Barbara M.A.} and {Van Der Burg}, Bart and Grasset, {Fabien L.} and Elisabeth Campillo and James Sherwood and Byrne, {Fergal P.} and Farmer, {Thomas J.}",

year = "2022",

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doi = "10.1071/CH22046",

language = "English",

volume = "75",

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Liu, X, Pollard, B, Banwell, MG, Yu, LJ, Coote, ML, Gardiner, MG, Van Vugt-Lussenburg, BMA, Van Der Burg, B, Grasset, FL, Campillo, E, Sherwood, J, Byrne, FP & 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, vol. 75, no. 5, pp. 331-344. 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 G.

AU - Yu, Li Juan

AU - Coote, Michelle L.

AU - Gardiner, Michael G.

AU - Van Vugt-Lussenburg, Barbara M.A.

AU - Van Der Burg, Bart

AU - Grasset, Fabien L.

AU - Campillo, Elisabeth

AU - Sherwood, James

AU - Byrne, Fergal P.

AU - Farmer, Thomas J.

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.

AB - 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.

KW - bio-derived

KW - Cyrene

KW - green solvent

KW - iso -Cyrene

KW - iso -levoglucosenone

KW - levoglucosenone

KW - physiochemical properties

KW - toxicity

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SN - 0004-9425

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JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 5

ER -

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

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Keywords

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