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

^*Corresponding author for this work

Research School of Chemistry

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

10 Citations (Scopus)

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 - Jul 2022

Access to Document

10.1071/CH22046

Cite this

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{d2e0beaf00084d2680eabf8918c3e94f,

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 = "Cyrene, bio-derived, 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.\}",

note = " {\textcopyright} 2022 The Author(s) ",

year = "2022",

month = jul,

doi = "10.1071/CH22046",

language = "English",

volume = "75",

pages = "331--344",

journal = "Australian Journal of Chemistry",

issn = "0004-9425",

publisher = "CSIRO Publishing",

number = "5",

}

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

TY - JOUR

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

Y1 - 2022/7

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 - Cyrene

KW - bio-derived

KW - green solvent

KW - iso -Cyrene

KW - iso -levoglucosenone

KW - levoglucosenone

KW - physiochemical properties

KW - toxicity

UR - https://www.scopus.com/pages/publications/85134744539

U2 - 10.1071/CH22046

DO - 10.1071/CH22046

M3 - Article

SN - 0004-9425

VL - 75

SP - 331

EP - 344

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^®

Abstract

Access to Document

Other files and links

Fingerprint

Controlling chemical reactions via pH-switchable electrostatic catalysis

Cite this

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

Abstract

Access to Document

Other files and links

Fingerprint

Projects

Controlling chemical reactions via pH-switchable electrostatic catalysis

Cite this

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