Cargando…

Geminal Diol of Dihydrolevoglucosenone as a Switchable Hydrotrope: A Continuum of Green Nanostructured Solvents

[Image: see text] The addition of water to dihydrolevoglucosenone (Cyrene) creates a solvent mixture with highly unusual properties and the ability to specifically and efficiently solubilize a wide range of organic compounds, notably, aspirin, ibuprofen, salicylic acid, ferulic acid, caffeine, and m...

Descripción completa

Detalles Bibliográficos
Autores principales: De bruyn, Mario, Budarin, Vitaliy L., Misefari, Antonio, Shimizu, Seishi, Fish, Heather, Cockett, Martin, Hunt, Andrew J., Hofstetter, Heike, Weckhuysen, Bert M., Clark, James H., Macquarrie, Duncan J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7493416/
https://www.ncbi.nlm.nih.gov/pubmed/32953281
http://dx.doi.org/10.1021/acssuschemeng.9b00470
_version_ 1783582563895345152
author De bruyn, Mario
Budarin, Vitaliy L.
Misefari, Antonio
Shimizu, Seishi
Fish, Heather
Cockett, Martin
Hunt, Andrew J.
Hofstetter, Heike
Weckhuysen, Bert M.
Clark, James H.
Macquarrie, Duncan J.
author_facet De bruyn, Mario
Budarin, Vitaliy L.
Misefari, Antonio
Shimizu, Seishi
Fish, Heather
Cockett, Martin
Hunt, Andrew J.
Hofstetter, Heike
Weckhuysen, Bert M.
Clark, James H.
Macquarrie, Duncan J.
author_sort De bruyn, Mario
collection PubMed
description [Image: see text] The addition of water to dihydrolevoglucosenone (Cyrene) creates a solvent mixture with highly unusual properties and the ability to specifically and efficiently solubilize a wide range of organic compounds, notably, aspirin, ibuprofen, salicylic acid, ferulic acid, caffeine, and mandelic acid. The observed solubility enhancement (up to 100-fold) can be explained only by the existence of microenvironments mainly centered on Cyrene’s geminal diol. Surprisingly, the latter acts as a reversible hydrotrope and regulates the polarity of the created complex mixture. The possibility to tune the polarity of the solvent mixture through the addition of water, and the subsequent generation of variable amounts of Cyrene’s geminal diol, creates a continuum of green solvents with controllable solubilization properties. The effective presence of microheterogenieties in the Cyrene/water mixture was adequately proven by (1) Fourier transform infrared/density functional theory showing Cyrene dimerization, (2) electrospray mass-spectrometry demonstrating the existence of dimers of Cyrene’s geminal diol, and (3) the variable presence of single or multiple tetramethylsilane peaks in the (1)H NMR spectra of a range of Cyrene/water mixtures. The Cyrene–water solvent mixture is importantly not mutagenic, barely ecotoxic, bioderived, and endowed with tunable hydrophilic/hydrophobic properties.
format Online
Article
Text
id pubmed-7493416
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-74934162020-09-16 Geminal Diol of Dihydrolevoglucosenone as a Switchable Hydrotrope: A Continuum of Green Nanostructured Solvents De bruyn, Mario Budarin, Vitaliy L. Misefari, Antonio Shimizu, Seishi Fish, Heather Cockett, Martin Hunt, Andrew J. Hofstetter, Heike Weckhuysen, Bert M. Clark, James H. Macquarrie, Duncan J. ACS Sustain Chem Eng [Image: see text] The addition of water to dihydrolevoglucosenone (Cyrene) creates a solvent mixture with highly unusual properties and the ability to specifically and efficiently solubilize a wide range of organic compounds, notably, aspirin, ibuprofen, salicylic acid, ferulic acid, caffeine, and mandelic acid. The observed solubility enhancement (up to 100-fold) can be explained only by the existence of microenvironments mainly centered on Cyrene’s geminal diol. Surprisingly, the latter acts as a reversible hydrotrope and regulates the polarity of the created complex mixture. The possibility to tune the polarity of the solvent mixture through the addition of water, and the subsequent generation of variable amounts of Cyrene’s geminal diol, creates a continuum of green solvents with controllable solubilization properties. The effective presence of microheterogenieties in the Cyrene/water mixture was adequately proven by (1) Fourier transform infrared/density functional theory showing Cyrene dimerization, (2) electrospray mass-spectrometry demonstrating the existence of dimers of Cyrene’s geminal diol, and (3) the variable presence of single or multiple tetramethylsilane peaks in the (1)H NMR spectra of a range of Cyrene/water mixtures. The Cyrene–water solvent mixture is importantly not mutagenic, barely ecotoxic, bioderived, and endowed with tunable hydrophilic/hydrophobic properties. American Chemical Society 2019-03-15 2019-04-15 /pmc/articles/PMC7493416/ /pubmed/32953281 http://dx.doi.org/10.1021/acssuschemeng.9b00470 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle De bruyn, Mario
Budarin, Vitaliy L.
Misefari, Antonio
Shimizu, Seishi
Fish, Heather
Cockett, Martin
Hunt, Andrew J.
Hofstetter, Heike
Weckhuysen, Bert M.
Clark, James H.
Macquarrie, Duncan J.
Geminal Diol of Dihydrolevoglucosenone as a Switchable Hydrotrope: A Continuum of Green Nanostructured Solvents
title Geminal Diol of Dihydrolevoglucosenone as a Switchable Hydrotrope: A Continuum of Green Nanostructured Solvents
title_full Geminal Diol of Dihydrolevoglucosenone as a Switchable Hydrotrope: A Continuum of Green Nanostructured Solvents
title_fullStr Geminal Diol of Dihydrolevoglucosenone as a Switchable Hydrotrope: A Continuum of Green Nanostructured Solvents
title_full_unstemmed Geminal Diol of Dihydrolevoglucosenone as a Switchable Hydrotrope: A Continuum of Green Nanostructured Solvents
title_short Geminal Diol of Dihydrolevoglucosenone as a Switchable Hydrotrope: A Continuum of Green Nanostructured Solvents
title_sort geminal diol of dihydrolevoglucosenone as a switchable hydrotrope: a continuum of green nanostructured solvents
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7493416/
https://www.ncbi.nlm.nih.gov/pubmed/32953281
http://dx.doi.org/10.1021/acssuschemeng.9b00470
work_keys_str_mv AT debruynmario geminaldiolofdihydrolevoglucosenoneasaswitchablehydrotropeacontinuumofgreennanostructuredsolvents
AT budarinvitaliyl geminaldiolofdihydrolevoglucosenoneasaswitchablehydrotropeacontinuumofgreennanostructuredsolvents
AT misefariantonio geminaldiolofdihydrolevoglucosenoneasaswitchablehydrotropeacontinuumofgreennanostructuredsolvents
AT shimizuseishi geminaldiolofdihydrolevoglucosenoneasaswitchablehydrotropeacontinuumofgreennanostructuredsolvents
AT fishheather geminaldiolofdihydrolevoglucosenoneasaswitchablehydrotropeacontinuumofgreennanostructuredsolvents
AT cockettmartin geminaldiolofdihydrolevoglucosenoneasaswitchablehydrotropeacontinuumofgreennanostructuredsolvents
AT huntandrewj geminaldiolofdihydrolevoglucosenoneasaswitchablehydrotropeacontinuumofgreennanostructuredsolvents
AT hofstetterheike geminaldiolofdihydrolevoglucosenoneasaswitchablehydrotropeacontinuumofgreennanostructuredsolvents
AT weckhuysenbertm geminaldiolofdihydrolevoglucosenoneasaswitchablehydrotropeacontinuumofgreennanostructuredsolvents
AT clarkjamesh geminaldiolofdihydrolevoglucosenoneasaswitchablehydrotropeacontinuumofgreennanostructuredsolvents
AT macquarrieduncanj geminaldiolofdihydrolevoglucosenoneasaswitchablehydrotropeacontinuumofgreennanostructuredsolvents