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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...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American
Chemical Society
2019
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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 |
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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 |
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