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Glycerol Acetals and Ketals as Bio-based Solvents: Positioning in Hansen and COSMO-RS spaces, Volatility and Stability towards Hydrolysis and Autoxidation

Moity, Laurianne and Benazzouz, Adrien and Molinier, Valérie and Nardello-Rataj, Véronique and Elmkaddem, Mohammed Kamal and De Caro, Pascale and Thiebaud-Roux, Sophie and Gerbaud, Vincent and Marion, Philippe and Aubry, Jean-Marie Glycerol Acetals and Ketals as Bio-based Solvents: Positioning in Hansen and COSMO-RS spaces, Volatility and Stability towards Hydrolysis and Autoxidation. (2015) Green Chemistry, vol. 17 (n° 3). pp. 1779-1792. ISSN 1463-9262

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Official URL: http://dx.doi.org/10.1039/c4gc02377c

Abstract

Four recently launched cyclic glycerol acetals or ketals are evaluated as bio-based solvents. Three of them are industrially available and result from the condensation of glycerol with formaldehyde, acetone and isobutyl methyl ketone. The fourth is under development and is prepared by the reaction of glycerol with benzaldehyde under heterogeneous acidic catalysis. Their solvent properties are evaluated through Hansen and COSMO-RS (COnductor-like Screening MOdel for Real Solvents) approaches, in comparison to traditional petrochemical solvents. Dioxolane- and dioxane-type isomers have close solubility parameters; however the nature of the starting aldehyde/ketone significantly impacts the solvency properties. Stability to hydrolysis depends heavily on both the aldehyde/ketone part and on the size of the ring. In acidic medium, acetals are found to be more stable than ketals and glycerol-based ketals are more stable than ethylene glycol-based ketals. In the case of benzaldehyde glycerol acetal, it is shown that the 6-member ring isomer (dioxane-type) is approximately 8 times more stable than the 5-member ring counterpart (dioxolane-type) at low pH. Stability towards autoxidation by O2 is high for formaldehyde and acetone-derived acetals and drops for the other two compounds. Glycerol acetals and ketals are promising potential alternatives to some harmful solvents such as glycol ethers and aniline.

Item Type:Article
Additional Information:Thanks to Royal Society of Chemistry editor. The definitive version is available at http://pubs.rsc.org The original PDF of the article can be found at Royal Society of Chemistry website : http://pubs.rsc.org/en/Content/ArticleLanding/2015/GC/c4gc02377c#!divAbstract
HAL Id:hal-01198815
Audience (journal):International peer-reviewed journal
Uncontrolled Keywords:
Institution:French research institutions > Centre National de la Recherche Scientifique - CNRS (FRANCE)
Other partners > Ecole Nationale Supérieure de Chimie de Lille - ENSCL (FRANCE)
Université de Toulouse > Institut National Polytechnique de Toulouse - INPT (FRANCE)
French research institutions > Institut National de la Recherche Agronomique - INRA (FRANCE)
Other partners > SOLVAY (FRANCE)
Université de Toulouse > Université Paul Sabatier-Toulouse III - UPS (FRANCE)
Other partners > Université Lille 1, Sciences et Technologies - Lille 1 (FRANCE)
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Deposited By: Vincent GERBAUD
Deposited On:11 Sep 2015 15:05

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