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Molecules 2011, 16(3), 2065-2074; doi:10.3390/molecules16032065

From Symmetric Glycerol Derivatives to Dissymmetric Chlorohydrins

, , , , *  and
Department of Chemistry, Lleida University, Alcalde Rovira Roure 191, 25198 Lleida, Spain
* Author to whom correspondence should be addressed.
Received: 9 December 2010 / Revised: 16 February 2011 / Accepted: 28 February 2011 / Published: 2 March 2011
(This article belongs to the Special Issue Asymmetric Synthesis)
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The anticipated worldwide increase in biodiesel production will result in an accumulation of glycerol for which there are insufficient conventional uses. The surplus of this by-product has increased rapidly during the last decade, prompting a search for new glycerol applications. We describe here the synthesis of dissymmetric chlorohydrin esters from symmetric 1,3-dichloro-2-propyl esters obtained from glycerol. We studied the influence of two solvents: 1,4-dioxane and 1-butanol and two bases: sodium carbonate and 1-butylimidazole, on the synthesis of dissymmetric chlorohydrin esters. In addition, we studied the influence of other bases (potassium and lithium carbonates) in the reaction using 1,4-dioxane as the solvent. The highest yield was obtained using 1,4-dioxane and sodium carbonate.
Keywords: glycerol; chlorohydrin esters; dissymmetry; 1-butanol; 1,4-dioxane glycerol; chlorohydrin esters; dissymmetry; 1-butanol; 1,4-dioxane
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Solarte, C.; Escribà, M.; Eras, J.; Villorbina, G.; Canela, R.; Balcells, M. From Symmetric Glycerol Derivatives to Dissymmetric Chlorohydrins. Molecules 2011, 16, 2065-2074.

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