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

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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Abstract

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 3.0).

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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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