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.
Highlights
Glycerol (1,2,3-propanetriol), is one of the most versatile and valuable chemicals known to man.Glycerol has over 1,500 known end uses, including applications as an ingredient or processing aid in cosmetics, toiletries, personal care products, pharmaceutical formulations and food [1]
We report the results obtained when two solvents (1,4-dioxane and 1-butanol) and different bases are used to prepare dissymmetric chlorohydrin esters from symmetric 1,3-dichloro-2propyl esters obtained from glycerol
Several 1,3-dichloro-2-propyl esters 1a–d were treated with water and an organic (1-butylimidazole) or inorganic base in two different solvents: 1,4-dioxane or 1-butanol (Table 1)
Summary
Glycerol (1,2,3-propanetriol), is one of the most versatile and valuable chemicals known to man. Glycerol has over 1,500 known end uses, including applications as an ingredient or processing aid in cosmetics, toiletries, personal care products, pharmaceutical formulations and food [1]. It is obtained as a by-product in four different processes: soap manufacture (saponification), fatty acid. Biodiesel is a common term for the different alkyl fatty esters formed by transesterification of vegetable oils or fats with an alcohol, usually methanol, with or without a catalyst It has been implemented as an alternative to transportation fuels in Europe, the United States, Brazil and other countries as a result of increased interest in using renewable energy sources to reduce greenhouse gas emissions and to alleviate the depletion of fossil fuel reserves [5,6]. We report the results obtained when two solvents (1,4-dioxane and 1-butanol) and different bases are used to prepare dissymmetric chlorohydrin esters from symmetric 1,3-dichloro-2propyl esters obtained from glycerol
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