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Low-Temperature Chemical Synthesis of High-Purity Diacylglycerols (DAG) from Monoacylglycerols (MAG)

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Lipids

Abstract

A chemical method was developed for low-temperature synthesis of DAG from MAG followed by an easy purification procedure in order to obtain high-purity DAG. Solvent-assisted and solvent-free reaction conditions were used, combined with different catalysts (sodium methoxide, p-toluenesulfonic acid, methanesulfonic acid, and sulfuric acid). All reactions were performed at 35 and 70 °C. By increasing both acidity and polarity of the catalyst the equilibrium shifts towards the formation of DAG. When using sulfuric acid in solvent-assisted condition at 70 °C, 88 % conversion was obtained after 20 min of reaction (77 % w/w DAG in the reaction mixture after evaporation of the solvent). After purifying by means of column chromatography, 96 % pure DAG were obtained. The overall yield of DAG was 81 %.

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Abbreviations

DAG:

Diacylglycerol(s)

FFA:

Free fatty acid(s)

GPC:

Gel permeation chromatography

MAG:

Monoacylglycerol(s)

MSA:

Methanesulfonic acid

PTSA:

p-Toluenesulfonic acid

SA:

Solvent-assisted

SF:

Solvent-free

SFA:

Sulfuric acid

TAG:

Triacylglycerol(s)

TLC:

Thin layer chromatography

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Acknowledgments

The authors thank Karel de Grote-Hogeschool for financial support and Oleon NV for providing the MAG.

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Authors and Affiliations

  1. Faculty of Applied Engineering, University of Antwerp, Salesianenlaan 90, 2660, Hoboken, Belgium

    Łukasz Pazdur & Serge M. F. Tavernier

  2. Department of Industrial Sciences and Technology, Karel de Grote University College, Salesianenlaan 90, 2660, Hoboken, Belgium

    Jeroen Geuens & Hannes Sels

Authors
  1. Łukasz Pazdur
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  2. Jeroen Geuens
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  3. Hannes Sels
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  4. Serge M. F. Tavernier
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Correspondence to Jeroen Geuens.

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Pazdur, Ł., Geuens, J., Sels, H. et al. Low-Temperature Chemical Synthesis of High-Purity Diacylglycerols (DAG) from Monoacylglycerols (MAG). Lipids 50, 219–226 (2015). https://doi.org/10.1007/s11745-014-3980-x

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  • DOI: https://doi.org/10.1007/s11745-014-3980-x

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