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Use of Glycerol Carbonate in an Efficient, One-Pot and Solvent Free Synthesis of 1,3-sn-Diglycerides

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Journal of the American Oil Chemists' Society

Abstract

An efficient solvent-free synthesis of a variety of highly pure 1,3-sn-diglycerides (1,3-sn-diacylglycerols) in a two-step one pot process is described. Heating glycerol carbonate (4-hydroxymethyl-1,3-dioxolan-2-one) with fatty acid anhydrides 2a–d affords 1:1 mixtures of glycerol carbonate fatty esters 3a–3d and the corresponding fatty acids. Further heating the reaction mixtures in the presence of catalytic amounts of 1,4-diazabicyclo[2.2.2]octane (DABCO) at 195–200 °C yields highly pure 1,3-sn-diglycerides 4a–4d.

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Notes

  1. The hydrophilic-lipophilic balance (HLB) of a surfactant is a measure of the degree to which it is hydrophilic or lipophilic, determined by calculating values for the different regions of the molecule, as described by Griffin in 1949.

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Authors and Affiliations

  1. Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran

    Mojgan Kargar & Rahim Hekmatshoar

  2. School of Chemistry, College of Science, University of Tehran, Tehran, Iran

    Mehdi Ghandi

  3. Industrial Chemical R&D Organization, Tehran, Iran

    AbdolJalil Mostashari

Authors
  1. Mojgan Kargar
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  2. Rahim Hekmatshoar
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  3. Mehdi Ghandi
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  4. AbdolJalil Mostashari
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Correspondence to Mojgan Kargar.

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Kargar, M., Hekmatshoar, R., Ghandi, M. et al. Use of Glycerol Carbonate in an Efficient, One-Pot and Solvent Free Synthesis of 1,3-sn-Diglycerides. J Am Oil Chem Soc 90, 259–264 (2013). https://doi.org/10.1007/s11746-012-2165-0

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  • DOI: https://doi.org/10.1007/s11746-012-2165-0

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