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

• Published in: Journal of the American Oil Chemists' Society Vol. 90; no. 2; pp. 259 - 264
• Main Authors: Kargar, Mojgan, Hekmatshoar, Rahim, Ghandi, Mehdi, Mostashari, AbdolJalil
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer-Verlag 01.02.2013; Springer Nature B.V
• Subjects: 1,3‐sn‐Diglycerides; Agriculture; anhydrides; Biomaterials; Biotechnology; Chemical synthesis; Chemistry; Chemistry and Materials Science; DABCO; Esters; Fatty acid anhydrides; Fatty acids; Food Science; glycerol; Glycerol carbonate; Glycerol carbonates fatty esters; heat treatment; Industrial Chemistry/Chemical Engineering; Low HLB surfactants; Oils & fats; Original Paper; Solvents; Surfactants; Glycerol carbonate; Glycerol carbonates fatty esters; Low HLB surfactants; Fatty acid anhydrides; 1,3; Diglycerides; DABCO
• ISSN: 0003-021X; 1558-9331
• DOI: 10.1007/s11746-012-2165-0

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.