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

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.

Acylglycerols of Myristic Acid as New Candidates for Effective Stigmasterol Delivery—Design, Synthesis, and the Influence on Physicochemical Properties of Liposomes

“…White crystals, mp 62–64 °C (lit. 64–66 °C [ 48 ]), R f = 0.22 (hexane:ethyl acetate, 5:1), 1 H NMR (400 MHz, CDCl 3 ): δ 0.87 (t, J = 7.1 Hz, 6H, 2 × -OC(O)(CH 2 ) 12 C H 3 ), 1.20–1.34 (m, 40H, 2 × -OC(O)CH 2 CH 2 (C H 2 ) 10 CH 3 ), 1.62 (m, 4H, 2 × -OC(O)CH 2 C H 2 (CH 2 ) 10 CH 3 ), 2.34 (t, J = 7.6 Hz, 4H, 2 × -OC(O)C H 2 (CH 2 ) 11 CH 3 ), 4.07 (m, 1H, H-2), 4.13 (dd, J = 11.3 Hz and 5.6 Hz, 2H, one of CH 2 -1 and one of CH 2 -3), 4.18 (dd, J = 11.3 Hz and 4.3 Hz, 2H, one of CH 2 -1 and one of CH 2 -3); 13 C NMR (100 MHz): δ 14.12 (2 × -OC(O)(CH 2 ) 12 C H 3 ), 22.68 (2 × -OC(O)(CH 2 ) 11 C H 2 CH 3 ), 24.86 (2 × -OC(O)CH 2 C H 2 (CH 2 ) 10 CH 3 ), 29.10, 29.23, 29.34, 29.43, 29.58, 29.63 and 29.66 (2 × -OC(O)CH 2 CH 2 ( C H 2 ) 8 CH 2 CH 2 CH 3 ), 31.90 (2 × -OC(O)(CH 2 ) 10 C H 2 CH 2 CH 3 ), 34.07 (2 × -OC(O) C H 2 (CH 2 ) 11 CH 3 ), 65.00 (C-1 and C-3), 68.33 (C-2), 173.95 (2 × -O C (O)(CH 2 ) 12 CH 3 ); IR (ATR, cm −1 ): 3484 (w), 1715 (s), 1732 (s), 1181 (s); HRMS (ESI): m/z calcd for C 31 H 58 O 5 : 535.4338 [ M +Na] + ; found: 535.4335.…”

Glycerol based solvents: synthesis, properties and applications

“…Thus, an efficient (98-100% yield) solvent-free synthesis of a variety of highly pure 1,3-sn-diacylglycerols has been recently proposed. 110 As previously mentioned, these products are popular in the food industry as benign low hydrophilic-lipophilic balance (co)emulsifiers, rheological modifiers and dietary fat and oils.…”

Lithium Zirconate as a Selective and Cost-Effective Mixed Metal Oxide Catalyst for Glycerol Carbonate Production

“…One of the applications of GL could be its utilization as a raw material for the synthesis of another value-added products, viz., glycerol carbonate (GLC). GLC is one of the nonfood derivative of GL which has diverse applications such as a green solvent, electrolyte ingredient, and liquid carrier in lithium-based batteries; a GL precursor in detergent synthesis; an intermediate to synthesize resins and plastics in polymers industry; for the formation of 1,3- sn -diglyceride in food industry; a potential solvent for gas separation; drug carriers; a wetting agent in cosmetics; and a curing agent in concrete industry. GLC can be synthesized through diverse direct (carboxylation) and indirect routes (phosgenation, glycerolysis, and transesterification) starting from GL, as shown in Scheme .…”