Convenient preparation of fatty ester cyclic carbonates

The cyclic carbonate moiety finds many industrial applications because of its unique chemistry and properties. Phosgene, a highly toxic and corrosive reagent, has been utilized in the past to prepare low yields of fatty ester compounds ( 1 ) that contain a five‐membered cyclic carbonate group. Herein, we show (CH 3 ) 4 N +− HCO 3 , tetramethylammonium hydrogen carbonate (TMAHC), to react efficiently with methyl or 2‐ethylhexyl 9(10)chloro‐10(9)‐hydroxyoctadecanoate at 50–55 °C to give methyl or 2‐ethylhexyl 8‐(2‐oxo‐5‐octyl‐1,3‐dioxolan‐4‐yl)octanoate, 1a and 1b , respectively. These fatty acid ester carbonates were isolated in good yields ranging from 84% to 91% after purification by vacuum distillation. The purified fatty ester carbonate compounds were characterized by 1 H and 13 C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and gas chromatography‐mass spectrometry using electron impact ionization and positive chemical ionization techniques. This work demonstrates that the five‐membered cyclic carbonate ring can be effectively introduced onto the alkyl chains of fatty acid esters using fatty ester chlorohydrins and (CH 3 ) 4 N +− HCO 3 chemistry. The well‐known lubricating and polymeric properties of the carbonate moiety make these interesting cyclic oleochemical carbonates potential candidates for industrial lubricant, plasticizer, or polymer applications.