Synthesis of long chain alkyl glyceryl ethers from triglycerides using boron trifluoride etherate and lithium aluminum hydride

Abstract

Abstract A procedure for direct conversion of long chain triglycerides to their corresponding ether derivatives has been accomplished using a combination of lithium aluminum hydride and boron trifluoride etherate. Reaction products obtained from reduction of tristearin or trimyristin were isolated by thin layer and column chromatography and identified using infrared spectroscopy. Glyceryl triethers, glyceryl monoethers, and aliphatic alcohols were the major reaction products, making up 2–3%, 9–19%, and 43–75%, respectively, of the theoretical molar yields. Yields of both ether derivatives were increased when a lithium aluminum hydride solution was added to a mixture of triglyceride and boron trifluoride etherate rather than adding a mixture of triglyceride and boron trifluoride etherate to lithium aluminum hydride. Increasing the quantities of lithium aluminum hydride increased glyceryl triether yield, but decreased glyceryl monoether yield.