Premium
Synthesis of long chain alkyl glyceryl ethers from triglycerides using boron trifluoride etherate and lithium aluminum hydride
Author(s) -
Go H. C.,
Branen A. L.
Publication year - 1975
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02545283
Subject(s) - boron trifluoride , chemistry , lithium (medication) , yield (engineering) , boron , aluminum hydride , hydride , ether , alkyl , lithium aluminium hydride , organic chemistry , inorganic chemistry , catalysis , materials science , medicine , hydrogen , methoxide , metallurgy , endocrinology
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.