Synthesis of secondary ethers derived from meadowfoam oil

Abstract

AbstractSecondary ethers can be obtained from meadow‐foam‐derived delta lactones or 5‐hydroxy fatty acids by using Lewis or Brønsted acid catalysts in good yield (70–90%). The conversion of δ‐lactone or 5‐hydroxy fatty acid to 5‐ethers is performed under atmospheric pressure between 67 and 125°C with 0.5–6.4 mole equivalents of acid catalyst in the presence of 2–40 equivalents of alcohol and a reaction time of 1–140 h. Acid catalysts include mineral acids, such as perchloric and sulfuric; Lewis acids, such as boron trifluoride; and heterogeneous catalysts, such as clays and ion‐exchange resins. Primary alcohols, such as methanol, butanol, decanol, and oleyl alcohol, or branched‐chain alcohols, such as 2‐ethylhexanol, can be used to make secondary ether fatty esters. The 5‐ether fatty esters and the process for their formation have not been previously known and appear to be limited to structures where stabilized cations can be formed. The novel ethers were fully characterized by nuclear magnetic resonance and gas chromatography‐mass spectrometry.