A sustainable tandem catalysis approach to plant oil based polyols via Schenck ‐Ene reaction and epoxidation

Abstract
Novel polyols were synthesized in a one‐pot, tandem reaction approach. First, singlet oxygen was used as oxidant in the photochemical Schenck‐Ene reaction to obtain allyl hydroperoxides of triglycerides, which were reacted in situ to the corresponding epoxy alcohols catalyzed by titanium(IV) isopropoxide. Subsequent acidic epoxide ring‐opening with perchloric acid yielded a triglyceride‐based polyol. Under basic conditions applying aqueous sodium hydroxide solution, cleavage of the ester bonds of the triglyceride and epoxide ring‐opening occurred simultaneously resulting in a fatty acid‐based polyol.Practical applications: Polyols, especially also based on renewable fatty acids, are valuable monomers for the synthesis of polyurethanes, polyester‐ and alkyd‐resins. With the here reported method, a maximum of three hydroxyl groups per double bond of the unsaturated triglyceride can be introduced, which cannot be realized with the methods reported to date.

Source: European Journal of Lipid Science and Technology - February 1, 2018 Category: Lipidology Authors: Maike Unverferth, Michael A. R. Meier Tags: Research Article Source Type: research