Synthesis of Chlorinated and Non‐chlorinated Polyols from Model Cross‐Metathesis Modified Triacylglycerols

Abstract

AbstractThree pure triacylglycerols (TAG) containing decenoic acid (D), and stearic acid (S), were hydroxylated into chlorinated and non‐chlorinated polyols and studied in detail. D is a fatty moiety that can result from the cross metathesis of small olefins with common vegetable oils such as soybean oil. A fundamental understanding relating chemical composition and derived structure, particularly the number and position of the hydroxyl groups, to physical properties was established allowing us to add some perspective to the growing body of knowledge on industrially relevant polyol and polyurethane systems produced with metathesis‐modified TAG (MTAG). The hydroxyl value, crystallization and melting behaviors, thermal degradation behavior of the polyols were directly related to their peculiar shortened and primary functionality inherited from the parent MTAG. The effect of regiochemistry on the physical properties of the polyols was investigated with the chromatography fractions of the trichlorinated polyol of propane‐1,2,3‐triyl tris(dec‐9‐enoate), giving an unhindered insight into the role of short and terminal functionality of MTAG polyols that will help select the optimal isomer composition for designer polyurethane materials.