Propargyl ether(s) produced from renewable raw materials - by reacting eugenol, iso-eugenol or vanillin with propargyl halide in presence of base, with iron@ or iron salt as catalyst

摘要

Propargyl ethers of formula HC=C-CH2-O-Ar-CH2-CH=CH2 (IA), HC=C-CH2-O-Ar-CH=CH-Me (IB) or HC=C-CH2-O-Ar-CHO (IC) are claimed, pref. (IA) or (IB), esp. pref. (IA), with Ar = a gp. of formula (II). Also claimed is a process for prepn. of (IA) and (IB) by reaction of 1 mol. eugenol (for IA) or isoeguenol (for IB) with 1-2 mols. propargyl halide in organic solvent (II) in the presence of 1-2 mols. base, with addn. of 0.0001-0.01 mol. Fe in the form of the element or Fe cpds.. USE/ADVANTAGE - (I) are useful for the prodn. of water-repellent thermosets, which combine the advantages of epoxy resins with that of low water absorption (see, e.g. High Performance Polymers 2 (1), 1990, 67-77). The invention enables the prodn. of new propargyl ethers from renewable natural raw materials, i.e. (iso)eugenol.