Synthesis and characterization of acrylated phosphonates and their polymers having 1,3‐dioxolane and 1,3‐dioxane moieties derived from brominated cyclic acetals of polyols through the Arbuzov reaction. II

Glycerol, D ‐mannitol, and D ‐sorbitol were converted into their mono‐ and di‐ O ‐1,3‐dioxolane and 1,3‐dioxane bromoethylidene derivatives through a transacetalation reaction with bormoacetaldehyde diethyl acetal under controlled conditions. These brominated dioxolane or dioxane derivatives were subsequently phosphonylated through the Arbuzov reaction. The phosphonylated cyclic acetals were used as precursors for the synthesis of acrylated phosphonate monomers. All these compounds have been characterized by elemental analysis and spectroscopic (IR, 1 H‐, 13 C‐, 31 P‐NMR and mass) methods. A mixture of 1,3‐dioxane and 1,3‐dioxolane derivatives was obtained with D ‐sorbitol, whereas the reaction products with glycerol and D ‐mannitol yielded primarily the 1,3‐dioxolane derivatives. The acrylated phosphonates of glycerol and mannitol have been polymerized and studied on the basis of gel permeation chromatography and their spectral and thermal properties. The acrylated phosphonates, monomers, and polymers, were shown to have a large capacity to solvate and dissolve heavy metal salts. This results in a dramatic increase (> 100°C) of the glass transition temperature of these polymers.