Synthesis of 3-chloro-2-hydroxy propyl methacrylate and ion exchange resins therefrom

Abstract

3-Chloro-2-hydroxy propyl methacrylate (CHPMA) was prepared using methacrylic acid and epichlorohydrin. The effect of catalyst and temperature on the rate of conversion was studied. Benzyl trimethyl ammonium chloride was found to be very effective as a catalyst. The chloromethyl moiety on the resultant polymer was utilized for synthesizing ion exchange resins. Polymers of CHPMA cross linked with DVB were prepared, which were then reacted with various amines to give ion exchange resins. Effect of dioxolane as a swelling agent, along with its recovery was also studied. The ion exchange resins were characterized by their capacity, consistency in capacity, void volume and water regain. These resins are likely to have superior hydrolytic stability compared to the conventional acrylic resins and a new plant could easily adopt this technology for manufacture of all anion resins in place of styrene-DVB type products involving intermediate chloromethyl methyl ether which is a proven carcinogen. This procedure is superior to the one reported by Hradil and Svec [React. Polym. 13 (1990) 43] as the same final products are produced without using yet another toxic and expensive monomer, glycidyl methacrylate.