Acrylate monomers from olefins via tertiary butyl hypochlorite

A variety of olefins were readily converted to acrylate monomers by combining them with t-butyl hypochlorite and acrylic or methacrylic acid at 25–65°C. The predominate product was the vicinal acyloxychloro derivative formed by addition at the olefinic double bond. By-products were the vicinal butoxychloro derivative and the still unsaturated chlorinated olefin. The main reaction was shown to occur by an ionic mechanism. 2-Chloro-1-methyl propyl methacrylate was isolated and identified as the main product of the reaction of 2-butene, methacrylic acid, and t-butyl hypochlorite. The crude olefin products readily homopolymerized and copolymerized with other vinyl monomers by incorporating free-radical initiators.