ethyl acetate. Removal of the ethyl acetate under vacuum and distillation of the residual brown oil gave 52% of material boiling at 121-127°/0.1 mm., re" 1.4755.

SynopsisThe aqueous suspension chlorination of poly( methyl methacrylate) using incandrsrrnt light produces polymer having up to one chlorine atom per monomer unit. The mrchmism of aqueous suspension chlorination is the same as that for solution chlorination, i.r., free radical substitution; the rate of chlorination a t constant chlorine flow rate drprnds on the time, the concentration of the polymer, and the size or porosity of the polymer particles. The structures of suspension and solution Chlorinated poly( methyl methacrylate) were established by comparison of their NMR spectra with those of poly(methy1 methacrylate), poly(chloromethy1 methacrylate), and a copolymer of methyl a-chloromethylacrylate with methyl methacrylate. In chlorinated poly( methyl methacrylate) having 0.5 chlorine atoms per monomer unit, hrtlf of the chlorine is on the ester methyl group and half is on the @-carbon atom. In the suspension chlorinated sample containing one chlorine per monomer unit, 20% of the chlorine is present as OCHC1, groups, 40% as OCHtC1 groups, 30% as -CHCl-groups, and lOyo as C-CH&1 groups. In a solution chlorinated sample containing two chlorine atoms per monomer unit, the chlorine is distributed: 40% as OCH,Cl, 40% as -CHCl-and/or C-CH,CI, and 20% as OCHCl?.