Methyl Methacrylate → Butyl prop-2-enoate--methyl 2-methylprop-2-enoate (1/1)

Participants

Reaction Steps

Cellulose (200 g, Harmac fully bleached Douglas Fir pulp available from MacMillan Bloedel, Stamford, CT) was dispersed in water (9.5 l) by mechanical agitation under nitrogen purging for two hours. A mixture of butyl acrylate (200 g) and methyl methacrylate (20 g) was vigorously stirred into the pulp for one-half hour. Graft copolymerization was initiated by addition of ceric ammonium nitrate (11 g, 0.02M) in 1M nitric acid (500 ml). The graft copolymerization was allowed to proceed for four hours, during which the color of the aqueous portion went from yellow (Ce4) to colorless (Ce3) indicating the oxidation of cellulose and initiation of polymerization. The reaction was neutralized with sodium carbonate (26.5 g, 0.25 M), filtered by suction, and washed with water (5 l). The sample was dried overnight at 90° C. to give a white fiber product (405 g, 93% conversion). The cellulose graft copolymer was extracted by refluxing with tetrahydrofuran (9 l) for three hours to remove homopolymer, filtered and dried to yield cellulose/butyl acrylate/methyl methacrylate fibers (200 g/177 g, 53 wt. % cellulose/47 wt. % butyl acrylate/methyl methacrylate, 86% graft efficiency).

Provenance & Evidence