A new phase-selectively soluble polymer has been prepared using 4-dodecylstyrene as the monomer with 1-5 mol% of 4-chloromethylstyrene as a comonomer. A fluorescent dye has been incorporated into the copolymer as a catalyst surrogate to measure polymer phase selective solubility in a heptane phase. Using the resulting labeled polymer we showed that poly(4-dodecylstyrene) copolymer exhibits 99.9 % phase selective solubility in heptane, making it a good polymer candidate for recycling of catalysts. A derivative of 4-(dimethylamino)pyridine (DMAP) was synthesized and then coupled to the poly(4-dodecylstyrene) copolymer via a piperazine moiety. The recyclability and the catalytic potential of this new copolymer was investigated in acylation reactions of 2,6-dimethylphenol with Boc anhydride in a latent biphasic system and  in acylation of glycidyl isopropyl ether with acetic anhydride in thermomorphic conditions. The polymer-supported catalyst could be recycled up to 20 times with a minimal leaching into the polar phase (ca. 0.1% per cycle). The catalytic activity of the polymer-supported DMAP was comparable with that of the low molecular weight DMAP.

Recoverable, reusable novel polymer-supported organocatalyst

244th National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.