Toward the synthesis of functionalized polymers via green chemistry: Studies of enzyme catalyzed transesterification

POLY 130

Joseph R. Kasper, joseph_kasper@mail.msj.edu1, Mustafa Y. Sen, mustafa@uakron.edu2, and Judit E. Puskas, jpuskas@uakron.edu2. (1) University of Akron, Cincinnati, OH 45233, (2) Department of Polymer Science, The University of Akron, 170 University Avenue, Akron, OH 44325
The goal of this research was to develop a novel, enzyme-mediated approach to polymer functionalization. Enzymes are environmentally friendly alternatives to classical catalysts and typically react under mild conditions. Conditions have recently been found under which poly(ethylene glycol)s PEGs could be functionalized with 100% efficiency via transesterification catalyzed by Candida antarctica lipase B (CALB). This research focused on finding conditions for the functionalization of polyisobutylenes bearing primary hydroxyl groups (PIB-OH), prepared with epoxy initiators in one step. Vinyl and ethyl acetate were transesterified with 2-phenyl-1-propanol, the model compound for PIB-OH. It was observed that the reaction was quantitative with vinyl acetate, because isomerization of the vinyl alcohol product rendered the transesterification irreversible. Comparison of the reactions catalyzed by CALB and a commercially available distannoxane catalyst was revealed that CALB was more effective. The products were characterized by thin layer chromatography (TLC) and NMR spectroscopy.
 

Undergraduate Research in Polymer Science
6:00 PM-8:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster

Division of Polymer Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008