Recent Research Developments

Dr. Donghui Zhang, a postdoctoral research associate working in the laboratories of Professors Marc Hillmyer and William Tolman, has developed a new procedure (Scheme 1) for preparing high molecular weight poly[3-hydroxypropionic acid] (P[3-HP]), a biorenewable and biodegradable plastic with attractive mechanical properties. In a paper recently published in Macromolecules [1] Donghui showed that 3-HP macrocyclic esters derived directly from 3-hydroxypropionic acid, a biorenewable resource resulting from the fermentation of sugars, could be readily polymerized by a Zn-based catalyst recently developed in the Hillmyer/Tolman laboratories [J. Am. Chem. Soc. 2003, 125, 11350]. Previously reported methodologies for preparing P[3-HP] are difficult to control or require the use of toxic monomers. This new procedure circumvents both of these problems and can be readily performed on a large scale.

Specifically, a 3-HP macrocylic ester mixture was obtained from a simple one-pot condensation reaction of a commercially available aqueous solution 3-HP. The 3-HP trimer (Scheme 1, n = 3) was isolated from the mixture and polymerization of this 12-membered ring occurred rapidly at room temperature to give high molecular weight P[3-HP] samples (up to 67 kg⋅mol^-1). Moreover, it was shown that 3-HP cyclic esters with larger ring sizes (n = 4 or 5) also could be polymerized. These results demonstrate the practicality of this new synthetic route to an environmentally friendly plastic.

[1] Zhang, D.; Hillmyer, M. A.; Tolman, W. B. “A New Synthetic Route to Poly[3-hydroxypropionic acid] (P[3-HP]): Ring-Opening Polymerization of 3-HP Macrocyclic Esters” Macromolecules 2004, 37, 8198

Where do you want to go? ------------------------ Chemistry Home Page University of Minnesota Welcome Research News Chemistry News Directory Graduate Program Course Pages Undergraduate Program Seminars Events Chemistry Outreach Facilities, Sup. Services, & Safety Search Links Summer Undergrad Research Job Openings
The University of Minnesota is an equal opportunity educator and employer.

Copyright 2005 by the Regents of the University of Minnesota.For questions or comments, contact the Chemistry Webmaster or read the University's Online Privacy Statement.