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ERIC Number: EJ1062304
Record Type: Journal
Publication Date: 2015-Apr
Pages: 6
Abstractor: As Provided
Reference Count: 28
ISBN: N/A
ISSN: ISSN-0021-9584
Organocatalytic Ring-Opening Polymerization of Trimethylene Carbonate to Yield a Biodegradable Polycarbonate
Chan, Julian M. W.; Zhang, Xiangyi; Brennan, Megan K.; Sardon, Haritz; Engler, Amanda C.; Fox, Courtney H.; Frank, Curtis W.; Waymouth, Robert M.; Hedrick, James L.
Journal of Chemical Education, v92 n4 p708-713 Apr 2015
In this laboratory experiment, students work in pairs to synthesize a simple aliphatic polycarbonate via ring-opening polymerization of trimethylene carbonate using 1,8-diazabicyclo[5.4.0]undec-7-ene and thiourea as organocatalysts. Following polymer isolation, students cool the material in a dry ice/acetone bath to observe its glass-transition behavior. This experiment is convenient to perform under teaching laboratory conditions and reinforces key concepts learned in second-year undergraduate organic chemistry, for example, nucleophilic acyl substitution, transesterification reactions, and Lewis acidity-basicity. Additionally, the experiment introduces students to polymer chemistry, heterocycles, materials science, and green chemistry. It also covers interesting concepts that are less frequently encountered at the undergraduate level such as biomimetic chemistry, bifunctional catalysis, and polymer-glass transitions.
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: National Science Foundation
Authoring Institution: N/A
IES Grant or Contract Numbers: NSF-CHE 957386