Sustainable polymers in the organic chemistry laboratory: Synthesis and characterization of a renewable polymer from δ-decalactone and l-lactide

Journal of Chemical Education

Volumn 91, Issue 1, 2014, Pages 131-135

  Schneiderman, Deborah K ^a   Gilmer, Chad ^b   Wentzel, Michael T ^b   Martello, Mark T ^a   Kubo, Tomohiro ^a   Wissinger, Jane E ^a  

^a University of Minnesota   (United States)

^b AUGSBURG COLLEGE   (United States)

Author keywords

Catalysis; Esters; Green Chemistry; Laboratory Instruction; Material Science; NMR Spectroscopy; Organic Chemistry; Polymer Chemistry; Polymerization; Second Year Undergraduate

Indexed keywords

EID: 84892607690     PISSN: 00219584     EISSN: 19381328     Source Type: Journal    
DOI: 10.1021/ed400185u     Document Type: Article

References (23)

1. Shakhashiri, B. Z. Chemical Demonstrations, A Handbook for Teachers of Chemistry; The University of Wisconsin Press: Madison, WI, 1983; Vol. 1, pp 213-215.
2. th ed.; Brooks/Cole, Cengage Learning: Belmont, CA, 2011; pp 763-765.
3. Mohrig, J. R.; Hammond, C. N.; Schatz, P. F.; Morrill, T. C. Modern Projects and Experiments in Organic Chemistry: Miniscale and Standard Taper Microscale, 2 nd ed.; W. H. Freeman and Company: New York, 2003; pp 143-149.
4. Lehman, J. W. Operational Organic Chemistry, 2 nd ed.; Pearson Education, Inc.: Upper Saddle River, NJ, 2009; pp 232-238.
5. Donahue, C. J.; Exline, J. A.; Warner, C. Chemical Recycling of Pop Bottles: The Synthesis of Dibenzyl Terephthalate from Plastic Polyethylene Terephthalate J. Chem. Educ. 2003, 80, 79-82
6. Kamber, N. E.; Tsujii, Y.; Keets, K.; Waymouth, R. M.; Pratt, R. C.; Nyce, G. W.; Hendrick, J. L. The Depolymerization of Poly(ethylene terephthalate) (PET) Using N-Heterocyclic Carbenes from Ionic Liquids J. Chem. Educ. 2010, 87, 519-521
7. Pappenfus, T. M.; Hermanson, D. L.; Kohl, S. G.; Melby, J. H.; Thoma, L. M.; Carpenter, N. E.; da Silva Filho, D. A.; Bredas, J.-L. Regiochemistry of Poly(3-hexylthiophene) Synthesis and Investigation of a Conducting Polymer J. Chem. Educ. 2010, 87, 522-525
8. Goto, H.; Yoneyama, H.; Togashi, F.; Ohta, R.; Tsujimoto, A.; Kita, E.; Ohshima, K.-i. Preparation of Conducting Polymers by Electrochemical Methods and Demonstration of a Polymer Battery J. Chem. Educ. 2008, 85, 1067-1070
9. Weizman, H.; Nielsen, C.; Weizman, O. S.; Nemat-Nasser, S. N. Synthesis of a Self-Healing Polymer Based on Reversible Diels-Alder Reaction: An Advanced Undergraduate Laboratory at the Interface of Organic Chemistry and Materials Science J. Chem. Educ. 2011, 88, 1137-1140
10. Pinto, M. L. Formulation, Preparation, and Characterization of Polyurethane Foams J. Chem. Educ. 2010, 87, 212-215
11. Stevens, E. S.; Poliks, M. D. Tensile Strength Measurements on Biopolymer Films J. Chem. Educ. 2003, 80, 810-812
12. Mc Ilrath, S. P.; Robertson, N. J.; Kuchta, R. J. Bustin' Bunnies: An Adaptable Inquiry-Based Approach Introducing Molecular Weight and Polymer Properties J. Chem. Educ. 2012, 89, 928-932
13. Robert, J. L.; Aubrecht, K. B. Ring-Opening Polymerization of Lactide to Form a Biodegradable Polymer J. Chem. Educ. 2008, 85, 258-260
14. Bennett, G. D. A Green Polymerization of Aspartic Acid for the Undergraduate Organic Laboratory J. Chem. Educ. 2005, 82, 1380-1381
15. Anastas, P. T.; Warner, J. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998.
16. Martello, M. T.; Burns, A.; Hillmyer, M. A. Bulk Ring-Opening Transesterification Polymerization of the Renewable Decalactone Using an Organocatalyst ACS Macro. Lett. 2012, 1, 131-135
17. Rali, T.; Wossa, S. W.; Leach, D. N. Comparative chemical analysis of the essential oil constituents in the bark, heartwood, and fruits of Cyptocarya massoy (Oken) Kosterm. (Lauraceae) from Papua New Guinea Molecules 2007, 12, 149-154
18. U.S. Food and Drug Administration. CFR Code of Federal Regulations, Title 21. http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?FR= 172.515 (accessed Nov 2013).
19. Sigma-Aldrich. δ -Decalactone. http://www.sigmaaldrich.com/catalog/ product/aldrich/w236101?lang=en®ion=US (accessed Nov 2013).
20. Smith, J. G. Organic Chemistry, 4 th ed.; McGraw-Hill: New York, 2014; pp 1243-1250 and
21. Wade, L. G. Organic Chemistry, 8 th ed.; Pearson Education, Inc.: New York, 2013; pp 1232-1238.
22. Engel, K.-H.; Flath, R. A.; Buttery, R. G.; Mon, T. R.; Ramming, D. W.; Teranishi, R. Investigation of Volatile Constituents in Nectarines. 1. Analytical and Sensory Characteristics of Aroma Components in Some Nectarine Cultivars J. Agric. Food Chem. 1988, 36, 549-553
23. Wanamaker, C. L.; Tolman, W. B.; Hillmyer, M. A. Hydrolytic Degradation Behavior of a Renewable Thermoplastic Elastomer Biomacromolecules 2009, 10, 443-448