Alternating copolymerization of propylene oxide with biorenewable terpene-based cyclic anhydrides: A sustainable route to aliphatic polyesters with high glass transition temperatures

Angewandte Chemie - International Edition

Volumn 54, Issue 9, 2015, Pages 2665-2668

  Van Zee, Nathan J ^a   Coates, Geoffrey W ^a  

^a Department of Obstetrics Gynecology   (United States)

Author keywords

Aluminum; Homogeneous catalysis; Ring opening polymerization; Sustainable chemistry; Terpenoids

Indexed keywords

ALUMINUM; CATALYSIS; CHROMIUM COMPOUNDS; COBALT COMPOUNDS; COPOLYMERIZATION; COPOLYMERS; GLASS; MOLECULAR WEIGHT; MOLECULAR WEIGHT DISTRIBUTION; OPTICAL SENSORS; POLYESTERS; POLYMERS; PROPYLENE; REACTION KINETICS; RING OPENING POLYMERIZATION; TEMPERATURE; TERPENES;

ALTERNATING COPOLYMERIZATION; ALUMINUM-SALEN COMPLEXES; HIGH MOLECULAR WEIGHT; HIGH-GLASS TRANSITION TEMPERATURES; HOMOGENEOUS CATALYSIS; POLYMERIZATION CONDITIONS; SUSTAINABLE CHEMISTRY; TERPENOIDS;

GLASS TRANSITION;

ACID ANHYDRIDE; EPOXIDE; GLASS; POLYESTER; PROPYLENE OXIDE; TERPENE;

CHEMICAL STRUCTURE; CHEMISTRY; POLYMERIZATION; SYNTHESIS; TRANSITION TEMPERATURE;

ANHYDRIDES; EPOXY COMPOUNDS; GLASS; MOLECULAR STRUCTURE; POLYESTERS; POLYMERIZATION; TERPENES; TRANSITION TEMPERATURE;

EID: 84923115847     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201410641     Document Type: Article

References (49)

1. a) A. J. Ragauskas, C. K. Williams, B. H. Davison, G. Britovsek, J. Cairney, C. A. Eckert, W. J. Frederick, Jr., J. P. Hallett, D. J. Leak, C. L. Liotta, J. R. Mielenz, R. Murphy, R. Templer, T. Tschaplinski, Science 2006, 311, 484-489;
2. b) A. Gandini, Green Chem. 2011, 13, 1061-1083;
3. c) C. Vilela, A. F. Sousa, A. C. Fonseca, A. C. Serra, J. F. J. Coelho, C. S. R. Freire, A. J. D. Silvestre, Polym. Chem. 2014, 5, 3119-3141.
4. a) W. Amass, A. Amass, B. Tighe, Polym. Int. 1998, 47, 89-144;
5. b) R. A. Gross, B. Kalra, Science 2002, 297, 803-807;
6. c) S. Mecking, Angew. Chem. Int. Ed. 2004, 43, 1078-1085;
7. Angew. Chem. 2004, 116, 1096-1104;
8. d) M. Vert, Biomacromolecules 2005, 6, 538-546;
9. e) O. Coulembier, P. Degée, J. L. Hedrick, P. Dubois, Prog. Polym. Sci. 2006, 31, 723-747;
10. f) C. K. Williams, Chem. Soc. Rev. 2007, 36, 1573-1580.
11. R.-J. Müller, I. Kleeberg,W.-D. Deckwer, J. Biotechnol. 2001, 86, 87-95.
12. Y. Ikada, T. Hideto, Macromol. Rapid Commun. 2000, 21, 117-132.
13. a) E. T. H. Vink, K. R. Rábago, D. A. Glassner, P. R. Gruber, Polym. Degrad. Stab. 2003, 80, 403-419;
14. b) R. Auras, B. Harte, S. Selke, Macromol. Biosci. 2004, 4, 835-864;
15. c) R. Datta, M. Henry, J. Chem. Technol. Biotechnol. 2006, 81, 1119-1129;
16. d) A. P. Gupta, V. Kumar, Eur. Polym. J. 2007, 43, 4053-4074.
17. G. Odian, Principles of Polymerization, 4th ed.,Wiley, Hoboken, 2004.
18. a) F. Fenouillot, A. Rousseau, G. Colomines, R. Saint-Loup, J. P. Pascault, Prog. Polym. Sci. 2010, 35, 578-622;
19. b) D. S. van Es, J. Renewable Mater. 2013, 1, 61-72;
20. c) C. Lavilla, A. Alla, A. Martinez de Ilarduya, S. Munoz-Guerra, Biomacromolecules 2013, 14, 781-793.
21. J. M. Becker, R. J. Pounder, A. P. Dove, Macromol. Rapid Commun. 2010, 31, 1923-1937.
22. F. Jing, M. R. Smith, G. L. Baker, Macromolecules 2007, 40, 9304-9312.
23. a) F. Jing, M. A. Hillmyer, J. Am. Chem. Soc. 2008, 130, 13826-13827;
24. b) G. L. Fiore, F. Jing, J. V. G. Young, C. J. Cramer, M. A. Hillmyer, Polym. Chem. 2010, 1, 870-877.
25. a) R. C. Jeske, A. M. DiCiccio, G.W. Coates, J. Am. Chem. Soc. 2007, 129, 11330-13331;
26. b) R. C. Jeske, J. M. Rowley, G. W. Coates, Angew. Chem. Int. Ed. 2008, 47, 6041-6044;
27. Angew. Chem. 2008, 120, 6130-6133.
28. a) A. M. DiCiccio, G.W. Coates, J. Am. Chem. Soc. 2011, 133, 10724-10727;
29. b) C. Robert, F. de Montigny, C. M. Thomas, Nat. Commun. 2011, 2, 586;
30. c) E. Hosseini Nejad, C. G. W. van Melis, T. J. Vermeer, C. E. Koning, R. Duchateau, Macromolecules 2012, 45, 1770-1776;
31. d) A. Bernard, C. Chatterjee, M. H. Chisholm, Polymer 2013, 54, 2639-2646.
32. a) S. Huijser, E. Hosseini Nejad, R. Sablong, C. de Jong, C. E. Koning, R. Duchateau, Macromolecules 2011, 44, 1132-1139;
33. b) D. J. Darensbourg, R. R. Poland, C. Escobedo, Macromolecules 2012, 45, 2242-2248;
34. c) J. Liu, Y.-Y. Bao, Y. Liu, W.-M. Ren, X.-B. Lu, Polym. Chem. 2013, 4, 1439-1444.
35. Z. Duan, X. Wang, Q. Gao, L. Zhang, B. Liu, I. Kim, J. Polym. Sci. Part A 2014, 52, 789-795.
36. a) K. A. D. Swift, Top. Catal. 2004, 27, 143-155;
37. b) C. S. Sell, Terpenoids, Kirk-Othmer Encycl. Chem. Tech., Vol. 24, 5th ed., Wiley, Hoboken, 2006, pp. 468-591;
38. c) A. Behr, L. Johnen, ChemSusChem 2009, 2, 1072-1095;
39. d) P. A. Wilbon, F. Chu, C. Tang, Macromol. Rapid Commun. 2013, 34, 8-37;
40. e) D. Dakshinamoorthy, A. K. Weinstock, K. Damodaran, D. F. Iwig, R. T. Mathers, ChemSusChem 2014, 7, 2923-2929.
41. A. H. Tullo, P. L. Short, Chem. Eng. News 2006, 84, 22-23.
42. a) E. Hosseini Nejad, A. Paoniasari, C. E. Koning, R. Duchateau, Polym. Chem. 2012, 3, 1308-1313;
43. b) E. H. Nejad, A. Paoniasari, C. G. W. van Melis, C. E. Koning, R. Duchateau, Macromolecules 2013, 46, 631-637.
44. A detailed discussion regarding the alternating microstructure of these polyesters can be found in the Supporting Information.
45. g of 105°C.
46. A detailed discussion regarding the epimerization of diester stereochemistry can be found in the Supporting Information.
47. (S)-PO was copolymerized with 1c using 2b under the conditions described for Table 2, entry 4. The polymer was degraded to yield (S)-3 with an e.r. of 97:3.
48. (S)-PO was copolymerized with 1c using 2c under the conditions described in Table 2, entry 6. The polymer was degraded to yield (S)-3 with an e.r. of 96:4.
49. Sequential monomer addition experiments excluded the possibility of irreversible catalyst deactivation after reaching high conversion of 1c ; please see the Supporting Information for details.