Copolymerization of carbon dioxide and butadiene via a lactone intermediate

Nature Chemistry

Volumn 6, Issue 4, 2014, Pages 325-331

  Nakano, Ryo ^a   Ito, Shingo ^a   Nozaki, Kyoko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84896988712     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1882     Document Type: Article

References (50)

1. Aresta, M. Carbon Dioxide as Chemical Feedstock (Wiley-VCH, 2010).
2. Sakakura, T., Choi, J. C. & Yasuda, H. Transformation of carbon dioxide. Chem. Rev. 107, 2365-2387 (2007).
3. Arakawa, H. et al. Catalysis research of relevance to carbon management: Progress, challenges, and opportunities. Chem. Rev. 101, 953-996 (2001).
4. Behr, A. Use of carbon dioxide in industrial organic syntheses. Chem. Eng. Technol. 10, 16-27 (1987).
5. Omae, I. Recent developments in carbon dioxide utilization for the production of organic chemicals. Coord. Chem. Rev. 256, 1384-1405 (2012).
6. Sumida, K. et al. Carbon dioxide capture in metal-organic frameworks. Chem. Rev. 112, 724-781 (2012).
7. Huang, K., Sun, C-L. & Shi, Z-J. Transition-metal-catalyzed C-C bond formation through the fixation of carbon dioxide. Chem. Soc. Rev. 40, 2435-2452 (2011).
8. Tsuji, Y. & Fujihara, T. Carbon dioxide as a carbon source in organic transformation: Carbon-carbon bond forming reactions by transition-metal catalysts. Chem. Commun. 48, 9956-9964 (2012).
9. Aresta, M., Dibenedetto, A. & Angelini, A. The use of solar energy can enhance the conversion of carbon dioxide into energy-rich products: Stepping towards artificial photosynthesis. Phil. Trans. R. Soc. A 371, 20120111 (2012).
10. Shaikh, A-A. G. & Sivaram, S. Organic carbonates. Chem. Rev. 96, 951-976 (1996).
11. Darensbourg, D. J. & Holtcamp, M. W. Catalysts for the reactions of epoxides and carbon dioxide. Coord. Chem. Rev. 153, 155-174 (1996).
12. Lu, X-B. & Darensbourg, D. J. Cobalt catalysts for the coupling of CO2 and epoxides to provide polycarbonates and cyclic carbonates. Chem. Soc. Rev. 41, 1462-1484 (2012).
13. Fukuoka, S. et al. A novel non-phosgene polycarbonate production process using by-product CO2 as starting material. Green Chem. 5, 497-507 (2003).
14. Coates, G. W. & Moore, D. R. Discrete metal-based catalysts for the copolymerization of CO2 and epoxides: Discovery, reactivity, optimization, and mechanism. Angew. Chem. Int. Ed. 43, 6618-6639 (2004).
15. Darensbroug, D. J. Making plastics from carbon dioxide: Salen metal complexes as catalysts for the production of polycarbonates from epoxides and CO2. Chem. Rev. 107, 2388-2410 (2007).
16. Sugimoto, H. & Inoue, S. Copolymerization of carbon dioxide and epoxide. J. Polym. Sci. A 42, 5561-5573 (2004).
17. Kember, M. R., Buchard, A. & Williams, C. K. Catalysts for CO2/epoxide copolymerisation. Chem. Commun. 47, 141-163 (2011).
18. Lejkowski, M. L. et al. The first catalytic synthesis of an acrylate from CO2 and an alkene-A rational approach. Chem. Eur. J. 18, 14017-14025 (2012).
19. Takaya, J., Sasano, K. & Iwasawa, N. Efficient one-To-one coupling of easily available 1,3-dienes with carbon dioxide. Org. Lett. 13, 1698-1701 (2011).
20. Williams, C. M., Johnson, J. B. & Rovis, T. Nickel-catalyzed reductive carboxylation of styrenes using CO2. J. Am. Chem. Soc. 130, 14936-14937 (2008).
21. Takimoto, M., Nakamura, Y., Kimura, K. & Mori, M. Highly enantioselective catalytic carbon dioxide incorporation reaction: Nickel-catalyzed asymmetric carboxylative cyclization of bis-1,3-dienes. J. Am. Chem. Soc. 126, 5956-5957 (2004).
22. Soga, K., Hosoda, S. & Ikeda, S. Copolymerization of carbon dioxide and some diene compounds. Die Makromol. Chemie 176, 1907-1911 (1975).
23. Soga, K., Hosoda, S., Tasuka, Y. & Ikeda, S. Copolymerization of carbon dioxide and ethyl vinyl ether. J. Polym. Sci. Polym. Lett. 13, 265-268 (1975).
24. Soga, K., Sato, M., Hosoda, S. & Ikeda, S. Copolymerization of methyl vinyl ether and carbon dioxide. J. Polym. Sci. Polym. Lett. 13, 543-548 (1975).
25. Chiang, W-Y. Copolymerization of carbon dioxide and acrylonitrile. Proc. Natl Sci. Council Republic of China 2, 170-176 (1978).
26. Price, C. J., Reich, B. J. E. & Miller, S. A. Thermodynamic and kinetic considerations in the copolymerization of ethylene and carbon dioxide. Macromolecules 39, 2751-2756 (2006).
27. Darensbourg, D. J. & Yeung, A. D. Thermodynamics of the carbon dioxide-epoxide copolymerization and kinetics of the metal-free degradation: A computational study. Macromolecules 46, 83-95 (2013).
28. Sasaki, Y., Inoue, Y. & Hashimoto, H. Reaction of carbon dioxide with butadiene catalysed by palladium complexes. Synthesis of 2-ethylidenehept-5-en- 4-olide. J. Chem. Soc. Chem. Commun. 605-606 (1976).
29. Behr, A. & Henze, G. Use of carbon dioxide in chemical syntheses via a lactone intermediate. Green Chem. 13, 25-39 (2011).
30. Musco, A. Co-oligomerization of butadiene and carbon dioxide catalysed by tertiary phosphine-palladium complexes. J. Chem. Soc. Perkin Trans. 1 693-698 (1980).
31. Behr, A. & Juszak, K-D. Palladium-catalyzed reaction of butadiene and carbon dioxide. J. Organomet. Chem. 255, 263-268 (1983).
32. Behr, A., He, R., Juszak, K-D., Kruger, C. & Tsay, Y-H. Steuerungsmöglichkeiten bei der ubergangsmetall-katalysierten umsetzung von 1,3-dienen mit kohlendioxid. Chem. Ber. 119, 991-1015 (1986).
33. Braunstein, P., Matt, D. & Nobel, D. Carbon dioxide activation and catalytic lactone synthesis by telomerization of butadiene and carbon dioxide. J. Am. Chem. Soc. 110, 3207-3212 (1988).
34. Dinjus, E. & Leitner, W. New insights into the palladium-catalysed synthesis of d-lactones from 1,3-dienes and carbon dioxide. Appl. Organomet. Chem. 9, 43-50 (1995).
35. Pitter, S. & Dinjus, E. Phosphinoalkyl nitriles as hemilabile ligands: New aspects in the homogeneous catalytic coupling of CO2 and 1,3-butadiene. J. Mol. Catal. A 125, 39-45 (1997).
36. Behr, A. & Heite, M. Telomerisation von kohlendioxid und 1,3-butadien: Verfahrensentwicklung via miniplant-Technik. Chem. Ing. Tech. 72, 58-61 (2000).
37. Behr, A. & Becker, M. The telomerisation of 1,3-butadiene and carbon dioxide: Process development and optimisation in a continuous miniplant. Dalton Trans. 4607-4613 (2006).
38. Behr, A., Bahke, P. & Becker, M. Palladium-katalysierte telomerisation von kohlendioxid mit butadien im labor-und miniplantmaß stab. Chem. Ing. Tech. 1828-1832 (2004).
39. Behr, A., Bahke, P., Klinger, B. & Becker, M. Application of carbonate solvents in the telomerisation of butadiene with carbon dioxide. J. Mol. Catal. A 267, 149-156 (2007).
40. Haack, V., Dinjus, E. & Pitter, S. Synthesis of polymers with an intact lactone ring structure in the main chain. Die Angew. Makromol. Chem. 257, 19-22 (1998).
41. Laible, R. C. Allyl polymerizations. Chem. Rev. 58, 807-843 (1958).
42. Miller, M. L. & Skogman, J. Polymerization of tert-butyl crotonate. J. Polym. Sci. A 2, 4551-4558 (1964).
43. Kassi, E. & Patrickios, C. S. Well-defined polymers from biosourced monomers: The case of 2-(methacryloyloxy)ethyl tiglate. Macromolecules 43, 1411-1415 (2010).
44. Kitayama, T. et al. Synthesis and polymerization of methyl 3-methylcyclobutene-1-carboxylate. Macromolecules 35, 1591-1598 (2002).
45. Chen, X-P., Sufi, B. A., Padias, A. B. & Hall, H. K. Jr. Controlled/'living' reverse atom transfer radical polymerization of a monocyclic olefin, methyl 1-cyclobutenecarboxylate. Macromolecules 35, 4277-4281 (2002).
46. Brandrup, J., Immergut, E H. & Grulke, E. A. Polymer Handbook 4th edn (Wiley, 1999).
47. Iio, K., Kobayashi, K. & Matsuo, M. Radical polymerization of allyl alcohol and allyl acetate. Polym. Adv. Technol. 18, 953-958 (2007).
48. Matyjaszewski, K., Nakagawa, Y. & Jasieczek, C. B. Polymerization of n-butyl acrylate by atom transfer radical polymerization: Remarkable effect of ethylene carbonate and other solvents. Macromolecules 31, 1535-1541 (1998).
49. Sato, T., Shimooka, S., Seno, M. & Tanaka, H. Radical polymerization of orthoformylphenyl crotonate involving intramolecular hydrogen-Abstraction. Eur. Polym. J. 28, 1357-1364 (1992).
50. Grub, J. & Löser, E. Butadiene. Ullmann's Encyclopedia of Industrial Chemistry (Wiley-VCH, 2011).