On the Diels-Alder approach to solely biomass-derived polyethylene terephthalate (PET): Conversion of 2,5-dimethylfuran and acrolein into p-xylene

Chemistry - A European Journal

Volumn 17, Issue 44, 2011, Pages 12452-12457

  Shiramizu, Mika ^a   Toste, F Dean ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

biomass; Diels Alder reactions; polyethylene terephthalate; sustainable chemistry

Indexed keywords

BIODIESEL PRODUCTION; DIELS-ALDER; DIELS-ALDER REACTION; ECONOMIC FEASIBILITIES; GLOBAL DEMAND; INDUSTRIAL SCALE; LIGNOCELLULOSIC BIOMASS; LOW TEMPERATURES; P-XYLENE; POLYMERIC MATERIAL; SIDE PRODUCTS; SUSTAINABLE CHEMISTRY; TEREPHTHALIC ACIDS; THERMODYNAMIC DATA;

ALDEHYDES; BIOMASS; CARBOXYLATION; GLYCEROL; HERBICIDES; METHANOL; OXIDATION; POLYESTERS; POLYETHYLENES; SYNTHESIS (CHEMICAL); XYLENE;

POLYETHYLENE TEREPHTHALATES;

2,5 DIMETHYLFURAN; 2,5-DIMETHYLFURAN; 4-XYLENE; 5 HYDROXYMETHYLFURFURAL; 5-HYDROXYMETHYLFURFURAL; ACROLEIN; BIOFUEL; DRUG DERIVATIVE; FURAN DERIVATIVE; FURFURAL; GLYCEROL; PARA XYLENE; POLYETHYLENE TEREPHTHALATE; XYLENE;

ARTICLE; BIOMASS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

ACROLEIN; BIOFUELS; BIOMASS; CATALYSIS; FURALDEHYDE; FURANS; GLYCEROL; MOLECULAR STRUCTURE; POLYETHYLENE TEREPHTHALATES; XYLENES;

EID: 80054773177     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201101580     Document Type: Article

References (41)

1. R. Rinaldi, F. Schuth, ChemSusChem 2009, 2, 1096-1107.
2. Q. Xiang, Y. Y. Lee, R. W. Torget, Appl. Biochem. Biotechnol. 2004, 115, 1127-1138.
3. G. W. Huber, S. Iborra, A. Corma, Chem. Rev. 2006, 106, 4044-4098
4. J. N. Chheda, Y. Roman-Leshkov, J. A. Dumesic, Green Chem. 2007, 9, 342-350.
5. J. B. Binder, R. T. Raines, J. Am. Chem. Soc. 2009, 131, 1979-1985
6. C. Li, Z. Zhang, Z. K. Zhao, Tetrahedron Lett. 2009, 50, 5403-5405.
7. P. Verdeguer, N. Merat, A. Gaset, J. Molec. Catal. 1993, 85, 327-344
8. Y. Y. Gorbanev, S. K. Klitgaard, J. M. Woodley, C. H. Christensen, A. Riisager, ChemSusChem 2009, 2, 672-675
9. O. Casanova, S. Iborra, A. Corma, ChemSusChem 2009, 2, 1138-1144.
10. Top Value Added Chemicals From Biomass, US Department of Energy, 2004
11. J. J. Bozell, G. R. Petersen, Green Chem. 2010, 12, 539-554.
12. B. Kuczenski, R. Geyer, Resour. Conserv. Recycl. 2010, 54, 1161-1169.
13. A. Gandini, Adv. Polym. Sci. 1977, 25, 47-96.
14. A. Gandini, A. J. D. Silvestre, C. P. Neto, A. F. Sousa, M. Gomes, J. Polym. Sci. Part A: Polym. Chem. 2009, 47, 295-298.
15. K. Takanishi, S. Sone, (Toray Industries, Tokyo, Japan), WO 2009110402A1, 2009
16. T. Brandvold, (UOP LLC, Illinois, USA), WO 2010151346A1, 2010.
17. In the course of our investigation, we also studied maleic anhydride and 2,2,2-trifluoroethyl acetate as alternative raw materials. p-Xylene was obtained in both cases in moderate overall yields. Acrylic acid is an oxidized form of acrolein and thus can be obtained from glycerol. Maleic acid can also be produced from bio-derived fumaric acid. See the Supporting Information for details.: B. Katryniok, S. Paul, V. Belliere-Baca, P. Rey, F. Dumeignil, Green Chem. 2010, 12, 2079-2098.
18. Ethylene glycol is conventionally produced from another petrochemical ethylene. However, its replacement with biomass-based ethylene glycol has already been successfully commercialized in some products, such as The Coca-Cola Company's PlantBottle; for methods of bio-derived ethylene glycol production, see: T. P. Binder, P. D. Bloom, G. B. Poppe, (Kirkpatrick&Lockhart Preston Gates Ellis LLP, Pittsburgh, PA), USA 20080103340Al, 2008
19. S. P. Chopade, D. J. Miller, J. E. Jackson, T. A. Werpy, J. G. Frye, A. H. Zacher, (Michigan State University, East Lansing, MI; Battelle Memorial Institute, Richland, WA), US-A 6291725B1, 2001.
20. N. Ji, T. Zhang, M. Zheng, A. Wang, H. Wang, X. Wang, J. G. Chen, Angew. Chem. 2008, 120, 8638-8641
21. Angew. Chem. Int. Ed. 2008, 47, 8510-8513.
22. Y. Román-Leshkov, C. J. Barrett, Z. Y. Liu, J. A. Dumesic, Nature 2007, 447, 982-985
23. M. Chidambaram, A. T. Bell, Green Chem. 2010, 12, 1253-1262
24. G. C. A. Luijkx, N. P. M. Huck, F. van Rantwijk, L. Maat, H. van Bekkum, Heterocycles 2009, 77, 1037-1044.
25. S. W. G. Dauben, H. O. Krabbenhoft, J. Am. Chem. Soc. 1976, 98, 1992-1993
26. P. Laszlo, J. Lucchetti, Tetrahedron Lett. 1984, 25, 4387-4388.
27. For aromatization of DMF through a Diels-Alder reaction with other dienophiles, see: A. de La Hoz, A. Diaz-Ortiz, J. M. Fraile, M. V. Gomez, J. A. Mayoral, A. Moreno, A. Saiz, E. Vazquez, Synlett 2001, 0753-0756
28. J. Fraile, J. Garca, M. A. Gmez, A. de La Hoz, J. Mayoral, A. Moreno, P. Prieto, L. Salvatella, E. Vzquez, Eur. J. Org. Chem. 2001, 2891-2899.
29. Y. Hayashi, M. Nakamura, S. Nakao, T. Inoue, M. Shoji, Angew. Chem. 2002, 114, 4253-4256
30. Angew. Chem. Int. Ed. 2002, 41, 4079-4082.
31. A. Raach, O. Reiser, J. Prakt. Chem. 2000, 342, 605-608
32. E. Dalcanale, F. Montanari, J. Org. Chem. 1986, 51, 567-569
33. F. E. Ziegler, Y. Wang, J. Org. Chem. 1998, 63, 7920-7930.
34. T. Chan, T. C. W. Mak, C. Poon, H. N. C. Wong, J. H. Jia, L. L. Wang, Tetrahedron 1986, 42, 655-661
35. G. P. Jana, B. K. Ghorai, Tetrahedron 2007, 63, 12015-12025
36. F. I. Zubkov, E. V. Boltukhina, K. F. Turchin, A. V. Varlamov, Tetrahedron 2004, 60, 8455-8463
37. A. D. Mance, B. Borovicka, B. Karaman, K. Jakopcic, J. Heterocycl. Chem. 1999, 36, 1337-1341.
38. F. Brion, Tetrahedron Lett. 1982, 23, 5299-5302
39. M. E. Bunnage, T. Ganesh, I. B. Masesane, D. Orton, P. G. Steel, Org. Lett. 2003, 5, 239-242.
40. W. A. Yarnall, E. S. Wallis, J. Org. Chem. 1939, 4, 270-283.
41. L. J. Gooßen, W. R. Thiel, N. Rodriguez, C. Linder, B. Melzer, Adv. Synth. Catal. 2007, 349, 2241-2246.