Synthesis of isoidide through epimerization of isosorbide using ruthenium on carbon

ChemSusChem

Volumn 6, Issue 4, 2013, Pages 693-700

  Nôtre, Jérôme Le ^a   Van Haveren, Jacco ^a   Van Es, Daan S ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

Carbohydrates; Heterogeneous catalysis; Isomerization; Renewable resources; Ruthenium

Indexed keywords

CARBOHYDRATES; CARBON; CATALYSIS; DISTILLATION; INDUSTRIAL APPLICATIONS; ISOMERIZATION; LOADING; RUTHENIUM; WATER CONSERVATION;

EQUILIBRIUM MIXTURES; HYDROGEN PRESSURES; NICKEL-BASED CATALYST; REACTION TEMPERATURE; RENEWABLE RESOURCE; SUBSTRATE CONCENTRATIONS; SUBSTRATE LOADING; THERMODYNAMIC EQUILIBRIA;

CATALYST SELECTIVITY;

CARBON; ISOSORBIDE; NICKEL; RUTHENIUM; SILICON DIOXIDE; SUGAR ALCOHOL;

ARTICLE; CATALYSIS; CHEMISTRY;

CARBON; CATALYSIS; ISOSORBIDE; NICKEL; RUTHENIUM; SILICON DIOXIDE; SUGAR ALCOHOLS;

EID: 84878288628     PISSN: 18645631     EISSN: 1864564X     Source Type: Journal    
DOI: 10.1002/cssc.201200714     Document Type: Article

References (60)

1. a) G.-Q. Chen, M. K. Patel, Chem. Rev. 2012, 112, 2082 -2099;
2. b) L. Shen, E. Worrell, M. Patel, Biofuels Bioprod. Biorefin. 2010, 4, 25-40.
3. a) http://www.braskem.com/site.aspx/green-products; accessed 22.02.2013;
4. b) A. Morschbacker, Polym. Rev. 2009, 49, 79- 84.
5. a) C. J. Weber, V. Haugaard, R. Festersen, G. Bertelsen, Food Addit. Contam. 2002, 19, 172 -177;
6. b) L.-T. Lim, R. Auras, M. Rubino, Prog. Polym. Sci. 2008, 33, 820 -852;
7. c) S. Philip, T. Keshavarz, I. Roy, J. Chem. Technol. Biotechnol. 2007, 82, 233 -247;
8. d) G.-Q. Chen, Chem. Soc. Rev. 2009, 38, 2434 -2446.
9. a) T. Werpy, G. Petersen, Top Value Added Chemicals from Biomass, US Department of Energy, Office of Scientific and Technical Information, 2004;
10. b) I. Bechthold, K. Bretz, S. Kabasci, R. Kopitzky, A. Springer, Chem. Eng. Technol. 2008, 31, 647 -654.
11. a) A. Gandini, Polym. Chem. 2010, 1, 245 -251;
12. b) C. Moreau, M. N. Belgacem, A. Gandini, Top. Catal. 2004, 27, 11 - 30.
13. a) M. Rose, R. Palkovits, ChemSusChem 2012, 5, 167 -176;
14. b) F. Fenouillot, A. Rousseau, G. Colomines, R. Saint-Loup, J.-P. Pascault, Prog. Polym. Sci. 2010, 35, 578 -622;
15. GB1012563 (Atlas Chem. Ind.), 1965;
16. W. C. Tate, G. J. Scruggs (Monsanto), US3223752, 1965;
17. e) F. L. Charbonneau, E. R. Johnson, B. H. Witteler, G. Khanarian (HNA Holdings Inc.), US5959066, 1999;
18. f) V. J. Kurian, Y. Liang (E. I. du Pont de Nemours and Co.), US6737481, 2004;
19. g) J. Thiem, H. Leders, Starch/Staerke 1984, 36, 170- 176;
20. h) J. Thiem, H. Lders, Polym. Bull. 1984, 11, 365 -369.
21. a) H. R. Kricheldorf, Z. Gomourachvili, Macromol. Chem. Phys. 1997, 198, 3149 -3160;
22. b) D. J. Adelman, L. F. Charbonneau, S. Ung (E. I. du Pont de Nemours and Co.), US6656577, 2003;
23. c) M. Okada, Y. Okada, K. Aoi, J. Polym. Sci. Part A 1995, 33, 2813 - 2820;
24. d) M. Okada, K. Tsunoda, K. Tachikawa, K. Aoi, J. Appl. Polym. Sci. 2000, 77, 338 -346;
25. e) R. Sablong, R. Duchateau, C. E. Koning, G. de Wit, D. S. van Es, R. Koelewijn, J. van Haveren, Biomacromolecules 2008, 9, 3090 -3097;
26. f) B. A. J. Noordover, R. J. Sablong, R. Duchateau, R. A. T. M. van Benthem, W. Ming, C. Koning, J. van Haveren (Dutch Polymer Institute), WO2008031592, 2008;
27. B. A. J. Noordover, V. G. van Staalduinen, R. Duchateau, C. E. Koning, R. A. T. M. van Benthem, M. Mak, A. Heise, A. E. Frissen, J. van Haveren, Biomacromolecules 2006, 7, 3406 -3416.
28. a) J. Wu, P. Eduard, S. Thiyagarajan, J. van Haveren, D. S. van Es, C. E. Koning, M. Lutz, F. Calia Guerra, ChemSusChem 2011, 4, 599 -603;
29. b) S. Thiyagarajan, L. Gootjes, W. Vogelzang, J. van Haveren, M. Lutz, D. S. van Es, ChemSusChem 2011, 4, 1823 -1829;
30. c) S. Thiyagarajan, L. Gootjes, W. Vogelzang, J. Wu, J. van Haveren, M. Lutz, D. S. van Es, Tetrahedron 2011, 67, 383- 389;
31. d) J. Thiem, Makromol. Chem. 1986, 187, 2775 -2785;
32. e) J. Thiem, F. Bachmann, Makromol. Chem. 1991, 192, 2163 -2182.
33. http://www.roquette.com; accessed 22.02.2013.
34. a) R. Storbeck, M. Rehahn, M. Ballauff, Makromol. Chem. 1993, 194, 53-64;
35. b) M. Okada, Y. Okada, A. Tao, K. Aoi, J. Appl. Polym. Sci. 1996, 62, 2257 -2265;
36. c) B. A. J. Noordover, A. Heise, P. Malanowksi, D. Senatore, M. Mak, L. Molhoek, R. Duchateau, C. E. Koning, R. A. T. M. van Benthem, Prog. Org. Coat. 2009, 65, 187- 196.
37. J. C. Goodwin, J. E. Hodge, D. Weisleder, Carbohydr. Res. 1980, 79, 133 - 141.
38. P. Fuertes (Roquette Frires), US7674381, 2010.
39. L. Wright, L. Hartman, J. Org. Chem. 1961, 26, 1588 -1596.
40. a) L. W. Wright, J. D. Brandner (Atlas Chem. Ind.), US3023223, 1962;
41. b) L. W. Wright, J. D. Brandner, J. Org. Chem. 1964, 29, 2979- 2982.
42. a) H. G. Fletcher, R. M. Goepp, J. Am. Chem. Soc. 1945, 67, 1042 -1043;
43. b) H. G. Fletcher, R. M. Goepp, J. Am. Chem. Soc. 1946, 68, 939-941;
44. c) C. Montassier, J. C. Menezo, J. Moukolo, J. Naja, L. C. Hoang, J. Barbier, J. P. Boitiaux, J. Mol. Catal. 1991, 70, 65- 84.
45. a) J. Bosson, S. P. Nolan, J. Org. Chem. 2010, 75, 2039 -2043;
46. b) R. Karvembu, R. Prabhakaran, M. Muthu Tamizh, K. Natarajan, C. R. Chim. 2009, 12, 951- 962.
47. A. C. Marr, C. L. Pollock, G. C. Saunders, Organometallics 2007, 26, 3283 - 3285.
48. T. Jerphagnon, A. J. A. Gayet, F. Berthiol, V. Ritleng, N. Mrsic, A. Meetsma, M. Pfeffer, A. J. Minnaard, B. L. Feringa, J. G. de Vries, Chem. Eur. J. 2009, 15, 12780 - 12790.
49. T. Maegawa, Y. Fujiwara, Y. Inagaki, Y. Monguchi, H. Sajiki, Adv. Synth. Catal. 2008, 350, 2215 -2218.
50. a) N. Li, G. W. Huber, J. Catal. 2010, 270, 48- 59;
51. b) N. Li, G. A. Tompsett, T. Zhang, J. Shi, C. E. Wyman, G. W. Huber, Green Chem. 2011, 13, 91-101.
52. a) J. Muzart, Tetrahedron 2003, 59, 5789- 5816;
53. "Catalytic oxidations of alcohols": R. A. Sheldon, I. W. C. E. Arends in Advances in Catalytic Activation of Dioxygen by Metal Complex (Ed.: L. I. Simandi), Kluwer Academic Publishers, Dordrecht, NL 2003, chap. 3, p. 123.
54. H. Esaki, R. Ohtaki, T. Maegawa, Y. Monguchi, H. Sajiki, J. Org. Chem. 2007, 72, 2143 -2150.
55. F. Abild-Pedersen, J. Greeley, F. Studt, J. Rossmeisl, T. R. Munter, P. G. Moses, E. Skulason, T. Bligaard, J. K. Norskov, Phys. Rev. Lett. 2007, 99, 016105.
56. a) P. W. J. G. Wijnen, T. P. M. Beelen, J. W. de Haan, C. P. J. Rummens, L. J. M. van de Ven, R. A. van Santen, J. Non-Cryst. Solids 1989, 109, 85-94;
57. b) S. Sjçberg, J. Non-Cryst. Solids 1996, 196, 51- 57;
58. c) C. Xu, Y. Hu, J. Rong, S. P. Jiang, Y. Liu, Electrochem. Commun. 2007, 9, 2009 - 2012;
59. d) Y. Niibori, M. Kunita, O. Tochiyama, T. Chida, J. Nucl. Sci. Technol. 2000, 37, 349- 357.
60. E. M. F. Muri, B. A. Abrahim, T. G. Barros, J. S. Williamson, O. A. C. Antunes, Mini-Rev. Org. Chem. 2010, 7, 75-83.