Catalyst activity and selectivity in the isomerising alkoxycarbonylation of methyl oleate

Chemistry - A European Journal

Volumn 19, Issue 50, 2013, Pages 17131-17140

  Christl, Josefine T ^a   Roesle, Philipp ^a   Stempfle, Florian ^a   Wucher, Philipp ^a   Göttker Schnetmann, Inigo ^a   Müller, Gerhard ^a   Mecking, Stefan ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

carbonylation; isomerisation; palladium; phosphines; renewable resources

Indexed keywords

CATALYTIC CONDITIONS; CATALYTIC CONVERSION; CATALYTICALLY ACTIVE SPECIES; ISOMERISATION; METHOXYCARBONYLATION; PHOSPHINES; RENEWABLE RESOURCE; TRIPHENYL PHOSPHINES;

CARBONYLATION; CATALYSIS; CATALYST ACTIVITY; HYDRIDES; ISOMERIZATION; LIGANDS; PALLADIUM; PHOSPHORUS; PHOSPHORUS COMPOUNDS; PRODUCTIVITY; SELF ASSEMBLY; VEGETABLE OILS; X RAY CRYSTALLOGRAPHY;

PALLADIUM COMPOUNDS;

EID: 84889595305     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301124     Document Type: Article

References (44)

1. U. Biermann, U. Bornscheuer, M. A. R. Meier, J. O. Metzger, H. J. Schäfer, Angew. Chem. 2011, 123, 3938-3956
2. Angew. Chem. Int. Ed. 2011, 50, 3854-3871
3. S. Chikkali, S. Mecking, Angew. Chem. Int. Ed. 2012, 51, 5802-5808.
4. S. Picataggio, T. Rohrer, K. Deanda, D. Lanning, R. Reynolds, J. Mielenz, L. D. Eirich, Nat. Biotechnol. 1992, 10, 894-898
5. U. Schörken, P. Kempers, Eur. J. Lipid Sci. Technol. 2009, 111, 627-645.
6. W. Lu, J. E. Ness, W. Xie, X. Zhang, J. Minshull, R. A. Gross, J. Am. Chem. Soc. 2010, 132, 15451-15455.
7. F. Stemple, P. Roesle, S. Mecking, ACS Symp. Series 1105 Biobased Monomers, Polymers and Materials (Ed.:, R. Gross, P. B. Smith,), 2012, pp. 151-163
8. M. B. Dinger, J. C. Mol, Adv. Synth. Catal. 2002, 344, 671-677
9. A. Behr, D. Obst, A. Westfechtel, Eur. J. Lipid Sci. Technol. 2005, 107, 213-219.
10. M. McCoy, J.-F. Tremblay, Chem. Eng. News 2009, 87, 9
11. B. Harris, Ingenia 2010, 45, 19-23.
12. Now: Mitsubishi Rayon; cf. Ref. [5a].
13. W. Clegg, G. R. Eastham, M. R. J. Elsegood, R. P. Tooze, X. L. Wang, K. Whiston, Chem. Commun. 1999, 1877-1878; for a prior report of the coordination chemistry of dtbpx, see
14. N. Carr, B. J. Dunne, A. G. Orpen, J. L. Spencer, J. Chem. Soc. Chem. Commun. 1988, 926-928.
15. R. I. Pugh, E. Drent, P. G. Pringle, Chem. Commun. 2001, 1476-1477
16. C. Jiménez-Rodriguez, D. F. Foster, G. R. Eastham, D. J. Cole-Hamilton, Chem. Commun. 2004, 1720-1721. Also cf
17. V. de La Fuente, M. Waugh, G. R. Eastham, J. A. Iggo, S. Castillõn, C. Claver, Chem. Eur. J. 2010, 16, 6919-6932.
18. P. Roesle, C. J. Dürr, H. M. Möller, L. Cavallo, L. Caporaso, S. Mecking, J. Am. Chem. Soc. 2012, 134, 17696-17703.
19. C. Jiménez-Rodriguez, G. R. Eastham, D. J. Cole-Hamilton, Inorg. Chem. Commun. 2005, 8, 878-881.
20. G. Walther, J. Deutsch, A. Martin, F. E. Baumann, D. Fridag, R. Franke, A. Köckritz, ChemSusChem 2011, 4, 1052-1054
21. M. R. L. Furst, R. Le Goff, D. Quinzler, S. Mecking, C. H. Botting, D. J. Cole-Hamilton, Green Chem. 2012, 14, 472-477.
22. D. Quinzler, S. Mecking, Angew. Chem. 2010, 122, 4402-4404
23. Angew. Chem. Int. Ed. 2010, 49, 4306-4308
24. F. Stempfle, D. Quinzler, I. Heckler, S. Mecking, Macromolecules 2011, 44, 4159-4166
25. S. Chikkali, F. Stempfle, S. Mecking, Macromol. Rapid Commun. 2012, 33, 1126-1129
26. F. Stempfle, P. Ortmann, S. Mecking, Macromol. Rapid Commun. 2013, 34, 47-50.
27. G. R. Eastham, P. I. Richards, (Lucite International UK Limited) WO 2009/010782 A1
28. T. Fanjul, G. Eastham, J. Floure, S. J. K. Forrest, M. F. Haddow, A. Hamilton, P. G. Pringle, A. G. Orpen, M. Waugh, Dalton Trans. 2013, 42, 100-115.
29. A. J. Rucklidge, G. E. Morris, A. M. Z. Slawin, D. J. Cole-Hamilton, Helv. Chim. Acta 2006, 89, 1783-1800.
30. P. Dierkes, P. W. N. M. van Leeuwen, Dalton Trans. 1999, 1519-1530.
31. G. P. C. M. Dekker, C. J. Elsevier, K. Vrieze, P. W. N. M. van Leeuwen, Organometallics 1992, 11, 1598-1603.
32. J. Ledford, C. S. Schultz, D. P. Gates, P. S. White, J. M. DeSimone, M. Brookhart, Organometallics 2001, 20, 5266-5276.
33. P. W. N. M. van Leeuwen, P. C. J. Kamer, J. N. H. Reek, Pure Appl. Chem. 1999, 71, 1443-14452.
34. G. R. Eastham, B. T. Heaton, J. A. Iggo, R. P. Tooze, R. Whyman, S. Zacchini, Chem. Commun. 2000, 609-610.
35. J. Goerlich, R. Schmutzler, Phosphorus Sulfur Silicon Relat. Elem. 1994, 88, 241-244.
36. P. W. N. M. van Leeuwen, Homogenous catalysis, understanding the art, Kluwer, 2004, 125, pp. 16-19.
37. D. J. Tempel, L. K. Johnson, R. L. Huff, P. S. White, M. Brookhart, J. Am. Chem. Soc. 2000, 122, 6686-6700.
38. E. Drent, W. W. Jager, R. I. Pugh, (Shell Oil Company) US 7265242 B2, 2007
39. M. Boutain, S. B. Duckett, J. P. Dunne, C. Godard, J. M. Hernández, A. J. Holmes, I. G. Khazal, J. L. Serrano, Dalton Trans. 2010, 39, 3495-3500
40. A. K. Ghosh, D. R. Nicponski, J. Kass, Tetrahedron Lett. 2012, 53, 3699-3702
41. M. Davis, F. G. Mann, J. Chem. Soc. 1964, 3786-3790
42. E. Drent, R. Ernst, W. W. Jager, (Shell Internationale Research Maatschappij) WO2004/103948A1.
43. W. Clegg, G. R. Eastham, M. R. J. Elsegood, B. T. Heaton, J. A. Iggo, R. P. Tooze, R. Whyman, S. Zacchini, Organometallics 2002, 21, 1832-1840
44. J. J. R. Frew, K. Damian, H. Van Rensburg, A. M. Z. Slawin, R. P. Tooze, M. L. Clarke, Chem. Eur. J. 2009, 15, 10504-10513.