Tandem isomerization-decarboxylation for converting alkenoic fatty acids into alkenes

ACS Catalysis

Volumn 4, Issue 10, 2014, Pages 3517-3520

  Murray, Rex E ^a,b   Walter, Erin L ^a   Doll, Kenneth M ^a  

^a NATIONAL CENTER FOR AGRICULTURAL UTILIZATION RESEARCH   (United States)

^b WAYNE STATE COLLEGE   (United States)

Author keywords

decarboxylation; isomerization; octadecenoic acid; ruthenium carbonyl carboxylate; triruthenuium dodecacarbonyl; unsaturated fatty acid

Indexed keywords

UNSATURATED FATTY ACIDS;

DECARBOXYLATION; OCTADECENOIC ACIDS; RUTHENIUM CARBONYL CARBOXYLATES; TRIRUTHENUIUM DODECACARBONYL;

ISOMERIZATION;

EID: 84907858566     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs501019t     Document Type: Article

References (40)

1. Adkins, H. J. Am. Chem. Soc. 1922, 44, 2175-2186
2. Santillan-Jimenez, E.; Crocker, M. J. Chem. Technol. Biotechnol. 2012, 87, 1041-1050
3. Zaccheria, F.; Psaro, R.; Ravasio, N. Green Chem. 2009, 11, 462-465
4. Immer, J. G.; Kelly, M. J.; Lamb, H. H. Appl. Catal., A 2010, 375, 134-139
5. Snåre, M.; Kubičková, I.; Mäki-Arvela, P.; Eränen, K.; Murzin, D. Y. Ind. Eng. Chem. Res. 2006, 45, 5708-5715
6. Ohlmann, D. M.; Tschauder, N.; Stockis, J.-P.; Goossen, K.; Dierker, M.; Goossen, L. J. J. Am. Chem. Soc. 2012, 134, 13716-13729
7. Prince, R. H.; Raspin, K. A. Chem. Commun. 1966, 156-157
8. Fenton, D. M. U.S. Patent 3,530,198, September 22, 1970.
9. Miller, J. A.; Nelson, J. A.; Byrne, M. U.S. Patent 5,077,447, December 31, 1991.
10. Miller, J. A.; Nelson, J. A.; Byrne, M. P. J. Org. Chem. 1993, 58, 18-20
11. Kraus, G. A.; Riley, S. Synthesis 2012, 44, 3003-3005
12. Stern, R.; Hillion, G. U.S. Patent 4,554,397, November 19, 1985.
13. Goossen, L. J.; Rodriguez, N. Chem. Commun. 2004, 724-725
14. Tanaka, S.; Shimizu, K.; Yamamoto, I. Chem. Lett. 1997, 12, 1277-1278
15. Maki-Arvela, P.; Kubickova, I.; Snare, M.; Eranen, K.; Murzin, D. Y. Energy Fuels 2006, 21, 30-41
16. Snare, M.; Kubickova, I.; Maki-Arvela, P.; Chichova, D.; Eranen, K.; Murzin, D. Y. Fuel 2008, 87, 933-945
17. Liu, Y.; Kim, K. E.; Herbert, M. B.; Fedorov, A.; Grubbs, R. H.; Stoltz, B. M. Adv. Synth. Catal. 2014, 356, 130-136
18. Miranda, M. O.; Pietrangelo, A.; Hillmyer, M. A.; Tolman, W. B. Green Chem. 2012, 14, 490-494
19. Gosselink, R. W.; Xia, W.; Muhler, M.; de Jong, K. P.; Bitter, J. H. ACS Catal. 2013, 3, 2397-2402
20. Foglia, T. A.; Barr, P. A. J. Am. Oil Chem. Soc. 1976, 53, 737-741
21. Fristad, W. E.; Fry, M. A.; Klang, J. A. J. Org. Chem. 1983, 48, 3575-3577
22. van der Klis, F.; Le Notre, J.; Blaauw, R.; van Haveren, J.; van Es, D. S. Eur. J. Lipid Sci. Technol. 2012, 114, 911-918
23. van der Klis, F.; van den Hoorn, M. H.; Blaauw, R.; van Haveren, J.; van Es, D. S. Eur. J. Lipid Sci. Technol. 2011, 113, 562-571
24. Berenblyum, A.; Shamsiev, R.; Podoplelova, T.; Danyushevsky, V. Russ. J. Phys. Chem. A 2012, 86, 1199-1203
25. Berenblyum, A. S.; Podoplelova, T. A.; Shamsiev, R. S.; Katsman, E. A.; Danyushevsky, V. Y. Pet. Chem. 2011, 51, 336-341
26. Arnold, R. T.; Danzig, M. J. J. Am. Chem. Soc. 1957, 79, 892-893
27. Arnold, R. T.; Elmer, O. C.; Dodson, R. M. J. Am. Chem. Soc. 1950, 72, 4359-4361
28. Fu, J.; Lu, X.; Savage, P. E. ChemSusChem 2011, 4, 481-486
29. Erdogan, G.; Grotjahn, D. B. J. Am. Chem. Soc. 2009, 131, 10354-10355
30. Grotjahn, D. B.; Larsen, C. R.; Gustafson, J. L.; Nair, R.; Sharma, A. J. Am. Chem. Soc. 2007, 129, 9592-9593
31. Czaun, M.; Goeppert, A.; May, R.; Haiges, R.; Prakash, G. K. S.; Olah, G. A. ChemSusChem 2011, 4, 1241-1248
32. Gao, Y.; Kuncheria, J.; Yap, G. P. A.; Puddephatt, R. J. Chem. Commun. 1998, 34, 2365-2366
33. Ohnishi, Y.-y.; Matsunaga, T.; Nakao, Y.; Sato, H.; Sakaki, S. J. Am. Chem. Soc. 2005, 127, 4021-4032
34. Casey, C. P.; Cyr, C. R. J. Am. Chem. Soc. 1973, 95, 2248-2253
35. Angelici, R. J.; Shih, K.-C. U.S. Patent 5,859,268, January 12, 1999.
36. Caulton, K. G.; Thomas, M. G.; Sosinsky, B. A.; Muetterties, E. L. Proc. Natl. Acad. Sci. U. S. A. 1976, 73, 4274-4276
37. Castiglioni, M.; Milone, L.; Osella, D.; Vaglio, G. A.; Valle, M. Inorg. Chem. 1976, 15, 394-396
38. Crooks, G. R.; Johnson, B. R. G.; Lewis, J.; Williams, I. G.; Gamlen, G. J. Chem. Soc., A 1969, 2761-2766
39. Salvini, A.; Frediani, P.; Piacenti, F. J. Mol. Catal., A 2000, 159, 185-195
40. Sivaramakrishna, A.; Mushonga, P.; Rogers, I. L.; Zheng, F.; Haines, R. J.; Nordlander, E.; Moss, J. R. Polyhedron 2008, 27, 1911-1916