Mechanistic Insight to C-C Bond Formation and Predictive Models for Cascade Reactions among Alcohols on Ca- and Sr-Hydroxyapatites

ACS Catalysis

Volumn 6, Issue 7, 2016, Pages 4170-4183

  Moteki, Takahiko ^a   Flaherty, David W ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

alcohol coupling; aldol condensation; cascade reaction; Guerbet reaction; hydroxyapatite; Meerwein Ponndorf Verley; step growth

Indexed keywords

ACETALDEHYDE; ALDEHYDES; CATALYSTS; CHEMICAL BONDS; CHEMICAL REACTIONS; CONDENSATION; COVALENT BONDS; ETHANOL; HYDROGENATION; HYDROXYAPATITE; KETONES;

ACTIVATION ENTHALPIES; ALDOL CONDENSATION; CARBON NUMBER DISTRIBUTION; CASCADE REACTIONS; CROSS COUPLING REACTIONS; GUERBET REACTION; ISOTOPE LABELING EXPERIMENTS; MEERWEIN-PONNDORF-VERLEY;

CONDENSATION REACTIONS;

EID: 84977119815     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/acscatal.6b00556     Document Type: Article

References (52)

1. Climent, M. J.; Corma, A.; Iborra, S. Green Chem. 2014, 16, 516-547 10.1039/c3gc41492b
2. World Energy Outlook 2014. http://www.worldenergyoutlook.org/publications/weo-2014/ (accessed Apr 6, 2016).
3. Serrano-Ruiz, J. C.; Dumesic, J. A. Energy Environ. Sci. 2011, 4, 83-99 10.1039/C0EE00436G
4. Demirbas, A. Prog. Energy Combust. Sci. 2007, 33, 1-18 10.1016/j.pecs.2006.06.001
5. Balat, M.; Balat, H.; Oz, C. Prog. Energy Combust. Sci. 2008, 34, 551-573 10.1016/j.pecs.2007.11.001
6. IEA. Energy Technology Essentials: Biofuel Production, January 2007. https://www.iea.org/publications/freepublications/publication/essentials2.pdf (accessed Apr 6, 2016).
7. Kozlowski, J. T.; Davis, R. J. ACS Catal. 2013, 3, 1588-1600 10.1021/cs400292f
8. Gabriëls, D.; Hernández, W. Y.; Sels, B.; Van Der Voort, P. V. D.; Verberckmoes, A. Catal. Sci. Technol. 2015, 5, 3876-3902 10.1039/C5CY00359H
9. Anbarasan, P.; Baer, Z. C.; Sreekumar, S.; Gross, E.; Binder, J. B.; Blanch, H. W.; Clark, D. S.; Toste, F. D. Nature 2012, 491, 235-239 10.1038/nature11594
10. Sun, J.; Wang, Y. ACS Catal. 2014, 4, 1078-1090 10.1021/cs4011343
11. Angelici, C.; Weckhuysen, B. M.; Bruijnincx, P. C. A. ChemSusChem 2013, 6, 1595-1614 10.1002/cssc.201300214
12. Ueda, W.; Kuwabara, T.; Ohshida, T.; Morikawa, Y. J. Chem. Soc., Chem. Commun. 1990, 1558-1559 10.1039/c39900001558
13. Ueda, W.; Ohshida, T.; Kuwabara, T.; Morikawa, Y. Catal. Lett. 1992, 12, 97-104 10.1007/BF00767192
14. Chieregato, A.; Velasquez Ochoa, J.; Bandinelli, C.; Fornasari, G.; Cavani, F.; Mella, M. ChemSusChem 2015, 8, 377-388 10.1002/cssc.201402632
15. Ndou, A. Appl. Catal., A 2003, 251, 337-345 10.1016/S0926-860X(03)00363-6
16. Marcu, I.-C.; Tanchoux, N.; Fajula, F.; Tichit, D. Catal. Lett. 2013, 143, 23-30 10.1007/s10562-012-0935-9
17. Carvalho, D. L.; de Avillez, R. R.; Rodrigues, M. T.; Borges, L. E. P.; Appel, L. G. Appl. Catal., A 2012, 415-416, 96-100 10.1016/j.apcata.2011.12.009
18. Ordóñez, S.; Díaz, E.; León, M.; Faba, L. Catal. Today 2011, 167, 71-76 10.1016/j.cattod.2010.11.056
19. Di Cosimo, J. I.; Apesteguía, C. R.; Ginés, M. J. L.; Iglesia, E. J. Catal. 2000, 190, 261-275 10.1006/jcat.1999.2734
20. Gines, M. J. L.; Iglesia, E. J. Catal. 1998, 176, 155-172 10.1006/jcat.1998.2009
21. Tsuchida, T.; Sakuma, S.; Takeguchi, T.; Ueda, W. Ind. Eng. Chem. Res. 2006, 45, 8634-8642 10.1021/ie0606082
22. Tsuchida, T.; Kubo, J.; Yoshioka, T.; Sakuma, S.; Takeguchi, T.; Ueda, W. J. Catal. 2008, 259, 183-189 10.1016/j.jcat.2008.08.005
23. Ogo, S.; Onda, A.; Iwasa, Y.; Hara, K.; Fukuoka, A.; Yanagisawa, K. J. Catal. 2012, 296, 24-30 10.1016/j.jcat.2012.08.019
24. Ogo, S.; Onda, A.; Yanagisawa, K. Appl. Catal., A 2011, 402, 188-195 10.1016/j.apcata.2011.06.006
25. Silvester, L.; Lamonier, J.-F.; Faye, J.; Capron, M.; Vannier, R.-N.; Lamonier, C.; Dubois, J.-L.; Couturier, J.-L.; Calais, C.; Dumeignil, F. Catal. Sci. Technol. 2015, 5, 2994-3006 10.1039/C5CY00327J
26. Ho, C. R.; Shylesh, S.; Bell, A. T. ACS Catal. 2016, 6, 939-948 10.1021/acscatal.5b02672
27. Scalbert, J.; Thibault-Starzyk, F.; Jacquot, R.; Morvan, D.; Meunier, F. J. Catal. 2014, 311, 28-32 10.1016/j.jcat.2013.11.004
28. Meunier, F. C.; Scalbert, J.; Thibault-Starzyk, F. C. R. Chim. 2015, 18, 345-350 10.1016/j.crci.2014.07.002
29. Hanspal, S.; Young, Z. D.; Shou, H.; Davis, R. J. ACS Catal. 2015, 5, 1737-1746 10.1021/cs502023g
30. Tsuchida, T.; Kubo, J.; Yoshioka, T.; Sakuma, S.; Takeguchi, T.; Ueda, W. J. Jpn. Pet. Inst. 2009, 52, 51-59 10.1627/jpi.52.51
31. Black, G.; Curran, H. J.; Pichon, S.; Simmie, J. M.; Zhukov, V. Combust. Flame 2010, 157, 363-373 10.1016/j.combustflame.2009.07.007
32. Rakopoulos, D. C.; Rakopoulos, C. D.; Hountalas, D. T.; Kakaras, E. C.; Giakoumis, E. G.; Papagiannakis, R. G. Fuel 2010, 89, 2781-2790 10.1016/j.fuel.2010.03.047
33. Alonso, D. M.; Bond, J. Q.; Dumesic, J. A. Green Chem. 2010, 12, 1493-1513 10.1039/c004654j
34. Nagaraja, V. In Indian Journal of Technology; Council of Scientific & Industrial Research in association with Indian National Science Academy: New Delhi, 1971; Vol. 9, pp 380 - 386.
35. Diallo-Garcia, S.; Laurencin, D.; Krafft, J.-M.; Casale, S.; Smith, M. E.; Lauron-Pernot, H.; Costentin, G. J. Phys. Chem. C 2011, 115, 24317-24327 10.1021/jp209316k
36. Diallo-Garcia, S.; Osman, M. B.; Krafft, J.-M.; Casale, S.; Thomas, C.; Kubo, J.; Costentin, G. J. Phys. Chem. C 2014, 118, 12744-12757 10.1021/jp500469x
37. Hill, I. M.; Hanspal, S.; Young, Z. D.; Davis, R. J. J. Phys. Chem. C 2015, 119, 9186-9197 10.1021/jp509889j
38. Witzke, M. E.; Dietrich, P.; Ibrahim, M.; Al-Bardan, K.; Triezenberg, M.; Flaherty, D. W. to be submitted.
39. Stille, J. K. J. Chem. Educ. 1981, 58, 862-866 10.1021/ed058p862
40. Fried, J. R. Polymer Science and Technology, 3 rd ed.; Prentice Hall: Upper Saddle River, NJ, 2014.
41. Wang, J.; Kispersky, V. F.; Nicholas Delgass, W.; Ribeiro, F. H. J. Catal. 2012, 289, 171-178 10.1016/j.jcat.2012.02.008
42. Gilkey, M. J.; Xu, B. ACS Catal. 2016, 6, 1420-1436 10.1021/acscatal.5b02171
43. Kibby, C. L.; Hall, W. K. J. Catal. 1973, 31, 65-73 10.1016/0021-9517(73)90271-6
44. Gilkey, M. J.; Panagiotopoulou, P.; Mironenko, A. V.; Jenness, G. R.; Vlachos, D. G.; Xu, B. ACS Catal. 2015, 5, 3988-3994 10.1021/acscatal.5b00586
45. Suzuoki, T.; Epstein, S. Geochim. Cosmochim. Acta 1976, 40, 1229-1240 10.1016/0016-7037(76)90158-7
46. Stošić, D.; Bennici, S.; Sirotin, S.; Calais, C.; Couturier, J.-L.; Dubois, J.-L.; Travert, A.; Auroux, A. Appl. Catal., A 2012, 447-448, 124-134 10.1016/j.apcata.2012.09.029
47. Ramesh, K.; Ling, E. G. Y.; Gwie, C. G.; White, T. J.; Borgna, A. J. Phys. Chem. C 2012, 116, 18736-18745 10.1021/jp304187v
48. Faria, R. M. B.; Cesar, D. V.; Salim, V. M. M. Catal. Today 2008, 133-135, 168-173 10.1016/j.cattod.2007.12.114
49. Griffiths, P. R.; Haseth, J. A. D. Fourier Transform Infrared Spectrometry, 2 nd ed.; John Wiley & Sons, Inc.: Hoboken, NJ, 2007.
50. Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry; University Science Books: Sausalito, CA, 2005.
51. ChemAxon, (2016. https://www.ChemAxon.com (accessed Apr 6, 2016).
52. Biloen, P.; Sachtler, W. M. H. In Adv. Catal.; Eley, D. D.; Pines, H.; Weisz, P. B., Eds.; Academic Press: New York, 1981; Vol. 30, pp 165-216.