Selective hydrogenation of ethyl-benzoylacetate to 3-hydroxy-3-phenyl-propionate catalyzed by Pd/C in EtOH as a solvent in the presence of KOH: The role of the enolate ion on the reaction mechanism

Applied Catalysis A: General

Volumn 355, Issue 1-2, 2009, Pages 50-60

  Ronchin, L ^a   Vavasori, A ^a   Bernardi, D ^a   Cavinato, G ^b   Toniolo, L ^a  

^a CA' FOSCARI UNIVERSITY OF VENICE   (Italy)

^b UNIVERSITY OF PADOVA   (Italy)

Author keywords

3 Hydroxy 3 phenyl propionate; Enolate adsorption; Ethyl benzoylacetate; Selective hydrogenation kinetics

Indexed keywords

ADSORPTION; DESORPTION; EQUILIBRIUM CONSTANTS; ESTERS; HYDROGEN; HYDROGENATION; KINETIC THEORY; PALLADIUM;

3-HYDROXY-3-PHENYL-PROPIONATE; ADSORPTION EQUILIBRIUM; ENOLATE ADSORPTION; ENOLATE ANIONS; ETHYL-BENZOYLACETATE; LANGMUIR-HINSHELWOOD; PD ATOMS; REACTION MECHANISMS; SELECTIVE HYDROGENATION KINETICS;

REACTION KINETICS;

EID: 58749100994     PISSN: 0926860X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.apcata.2008.11.028     Document Type: Article

References (47)

1. Ringk W.F. In: Kirk Othmer (Ed). Enciclopaedia of Chemical Technology vol. 6 (1980), John Wiley & Sons 142
2. D. Anderson, G. Frater, US Pat. 6,348,618 B1 (2002).
3. Sabbatier P., and Senderens J.B. Compt. Rend. 137 (1904) 301
4. Augustine R.L. Catal. Today 37 (1997) 419
5. Baltzly R. J. Org. Chem. 41 (1976) 920
6. Rocchini E., Spogliarich R., and Graziani M. J. Mol. Catal. 91 (1994) 313
7. Rylander P.N. Hydrogenation Methods (1985), Academic Press
8. Aramendia M.A., Borau V., and Gomez J.F. J. Catal. 140 (1993) 335
9. Van Bekkum H., Kieboom A.P.G., and Van de Putte K.J.G. Rec. Trav. Chim. 88 (1969) 52
10. Bonnet M., Geneste P., and Lonzano Y. C.R. Acad. Sci. Paris Ser. C 282 (1976) 1009
11. Rajashekharam M.V., and Chaudhari R.V. Chem. Eng. Sci. 51 (1996) 1663
12. Rylander P.N. Catalysis in Organic Synthesis (1978), Academic Press 155
13. Breitner E., Roginski E., and Rylander P.N. J. Org. Chem. 24 (1959P) 1855
14. Malyala R.V., Rode C.V., Arai M., Hegde S.G., and Chaudari R.V. Appl. Catal. A: Gen. 193 (2000) 71
15. Maki-Arvela P., Sahin S., Kumar N., Heikkila T., Lehto V., Salmi T., and Murzin D.Y. Appl. Catal. A: Gen. 350 (2008) 24
16. Zaccheria F., Ravasio N., and Psaro R.A. Fusia Tetrahedron Lett. 46 (2005) 3695
17. Bertero N.M., Apesteguia C.R., and Marchi A.J. Appl. Catal. A: Gen. 349 (2008) 100
18. Ronchin L., Toniolo L., and Cavinato G. Appl. Catal. A: Gen. 165 (1997) 133
19. Diezi S., Reimann S., Bonalumi N., Mallat T., and Baiker A. J. Catal. 239 (2006) 255
20. Singh U.K., and Vannice M.A. Appl. Catal. A: Gen. 213 (2001) 1
21. Osawa T., Hagino Y., Harada T., and Takayasu O. Catal. Lett. 112 (2006) 57
22. Osawa T., Amayaa Y., Harada T., and Takayasu O. J. Mol. Catal. A 211 (2004) 93
23. Klabunovskii E.I. Kinet. Catal. 33 (1992) 233
24. Szollosi G., Herman B., Felfoldi K., Fulopa F., and Bartok M. J. Mol. Catal. A 290 (2008) 54
25. Bucsi I., Sutyinszki M., Felfoldi K., and Bartok M. Catal. Commun. 7 (2006) 104
26. Nakagawa S., Tai A., Okuyama T., and Sugimura T. Top. Catal. 13 (2000) 187
27. Ronchin L., and Toniolo L. React. Kinet. Catal. Lett. 78 (2003) 281
28. Ronchin L., and Toniolo L. Appl. Catal. A: Gen. 208 (2001) 77
29. Bates D.M., and Watts D.G. Non-linear Regression Analysis & its Applications (1988), John Wiley & Sons, New York
30. Abell M.L., and Braselton J.P. The Mathematica Handbook (1992), Academic Press
31. Chang N., Aldrett S., Holtzapple M.T., and Davison R.R. Chem. Eng. Sci 55 (2000) 5721
32. Satterfield C.N. Heterogeneous Catalysis in Industrial Practice. II ed. (1991), McGraw-Hill
33. Philipsen P.H.T., and Baerends E.J. J. Phys. Chem. B 110 (2006) 12470
34. Pallassana V., and Neurock M. J. Phys. Chem. B 104 (2000) 9449
35. Roques J., Lacaze-Dufaure C., and Mijoule C. J. Chem. Theory Comput. 3 (2007) 878
36. But J.B. Reaction Kinetics and Reactor Design. 2nd ed. (2000), Marcel-Dekker, NY pp. 169
37. Singer S., and Zuman P. J. Org. Chem. 39 (1974) 836
38. Roberts G.W. In: Rylander P.N., and Greenfield H. (Eds). Catalysis in Organic Synthesis (1976), Academic Press 1
39. Ramachadran e P.A., and Chaudhari R.V. Three-phase Catalytic Reactors (1982), Gordon and Breach Sciences Publisher
40. Boudart M. Ind. Eng. Chem. Fundam. 28 (1986) 656
41. Jeffery E.L., Mann R.K., Hutchings G.J., Taylor S.H., and David J.W. Catal. Today 105 (2005) 85
42. Van Der Burg A., Doornbos J., Kos N.J., Ultee W.J., and Ponec V. J. Catal. 54 (1978) 243
43. van Druten G.M.R., Aksu L., and Ponec V. Appl. Catal. A: Gen. 149 (1997) 181
44. Van Druten G.M.R., and Ponec V. Appl. Catal. A: Gen. 191 (2000) 153
45. Van Druten G.M.R., and Ponec V. Appl. Catal. A: Gen. 191 (2000) 163
46. Blaser H.U., Jalett H.P., Garland M., Studer M., Thies H., and -Tijani A. J. Catal. 173 (1998) 282
47. Draper N.R., and Smith H. Applied Regression Analysis (1966), John Wiley & Sons, New York pp. 86