Mild electrocatalytic hydrogenation of lactic acid to lactaldehyde and propylene glycol

Journal of Catalysis

Volumn 246, Issue 1, 2007, Pages 15-28

  Dalavoy, Tulika S ^a   Jackson, James E ^a   Swain, Greg M ^a   Miller, Dennis J ^b   Li, Jie ^c   Lipkowski, Jacek ^c  

^a MICHIGAN STATE UNIVERSITY   (United States)

^b Michigan State University   (United States)

^c UNIVERSITY OF GUELPH   (Canada)

Author keywords

ATR; Electrocatalytic hydrogenation; Electrosynthesis; FTIR; Green chemistry; Lactaldehyde; Lactic acid; Organic electrochemistry; Propylene glycol; Reticulated vitreous carbon; SEIRAS

Indexed keywords

ADSORPTION; ELECTRODES; ELECTROLYSIS; HYDROGENATION; NEGATIVE IONS;

ELECTROCATALYTIC HYDROGENATION; GREEN CHEMISTRY; ORGANIC ELECTROCHEMISTRY; RETICULATED VITREOUS CARBON (RVC) ELECTRODE;

ORGANIC ACIDS;

EID: 33846203236     PISSN: 00219517     EISSN: 10902694     Source Type: Journal    
DOI: 10.1016/j.jcat.2006.11.009     Document Type: Article

References (59)

1. Zhang Z., Jackson J.E., and Miller D.J. Appl. Catal. A 219 (2001) 89
2. Zhang Z., Jackson J.E., and Miller D.J. Ind. Eng. Chem. Res. 41 (2002) 691
3. Jere F.T., Miller D.J., and Jackson J.E. Org. Lett. 5 (2003) 527
4. Jere F.T., Jackson J.E., and Miller D.J. Ind. Eng. Chem. Res. 43 (2004) 3297
5. Laplante F., Brossard L., and Menard H. Can. J. Chem. 81 3 (2003) 258
6. Ilikti H., Rekik N., and Thomalla M.J. J. Appl. Electrochem. 32 (2002) 603
7. Ilikti H., Rekik N., and Thomalla M.J. J. Appl. Electrochem. 34 (2004) 127
8. Cheong A.K., Bolduc Y., and Lessard J. Can. J. Chem. 71 (1993) 1850
9. Mahdavi B., Chambrion P., Binette J., Martel E., and Lessard J. Can. J. Chem. 73 (1995) 846
10. Polcaro A.M., Palmas S., and Dermini S. Ind. Eng. Chem. Res. 32 (1993) 1315
11. J. Farrugia, unpublished work
12. Cyr A., Chiltz F., Jeanson P., Martel A., Brossard L., Lessard J., and Menard H. Can. J. Chem. 78 (2000) 307
13. Dabo P., Cyr A., Lessard J., Brossard L., and Menard H. Can. J. Chem. 77 (1999) 1225
14. Ruest L., Menard H., Moreau V., and Laplante F. Can. J. Chem. 80 (2002) 1662
15. Dube P., Kerdouss F., Proulx P., Brossard L., and Menard H. J. Appl. Electrochem. 33 (2003) 541
16. Miyake H., Ye S., and Osawa M. Electrochem. Commun. 4 (2002) 973
17. Curtiss L.A., Raghavachari K., Redfern P.C., Rassolov V., and Pople J.A. J. Chem. Phys. 109 (1998) 7764
18. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B.G. Johnson, W. Chen, M.W. Wong, J.L. Andres, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98 (Revision A.7), Gaussian, Inc., Pittsburgh, PA, 1998
19. Miertus S., Scrocco E., and Tomasi J. J. Chem. Phys. 55 (1981) 117
20. Miertus S., and Tomasi J. Chem. Phys. 65 (1982) 239
21. Cossi M., Barone V., Cammi R., and Tomasi J. Chem. Phys. Lett. 255 (1996) 327
22. Barone V., Cossi M., and Tomasi J. J. Comput. Chem. 19 (1998) 404
23. Nambiar K.P., Stauffer D.M., Kolodziej P.A., and Benner S.A. J. Am. Chem. Soc. 105 (1983) 5886
24. Hu X.E., Yang H.W., Wang X.J., and Bai R.S. J. Appl. Electrochem. 32 (2002) 321
25. Amouzegar K., and Savadogo O. Electrochim. Acta 39 4 (1994) 557
26. Roessler A., Dossenbach O., and Rys P. J. Electrochem. Soc. 150 1 (2003) D1
27. Bryan A., and Grimshaw J. Electrochim. Acta 42 13-14 (1997) 2101
28. Senda Y., Tateoka M., Itoh H., and Ishiyama J. Bull. Chem. Soc. Jpn. 64 (1991) 3302
29. Nielsen H., and Sorensen P.E. Acta Chem. Scand. A 31 (1977) 739
30. Lamy-Pitara E., El Mouahid S., and Barbier J. Electrochim. Acta 43 (2000) 4299
31. Horanyi G. Electrochim. Acta 36 (1991) 1453
32. Hadzi-Jordanov S., Angerstein-Koziowska H., Yukovic M., and Conway B.E. J. Phys. Chem. 81 24 (1977) 2271
33. Sawatari Y., Inukai J., and Ito M. J. Electron Spectrosc. Relat. Phenom. 64/65 (1993) 515
34. Hoshi N., Kuroda M., Ogawa T., Koga O., and Hori Y. Langmuir 20 (2004) 5066
35. Shingaya Y., and Ito M. Electrochim. Acta 37 (1992) 365
36. Colom F., and Gonzalez-Tejera M.J. J. Electroanal. Chem. 190 (1985) 243
37. Marinkovic N.S., Wang J.X., Zajonz H., and Adzic R.R. J. Electroanal. Chem. 500 1-2 (2001) 388
38. Shingaya Y., and Ito M. J. Electroanal. Chem. 467 (1999) 299
39. Ahmadi A., Evans R.W., and Attard G. J. Electroanal. Chem. 350 (1993) 279
40. Horanyi G., and Rizmayer E.M. J. Electroanal. Chem. 181 (1984) 199
41. Osawa M., and Ikeda M. J. Phys. Chem. 95 (1991) 9914
42. Ataka K., Yotsuyanigi T., and Osawa M. J. Phys. Chem. 100 (1996) 10664
43. Ataka K., and Osawa M. Langmuir 14 (1998) 951
44. Pretsch E., Seibl J., Clerc D., and Simon W. Tables of Spectral Data for Structure Determination of Organic Compounds. second ed. (1985), Springer-Verlag p. I85
45. Thiel P.A., Hoffman E.M., and Weinberg W.H. J. Chem. Phys. 75 (1981) 5556
46. Thiel P.A., DePaola R.A., and Weinberg W.H. J. Chem. Phys. 80 (1984) 5326
47. Brink G., and Falk M. Can. J. Chem. 48 (1970) 2096
48. Walrafen G.E. J. Chem. Phys. 36 (1962) 1035
49. Walrafen G.E. J. Chem. Phys. 55 (1971) 768
50. Kitamura F., Nanbu N., Ohsaka T., and Tokuda K. J. Electroanal. Chem. 452 (1998) 241
51. Vassilev P., Van Santen R.A., and Koper M.T.M. J. Chem. Phys. 122 (2005) 054701
52. Kunimatsu K., Uchida H., Osawa M., and Watanabe M. J. Electroanal. Chem. 587 (2006) 299
53. Kunimatsu K., Senzaki T., Tsushima M., and Osawa M. Chem. Phys. Lett. 401 (2005) 451
54. Yokoyama T., and Yamagata N. Appl. Catal. A Gen. 221 (2001) 227
55. L. Peereboom, unpublished results
56. Cortright R.D., Sanchez-Castillo M., and Dumesic J.A. Appl. Catal. B 39 (2002) 353
57. Cortright R.D., and Dumesic J.A. Adv. Catal. 46 (2001) 161
58. Falorni M., Giacomelli G., Porcheddu A., and Taddei M. J. Org. Chem. 64 (1999) 8962
59. D.G. Kovacs, in preparation