Abstract
The electrocatalytic hydrogenation of benzene, aniline, and nitrobenzene was investigated at a Raney nickel powder cathode. The single phase electrolyte consisted of t-butanol, water, and a hydrotropic salt, either sodium or tetraethylammoniump-toluenesulphonate (TEATS). The hydrogenation of benzene was achieved only in the latter case; the only product detected was cyclohexane. The highest current efficiency (73%) was obtained at 50° C, 1.0m benzene, 2.5m TEATS, and at an apparent current density of 4.0 mA cm−2. Aniline was electrocatalytically hydrogenated to cyclohexylamine only in the presence of a quaternary ammonium ion supporting electrolyte (containing either Br− orp-toluenesulphonate anions), with product current efficiencies of ∼40%. When nitrobenzene was hydrogenated with a sodiump-toluenesulphonate supporting electrolyte, only nitro group reduction was observed. When the supporting electrolyte was TEATS, both nitro group reduction and aromatic ring hydrogenation occurred.
Similar content being viewed by others
References
L. L. Miller and L. Christensen,J. Org. Chem. 43 (1978) 2059.
K. Park, P. N. Pintauro, M. M. Baizer and K. Nobe,J. Electrochem. Soc. 132 (1985) 1850.
,J. Appl. Electrochem. 16 (1986) 941.
A. P. Tomilov, S. L. Kirilyus and I. P. AndriyanovaSov. Electrochem. 8 (1972) 1050.
Y. Song and P. N. Pintauro,J. Appl. Electrochem. 21 (1991) 21.
T. Chiba, M. Okimoto, H. Nagai and T. Takata,Bull. Chem. Soc. Jpn. 56 (1983) 719.
G. Belot, S. Desjardins and J. Lessard,Tetrahedron Lett. 25 (1984) 5347.
A. Cyr, P. Huot, G. Belot and J. Lessard,Electrochim. Acta 35 (1990) 147.
P. N. Pintauro, H. Phan, M. M. Baizer and K. Nobe.AIChE Symposium Series No. 254 83 (1987) 34.
J. Wisniak, M. Hershkowitz and S. Stein,Ind Eng. Chem. Proc. Res. Dev. 13 (1974) 232.
H. W. Haines,Ind. Eng. Chem. 54 (1962) 23.
T. Hatayama, US Patent 3 700 572 (24 Oct. 1973).
J. P. Coleman and J. H. Wagenknecht,J. Electrochem. Soc. 128 (1981) 322.
W. H. Sternberg, R. Markby and I. Vendor,110 (1963) 425.
A. R. Benkeser, E. M. Kaiser and R. F. Lambert,J. Am. Chem. Soc. 86 (1964) 5272.
D. Pasquariello, J. Foise, R. Kershaw, G. Zoski, K. Dwight and A. Wold,J. Phys. Chem. 89 (1985) 1243.
M. M. Baizer and H. Lund, ‘Organic Electrochemistry’, 2nd ed., Marcel Dekker, New York (1983), pp. 285–313.
R. H. McKee,Ind. Eng. Chem. 38 (1946) 382.
Idem R. H. McKee, US Patent 1 932 908 (31 Oct. 1933).
R. H. McKee and J. R. Heard,Trans. Electrochem. Soc. 65 (1934) 301.
M. M. Baizer,J. Electrochem. Soc. 111 (1964) 215.
R. Mozingo, ‘Organic Syntheses’, Coll Vol. III, John Wiley, New York (1964), p. 181.
A. P. Tomilov S. G. Mairanovskii, M. Ya. Fioshin and V. A. Smirnov, ‘Electrochemistry of Organic Compounds,’, Halsted Press, New York (1972), p. 351.
J. Bontha, ‘The Electrocatalytic Hydrogenation of Organic Compounds on Raney Nickel’, M. S. Thesis. Tulane University (1990).
T. C. Franklin and T. Jimbo,J. Electrochem. Soc. 134 (1987) 2169.
M. M. Baizer and J. P. Petrovich,114 (1967) 1023.
F. Beck,Angew. Chem. Int. Ed. Eng. 11 (1972) 760.
P. N. Pintauro, D. K. Johnson, K. Park, M. M. Baizer and K. Nobe,J. Appl. Electrochem. 14 (1984) 209.
‘Chemical Engineer's Handbook’, 6th Edition (edited by R. H. Perry and C. H. Chilton) Mc-Graw-Hill, New York (1987).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Pintauro, P.N., Bontha, J.R. The role of supporting electrolyte during the electrocatalytic hydrogenation of aromatic compounds. J Appl Electrochem 21, 799–804 (1991). https://doi.org/10.1007/BF01402817
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF01402817