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Catalytic Hydrogenation of Cinnamic Acid and Salicylic Acid
Corresponding Author(s) : Sunil B. Shinde
Asian Journal of Chemistry,
Vol. 32 No. 2 (2020): Vol 32 Issue 2
Abstract
Hydrogenation of cinnamic acid and salicylic acid was carried out using 5 %Ru/C, 5 % Pd/C and Ru-Sn/Al2O3 catalyst at 493 K and 6.89 MPa of hydrogen partial pressure. Ru-Sn/Al2O3 catalyst was found to be active for hydrogenation -COOH group to give cinnamyl alcohol. The selectivity to cinnamyl alcohol was low (15 %) as absolute inhibition of C=C bond hydrogenation in cinnamic acid is challenging. 5 %Pd/C catalyst was found to hydrogenate C=C bond and aromatic ring in cinnamic acid. 5 %Ru/C catalyst was found to be least selective catalyst as it hydrogenated C=C bond, aromatic ring and -COOH group in cinnamic acid. Hydrogenation of salicylic acid is not possible at 493 K as decarboxylation of salicylic acid occurs.
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- B. Chen, U. Dingerdissen, J. Ge Krauter, H.G.J. Lansink-Rotgerink, K. Mobus, D.J. Ostgard, P. Panster, T.H. Riermeier, S. Seebald, T. Tacke and H. Trauthwein, Appl. Catal. A, 17, 280 (2005); https://doi.org/10.1016/j.apcata.2004.08.025.
- R.L. Augustine, Heterogeneous Catalysis for the Synthetic Chemist, Marcel Dekker: New York (1996).
- A. Tungler, T. Taranai, L. Hegedus and K. Fodor, Platinum Met. Rev., 42, 108 (1998).
- R.L. Augustine, Catal. Today, 37, 419 (1997); https://doi.org/10.1016/S0920-5861(97)00025-4.
- J. Ishiyama, S. Maeda, K. Takahashi, Y. Senda and S. Imaizumi, Bull. Chem. Soc. Jpn., 60, 1721 (1987); https://doi.org/10.1246/bcsj.60.1721.
- J. Basters, H. van Bekkum and L.L. van Reijen, Rec. Trav. Chim. Pays-Bas, 89, 491 (1970); https://doi.org/10.1002/recl.19700890506.
- W. Feng, H. Dong, L. Niu, X. Wen, L. Huo and G. Bai, J. Mater. Chem. A Mater. Energy Sustain., 3, 19807 (2015); https://doi.org/10.1039/C5TA04894J.
- G. Lanchec, B. Blouri and P. Rumf, Bull. Soc. Chim. Fr., 3978 (1966).
- M.P. Wiesenfeldt, Z. Nairoukh, T. Dalton and F. Glorius, Angew. Chem. Int. Ed., 58, 10460 (2019); https://doi.org/10.1002/anie.201814471.
- K. Hattori, H. Sajiki and K. Hirota, Tetrahedron, 57, 4817 (2001); https://doi.org/10.1016/S0040-4020(01)00421-5.
- R.V. Chaudhari, C.V. Rode, R.M. Deshpande, R. Jaganathan, T.M. Leib and P.L. Mills, Chem. Eng. Sci., 58, 627 (2003); https://doi.org/10.1016/S0009-2509(02)00588-2.
- S.B. Shinde and R.M. Deshpande, Asian J. Chem., 24, 2767 (2012).
- A.I. Vogel, Textbook of Quantitative Inorganic Analysis: Including Elementary Instrumental Analysis, Longman Group: UK Ltd., vol. 3 (1961).
References
B. Chen, U. Dingerdissen, J. Ge Krauter, H.G.J. Lansink-Rotgerink, K. Mobus, D.J. Ostgard, P. Panster, T.H. Riermeier, S. Seebald, T. Tacke and H. Trauthwein, Appl. Catal. A, 17, 280 (2005); https://doi.org/10.1016/j.apcata.2004.08.025.
R.L. Augustine, Heterogeneous Catalysis for the Synthetic Chemist, Marcel Dekker: New York (1996).
A. Tungler, T. Taranai, L. Hegedus and K. Fodor, Platinum Met. Rev., 42, 108 (1998).
R.L. Augustine, Catal. Today, 37, 419 (1997); https://doi.org/10.1016/S0920-5861(97)00025-4.
J. Ishiyama, S. Maeda, K. Takahashi, Y. Senda and S. Imaizumi, Bull. Chem. Soc. Jpn., 60, 1721 (1987); https://doi.org/10.1246/bcsj.60.1721.
J. Basters, H. van Bekkum and L.L. van Reijen, Rec. Trav. Chim. Pays-Bas, 89, 491 (1970); https://doi.org/10.1002/recl.19700890506.
W. Feng, H. Dong, L. Niu, X. Wen, L. Huo and G. Bai, J. Mater. Chem. A Mater. Energy Sustain., 3, 19807 (2015); https://doi.org/10.1039/C5TA04894J.
G. Lanchec, B. Blouri and P. Rumf, Bull. Soc. Chim. Fr., 3978 (1966).
M.P. Wiesenfeldt, Z. Nairoukh, T. Dalton and F. Glorius, Angew. Chem. Int. Ed., 58, 10460 (2019); https://doi.org/10.1002/anie.201814471.
K. Hattori, H. Sajiki and K. Hirota, Tetrahedron, 57, 4817 (2001); https://doi.org/10.1016/S0040-4020(01)00421-5.
R.V. Chaudhari, C.V. Rode, R.M. Deshpande, R. Jaganathan, T.M. Leib and P.L. Mills, Chem. Eng. Sci., 58, 627 (2003); https://doi.org/10.1016/S0009-2509(02)00588-2.
S.B. Shinde and R.M. Deshpande, Asian J. Chem., 24, 2767 (2012).
A.I. Vogel, Textbook of Quantitative Inorganic Analysis: Including Elementary Instrumental Analysis, Longman Group: UK Ltd., vol. 3 (1961).