Catalytic Hydrogenation Products of Aromatic and Aliphatic Dicarboxylic Acids

Sunil B. Shinde; Raj M. Deshpande

doi:10.14233/ajchem.2019.21921

Issue

Vol. 31 No. 5 (2019): Vol 31 Issue 5

Issue Published : March 28, 2019

This work is licensed under a Creative Commons Attribution 4.0 International License.

Catalytic Hydrogenation Products of Aromatic and Aliphatic Dicarboxylic Acids

https://doi.org/10.14233/ajchem.2019.21921

Sunil B. Shinde

National Chemical Laboratory, Dr. Homibaba Road, Pune-411007, India; Post Graduate Department of Chemistry, Sir Parashurambahu College (Affiliated to Savitribai Phule Pune University), Tilak Road, Pune-411030, India

Raj M. Deshpande

National Chemical Laboratory, Dr. Homibaba Road, Pune-411007, India

Corresponding Author(s) : Sunil B. Shinde

sunil.shinde@spcollegepune.ac.in

Asian Journal of Chemistry, Vol. 31 No. 5 (2019): Vol 31 Issue 5
Article Published : March 28, 2019

Abstract

Hydrogenation of aromatic dicarboxylic acids gave 100 % selectivity to respective cyclohexane dicarboxylic acid with 5 % Pd/C catalyst. 5 % Ru/C catalyst was observed to give over hydrogenation products at 493 K and at lower temperature (453 K) the selectivity for cyclohexane dicarboxylic acids was increased. Hydrogenation of phthalic acid with Ru-Sn/Al₂O₃ catalyst was observed to give phthalide instead of 1,2-benzene dimethanol or 2-hydroxy methyl benzoic acid. Ru-Sn/Al₂O₃ catalyst selectively hydrogenated the carboxylic group of cyclohexane dicarboxylic acids to give cyclohexane dimethanol. Use of proper catalysts and reaction conditions resulted in desired products.

Keywords

Hydrogenation Dicarboxylic acids Catalyst Ru-Sn/Al2O3 Selectivity

Shinde, S. B., & Deshpande, R. M. (2019). Catalytic Hydrogenation Products of Aromatic and Aliphatic Dicarboxylic Acids. Asian Journal of Chemistry, 31(5), 1137–1142. https://doi.org/10.14233/ajchem.2019.21921

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References

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References

A.J. McAlees and R. McCrindle, J. Chem. Soc. C, 2425 (1969); https://doi.org/10.1039/j39690002425.

T. Turek, D.L. Trimm and N.W. Cant, Catal. Rev., Sci. Eng., 36, 645 (1994); https://doi.org/10.1080/01614949408013931.

P. Louessard, J.P. Candy, J.P. Bourneville and J.M. Basset, Structure and Reactivity of Surface, Elsevier: Amsterdam, p. 591 (1989).

K.Y. Cheah, T.S. Tang, F. Mizukami, S. Niwa, M. Toba and Y.M. Choo, J. Am. Oil Chem. Soc., 69, 410 (1992); https://doi.org/10.1007/BF02540940.

M. Toba, S. Tanaka, S. Niwa, F. Mizukami, Z. Koppány, L. Guczi, K.- Y. Cheah and T.-S. Tang, J. Appl. Catal. A, 189, 243 (1999); https://doi.org/10.1016/S0926-860X(99)00281-1.

R.M. Deshpande, V.V. Buwa, C.V. Rode, R.V. Chaudhari and P.L. Mills, Catal. Commun., 3, 269 (2002); https://doi.org/10.1016/S1566-7367(02)00119-X.

Y. Takeda, M. Tamura, Y. Nakagawa, K. Okumura and K. Tomishige, Catal. Sci. Technol., 6, 5668 (2016); https://doi.org/10.1039/C6CY00335D.

T. Toyao, S.M.A.H. Siddiki, A.S. Touchy, W. Onodera, K. Kon, Y. Morita, T. Kamachi, K. Yoshizawa and K. Shimizu, Eur. J. Chem., 23, 1001 (2017); https://doi.org/10.1002/chem.201604762.

D.R. Fagerburg, Polyester auf basis von 1,4- Cyclohexandicarbonsaeure und 1,4-Cyclohexandimethanol, DE 2655434 (1977).

Z. Zhu, Z. Lu, B.G.S. Li and S. Guo, Appl. Catal. A Gen., 302, 208 (2006); https://doi.org/10.1016/j.apcata.2006.01.005.

A.I. Vogel, Text book of Quantitative Inorganic Analysis: Including Elementary Instrumental Analysis, Longman Group: UK Ltd., edn 3 (1961).

Y. Hara and K. Endou, Appl. Catal. A Gen., 239, 181 (2003); https://doi.org/10.1016/S0926-860X(02)00388-5.

J.E. Carnahan, T.A. Ford, W.F. Gresham, W.E. Grigsby and G.F. Hager, J. Am. Chem. Soc., 77, 3766 (1955); https://doi.org/10.1021/ja01619a025.

P.Y. Bruice, Organic Chemistry, Prentice Hall, vol. 4, p. 717 (2003).

L.D. Lillwitz, Preparation of Cyclohexane Dicarboxylic Acids, US Patent 4754064 (1988).

T. Yoshiaki, S. Chihaya, T. Kotone, M. Mitsuo, O. Naoki and K. Kazuaki, EP 603825 (1994).

C.E. Sumner and B.L. Gustafson, Hydrogenation of Phthalic Acids, WO 2000078701 (2000).

Issue

Vol. 31 No. 5 (2019): Vol 31 Issue 5

Catalytic Hydrogenation Products of Aromatic and Aliphatic Dicarboxylic Acids

Corresponding Author(s) : Sunil B. Shinde

Abstract

Keywords

Full Article

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References

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