Effect of alkali metal promoters on catalytic performance of Co-based catalysts in selective hydrogenation of aniline to cyclohexylamine

1 Chaudhari, Ch., Sato, K., Ikeda, Y., Terada, K., Abe, N. & Nagaoka, K. (2021). One-pot synthesis of cyclohexylamine and N-aryl pyrroles via hydrogenation of nitroarenes over the Pd_0.5Ru_0.5-PVP catalyst. New. J. Chem. 45, 9743–9746. DOI: 10.1039/D1NJ00922B. Open DOISearch in Google Scholar

2 Araki, S., Nakanishi, K., Tanaka, A. & Kominami, H. (2020). A ruthenium and palladium bimetallic system superior to a rhodium co-catalyst for TiO₂-photocatalyzed ring hydrogenation of aniline to cyclohexylamine. J. Catal. 389, 212–217. DOI: 10.1016/j.jcat.2020.05.035. Open DOISearch in Google Scholar

3 Ásgeirsson, B., Markússon, S., Hlynsdóttir, S.S., Hel-land, R. & Hjörleifsson, J.G. (2020). X-ray crystal structure of Vibrio alkaline phosphatase with the non-competitive inhibitor cyclohexylamine. Biochem. Biophys. Rep. 24, 100830–100840. DOI: 10.1016/j.bbrep.2020.100830. Open DOISearch in Google Scholar

4 Ranjbar, S., Soltanabadi, A. & Fakhri, Z. (2016). Experimental and Computational Studies of Binary Mixtures of Isobutanol + Cyclohexylamine. J. Chem. Eng. Data. 61(9), 3077–3089. DOI: 10.1021/acs.jced.6b00158. Open DOISearch in Google Scholar

5 Senthil, K., Elangovan, K., Senthil, A. & Vinitha, G. (2021). Synthesis, growth, optical, mechanical, thermal, dielectric and third order nonlinear optical properties of cyclohexylamine derivative single crystals. Spectrochim. Acta. A: Mol. Biomol. Spectrosc. 247, 119063–119071. DOI: 10.1016/j.saa.2020.119063. Open DOISearch in Google Scholar

6 Beepala, S.K., Mitta, H., Sk, H., Balla, P. & Komandur, V.R.Ch. (2022). Reductive amination of cyclohexanol/cyclohexanone to cyclohexylamine using SBA-15 supported copper catalysts. J. Indian. Chem. Soc. 99(6), 100451–100458. DOI: 10.1016/j.jics.2022.100451. Open DOISearch in Google Scholar

7 Churro, R., Mendes, F., Araújo, P., Ribeiro, F., Peres, J. & Madeira, L.M. (2021). Statistical modelling of the amination reaction of cyclohexanol to produce cyclohexylamine over a commercial Ni-based catalyst. Chem. Eng. Res. Des. 170, 189–200. DOI: 10.1016/j.cherd.2021.03.029. Open DOISearch in Google Scholar

8 Wen, J., You, K., Liu, X., Jian, J., Zhao, F., Liu, P., Ai, Q. & Luo, H. (2019). Highly selective one-step catalytic amination of cyclohexene to cyclohexylamine over HZSM-5. Catal. Commun. 127, 64–68. DOI: 10.1016/j.catcom.2019.05.007. Open DOISearch in Google Scholar

9 Kowalewski, E., Krawczyk, M., Słowik, G., Kocik, J., Pieta, I.S., Chernyayeva, O., Lisovytskiy, D., Matus, K. & Śrębowata, A. (2021). Continuous-flow hydrogenation of nitrocyclohexane toward value-added products with CuZnAl hydrotalcite derived materials. Appl. Catal. A: Gen. 618, 118134–118145. DOI: 10.1016/j.apcata.2021.118134. Open DOISearch in Google Scholar

10 Axet, M.R., Conejero, S. & Gerber, I.C. (2018). Ligand Effects on the Selective Hydrogenation of Nitrobenzene to Cyclohexylamine Using Ruthenium Nanoparticles as Catalysts. Appl. Nano. Mater. 1(10), 5885–5894. DOI: 10.1021/acsanm.8b01549. Open DOISearch in Google Scholar

11 Li, X., Wang, Z., Mao, S., Chen, Y., Tang, M., Li, H. & Wang, Y. (2018). Insight into the Role of Additives in Catalytic Synthesis of Cyclohexyl-amine from Nitrobenzene. Chin. J. Chem. 36, 1191–1196. DOI: 10.1002/cjoc.201800380. Open DOISearch in Google Scholar

12 Chatterjee, M., Sato, M., Kawanami, H., Ishizaka, T., Yokoyama, T. & Suzuki, T. (2011). Hydrogenation of aniline to cyclohexylamine in supercritical carbon dioxide: Significance of phase behaviour. Appl. Catal. A: Gen. 396, 186–193. DOI: 10.1016/j.apcata.2011.02.016. Open DOISearch in Google Scholar

13 Greenfield, H. (1964). Hydrogenation of Aniline to Cyclohexylamine with Platinum Metal Catalysts. J. Org. Chem. 29(10), 3082–3084. DOI: 10.1021/jo01033a512. Open DOISearch in Google Scholar

14 Yin, Z., Zeng, H., Wu, J., Zheng, S. & Zhang, G. (2016). Cobalt-Catalyzed Synthesis of Aromatic, Aliphatic, and Cyclic Secondary Amines via a “Hydrogen-Borrowing” Strategy. ACS Catal. 6(10), 6546–6550. DOI: 10.1021/acscatal.6b02218. Open DOISearch in Google Scholar

15 Valeš, R., Dvořák, B. & Krupka, J. (2021). Thermodynamic analysis on disproportionation process of cyclohexylamine to dicyclohexylamine. Pol. J. Chem. Tech. 23(3), 63–48. DOI: 10.2478/pjct-2021-0029. Open DOISearch in Google Scholar

16 Hagihara, H. & Etsuro, E. (1965). The Catalytic Hydrogenation of Aniline. Bull. Chem. Soc. Jpn. 38(12), 2094–2100. DOI: 10.1246/bcsj.38.2094. Open DOISearch in Google Scholar

17 Mink, G. & Horváth, L. (1998). Hydrogenation of aniline to cyclohexylamine on NaOH-promoted or lanthana supported nickel. React. Kinet. Catal. Lett. 65, 59–65. DOI: 10.1007/BF02475316. Open DOISearch in Google Scholar

18 Roose, P., Eller, K., Henkes, E., Rossbacher, R. & Höke, H. (2015). Amines, Aliphatic. In Ullmann‘s Encyclopedia of Industrial Chemistry. Weinhelm, Germany: Wiley-VCH Verlag GmbH & Co. KGaA. DOI: 10.1002/14356007.a02_001.pub2. Open DOISearch in Google Scholar

19 Narayanan, K. & Unnikrishnan, R.P. (1997). Comparison of hydrogen adsorption and aniline hydrogenation over co-precipitated Co/Al₂O₃ and Ni/Al2O₃ catalysts. J. Chem. Soc., Faraday Trans. 93(10), 2009–2013. DOI: 10.1039/A608074J. Open DOISearch in Google Scholar

20 Nishimura, S., Yutaka, K., Yoshiharu, O. & Yoshio, F. (1971). The Ruthenium-Catalyzed Hydrogenation of Aromatic Amines Promoted by Lithium Hydroxide. Bull. Chem. Soc. Jpn. 44(1), 240–243. DOI: 10.1246/bcsj.44.240. Open DOISearch in Google Scholar

21 Nishimura, S., Shu, T., Hara, T. & Takagi, Y. (1966). The Hydroxide-Blacks of Ruthenium and Rhodium as Catalysts for the Hydrogenation of Organic Compounds. II. The Effects of Solvents and Added Alkalis in the Hydrogenation of Aniline. Bull. Chem. Soc. Jpn. 39(2), 329–333. DOI: 10.1246/bcsj.39.329. Open DOISearch in Google Scholar

22 Valeš, R., Dvořák, B. & Krupka, J. (2021). The effect of water and substituents of aromatic ring on its hydrogenation over a cobalt catalyst. Revealed in Reference: 8^th International Conference on Chemical Technology, 3-5 May 2021 (pp. 98–103). Prague, Czech Republic: Czech Society of Industrial Chemistry. ebook: 978-80-88307-08-2. Search in Google Scholar

23 Díaz, A., Acosta, D.R., Odriozola, J.A. & Montes, M. (1997). Characterization of Alkali-Doped Ni/SiO₂ Catalysts. J. Phys. Chem. B. 101(10), 1782–1790. DOI: 10.1021/jp963145u. Open DOISearch in Google Scholar

24 Dvořák, B. & Pašek, J. (1967). Einfluss der Zusammensetzung, der Herstellungsbedingungen und der Struktur des Kobaltkatalysators auf seine katalytische Aktivität für die Anilinhydrierung in der Gasphase. Collect. Czech. Chem. Commun. 32(10), 3476–3492. DOI: 10.1135/cccc19673476. Open DOISearch in Google Scholar

25 Strejcová, D. (2008). Effect of alkali metals carbonates on reduction rate of Co₃O₄ and strength of interactions between hydrogen and cobalt metal. Published bachelor thesis, University of Chemistry and Technology, Prague, Czech Republic. Search in Google Scholar

26 Veselá, D. (2016). Study of selected properties of cobalt catalysts. Published doctoral dissertation, University of Chemistry and Technology, Prague, Czech Republic. Search in Google Scholar

27 Li, D., Ichikuni, N., Shimazu, S. & Uematsu, T. (1998). Catalytic properties of sprayed Ru/Al₂O₃ and promoter effects of alkali metals in CO₂ hydrogenation. Appl. Catal. A: Gen. 172(2), 351–358. DOI: 10.1016/S0926-860X(98)00139-2. Open DOISearch in Google Scholar

28 Shi, H., Yang, H., Gao, P., Chen, X., Liu, H., Zhong, L., Wang, H., Wei, W. & Sun, Y. (2018). Effect of alkali metals on the performance of CoCu/TiO₂ catalysts for CO2 hydrogenation to long-chain hydrocarbons. Chin. J. Catal. 39(8), 1294–1302. DOI: 10.1016/S1872-2067(18)63086-4. Open DOISearch in Google Scholar

29 Pradeep, S.M., Weibin, L., Yijiao, J. & Huang, J. (2021). Cu-Based Nanocatalysts for CO₂ Hydrogenation to Methanol. Energy Fuels. 35(10), 8558–8584. DOI: 10.1021/acs. energyfuels.1c00625. Open DOISearch in Google Scholar