Abstract
2-Methyl-3’-hydroxydiphenylamine was synthesized from the mixture of 3-aminophenol, 3-nitrophenol, and 2-methylcyclohexanone in the presence of Pd/C catalyst. The optimum composition of the reaction mixture was determined for maximum yield of the diphenylamine derivative: with the molar ratio of 3-aminophenol: 3-nitrophenol fixed at 1 mmol: 2 mmol, the relative molar amounts of 2-methylcyclohexanone were varied between 3 and 96. At the optimum composition the amounts of Pd/C catalyst were varied threefold in order to investigate the effect of Pd on the product yield. The results obtained from the reaction mixture containing 1 mmol of 3-aminophenol were satisfactorily reproduced for the reaction mixture containing more than 10 mmol of 3-aminophenol. The formation of this diphenylamine derivative could be interpreted using the mechanism for the catalytic synthesis of 2-methyl-4-methoxydiphenylamine which we had optimized previously.
Article PDF
Similar content being viewed by others
Explore related subjects
Discover the latest articles, news and stories from top researchers in related subjects.Avoid common mistakes on your manuscript.
References
Akamatsu, N., “improved Preparation of Diphenylamine Derivatives Comprising Reaction of Nitrobenzenes with Anilines and Cyclohexanone in Presence of Palladium Catalyst”, Japanese Patent 05-117214 (1993).
Cho, J. W., Kim, K. S., Lee, T. J., Kim, J. C. and Kim, D. H., “Optimization of Catalytic Synthesis of Diphenylamine Derivative”,Theories and Applications of Chem. Eng.,1, 89 (1995).
Elmar, R. S. and Somerville, N. J., “Preparation of Hydroxy Substituted Diarylamines”, U.S. Patent 3,450,764 (1969).
Friedrich, W. C. and Heinz, U. B., “Process for the Preparation of Hydroxydiphenylamines”, U.S. Patent 4,265,833 (1981).
Industry Research Institute Report, Korea (1990). Kim, K. S., Lee, T. J., Kim, J. C. and Kim, D. H., “Optimization of Catalytic Synthesis of Diphenylamine Derivative”, Proceedings of 7th Japan-China-USA Symp. on Catalysis, Tokyo, Japan, 41 (1995).
Nagata, T., Kusuda, C. and Wada, M., “Process for the Preparation of Diphenylamine of Nucleus-substituted Derivative Thereof”, U.S. Patent 5,545,752 (1996).
Otto, I. K., Gerhard, D. and Hans, J. B., “Process for Preparation of Diphenylamine”, U.S. Patent 5,338,885 (1994); “Process for Preparing Diphenylamine”, U.S. Patent 5,344,987 (1994).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kim, BS., Jung, DG., Kim, K. et al. Synthesis of diphenylamine derivatives on Pd/C catalyst. Korean J. Chem. Eng. 15, 522–526 (1998). https://doi.org/10.1007/BF02707103
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02707103