Continuous Synthesis of Triacetonamine Over Cation-Exchange Resin

Xiaobao Du; Ge Song; Jun Tian; Yang Li

doi:10.14233/ajchem.2015.17022

Issue

Vol. 27 No. 2 (2015): Vol 27 Issue 2

Issue Published : January 10, 2015

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

Continuous Synthesis of Triacetonamine Over Cation-Exchange Resin

https://doi.org/10.14233/ajchem.2015.17022

Xiaobao Du

School of Chemical Engineering and Technology, Tianjin University, Tianjin, P.R. China

Ge Song

School of Chemical Engineering and Technology, Tianjin University, Tianjin, P.R. China

Jun Tian

School of Chemical Engineering and Technology, Tianjin University, Tianjin, P.R. China

Yang Li

School of Chemical Engineering and Technology, Tianjin University, Tianjin, P.R. China

Corresponding Author(s) : Yang Li

liyang777@tju.edu.cn

Asian Journal of Chemistry, Vol. 27 No. 2 (2015): Vol 27 Issue 2
Article Published : January 10, 2015

Abstract

A continuous process for the synthesis of triacetonamine, which is the sole precursor of most hindered amine light stabilizers, from acetone and ammonia was carried out with NKC-9 cation-exchange resin in a fixed bed reactor. The plausible reaction mechanism was also discussed. The effect of different reaction parameters including molar ratio of reactants, gas hour space velocity and reaction temperature have been investigated to obtain the optimal conditions. The activity, selectivity and stability of the catalyst were demonstrated and a continuous process for production of triacetonamine from acetone and ammonia has been established.

Keywords

Cation-exchange resin Triacetonamine Acetone Ammonia Light stabilizer Continuous process

Du, X., Song, G., Tian, J., & Li, Y. (2015). Continuous Synthesis of Triacetonamine Over Cation-Exchange Resin. Asian Journal of Chemistry, 27(2), 541–543. https://doi.org/10.14233/ajchem.2015.17022

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References

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H.K. Hall Jr., J. Am. Chem. Soc., 79, 5444 (1957); doi:10.1021/ja01577a031.
G. Cantatore and P. Cassandrini, Process for Preparing 2,2,6,6-Tetramethyl-4-piperidone, US Patent 4536581 (1985).
J. Gangadwala, S. Mankar, S. Mahajani, A. Kienle and E. Stein, Ind. Eng. Chem. Res., 42, 2146 (2003); doi:10.1021/ie0204989.
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D.B. Taylor and B. Milligan, Process for Preparing Triacetone Amine and Other Oxopiperidines, US Patent 4831146 (1989).

References

M. Dagonneau, E.S. Kagan, V.I. Mikhailov, E.G. Rozantsev and V.D. Sholle, Synthesis, 895 (1984); doi:10.1055/s-1984-31014.

L. Volodarsky and V. Kosover, Tetrahedron Lett., 41, 179 (2000); doi:10.1016/S0040-4039(99)02049-3.

W. Huang, R. Chiarelli and A. Rassat, Tetrahedron Lett., 41, 8787 (2000); doi:10.1016/S0040-4039(00)01557-4.

H. Wiezer, G. Nowy and H. Haberlein, Process for the Preparation of 2,2,6,6- Tetramethylpiperidone-4, US Patent 4356308 (1982).

T. Haruna, A. Nishimura and K. Sugibuchi, Method for preparing 2,2,6,6- tetramethyl-4-oxopiperidine, Patent 4663459 (1987).

M. Julius, D. Hermeling, H. Siegel and W. Harder, Preparation of 2,2,6,6-tetramethyl- piperidin-4-one, US Patent 5856494 (1999).

A. Wu, W. Yang and X. Pan, Synth. Commun., 26, 3565 (1996); doi:10.1080/00397919608003766.

R.E. Malz Jr., Y-C. Son and S.L. Suib, Process for the Synthesis of 2,2,6,6-Tetramethyl- 4-Oxopiperidine, US Patent US 6,646,127 B2 (2003).

H.K. Hall Jr., J. Am. Chem. Soc., 79, 5444 (1957); doi:10.1021/ja01577a031.

G. Cantatore and P. Cassandrini, Process for Preparing 2,2,6,6-Tetramethyl-4-piperidone, US Patent 4536581 (1985).

J. Gangadwala, S. Mankar, S. Mahajani, A. Kienle and E. Stein, Ind. Eng. Chem. Res., 42, 2146 (2003); doi:10.1021/ie0204989.

S.S. Mahajan, M.M. Sharma and T. Sridhar, Ind. Eng. Chem. Res., 45, 5246 (2006); doi:10.1021/ie050059k.

E. Sert and F.S. Atalay, Ind. Eng. Chem. Res., 51, 6350 (2012); doi:10.1021/ie300350r.

P. Delgado, M.T. Sanz and S. Beltrán, Chem. Eng. J., 126, 111 (2007); doi:10.1016/j.cej.2006.09.004.

D.B. Taylor and B. Milligan, Process for Preparing Triacetone Amine and Other Oxopiperidines, US Patent 4831146 (1989).

Issue

Vol. 27 No. 2 (2015): Vol 27 Issue 2

Continuous Synthesis of Triacetonamine Over Cation-Exchange Resin

Corresponding Author(s) : Yang Li

Abstract

Keywords

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