Kinetic analysis of experiment data for the formation of C.I. Acid Blue 9 leuco compound

doi:10.1016/j.cjche.2017.01.004

›› 2017, Vol. 25 ›› Issue (10): 1422-1426.DOI: 10.1016/j.cjche.2017.01.004

• Catalysis, Kinetics and Reaction Engineering • Previous Articles Next Articles

Kinetic analysis of experiment data for the formation of C.I. Acid Blue 9 leuco compound

Rongwen Lu, Ziang Zhao, Xinyu Hao, Beibei Shao, Shufen Zhang

State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China

Received:2016-09-23 Revised:2017-01-18 Online:2017-01-26 Published:2017-10-28
Supported by:
Supported by the National Natural Science Foundation of China (U1608223, 21576044, 21421005, 21536002) and the Dalian University of Technology Innovation Team (DUT2016TB12).

Kinetic analysis of experiment data for the formation of C.I. Acid Blue 9 leuco compound

Rongwen Lu, Ziang Zhao, Xinyu Hao, Beibei Shao, Shufen Zhang

State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China

通讯作者: Rongwen Lu,E-mail address:lurw@dlut.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China (U1608223, 21576044, 21421005, 21536002) and the Dalian University of Technology Innovation Team (DUT2016TB12).

Abstract

Abstract: A systematic study of the synthesis of C.I. Acid Blue 9 leuco compound in water is reported. The kinetic analysis of experimental data for the condensation reaction between 2-formylbenzenesulfonic acid sodium and N-ethyl-N-(3'-sulfonic acid benzyl) aniline obtained at four different temperatures ranging between 85 and 100℃ is discussed. It is shown that the reaction followed second-order rate kinetics. The overall rate constant (k) increased with the increase of temperature. On the basis of the value of k, activation energy (E_a) of the reaction was evaluated. Importantly, it is found that reactant concentration has great effect on the formation of C.I. Acid Blue 9 leuco compound, implying that it is not enough to improve the conversion of N-ethyl-N-(3'-sulfonic acid benzyl) aniline by only prolonging reaction time in the late period of the reaction.

Key words: Triphenylmethane dyes, C.I.Acid blue 9 leuco compound, Kinetics, Condensation

摘要： A systematic study of the synthesis of C.I. Acid Blue 9 leuco compound in water is reported. The kinetic analysis of experimental data for the condensation reaction between 2-formylbenzenesulfonic acid sodium and N-ethyl-N-(3'-sulfonic acid benzyl) aniline obtained at four different temperatures ranging between 85 and 100℃ is discussed. It is shown that the reaction followed second-order rate kinetics. The overall rate constant (k) increased with the increase of temperature. On the basis of the value of k, activation energy (E_a) of the reaction was evaluated. Importantly, it is found that reactant concentration has great effect on the formation of C.I. Acid Blue 9 leuco compound, implying that it is not enough to improve the conversion of N-ethyl-N-(3'-sulfonic acid benzyl) aniline by only prolonging reaction time in the late period of the reaction.

关键词: Triphenylmethane dyes, C.I.Acid blue 9 leuco compound, Kinetics, Condensation

Rongwen Lu, Ziang Zhao, Xinyu Hao, Beibei Shao, Shufen Zhang. Kinetic analysis of experiment data for the formation of C.I. Acid Blue 9 leuco compound[J]. , 2017, 25(10): 1422-1426.

References

[1] H. Zollinger, Color Chemistry, third ed. Wiley-VCH Verlag GmBH & Co.KGaA, 2001.
[2] D.F. Duxbury, The photochemistry and photophysics of triphenylmethane dyes in solid and liquid media, Chem. Rev. 93(1) (1993) 381-433.
[3] V. Nair, S. Thomas, S.C. Mathew, K.G. Abhilash, Recent advances in the chemistry of triaryl-and triheteroarylmethanes, Tetrahedron 62(29) (2006) 6731-6747.
[4] A. Noack, A. Schröder, H. Hartmann, Synthesis and spectral characterisation of a series of new heterocyclic triphenylmethane analogues, Dyes Pigments 57(2) (2003) 131-147.
[5] R. Christie, Colour Chemistry, RSC Publishing, UK, 2001.
[6] Z. Li, Z. Duan, J. Kang, H. Wang, L. Yu, Y. Wu, A simple access to triarylmethane derivatives from aromatic aldehydes and electron-rich arenes catalyzed by FeCl₃, Tetrahedron 64(8) (2008) 1924-1930.
[7] X. Wang, Y. Wang, D.M. Du, J. Xu, Solvent-free, AlCl₃-promoted tandem Friedel-Crafts reaction of arenes and aldehydes, J. Mol. Catal. A Chem. 255(1-2) (2006) 31-35.
[8] B.M. Babu, P.B. Thakur, V.M. Bangade, H.M. Meshram, Novel and highly efficient one pot protocol for the synthesis of diversely functionalized triarylmethanes, Tetrahedron Lett. 56(6) (2015) 766-771.
[9] V. Nair, K.G. Abhilash, N. Vidya, Practical synthesis of triaryl-and triheteroarylmethanes by reaction of aldehydes and activated arenes promoted by Gold(Ⅲ) chloride, Org. Lett. 7(26) (2005) 5857-5859.
[10] J. Jaratjaroonphong, S. Sathalalai, P. Techasauvapak, V. Reutrakul, Iodine-catalyzed Friedel-Crafts alkylation of electron-rich arenes with aldehydes:Efficient synthesis of triarylmethanes and diarylalkanes, Tetrahedron Lett. 50(44) (2009) 6012-6015.
[11] M. Yao, L. Cheng, J. Wang, Principle for the Synthesis of Fine Chemicals, second ed. China Petrochemical Press, Beijing, 2000(in Chinese).
[12] W.H. Stockmayer, The steady-state approximation in polymerization kinetics, J. Chem. Phys. 12(1944) 143-144.
[13] X. Fu, Physical Chemistry, fifth ed. China Higher Education Press, Beijing, 2005(in Chinese).

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Kinetic analysis of experiment data for the formation of C.I. Acid Blue 9 leuco compound

Kinetic analysis of experiment data for the formation of C.I. Acid Blue 9 leuco compound

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