Abstract
An online Raman analysis technique was used for the first time to study the mechanism underlying the synthesis of 5-bromomethylpyridine-2,3-dicarboxylic acid methyl ester (CMPE) via a bromination reaction with 5-methylpyridine-2,3-dicarboxylic acid dimethyl ester (MPE) as the raw material, N-bromosuccinimide (NBS) as the brominating reagent, and azobisisobutyronitrile (AIBN) as an initiator. The apparent thermodynamics and the reaction kinetics of bromination reaction of MPE were explored, a reaction kinetics model was established, and the bromination reaction of MPE was a typical reaction initiated by free radicals. The activation energy of bromination of MPE was 37.02 kJ mol–1, and the apparent reaction heat was 2.23 kJ mol–1 (calculated in the moles of NBS). The adiabatic temperature rise was 6.30°C under thermal runaway. The kinetic equation of the synthesis reaction: r = 3.26 × 106exp(–37.02/RT)\(C_{{{\text{NBS}}}}^{{1.52}}\).
This is a preview of subscription content, log in via an institution to check access.
REFERENCES
E. A. Braude and E. S. Waight, Nature (London, U.K.) 164 (4162), 241 (1949).
Sui Xiaofeng, Yuan Jinying, Zhou Mi, et al., Org. Chem. 26 (11), 7 (2006).
E. E. Kolvari, A. Ghorbani-Choghamarani, P. Salehi, et al., J. Iran. Chem. Soc. 4, 126 (2007).
Lu Bai, Tianjin Chem. Ind., 2 (1998).
A.-R. Allouche, J. Comput. Chem. 32, 174 (2012).
Xu Fengjie, Guangdong Chem. Ind. 45 (10), 3 (2018).
Mingxing Guan, Yingtao Tian, Jibin Zhao, et al., Org. Process Res. Developm. 25, 1375 (2021).
Cheng Chunsheng, Lin Yang, Yang Zhaoguo, et al., Patent CN109467548A (2019).
Ding Mingwu, Xu Zhifeng, Liu Zhaojie, et al., Chin. J. Appl. Chem. 18 (8), 3 (2001).
Y. Chae, S. Min, E. Park, et al., Anal. Chem. (2021).
J. Hu, C. S. Cheng, X. Liu, et al., RSC Adv. 12, 2270 (2022).
Xing Qiyi, Basic Organic Chemistry (Higher Education Press, 1983).
Wan Wei, Chen Wanghua, Wei Shui’ai, et al., Chin. J. Safety Sci. 22 (8), 7 (2012).
Cheng Chunsheng and Wei Zhenyun, Risk and Control of Fine Chemical Reaction (Chem. Ind. Press, Moscow, 2020).
Fu Xiancai, Physical Chemistry, 5th ed. (Higher Education Press, Moscow, 2005).
Cheng Chunsheng, Xu Weichang, Wei Zhenyun, et al., Fine Chemical Reaction Risk and Control (Chemical Industry Press, Moscow, 2020).
Cheng Chunsheng, Wei Zhenyun, Li Quanguo, et al., Pesticides 53 (2), 4 (2014).
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
The authors declare that they have no conflicts of interest.
Rights and permissions
About this article
Cite this article
Ma, X., Liu, X., Ming, X. et al. Mechanism and Kinetics of Bromination of 5-Methylpyridine-2,3-dicarboxylic Acid Dimethyl Ester. Russ. J. Phys. Chem. 97, 73–79 (2023). https://doi.org/10.1134/S0036024423010338
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0036024423010338