Effects of Assistant Solvents and Mixing Intensity on the Bromination Process of Butyl Rubber

doi:10.1016/S1004-9541(14)60052-5

Chin.J.Chem.Eng. ›› 2014, Vol. 22 ›› Issue (4): 398-404.DOI: 10.1016/S1004-9541(14)60052-5

• CATALYSIS, KINETICS AND REACTION ENGINEERING • Previous Articles Next Articles

Effects of Assistant Solvents and Mixing Intensity on the Bromination Process of Butyl Rubber

WANG Wei^1,2, ZOU Haikui^1,, CHU Guangwen^1,2, XIANG Yang¹, PENG Han¹, CHEN Jianfeng^1,2

1 Research Center of the Ministry of Education for High Gravity Engineering and Technology, Beijing University of Chemical Technology, Beijing 100029, China;
2 State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029, China

Received:2013-07-10 Revised:2013-12-19 Online:2014-04-04 Published:2014-04-28
Supported by:
Supported by the National Natural Science Foundation of China (21176014, 20990221, 21121064) and the Science-Technology Project for Supervisors of Excellent Doctor Degree Thesis of Beijing (20111001001).

Effects of Assistant Solvents and Mixing Intensity on the Bromination Process of Butyl Rubber

王伟^1,2, 邹海魁^1,, 初广文^1,2, 向阳¹, 彭晗¹, 陈建峰^1,2

1 Research Center of the Ministry of Education for High Gravity Engineering and Technology, Beijing University of Chemical Technology, Beijing 100029, China;
2 State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029, China

通讯作者: ZOU Haikui, CHEN Jianfeng
基金资助:
Supported by the National Natural Science Foundation of China (21176014, 20990221, 21121064) and the Science-Technology Project for Supervisors of Excellent Doctor Degree Thesis of Beijing (20111001001).

Abstract

Abstract: A slow bromination process of butyl rubber (IIR) suffers from low efficiency and low selectivity (S) of target-product. To obtain suitable approach to intensify the process, effects of assistant solvents and mixing intensity on the bromination process were systemically studied in this paper. The reaction process was found constantly accelerated with the increasing dosage and polarity of assistant solvent. Hexane with 30% (by volume) dichloromethane was found as the suitable solvent component, where the stable conversion of 1,4-isoprene transferring to target product (x_A1s) of 80.2% and the corresponding S of 91.2% were obtained in 5 min. The accelerated reaction process was demonstrated being remarkably affected by mixing intensity until the optimal stirring rate of 1100 r·min^-1 in a stirred tank reactor. With better mixing condition, a further intensification of the process was achieved in a rotating packed bed (RPB) reactor, where x_A1s of 82.6% and S of 91.9% were obtained in 2 min. The usage of the suitable solvent component and RPB has potential application in the industrial bromination process intensification.

Key words: bromination of butyl rubber, process intensification, assistant solvent, mixing intensity

摘要： A slow bromination process of butyl rubber (IIR) suffers from low efficiency and low selectivity (S) of target-product. To obtain suitable approach to intensify the process, effects of assistant solvents and mixing intensity on the bromination process were systemically studied in this paper. The reaction process was found constantly accelerated with the increasing dosage and polarity of assistant solvent. Hexane with 30% (by volume) dichloromethane was found as the suitable solvent component, where the stable conversion of 1,4-isoprene transferring to target product (x_A1s) of 80.2% and the corresponding S of 91.2% were obtained in 5 min. The accelerated reaction process was demonstrated being remarkably affected by mixing intensity until the optimal stirring rate of 1100 r·min^-1 in a stirred tank reactor. With better mixing condition, a further intensification of the process was achieved in a rotating packed bed (RPB) reactor, where x_A1s of 82.6% and S of 91.9% were obtained in 2 min. The usage of the suitable solvent component and RPB has potential application in the industrial bromination process intensification.

关键词: bromination of butyl rubber, process intensification, assistant solvent, mixing intensity

WANG Wei, ZOU Haikui, CHU Guangwen, XIANG Yang, PENG Han, CHEN Jianfeng. Effects of Assistant Solvents and Mixing Intensity on the Bromination Process of Butyl Rubber[J]. Chin.J.Chem.Eng., 2014, 22(4): 398-404.

王伟, 邹海魁, 初广文, 向阳, 彭晗, 陈建峰. Effects of Assistant Solvents and Mixing Intensity on the Bromination Process of Butyl Rubber[J]. Chinese Journal of Chemical Engineering, 2014, 22(4): 398-404.

References

1 Storey, R.F., Lee, Y., "Sulfonation of tert-alkyl chlorides: Application to the tert-chloride-terminated polyisobutylene system", J. Polym. Sci. Part A: Polym. Chem., 29 (3), 317-325 (1991).

2 Chu, C.Y., Vukov, R., "Determination of the structure of butyl rubber by NMR spectroscopy", Macromolecules, 18 (7), 1423-1430 (1985).

3 Gardner, I.J., Fusco, J.V., Newman, I.F., Kowalski, R.C., Davis, W.M., Baldwin, F.P., "Halogenated butyl rubber", U.S. Pat., 4632963 (1986).

4 Sumner, A., Kelbch, S., Verbiest, A., "Halogenated butyl rubbers having a low halogen content", U.S. Pat., 5886106 (1999).

5 Shan, B.T., "Preparation of bromobutyl rubber and characterization of its structure and property", Master Thesis, Beijing Univ. of Chem. Tech., Beijing (2010). (in Chinese)

6 Baade, W., Konigshofen, H., Kaszas, G., "Process for the bromination of alkyl rubbers", U.S. Pat., 5569723 (1996).

7 Liang, X.Y., Application Technology of Butyl Rubber, Chemical Industry Press, Beijing (2004). (in Chinese)

8 Parker, P.T., Baton, R.L., John, L., Bryan, J., "Continuous chlorination and bromination of butyl rubber", U.S. Pat., 3099644 (1963).

9 Kowalski, R.C., Davis, W.M., Newman, N.F., Foroulis, Z.A., Baldwin, F.P., "Extrusion process for preparing improved brominated butyl rubber", U.S. Pat., 4563506 (1986).

10 Kaszas, G., "Bromination of butyl rubber in the presence of electrophilic solvents and oxidizing agents", Rubber Chem. Technol., 73 (2), 356-365 (2000).

11 Irving, K., Roselle, P., Francis, P., Robert, M.T., George, E.S., Roselle, N.J., "Nitrogen cured halogenated butyl rubber compositions", U.S. Pat., 3104235 (1963).

12 Kenneth, W.P., Berkeley, H., Hsien, C.W., "Halogenation of star-branched butyl rubber with improved neutralization", U.S. Pat., 5286804 (1994).

13 Delmer, L.C., Highland Park, N.J., "Halogenation of low unsaturation rubbery polymers in the presence of oxidizing agent", U.S. Pat., 3018275 (1962).

14 Kaszas, G., "Kinetics and mechanism of the bromination of butyl rubber", Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.), 40, 579-580 (1999).

15 Yang, H.J., Chu, G.W., Zhang, J.W., Shen, Z.G., Chen, J.F., "Micromixing efficiency in a rotating packed bed: Experiments and simulation", Ind. Eng. Chem. Res., 44 (20), 7730-7737 (2005).

16 Chen, J.F., Zheng, C., Chen, G.T., "Interaction of macro- and micromixing on particle size distribution in reactive precipitation", Chem. Eng. Sci., 51 (10), 1957-1966 (1996).

17 Chen, J.F., Gao, H., Zou, H.K., Chu, G.W., Zhang, L., Shao, L., Xiang, Y., Wu, Y.X., "Cationic polymerization in rotating packed bed reactor: experimental and modeling", AIChE J., 56 (4), 1053-1062 (2010).

18 Chen, J.F., High Gravity Technology and Application—A New Generation of Reaction And Separation Technology, Chemical Industry Press, Beijing (2003). (in Chinese)

19 Yang, H.J., Chu, G.W., Xiang, Y., Chen, J.F., "Characterization of micromixing efficiency in rotating packed beds by chemical methods", Chem. Eng. J., 121 (2), 147-152 (2006).

20 Yang, K., Chu, G.W., Shao, L., Luo, Y., Chen, J.F., "Micromixing efficiency of rotating packed bed with premixed liquid distributor", Chem. Eng. J., 153 (1), 222-226 (2009).

21 Li, W.Y., Wu, W., Zou, H.K., Chu, G.W., Shao, L., Chen, J.F., "Process intensification of VOC removal from high viscous media by rotating packed bed", Chin. J. Chem. Eng., 17 (3), 389-393 (2009).

22 Li, W.Y., Wu, W., Zou, H.K., Chu, G.W., Shao, L., Chen, J.F., "A mass transfer model for devolatilization of highly viscous media in rotating packed bed", Chin. J. Chem. Eng., 18 (2), 194-201 (2010).

23 Xiang, Y., Wen, L.X., Chu, G.W., Shao, L., Xiao, G.T., Chen, J.F., "Modeling of the precipitation process in a rotating packed bed and its experimental validation", Chin. J. Chem. Eng., 18 (2), 249-257 (2010).

24 Zhang, L.L., Wang, J.X., Sun, Q., Zeng, X.F., Chen, J.F., "Removal of nitric oxide in rotating packed bed by ferrous chelate solution", Chem. Eng. J., 181, 624-629 (2012).

25 Cheng, D.M., Gardner, I.J., Wang, H.C., Frederick, C.B., Dekmezian, A.H., Hous, P., "Spectroscopic studies of the structures of butyl and bromobutyl rubbers", Rubber Chem. Technol., 63 (2), 265-275 (1990).

26 Chu, C.Y., Watson, K.N., Vukov, R., "Determination of the structure of chlorobutyl and bromobutyl rubber by NMR spectroscopy", Rubber Chem. Technol., 60 (4), 636-646 (1987).

27 Smith, M.B., March's Advanced Organic Chemistry: Reactions, Mechanisms, And Structure, John and Wiley Sons, Inc., New Jersey (2013).

[1]	Pengcheng Zou, Kai Wang. Methanolysis of amides under high-temperature and high-pressure conditions with a continuous tubular reactor [J]. Chinese Journal of Chemical Engineering, 2023, 58(6): 170-178.
[2]	Shuangfei Zhao, Yingying Nie, Wenyan Zhang, Runze Hu, Lianzhu Sheng, Wei He, Ning Zhu, Yuguang Li, Dong Ji, Kai Guo. Microfluidic field strategy for enhancement and scale up of liquid–liquid homogeneous chemical processes by optimization of 3D spiral baffle structure [J]. Chinese Journal of Chemical Engineering, 2023, 56(4): 255-265.
[3]	Yongbo Zhou, Yang Jin, Jun Li, Qinyan Wang, Ming Chen. Numerical study on the hydrodynamics behavior of a central insert microchannel [J]. Chinese Journal of Chemical Engineering, 2023, 53(1): 361-373.
[4]	Yang Han, Yuanyuan Liu, Shiwei Wang, Xuehui Ge, Xiaoda Wang, Ting Qiu. High-efficiency and safe synthesis of tonalid via two Friedel-Crafts reactions in continuous-flow microreactors [J]. Chinese Journal of Chemical Engineering, 2022, 52(12): 126-135.
[5]	Ye Wan, Wenhui Guo, Jin Xiao, Dazhou Yan, Xiong Zhao, Shuhu Guo, Jianhua Liu, Qifan Zhong, Tao Yang, Yu Zhao, Xin Chang, Xin Gao. Integrated UV-based photo microreactor-distillation technology toward process intensification of continuous ultra-high-purity electronic-grade silicon tetrachloride manufacture [J]. Chinese Journal of Chemical Engineering, 2020, 28(9): 2248-2255.
[6]	Rongrui Deng, Hao Xiao, Zhaoming Xie, Zuohua Liu, Qiang Yu, Geng Chen, Changyuan Tao. A novel method for extracting vanadium by low temperature sodium roasting from converter vanadium slag [J]. Chinese Journal of Chemical Engineering, 2020, 28(8): 2208-2213.
[7]	Yuan Pu, Lifeng Lin, Jun Liu, Jiexin Wang, Dan Wang. High-gravity-assisted green synthesis of rare-earth doped calcium molybdate colloidal nanophosphors [J]. Chinese Journal of Chemical Engineering, 2020, 28(6): 1744-1751.
[8]	Yazhao Liu, Zhi hao Li, Guangwen Chu, Lei Shao, Yong Luo, Jianfeng Chen. Liquid-solid mass transfer in a rotating packed bed reactor with structured foam packing [J]. Chinese Journal of Chemical Engineering, 2020, 28(10): 2507-2512.
[9]	Harrson S. Santana, Alan C. Rodrigues, Mariana G. M. Lopes, Felipe N. Russo, Jo?o L. Silva Jr, Osvaldir P. Taranto. 3D printed millireactors for process intensification [J]. Chinese Journal of Chemical Engineering, 2020, 28(1): 180-190.
[10]	Yumeng Zhang, Yudan Zhu, Anran Wang, Qingwei Gao, Yao Qin, Yaojia Chen, Xiaohua Lu. Progress in molecular-simulation-based research on the effects of interface-induced fluid microstructures on flow resistance [J]. Chinese Journal of Chemical Engineering, 2019, 27(6): 1403-1415.
[11]	Chunli Li, Cong Duan, Jing Fang, Hongshi Li. Process intensification and energy saving of reactive distillation for production of ester compounds [J]. Chinese Journal of Chemical Engineering, 2019, 27(6): 1307-1323.
[12]	Hong Li, Chuanhui Wu, Zhiqiang Hao, Xingang Li, Xin Gao. Process intensification in vapor-liquid mass transfer: The state-of-the-art [J]. Chinese Journal of Chemical Engineering, 2019, 27(6): 1236-1246.
[13]	Wei Deng, Xuan He, Chao Zhang, Yunyi Gao, Xuedong Zhu, Kake Zhu, Qisheng Huo, Zhijie Zhou. Promoting Xylene Production in Benzene Methylation using Hierarchically Porous ZSM-5 Derived from a Modified Dry-gel Route [J]. Chin.J.Chem.Eng., 2014, 22(8): 921-929.
[14]	Andreas Harwardt, Korbinian Kraemer, Bettina Rüngeler, Wolfgang Marquardt. Conceptual Design of a Butyl-levulinate Reactive Distillation Process by Incremental Refinement [J]. , 2011, 19(3): 371-379.
[15]	ZHANG Wei. A Review of Techniques for the Process Intensification of Fluidized Bed Reactors [J]. , 2009, 17(4): 688-702.

Effects of Assistant Solvents and Mixing Intensity on the Bromination Process of Butyl Rubber

Effects of Assistant Solvents and Mixing Intensity on the Bromination Process of Butyl Rubber

PDF (PC)

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments