Simulation and Optimization in the Process of Toluene Liquid-phase Catalytic Oxidation

摘要/Abstract

摘要： Liquid-phase oxidation of toluene with air has become the main technology for producing benzoic acid in a reactor at present. Based on the kinetic model of the toluene oxidation process obtained from laboratory and mass balance of key component, a novel model is established to simulate the industrial toluene oxidation process, in which the effects of benzaldehyde and benzyl alcohol are considered and the kinetic parameters are revised by industrial data. The simulation results show that the error of benzoic acid yield is within 3.5%. Based on the simulation model, to maximize the benzoic acid yield, an optimization model is proposed to optimize the operating parameters, including toluene feed-in mass flux and temperature. The optimization result indicates that on the allow-able operating conditions, the maximum benzoic acid yield obtained with the reaction temperature at 167.2℃ and the mass flux at 104.1 t·h^-1 is greater than the current one, which can be used to guide industrial reactor’s operation.

关键词: toluene, benzoic acid, catalytic oxidation, simulation, optimization

Abstract: Liquid-phase oxidation of toluene with air has become the main technology for producing benzoic acid in a reactor at present. Based on the kinetic model of the toluene oxidation process obtained from laboratory and mass balance of key component, a novel model is established to simulate the industrial toluene oxidation process, in which the effects of benzaldehyde and benzyl alcohol are considered and the kinetic parameters are revised by industrial data. The simulation results show that the error of benzoic acid yield is within 3.5%. Based on the simulation model, to maximize the benzoic acid yield, an optimization model is proposed to optimize the operating parameters, including toluene feed-in mass flux and temperature. The optimization result indicates that on the allow-able operating conditions, the maximum benzoic acid yield obtained with the reaction temperature at 167.2℃ and the mass flux at 104.1 t·h^-1 is greater than the current one, which can be used to guide industrial reactor’s operation.

Key words: toluene, benzoic acid, catalytic oxidation, simulation, optimization

张玉坤, 李初福, 何小荣, 陈丙珍. Simulation and Optimization in the Process of Toluene Liquid-phase Catalytic Oxidation[J]. Chinese Journal of Chemical Engineering, 2008, 16(1): 36-38.

ZHANG Yukun, LI Chufu, HE Xiaorong, CHEN Bingzhen. Simulation and Optimization in the Process of Toluene Liquid-phase Catalytic Oxidation[J]. Chin.J.Chem.Eng., 2008, 16(1): 36-38.

参考文献

1 Wei, W.D., Encyclopedia of Organic Chemical Materials, Chemical Industry Press, Beijing (1999). (in Chinese)

2 Wu, X.G., Chen, S.F., “Synthesis and refining of benzoic acid”, Mod. Chem. Ind., 20 (8), 10-14 (2000).

3 Bhattacharya, D., Guba, D.K., Rooy, N.H., “Liquid phase air-oxidation of toluene to benzoic acid (II) Kinetics and mechanism”, Chemical Age of India, 24 (2), 87-90 (1973).

4 Yu, Z., “Dynamic simulation for reactor process of preparation benzoic acid by oxidation of toluene”, Ph.D. Thesis, Beijing University of Chemical Technology, Beijing (2003). (in Chinese)

5 Tang, S.W., “An investigation on the liquid phase oxidation of toluene by air”, Ph.D. Thesis, Sichuan University, Chengdu (2005).

6 Borgaonkar, H.V., Raverkar, S.R., Chandalla, S.B., “Liquid-phase air oxidation of toluene to benzaldehyde by air”, Ind. Eng. Chem. Prod. Res. Dev., 23, 455-458 (1984).

7 Wang, Z.Y., Zhang, Y.X., “Liquid-phase oxidation of toluene to benzoic acid”, Heilongjiang Petrochemicals, 7, 1-3 (1996). (in Chinese)

8 Guo, C.C., Liu, Q., Wang, X.T., Hu, H.Y., “Selective liquid phase oxidation of toluene with air”, Appl.Catal. A. Gen., 282, 55-59 (2005).

9 Kantam, M.L., Sreekanth, P., Rao, K.K., Kumar, T.P., Rao, B.P.C., Choudary, B.M., “An improved process for selective liquid-phase air oxidation of toluene”, Catal. Lett., 81, 223-232 (2002).

10 Li, M.S., Zhang, Z.J., Ma, Y.X., “Liquid phase oxidation of toluene to benzoic acid and benzaldehyde”, J. Lanzhou Univ., 1, 89-94 (1981). (in Chinese)

11 Morimoto, T., Ogata, Y., “Kinetics of the autoxidation of toluene catalysed by cobaltic acetate”, J. Chem. Soc. (B), 1, 62-66 (1967).

12 Morimoto, T., Ogata, Y., “Kinetics of the autoxidation of toluene catalysed by cobaltic acetate (II) Effects of benzaldehyde, cobalt, and substituent”, J. Chem. Soc. (B): Phys. Org., 12, 1353-1357 (1967).

13 Scott, E., Chester, W., “Kinetics of the cobalt-catalyzed autoxidation of toluene in acetic acid—The role of cobalt”, J. Phys. Chem., 76 (11), 1520-1524 (1972).

14 Milani-Nejad, F., “Kinetic studies of the catalytic oxidation of toluene to benzoic acid in the liquid phase”, Iran. J. Chem. Chem. Eng., 16 (1), 8-9 (1997).

15 Tang, S.W., Liang, B., Wu, P., Zhang, Q.Z., Liu, C.J., “Kinetics of liquid-phase oxidation of toluene to benzoic acid by air”, Chem. React. Eng. Technol., 21 (1), 333-339 (2005).

16 Lozar, J., Falgayrac, G., Savall, A., “Kinetics of the electrochemically assisted autoxidation of toluene in acetic acid”, Ind. Eng. Chem. Res., 40, 6055-6062 (2001).

17 Hanotier, J., Hanotier-Bridoux, M., “Mechanism of the liquid phase homogeneous oxidation of alkylaromatic hydrocarbons by cobalt salts”, J. Mol. Catal., 12, 133-147 (1981).

18 Tang, S.W., Liu, C.J., Wu, P., Zhang, Q.Z., Liang, B., “Effects of operation parameters on liquid-phase oxidation of toluene by air”, Petrochem. Technol., 34 (2), 116-121 (2005).

19 Czytko, M.P., Bub, G.K., “Oxidation of toluene by cobalt (III) Acetate in acetic acid solutions-influence of water”, Ind. Eng. Chem. Prod. Res. Dev., 20, 481-486 (1981).

20 Li, Y.F., Yan, X.H., Jiang, G.F., Liu, Q., Song, J.X., Guo, C.C., “Toluene oxyfunctionalization with air over metalloporphyrins and reaction condition optimization”, Chin. J. Chem. Eng., 15 (3), 453-457 (2007).

[1]	Chuang Liang, Zhihao Liu, Baochang Sun, Haikui Zou, Guangwen Chu. Improvement in discharge characteristics and energy yield of ozone generation via configuration optimization of a coaxial dielectric barrier discharge reactor[J]. 中国化学工程学报, 2023, 60(8): 61-68.
[2]	Jiahao Xing, Huaizhi Han, Ruitian Yu, Wen Luo. Numerical simulation of flow and heat transfer of n-decane in sub-millimeter spiral tube at supercritical pressure[J]. 中国化学工程学报, 2023, 60(8): 173-185.
[3]	Jindong Dai, Chi Zhai, Jiali Ai, Guangren Yu, Haichao Lv, Wei Sun, Yongzhong Liu. A cellular automata framework for porous electrode reconstruction and reaction-diffusion simulation[J]. 中国化学工程学报, 2023, 60(8): 262-274.
[4]	Lijuan Zhao, Zhe Tan, Xiaoguang Zhang, Qijun Zhang, Wei Wang, Qiang Deng, Jie Ma, De'an Pan. Research on process modeling and simulation of spent lead paste desulfurization enhanced reactor[J]. 中国化学工程学报, 2023, 60(8): 293-303.
[5]	Jian Han, Xinhua Liu, Shanwei Hu, Nan Zhang, Jingjing Wang, Bin Liang. Optimization of decoupling combustion characteristics of coal briquettes and biomass pellets in household stoves[J]. 中国化学工程学报, 2023, 59(7): 182-192.
[6]	Yaran Bu, Changchun Wu, Lili Zuo, Qian Chen. The calculation and optimal allocation of transmission capacity in natural gas networks with MINLP models[J]. 中国化学工程学报, 2023, 59(7): 251-261.
[7]	Danlei Chen, Yiqing Luo, Xigang Yuan. Cascade refrigeration system synthesis based on hybrid simulated annealing and particle swarm optimization algorithm[J]. 中国化学工程学报, 2023, 58(6): 244-255.
[8]	Wende Tian, Jiawei Zhang, Zhe Cui, Haoran Zhang, Bin Liu. Microscopic mechanism study and process optimization of dimethyl carbonate production coupled biomass chemical looping gasification system[J]. 中国化学工程学报, 2023, 58(6): 291-305.
[9]	Huan-Huan Yin, Yin-Lei Han, Xiao Yan, Yi-Xin Guan. Proanthocyanidins prevent tau protein aggregation and disintegrate tau filaments[J]. 中国化学工程学报, 2023, 57(5): 63-71.
[10]	Chenyang Zhao, Yinhan Cheng, Guangfei Qu, Yongheng Yuan, Fenghui Wu, Ye Liu, Shan Liu, Junyan Li, Ping Ning. High-performance liquid-phase catalytic purification of phosphine in tail gas using Pd(II)/Cu(II) composite[J]. 中国化学工程学报, 2023, 57(5): 98-108.
[11]	Jixiang Liu, Xin Zhou, Gengfei Yang, Hui Zhao, Zhibo Zhang, Xiang Feng, Hao Yan, Yibin Liu, Xiaobo Chen, Chaohe Yang. Conceptual carbon-reduction process design and quantitative sustainable assessment for concentrating high purity ethylene from wasted refinery gas[J]. 中国化学工程学报, 2023, 57(5): 290-308.
[12]	Shengfeng Luo, Song Zhang, Yiping Zeng, Hui Zhang, Lili Zheng, Zhaopeng Xu. Study on oxygen transport and titanium oxidation in coating cracks under parallel gas flow based on LBM modelling[J]. 中国化学工程学报, 2023, 56(4): 15-24.
[13]	Peiyin Chen, Yanxiong Fang, Kaihong Xie, Yao Chen, Yang Liu, Hongliang Zuo, Weijian Lu, Baoyu Liu. Lacunary silicotungstic heteropoly salts as high-performance catalysts in oxidation of cyclopentene[J]. 中国化学工程学报, 2023, 56(4): 152-159.
[14]	Jikai Dong, Bing Wang, Xinjie Wang, Chenxi Cao, Shikuan Chen, Wenli Du. Optimization of sensor deployment sequences for hazardous gas leakage monitoring and source term estimation[J]. 中国化学工程学报, 2023, 56(4): 169-179.
[15]	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]. 中国化学工程学报, 2023, 56(4): 255-265.