Global multi-objective optimization of trimethyl orthoformate-acetic acid extractive distillation

doi:10.11949/0438-1157.20220747

Abstract

Abstract:

The highest azeotrope exists between the reactant trimethyl orthoformate (TMOF) and the product acetic acid (HAc) in the production of 3- (methoxy methotenyl) - 2 (3H) benzofuranone, which leads to the accumulation of reactants and the loss of raw materials and is not conducive to the forward reaction. For TMOF-HAc system, vapor-liquid equilibrium was calculated and analyzed by Hayden-O'Connell's UNIFAC group contribution method with modified fugability coefficient. After error verification, NRTL-HOC model was used as the basis of simulation distillation. The azeotrope can be separated by empirical extractive distillation. The entrainment performance of HAc with N-methyl acetamide (NMA) and N-methyl pyrrolidone (NMP) was compared, and NMP was selected as the extractant. Conventional extractive distillation (CED), side-stream (liquid) extractive distillation (SED) and extractive dividing-wall column (EDWC) were designed with the objective of molar purity of system recovered components, reboiler thermal load (Q) and annual total cost (TAC). Sensitivity analysis was used to adjust the parameters of the three processes in advance. Based on the multi-objective constraints, the optimal parameter range was divided as the initial data of Box-Behnken response surface method (BBD-RSM) optimization, and then the global optimization of the three processes was further conducted by BBD within the specified range. The most economical scheme was formulated by optimizing the data regression multi-objective equation, and the mole purity was 99.8% HAc and 99.9% TMOF. The results show that EDWC and SED can save more economic input and reboiler heat load than CED under the same separation purity condition. SED can save 10.37% TAC and 6.88% heat load, and EDWC can save 10.65% TAC and 10.53% heat load. The results show that there is a good fitting relationship between the predicted value and the actual value, and the prediction errors of TAC and Q by CED, SED and EDWC are all less than 1%. All three process schemes can provide theoretical basis for actual chemical production.

Key words: azeotrope, computer simulation, economics, group contribution method, extractive distillation, multi-objective optimization

摘要：

在生产杀菌剂嘧菌酯中间体过程中，反应物原甲酸三甲酯（TMOF）与生成物醋酸（HAc）发生共沸，导致反应物堆积和原料损耗。为解决共沸物分离问题，使用Hayden-O'Connell修正的UNIFAC基团贡献法研究其汽液平衡，设计常规萃取精馏（CED）、侧线萃取精馏（SED）、隔壁塔萃取精馏（EDWC）三种工艺，以分离组分摩尔纯度、再沸器热负荷（Q）、年度总费用（TAC）为目标，运用灵敏度耦合箱线图响应面法（S-BBD）对三种工艺参数分别优化。结果表明，优化方法预测值与实际值存在较优拟合关系， CED、SED、EDWC对TAC和Q的预测误差均不超过1%。分离纯度相同时，SED较CED节约10.37%TAC和6.88%热负荷，EDWC较CED节约10.65%TAC和10.53%热负荷，三种工艺方案均可为化工实际生产提供理论基础。

关键词: 共沸物, 计算机模拟, 经济, 基团贡献法, 萃取精馏, 多目标优化

CLC Number:

TQ 028.3

Xu LIU, Songlin XU, Yanfei WANG. Global multi-objective optimization of trimethyl orthoformate-acetic acid extractive distillation[J]. CIESC Journal, 2022, 73(10): 4518-4526.

柳旭, 许松林, 王燕飞. 原甲酸三甲酯-醋酸萃取精馏全局多目标优化[J]. 化工学报, 2022, 73(10): 4518-4526.

Figures/Tables 17

Table 1 UNIFAC group volume RK and group surface area QK

基团	R_K	Q_K
CH—	0.4469	0.228
CH₃O—	1.1450	1.088
CH₃—	0.9011	0.848
COOH—	1.3013	1.224

Table 2 Interaction parameters of UNIFAC groups

基团	CH—	CH₃O—	CH₃—	COOH—
CH—	0	251.5	0	663.5
CH₃O—	83.36	0	83.36	664.6
CH₃—	0	251.5	0	663.5
COOH—	315.3	-338.5	315.3	0

Table 3 HAc-TMOF vapor-liqid equilibrium data of UNIFAC group contribution method

温度/K	x₁	x₂	y₁	y₂	γ₁	γ₂
391.581	0.98	0.02	0.99	0.01	0.9998	0.5819
391.985	0.96	0.04	0.97	0.03	0.9990	0.5972
392.366	0.94	0.06	0.96	0.04	0.9977	0.6128
392.721	0.92	0.08	0.94	0.06	0.9960	0.6285
393.046	0.90	0.10	0.93	0.07	0.9936	0.6444
393.336	0.88	0.12	0.91	0.09	0.9908	0.6605
393.589	0.86	0.14	0.89	0.11	0.9874	0.6766
393.833	0.70	0.30	0.66	0.34	0.9399	0.8057
393.605	0.68	0.32	0.63	0.37	0.9314	0.8215
392.557	0.62	0.38	0.52	0.48	0.9027	0.8673
389.704	0.52	0.48	0.35	0.65	0.8452	0.9376
386.690	0.44	0.56	0.23	0.77	0.7933	0.9856
385.882	0.42	0.58	0.21	0.79	0.7800	0.9961
374.159	0.06	0.94	0.01	0.99	0.9008	1.0118
373.763	0.04	0.96	0.01	0.99	1.0038	1.0060

Fig.1 T-xy diagram of TMOF-HAc at different pressures

Fig.2 x-y diagram of HAc with/without extractant

Table 4 CED sensitivity analysis process parameters range and results

N_T	R	N_F	S	N_S	N_T′	N_F′	R′
25~35	0.4~1.0	9~13	0.8~1.6	4~8	20~30	6~12	2.5~3.5

Table 5 CED process parameters optimization results

N_T	S	R	N_F	N_S	N_T′	N_F′	R′
34	1.02	0.40	13	6	20	7	2.50

Fig.3 Schematic diagram of lateral extraction distillation process

Table 6 Process parameters range and results of SED sensitivity analysis

N₁	R₁	N_A	S₁	N	L/(kmol/h)	N_L	N₂	N_A′	R₂
36~40	0.4~0.6	8~10	1.0~1.2	5~7	80~100	30~34	16~20	6~10	1.4~2.5

Table 7 Optimization results of SED process parameters

N₁	S₁	R₁	N	N_A	L/(kmol/h)	N_L	N₂	$N A'$	R₂
37	1.01	0.42	7	8	83	31	17	6	1.47

Table 7 Optimization results of SED process parameters

N₁	S₁	R₁	N	N_A	L/(kmol/h)	N_L	N₂	$N A'$	R₂
37	1.01	0.42	7	8	83	31	17	6	1.47

Fig.4 TAC response curve and coutour of L and NL changes

Fig.5 Process diagram of EDWC

Table 8 Process parameters range and results of EDWC sensitivity analysis

N_M	R_W	N_W	S_W	$N W'$	V/(kmol/h)	N_V	N_R
38~40	0.3~0.5	9~11	0.85~1.00	5~7	60~70	28~30	16~20

Table 8 Process parameters range and results of EDWC sensitivity analysis

N_M	R_W	N_W	S_W	$N W'$	V/(kmol/h)	N_V	N_R
38~40	0.3~0.5	9~11	0.85~1.00	5~7	60~70	28~30	16~20

Fig.6 TAC response curve and coutour of V and NV changes

Fig.7 MC tray position and component molar fraction curve

Table 9 Optimization results of EDWC process parameters

N_M	S_W	R_W	N_W	$N W'$	V/(kmol/h)	N_V	N_R
38	0.88	0.38	11	6	65	29	18

Table 9 Optimization results of EDWC process parameters

N_M	S_W	R_W	N_W	$N W'$	V/(kmol/h)	N_V	N_R
38	0.88	0.38	11	6	65	29	18

Table 11 Optimization results of BBD response surface

工艺	响应值	平方和	自由度	均方	F值	R²
CED	TMOF 摩尔纯度	3.00×10^-4	44	7.11×10^-6	46.16	0.96
	HAc 摩尔纯度	3.60×10^-3		1.00×10^-4	18.86	0.92
	NMP 摩尔纯度	1.00×10^-4		3.24×10^-6	21.46	0.93
	TAC	5.90×10¹¹		1.34×10¹⁰	9.84	0.85
	Q	8.24×10⁶		1.03×10⁶	74.75	0.85
SED	TMOF 摩尔纯度	8.00×10^-4	65	0	13.32	0.89
	HAc 摩尔纯度	7.00×10^-3		1.00×10^-4	6.91	0.81
	NMP 摩尔纯度	7.00×10^-4		0	7.92	0.83
	TAC	3.38×10¹¹		5.20×10⁹	337.24	0.99
	Q	4.65×10⁶		7.15×10⁴	344.64	0.99
EDWC	TMOF 摩尔纯度	2.00×10^-4	44	4.19×10^-6	21.84	0.97
	HAc 摩尔纯度	1.00×10^-3		0	20.45	0.97
	NMP 摩尔纯度	0		5.49×10^-7	78.61	0.99
	TAC	5.97×10¹⁰		1.36×10⁹	10.80	0.94
	Q	7.08×10⁵		1.61×10⁴	11.28	0.94

References 34

1	Venkatesan V, Viswanathan K S. Conformations of trimethoxymethane: matrix isolation infrared and ab initio studies[J]. Journal of Molecular Structure, 2010, 973(1/2/3): 89-95.
2	Teloxa S F, Kennington S C D, Camats M, et al. Direct, enantioselective, and nickel(Ⅱ) catalyzed reactions of N-azidoacetyl thioimides with trimethyl orthoformate: a new combined methodology for the rapid synthesis of lacosamide and derivatives[J]. Chemistry - A European Journal, 2020, 26(50): 11540-11548.
3	Kariofillis S K, Shields B J, Tekle-Smith M A, et al. Nickel/photoredox-catalyzed methylation of (hetero)aryl chlorides using trimethyl orthoformate as a methyl radical source[J]. Journal of the American Chemical Society, 2020, 142(16): 7683-7689.
4	Shan J J, Li M W, Allard L F, et al. Mild oxidation of methane to methanol or acetic acid on supported isolated rhodium catalysts[J]. Nature, 2017, 551(7682): 605-608.
5	Balba H. Review of strobilurin fungicide chemicals[J]. Journal of Environmental Science and Health, Part B, 2007, 42(4): 441-451.
6	许标. 3-(α-甲氧基)甲烯基苯并呋喃-2(3H)-酮的合成[J]. 山东化工, 2017, 46(17): 42-43.
	Xu B. Synthesis of 3-(α-methoxy) methylenebezofuran-2(3H)-ketone[J]. Shandong Chemical Industry, 2017, 46(17): 42-43.
7	杨朋. 杀菌剂嘧菌酯的合成和工艺优化[D]. 杭州: 浙江工业大学, 2013.
	Yang P. Process optimization on the synthesis of fungicide azoxystrobin[D]. Hangzhou: Zhejiang University of Technology, 2013.
8	刘长庆, 徐小兵, 黄显超, 等. 一种甲氧基苯并呋喃酮的分离提纯工艺: 109651316A[P]. 2019-04-19.
	Liu C Q, Xu X B, Huang X C, et al. Separation and purification process of methoxyl benzofuranone: 109651316A[P]. 2019-04-19.
9	黄显超, 徐小兵, 程伟家, 等. 一种甲氧基苯并呋喃酮的合成方法: 109678825A[P]. 2019-04-26.
	Huang X C, Xu X B, Cheng W J, et al. Synthesis method of methoxybenzofuranone: 109678825A[P]. 2019-04-26.
10	Fredenslund A, Jones R L, Prausnitz J M. Group-contribution estimation of activity coefficients in nonideal liquid mixtures[J]. AIChE Journal, 1975, 21(6): 1086-1099.
11	Wittig R, Lohmann J, Gmehling J. Vapor-liquid equilibria by UNIFAC group contribution.6. Revision and extension[J]. Industrial & Engineering Chemistry Research, 2003, 42(1): 183-188.
12	Kamesh R, Kumari A, Rani K Y. Measurements, correlations, and modified UNIFAC predictions of isobaric vapor-liquid equilibrium data for the binary system of dimethyl carbonate + anisole at different pressures[J]. Journal of Chemical & Engineering Data, 2021, 66(10): 3788-3801.
13	张莘, 高伟, 齐鸣, 等. 基于多目标优化精馏系统综述[J]. 化工进展, 2019, 38(S1): 1-9.
	Zhang S, Gao W, Qi M, et al. A review of optimization rectification systems based on multi-objective[J]. Chemical Industry and Engineering Progress, 2019, 38(S1): 1-9.
14	Weerachaipichasgul W, Wanwongka A, Saengdaw S, et al. Response surface methodology to evaluate energy in extractive distillation process for the mixture of methylal and methanol with glycerol as entrainer[J]. Journal of Engineering Science and Technology, 2021, 16(5): 4235-4249.
15	杨涛, 李肖, 宁阳坤, 等. 双塔精馏回收环己醇工艺模拟与优化[J]. 现代化工, 2017, 37(8): 195-199.
	Yang T, Li X, Ning Y K, et al. Simulation and optimization of cyclohexanol recovery by twin towers distillation[J]. Modern Chemical Industry, 2017, 37(8): 195-199.
16	肖武, 李明月, 阮雪华, 等. 响应面法优化一水硫酸氢钠流化催化精馏生产乙酸乙酯工艺条件[J]. 化工学报, 2014, 65(11): 4465-4471.
	Xiao W, Li M Y, Ruan X H, et al. Optimization of ethyl acetate process conditions for sodium bisulfate fluidized catalytic distillation using response surface methodology[J]. CIESC Journal, 2014, 65(11): 4465-4471.
17	Liang J, Wang H H, Wang Z, et al. Optimal separation of acetonitrile and pyridine from industrial wastewater[J]. Chemical Engineering Research and Design, 2021, 169: 54-65.
18	黄国强, 靳权. 隔壁精馏塔的设计、模拟与优化[J]. 天津大学学报(自然科学与工程技术版), 2014, 47(12): 1057-1064.
	Huang G Q, Jin Q. Design, simulation and optimization of divided wall column[J]. Journal of Tianjin University(Science and Technology), 2014, 47(12): 1057-1064.
19	Patrut C, Udrea E C, Bildea C S. Sepation of water-acetic acid mixtures by cyclic distillation[J]. Chemistry and Materials Science, 2018, 80(4): 49-66.
20	Bishop K, O'Connell J P. Aqueous cross second virial coefficients with the correlation[J]. Industrial & Engineering Chemistry Research, 2005, 44(3): 630-633.
21	魏静, 解新安, 丁年平, 等. UNIFAC基团贡献法研究及应用进展[J]. 当代化工, 2008, 37(6): 659-665.
	Wei J, Xie X N, Ding N P, et al. The development of research and applications for UNIFAC group contribution method[J]. Contemporary Chemical Industry, 2008, 37(6): 659-665.
22	郭天民, 钟银珠, 李再琮. 四种活度系数模型在汽液平衡和精馏计算中的应用和比较[J]. 化工学报, 1980, 31(2): 173-190.
	Guo T M, Zhong Y Z, Li Z C. The application and comparison of four activity coefficient models in vapor-liquid equilibrium and distillation calculations[J]. Journal of Chemical Industry and Engineering (China), 1980, 31(2): 173-190.
23	商文砚. 以离子液体为萃取剂萃取精馏分离甲醇-乙酸甲酯共沸物[D]. 天津: 天津大学, 2019.
	Shang W Y. Extractive distillation for azeotropic mixture of methanol and methyl acetate with ionic liquids as solvent[D]. Tianjin: Tianjin University, 2019.
24	Shan B M, Zheng Q, Chen Z R, et al. Dynamic control and performance comparison of conventional and dividing wall extractive distillation for benzene/isopropanol/water separation[J]. Journal of the Taiwan Institute of Chemical Engineers, 2021, 128: 73-86.
25	张莉平. 醋酸废水萃取精馏研究[D]. 杭州: 浙江大学, 2020.
	Zhang L P. Study on the extractive distillation of acetic acid wastewater[D]. Hangzhou: Zhejiang University, 2020.
26	王萌萌, 吴莉莉, 陈学梅. N-甲基吡咯烷酮分离醋酸-水体系微观机理分析[J].化学工程与装备, 2016(7): 21-26.
	Wang M M, Wu L L, Chen X M. Microscopic mechanism analysis of N-methylpyrrolidone separation system of acetic acid-water[J]. Chemical Engineering & Equipment, 2016(7): 21-26.
27	平丽娟, 彭勇, 毛建卫. 26.67kPa下醋酸-水-N-甲基吡咯烷酮体系汽液相平衡的研究[J]. 高校化学工程学报, 2011, 25(4): 554-558.
	Ping L J, Peng Y, Mao J W. Vapor-liquid equilibria of acetic acid-water-N-methylpyrrolidone system at 26.67kPa[J]. Journal of Chemical Engineering of Chinese Universities, 2011, 25(4): 554-558.
28	You X Q, Gu J L, Peng C J, et al. Optimal design of extractive distillation for acetic acid dehydration with N-methyl acetamide[J]. Chemical Engineering and Processing-Process Intensification, 2017, 120: 301-316.
29	Cui F G, Cui C T, Sun J S. Simultaneous optimization of heat-integrated extractive distillation with a recycle feed using pseudo transient continuation models[J]. Industrial & Engineering Chemistry Research, 2018, 57(45): 15423-15436.
30	Luyben W L. Comparison of extractive distillation and pressure-swing distillation for acetone/chloroform separation[J]. Computer & Chemical Engineering, 2013, 50: 1-7.
31	Wang C, Guang C, Cui Y, et al. Compared novel thermally coupled extractive distillation sequences for separating multi-azotropic mixture of acetonitrile/benzene/methanol[J]. Chemical Engineering Research and Design, 2018, 136: 513-528.
32	叶贞成, 倪泽雨, 程辉. 一种改进的分隔壁精馏塔简捷计算方法[J]. 华东理工大学学报(自然科学版), 2021, 47(1): 26-34.
	Ye Z C, Ni Z Y, Cheng H. An improved shortcut design method for dividing wall column[J]. Journal of East China University of Science and Technology, 2021, 47(1): 26-34.
33	Ling H, Qiu J, Hua T, et al. Remixing analysis of four-product dividing-wall columns[J]. Chemical Engineering & Technology, 2018, 41(7): 1359-1367.
34	Yu H, Ye Q, Xu H, et al. Design and control of dividing-wall column for tert-butanol dehydration system via heterogeneous azeotropic distillation[J]. Industrial & Engineering Chemistry Research, 2015, 54(13): 3384-3397.

[1]	Zhewen CHEN, Junjie WEI, Yuming ZHANG. System integration and energy conversion mechanism of the power technology with integrated supercritical water gasification of coal and SOFC [J]. CIESC Journal, 2023, 74(9): 3888-3902.
[2]	Lizhi WANG, Qiancheng HANG, Yeling ZHENG, Yan DING, Jiaji CHEN, Qing YE, Jinlong LI. Separation of methyl propionate + methanol azeotrope using ionic liquid entrainers [J]. CIESC Journal, 2023, 74(9): 3731-3741.
[3]	Yuanchao LIU, Bin GUAN, Jianbin ZHONG, Yifan XU, Xuhao JIANG, Duan LI. Investigation of thermoelectric transport properties of single-layer XSe₂(X=Zr/Hf) [J]. CIESC Journal, 2023, 74(9): 3968-3978.
[4]	Zhaolun WEN, Peirui LI, Zhonglin ZHANG, Xiao DU, Qiwang HOU, Yegang LIU, Xiaogang HAO, Guoqing GUAN. Design and optimization of cryogenic air separation process with dividing wall column based on self-heat regeneration [J]. CIESC Journal, 2023, 74(7): 2988-2998.
[5]	Yuanzhe SHAO, Zhonggai ZHAO, Fei LIU. Quality-related non-stationary process fault detection method by common trends model [J]. CIESC Journal, 2023, 74(6): 2522-2537.
[6]	Shanghao LIU, Shengkun JIA, Yiqing LUO, Xigang YUAN. Optimization of ternary-distillation sequence based on gradient boosting decision tree [J]. CIESC Journal, 2023, 74(5): 2075-2087.
[7]	Mujin LI, Song HU, Depan SHI, Peng ZHAO, Rui GAO, Jinlong LI. A process for offgas absorption and purification of 1,2-butylene oxide [J]. CIESC Journal, 2023, 74(4): 1607-1618.
[8]	Sheng’an ZHANG, Guilian LIU. Multi-objective optimization of high-efficiency solar water electrolysis hydrogen production system and its performance [J]. CIESC Journal, 2023, 74(3): 1260-1274.
[9]	Nini YUAN, Tuo GUO, Hongcun BAI, Yurong HE, Yongning YUAN, Jingjing MA, Qingjie GUO. Reaction process of CH₄ on the surface of Fe₂O₃/Al₂O₃ oxygen carrier in chemical looping combustion: ReaxFF-MD simulation [J]. CIESC Journal, 2022, 73(9): 4054-4061.
[10]	Weiwei LIU, Guomin CUI, Lu ZHANG, Yuan XIAO, Qiguo YANG, Guanhua ZHANG. Damping optimization method for heat exchange network synthesis [J]. CIESC Journal, 2022, 73(5): 2060-2072.
[11]	Qiwang HOU, Zhaolun WEN, Zhonglin ZHANG, Yegang LIU, Jingxuan YANG, Dongliang CHEN, Xiaogang HAO, Guoqing GUAN. Design and evaluation of a coal-based polygeneration system with carbon cycle [J]. CIESC Journal, 2022, 73(5): 2073-2082.
[12]	Qucheng LIN, Zuwei LIAO. Multi-objective optimization of work and heat exchange networks based on a decomposition algorithm [J]. CIESC Journal, 2022, 73(11): 5047-5055.
[13]	Kefan ZHAO, Shengkun JIA, Yiqing LUO, Xigang YUAN. Optimal design for dividing wall column using online Kriging surrogate model-based optimization method [J]. CIESC Journal, 2022, 73(1): 332-341.
[14]	WANG Zhaoqi, LI Mengshan, HU Haitao, WEI Wenjian. Development of simulation model for double row folded microchannel heat exchanger [J]. CIESC Journal, 2021, 72(S1): 113-119.
[15]	Yegang LIU, Zhonglin ZHANG, Qiwang HOU, Jingxuan YANG, Dongliang CHEN, Xiaogang HAO. Process design and simulation of synthesis gas to methanol in TBCFB system [J]. CIESC Journal, 2021, 72(9): 4838-4846.