酯交换法制备醋酸正丁酯的催化精馏实验研究及过程模拟
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摘要
醋酸甲酯(MeOAc)作为一种化工原料,其主要用途是作为硝基纤维素和醋酸纤维素的快干性溶剂;还可以作为油漆涂料、人造革和香料制造的原料以及用作油脂的萃取剂等,但与同族其它酯类相比,其需求量不是很大。它在工业生产中,往往作为副产品大量出现,如聚乙烯醇(PVA)生产过程中有大量的副产物醋酸甲酯,据估计,每生产一吨PVA将副产1.5～1.7吨的醋酸甲酯。目前,PVA生产厂家均采用将其水解生成醋酸和甲醇的方法加以利用,因醋酸和甲醇可用作生产PVA的原料。醋酸正丁酯为无色透明液体,是重要的有机溶剂、萃取剂和脱水剂,在工业上用途广泛。本文采用酯交换法将醋酸甲酯转化为醋酸丁酯,可以为醋酸甲酯提供一种效益更高的利用方法。
本论文对反应动力学进行实验研究,计算出活化能及指前因子,为后续的精馏实验及模拟提供依据。通过催化精馏实验,改变操作条件,考察进料方式、进料组成、回流比及进料总量等操作条件的变化对醋酸甲酯转化率的影响,并根据结果选择最优的操作条件。在实验范围内,催化精馏过程适宜的操作条件为:回流比10;进料醇酯摩尔比3:1;进料总量22mol/h;进料采用重组分正丁醇在反应段上部进料,轻组分醋酸甲酯在反应段下部进料。
借助ASPEN PLUS软件对反应精馏制醋酸正丁酯的过程进行模拟计算,将模拟值与实验值进行对比,从而验证计算的可靠性。进一步模拟优化,以模拟计算结果为依据,为后续的实验研究提供指导依据。结果显示,该模拟结果与实验值的相对误差最大不超过8%,在可接受范围内,故认为模拟值是可靠的。分别改变正丁醇和醋酸甲酯的进料位置,结果表明,反应段的长度越大转化率越高。增加反应段的理论塔板数,在实际实验中则表现为反应段与填料段交叉排列,能提高醋酸甲酯的转化率。
As a chemical raw material methyl acetate (MeOAc) mainly is used as a fast-drying solvent of nitro-cellulose and cellulose acetate; it can also be raw materials for paint, leather and spices, and for oil extraction etc., but comparing with other esters in the same race, its demand is not great. In industrial production, it is often used as a by-product, such as in process of polyvinyl alcohol (PVA) with a large number of by-products of methyl acetate. It is estimated that it will produce 1.5 to 1.7 tons of MeOAc for each ton product of PVA. At present, PVA manufacturers are used to hydrolyze methyl acetate, because acetic acid and methanol can be used for the production of PVA as raw materials. N-butyl acetate is a colorless, transparent liquid, which is important organic solvent, extractant and dehydrating agent, widely used in industry. In this paper, methyl acetate will be converted into n-butyl acetate by transesterification, which can provide a more efficient use of methyl acetate.
In this paper, reaction kinetics was experimentally studied and pre exponential factor and the activation energy were calculated for follow-up experimental research and simulation. Then, catalytic distillation experiment was done while changing operating conditions to inspect the influence of feed mode, feed composition, reflux ratio and total feed flow on conversion of methyl acetate. According to the results the best operating conditions have been chosen. Best operating conditions for catalytic distillation process are as follows: reflux ratio 10; mole ratio of alcohol and ester 3:1; total feed flow 22mol/h; n-butanol feed at the upper part, methyl acetate feed at the lower part.
Process simulation data done by Aspen Plus was compared with experimental data. The error being within an acceptable bound, the results of process simulation are credible. After the simulation process further optimized, the results can provide guidance for following experimental study. The results revealed that the error between the simulation and experiment was less than 8% within an acceptable range, so the simulation is reliable. By respectively changing the feed position of n-butanol and methyl acetate, results showed that the greater the length of reaction part was, the higher the conversion rate would be. Increasing the theory plate number of reaction part by adding certain height of packing in actual experiment can increase the conversion rate of methyl acetate.
本论文对反应动力学进行实验研究,计算出活化能及指前因子,为后续的精馏实验及模拟提供依据。通过催化精馏实验,改变操作条件,考察进料方式、进料组成、回流比及进料总量等操作条件的变化对醋酸甲酯转化率的影响,并根据结果选择最优的操作条件。在实验范围内,催化精馏过程适宜的操作条件为:回流比10;进料醇酯摩尔比3:1;进料总量22mol/h;进料采用重组分正丁醇在反应段上部进料,轻组分醋酸甲酯在反应段下部进料。
借助ASPEN PLUS软件对反应精馏制醋酸正丁酯的过程进行模拟计算,将模拟值与实验值进行对比,从而验证计算的可靠性。进一步模拟优化,以模拟计算结果为依据,为后续的实验研究提供指导依据。结果显示,该模拟结果与实验值的相对误差最大不超过8%,在可接受范围内,故认为模拟值是可靠的。分别改变正丁醇和醋酸甲酯的进料位置,结果表明,反应段的长度越大转化率越高。增加反应段的理论塔板数,在实际实验中则表现为反应段与填料段交叉排列,能提高醋酸甲酯的转化率。
As a chemical raw material methyl acetate (MeOAc) mainly is used as a fast-drying solvent of nitro-cellulose and cellulose acetate; it can also be raw materials for paint, leather and spices, and for oil extraction etc., but comparing with other esters in the same race, its demand is not great. In industrial production, it is often used as a by-product, such as in process of polyvinyl alcohol (PVA) with a large number of by-products of methyl acetate. It is estimated that it will produce 1.5 to 1.7 tons of MeOAc for each ton product of PVA. At present, PVA manufacturers are used to hydrolyze methyl acetate, because acetic acid and methanol can be used for the production of PVA as raw materials. N-butyl acetate is a colorless, transparent liquid, which is important organic solvent, extractant and dehydrating agent, widely used in industry. In this paper, methyl acetate will be converted into n-butyl acetate by transesterification, which can provide a more efficient use of methyl acetate.
In this paper, reaction kinetics was experimentally studied and pre exponential factor and the activation energy were calculated for follow-up experimental research and simulation. Then, catalytic distillation experiment was done while changing operating conditions to inspect the influence of feed mode, feed composition, reflux ratio and total feed flow on conversion of methyl acetate. According to the results the best operating conditions have been chosen. Best operating conditions for catalytic distillation process are as follows: reflux ratio 10; mole ratio of alcohol and ester 3:1; total feed flow 22mol/h; n-butanol feed at the upper part, methyl acetate feed at the lower part.
Process simulation data done by Aspen Plus was compared with experimental data. The error being within an acceptable bound, the results of process simulation are credible. After the simulation process further optimized, the results can provide guidance for following experimental study. The results revealed that the error between the simulation and experiment was less than 8% within an acceptable range, so the simulation is reliable. By respectively changing the feed position of n-butanol and methyl acetate, results showed that the greater the length of reaction part was, the higher the conversion rate would be. Increasing the theory plate number of reaction part by adding certain height of packing in actual experiment can increase the conversion rate of methyl acetate.
引文
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[12]王龙延,催化蒸馏技术,现代化工,1990,10(2):43～47
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[14]Jian Xiao, Jiaqi Liu, Juntai Li et al. Increase MeOAc conversion in PVA production by replacing the fixed bed reactor with a catalytic distillation column. Chemical Engineering Science, 2001, 56 (23): 6553～6562
[15] Degnan T F, Smith C M, Venkat C R. Alkylation of aromatics with ethylene and propylene: recent developments in commercial processes. Applied Catalysis A: General, 2001, 221:283～294
[16] Zhang Jirui, Li Dongfeng, Fu Jiquan et al. Process and apparatus for preparation of ethylbenzene by alkylation of benzene with dilute ethylene contained in dry gas by catalytic distillation. US: 6504071, 2003-01-07
[27]张瑞生,张家庭,宋宏宇,环氧丙烷水合制丙二醇反应精馏新工艺,化学工程,1993,21(1):22~26
[18]Lawrence A, Smith Jr. Method for operating a catalytic distillation process. US: 5221441, 1993-06-22
[19] Marker T L, Funk G A, Barge P T, et al. Two-stage process for producing diisopropyl ether using catalytic distillation. US: 5504258, 1996-04-02
[20] Huss A J, Kennedy C R. Hydrocarbon processes comprised of catalytic distillation using lewis acid promoted inorganic oxide catalyst systems. US: 4935577, 1990-06-19
[21]Masamoto J, Ohtake J, Kawamura M. Process for producing formaldehyde and derivatives thereof. US: 4967014, 1990-10-30
[22]周伟,谢敏明,马建新等,催化精馏在合成甲缩醛中的应用,工业催化, 1998,6(1):35~39
[23]曹海波,乔旭,流化催化精馏合成甲缩醛技术,南京化工大学学报,1998,20(3):19~22
[24]施云海,乐清华,许振良,用反应蒸馏技术制备碳酸二甲酯,齐鲁石油化工,2000,28(1):23～26
[25]王晓立,李萍,王茹,反应精馏法合成N,N-二甲基乙酰胺,石油化工高等学校学报,2003,16(1):20~ 23
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[30]Castier M, Rasmussen P, Frednenslund A. Calculation of simulation chemical and phase equilibrium in nonideal systems. Chemical Engineering Science, 1989, 44(2):237
[31]Michelson M L. The isothermal flash problem. Part1. Stability analysis. Fluid phase Equilibria, 1982, 9:1
[32]Xiao W., Zhu K., Yun W. et al, An algorithm for simultaneous chemical and equilibrium calculation. AIChE, 1989, 35 (11):1813
[33]Barbosa D, Doherty M F. The influence of equilibrium chemical reactions on vapor-liquid calculation. Chemical Engineering Science.1988, (43):539
[34]匡建武,反应精馏传质过程和级效率的研究:[博士学位论文],大津:天津大学化工学院,1991
[35]Krishna R, Wesselingh J A. The Maxwell-Stefan approach to mass transfer, Chemical Engineering Science.1997, 52: 861
[36]Lee J H, Dudukovic M P. A comparison of the equilibrium and nonequilibrium models for a multicomponent reactive distillation column. Computers and Chemical Engineering, 1998, 23:159
[37]Smith L A, Catalyst structure and a process for its separation .USP: 4250052, 1981
[38]Fuchigami Y, Hydrolysis of methyl acetate in distillation column packed with reactive packing of ion exchange resin. Journal of Chemical Engineering Japan, 1991, 23 (3): 354
[39]Smith L A, Process for separation isobutene from C4 streams .USP:4242530, 1980
[40]Degatmo J L, Parulelzar V N, Pinjala V. Consider Reactive Distillation. Chemical Engineering Progress.1992, 88 (3):43
[41]Reactive distillation with Katapak-S, Sulzer Chemtech
[42]Taylor R, Krishna R. Modeling reactive distillation. Chemical Engineering Science, 2000, 55 (22):5183
[43]吴燕翔,王良恩,二对角矩阵法及其在催化精馏塔模拟计算中的应用,福州大学学报:自然科学版,2000,28(1):82
[44]Carra S, Mobidelli M, Santacessania E, et al. Synthesis of propylene oxide from propylene chlorohydrins-Ⅱ. Chemical Engineering Science.1979, 34: 1133
[45]Komatsu H. Application of relaxation method of solving reacting distillation problems. Journal of Chemical Engineering Japan.1977, 10:292
[46]Chang Y A, Seader J D. Simulation of continuous reactive distillation by a homotopy continuation method. Computers and Chemical Engineering, 1988, 12: 1243
[47]Zheng Y ,Xu X .Study on Catalytic Distillation Processes, partⅠ.Mass transfer Characteristics in catalyst bed within column .Chemical Engineering Research and Design.1992, 70 (A):459
[48]Zheng Y, Xu X. Study on catalytic distillation processes, part II. Simulation of distillation processes-quasi-homogeneous and rate-based model. Chemical Engineering Research and Design.1992, 70(A):465
[49]Venimadhavam G., Barbosa D, Doherty M. Bifurcation study of kinetic effect in reactive distillation .AIChE Journal, 1999, 45(3):546
[50]Higler A, Krishna R, Taylor R . A non-equilibrium cell model for multicomponent (reactive) separation processes .AIChE Journal, 1999, 45:2357
[51]Higler A , Krishna R ,Taylor R .A non-equilibrium cell model for packed distillation columns :the influence of maldistribution .Industrial and Engineering Chemistry Research,1999,38:3988
[52]张瑞生,韩英,Hoffmann U,非均相催化精馏过程的模拟计算,化工学报,1989,40(6):693
[53]韩英,张瑞生,全回流催化精馏塔的模拟计算,华东化工学院学报,1989, 15(3):331
[54]漆志文,孙海军,伴有多反应的精馏过程数学模型.化工学报,1999,50(4):563
[55]杨照,王志祥,反应精馏技术及其应用,化工时刊,2004,18(11): 10-12
[56]Fuchigami Y. J. Chem. Eng. Jpn., 1990, 23(3):354
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[63]ASPEN Technology Inc., ASPEN PLUS USER GUIDE, 1994
[2]Sawistowski H, Pilavakis P A. Distillation with Chemical Reaction in a Packed Column .Institute of chemical engineers symposium series, 1979, 56: 49~63
[3]Smith L A Jr, Laurence A. Catalytic Distillation Process and Catalyst. Eur Pat: 0008860(1985)
[4]Smith L A Jr,Huddleston M N, New MTBE Design now commercial, Hydrocarbon Processing, 1982, 61(3): 121~123
[5]杨华琮,催化精馏工艺和甲基叔丁基醚的生产,石油化工译从,1989,10(3): 23~28
[6]王进善,栾祥山,杨宗人等,固定床和催化精馏MTBE生产技术的开发,炼油设计,1991,21(5):15~22
[7]Zhang Jirui, et al, Process and apparatus for preparation of ethyl benzene by alkylation of benzene with dilute ethylene contained in dry gas by catalytic distillation. US patent Application: 20010018545, 2001
[8]G.G. Podrebarace, F.T.T. Ng G.. L. Rempel CHEMTECH, 1997. May: 37
[9]冯国红,人工神经网络在萃取精馏、反应精馏模拟中的应用:[硕士学位论文],天津;天津大学,2007
[10] Rock K, Gilbert G R, Guirk T. Catalytic distillation. Chemical Engineering, 1997, 7:78～84
[11]王志亮,叶明汤,杨宗仁等,催化反应精馏塔及其用途,中国专利,1060228, 1992-04-15
[12]王龙延,催化蒸馏技术,现代化工,1990,10(2):43～47
[13]吴文炳,陈梁,张世玲,乙酸甲酯的合成与应用新进展,江苏化工,2004,32(5):11～14
[14]Jian Xiao, Jiaqi Liu, Juntai Li et al. Increase MeOAc conversion in PVA production by replacing the fixed bed reactor with a catalytic distillation column. Chemical Engineering Science, 2001, 56 (23): 6553～6562
[15] Degnan T F, Smith C M, Venkat C R. Alkylation of aromatics with ethylene and propylene: recent developments in commercial processes. Applied Catalysis A: General, 2001, 221:283～294
[16] Zhang Jirui, Li Dongfeng, Fu Jiquan et al. Process and apparatus for preparation of ethylbenzene by alkylation of benzene with dilute ethylene contained in dry gas by catalytic distillation. US: 6504071, 2003-01-07
[27]张瑞生,张家庭,宋宏宇,环氧丙烷水合制丙二醇反应精馏新工艺,化学工程,1993,21(1):22~26
[18]Lawrence A, Smith Jr. Method for operating a catalytic distillation process. US: 5221441, 1993-06-22
[19] Marker T L, Funk G A, Barge P T, et al. Two-stage process for producing diisopropyl ether using catalytic distillation. US: 5504258, 1996-04-02
[20] Huss A J, Kennedy C R. Hydrocarbon processes comprised of catalytic distillation using lewis acid promoted inorganic oxide catalyst systems. US: 4935577, 1990-06-19
[21]Masamoto J, Ohtake J, Kawamura M. Process for producing formaldehyde and derivatives thereof. US: 4967014, 1990-10-30
[22]周伟,谢敏明,马建新等,催化精馏在合成甲缩醛中的应用,工业催化, 1998,6(1):35~39
[23]曹海波,乔旭,流化催化精馏合成甲缩醛技术,南京化工大学学报,1998,20(3):19~22
[24]施云海,乐清华,许振良,用反应蒸馏技术制备碳酸二甲酯,齐鲁石油化工,2000,28(1):23～26
[25]王晓立,李萍,王茹,反应精馏法合成N,N-二甲基乙酰胺,石油化工高等学校学报,2003,16(1):20~ 23
[26]Ancillotti F, Mauri M M, Pescarollo E. Ion exchange resin catalyzed addition of alcohols to olefins. Catal, 1977, 46(1):49
[27]Ancillotti F ,Mauri M M, Pescarollo E. Mechanisms in the reaction between olefins and alcohols catalyzed by ion exchange resins. Mol. Catal, 1978, 4(1):37
[28]Smith W R, Missen R W. Chemical Reaction Equilibrium Analysis: Theory and Algorithms, Wiley, New York, 1982
[29]Gautam R, Seider W D, Computation of phase and chemical equilibrium. AIChE, 1979, 25 (6):991
[30]Castier M, Rasmussen P, Frednenslund A. Calculation of simulation chemical and phase equilibrium in nonideal systems. Chemical Engineering Science, 1989, 44(2):237
[31]Michelson M L. The isothermal flash problem. Part1. Stability analysis. Fluid phase Equilibria, 1982, 9:1
[32]Xiao W., Zhu K., Yun W. et al, An algorithm for simultaneous chemical and equilibrium calculation. AIChE, 1989, 35 (11):1813
[33]Barbosa D, Doherty M F. The influence of equilibrium chemical reactions on vapor-liquid calculation. Chemical Engineering Science.1988, (43):539
[34]匡建武,反应精馏传质过程和级效率的研究:[博士学位论文],大津:天津大学化工学院,1991
[35]Krishna R, Wesselingh J A. The Maxwell-Stefan approach to mass transfer, Chemical Engineering Science.1997, 52: 861
[36]Lee J H, Dudukovic M P. A comparison of the equilibrium and nonequilibrium models for a multicomponent reactive distillation column. Computers and Chemical Engineering, 1998, 23:159
[37]Smith L A, Catalyst structure and a process for its separation .USP: 4250052, 1981
[38]Fuchigami Y, Hydrolysis of methyl acetate in distillation column packed with reactive packing of ion exchange resin. Journal of Chemical Engineering Japan, 1991, 23 (3): 354
[39]Smith L A, Process for separation isobutene from C4 streams .USP:4242530, 1980
[40]Degatmo J L, Parulelzar V N, Pinjala V. Consider Reactive Distillation. Chemical Engineering Progress.1992, 88 (3):43
[41]Reactive distillation with Katapak-S, Sulzer Chemtech
[42]Taylor R, Krishna R. Modeling reactive distillation. Chemical Engineering Science, 2000, 55 (22):5183
[43]吴燕翔,王良恩,二对角矩阵法及其在催化精馏塔模拟计算中的应用,福州大学学报:自然科学版,2000,28(1):82
[44]Carra S, Mobidelli M, Santacessania E, et al. Synthesis of propylene oxide from propylene chlorohydrins-Ⅱ. Chemical Engineering Science.1979, 34: 1133
[45]Komatsu H. Application of relaxation method of solving reacting distillation problems. Journal of Chemical Engineering Japan.1977, 10:292
[46]Chang Y A, Seader J D. Simulation of continuous reactive distillation by a homotopy continuation method. Computers and Chemical Engineering, 1988, 12: 1243
[47]Zheng Y ,Xu X .Study on Catalytic Distillation Processes, partⅠ.Mass transfer Characteristics in catalyst bed within column .Chemical Engineering Research and Design.1992, 70 (A):459
[48]Zheng Y, Xu X. Study on catalytic distillation processes, part II. Simulation of distillation processes-quasi-homogeneous and rate-based model. Chemical Engineering Research and Design.1992, 70(A):465
[49]Venimadhavam G., Barbosa D, Doherty M. Bifurcation study of kinetic effect in reactive distillation .AIChE Journal, 1999, 45(3):546
[50]Higler A, Krishna R, Taylor R . A non-equilibrium cell model for multicomponent (reactive) separation processes .AIChE Journal, 1999, 45:2357
[51]Higler A , Krishna R ,Taylor R .A non-equilibrium cell model for packed distillation columns :the influence of maldistribution .Industrial and Engineering Chemistry Research,1999,38:3988
[52]张瑞生,韩英,Hoffmann U,非均相催化精馏过程的模拟计算,化工学报,1989,40(6):693
[53]韩英,张瑞生,全回流催化精馏塔的模拟计算,华东化工学院学报,1989, 15(3):331
[54]漆志文,孙海军,伴有多反应的精馏过程数学模型.化工学报,1999,50(4):563
[55]杨照,王志祥,反应精馏技术及其应用,化工时刊,2004,18(11): 10-12
[56]Fuchigami Y. J. Chem. Eng. Jpn., 1990, 23(3):354
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