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1 Jungho Cho, So-Jin Park,, Myung-Jae Choi,, Seong-Bo Kim,Hai-SongBae, and Jeong-Sik Han Department of Chemical Engineering, Dong-Yang University, Kyoungbuk, , Korea *Department of Chemical Engineering, Chungnam National University, Daejeon , Korea **Advanced Chemical Technology Division, Korea Research Institute of Chemical Technology, Daejeon, Korea ***ADD (Agency for Defence Development), Daejeon, Korea Received October 12, 2006; Accepted June 12, 2007 Abstract: In this study, simulation of distillation process for the mixture of exo-tetrahydrodicylcopentadiene (exo-thdcp) and endo-tetrahydrodicyclopentadiene (endo-thdcp) was carried out. Minimum reflux ratio and minimum number of stages were calculated to obtain products having 99.0 wt% of each components, respectively. Theoretical number of stages was estimated from the correlation of number of stages and reflux ratio. Optimal feed tray location that minimized the reboiler heat duty was also determined. Besides, the vapor-liquid equilibria for this mixture at kpa were reported. Keywords: exo-tetrahydrodicylcopentadiene, endo-tetrahydrodicylcopentadiene, separation, simulation, optimization Introduction 1) Exo-tetrahydrodicyclopentadiene (THDCP), a highdensity liquid fuel can be easily synthesized by the hydrogenation reaction of dicylcopentadiene isomeric mixture. One major disadvantage of the hydrogenation and isomerization process is the co-production of endo- THDCP, which should be separated from the product mixture. Scheme 1 shows isomerization mechanism of endo-thdcp into exo-thdcp and fundamental physical properties of THDCP isomers are listed in Table 1. Despite the industrial importance of THDCP isomers, very little is reported so far on their physical and equilibrium properties. Primary objective of this study is therefore to develop a process for separating isomeric mixtures of exo- and endo-thdcp by obtaining property data for each isomer To whom all correspondence should be addressed. ( sjpark@cnu.ac.kr, smjchoi@krict.re.kr) and their binary isobaric vapor-liquid equilibrium data at different pressures. Secondary objective, a main purpose of this work, is to model and optimize the distillation column to obtain each isomer with 99 wt% purity both at the top and the bottom, respectively. Our earlier published vapor pressures for both isomers and isobaric VLE, directly measured using a glass still at different pressures, were used for the simulation of distillation column in this work [1]. Antoine equation and NRTL liquid activity coefficient model [2] were used for regression of the experimental VLE data. Since exo- and endo-thdcp components are not builtin the pure component database of the general-purpose chemical process simulator, PRO/II with PROVISION [3-8], we used UNIFAC group contribution method [9] to estimate the pure component physical properties such as normal boiling temperature, critical properties, standard liquid density, standard heat of formation, and so on. We used SHORTCUT module built-in PRO/II with PROVISION simulator to predict the minimum number

2 Simulation and Optimization Study on the Separation of Exo-Tetrahydrodicyclopentadiene from Endo-Tetrahydrodicylcopentadiene Through Distillation 713 Table 1. The Basic Properties of Exo-THDCP and Endo- THDCP Properties Exo-THDCP Endo-THDCP Molecular weight Molecular formula Normal boiling point (K) Specific gravity Critical temperature (K) Critical compressibility factor C 10H C 10H Table 2. Coefficients in Vapor Pressure Correlation of Exo- THDCP and Endo-THDCP Coefficients Exo-THDCP Endo-THDCP A i B i C i D i , , AAD (%) ln (2) Scheme 1. Wagner-Meerwein type ionic chain mechanism. of stages and minimum reflux ratio for separation. We also used COLUMN and OPTIMIZER module in PRO/II with PROVISION to determine the theoretical number of stages and optimal feed tray location that minimizes the reboiler heat duty. Experimental Works Pure component vapor pressure of exo- and endo- THDCP and VLE data of this mixture, used in this simulation, were directly determined using Dr. Sieg and Roeck type recirculating still. The detailed description of the measuring procedure has been described elsewhere [1]. The experimental pressure range was ca. 10 to kpa. Experimental works for bubble temperature and compositions were performed at kpa. Pure component experimental vapor pressure data of exo- and endo- THDCP vs. temperature were correlated using four parameters Antoine equation shown in the equation (1). log (1) Table 2 shows regressed coefficients of each component. Average absolute deviations in prediction of vapor pressures for exo- and endo-thdcp are and %, respectively. Theory The non-random two-liquid (NRTL) activity coefficient model, equation (2), was used to correlate the binary VLE data of exo- and endo-thdcp system and for the distillation column simulations containing component exhibiting non-ideal vapor-liquid equilibrium phase behavior [10]. In equation (2), and G ij are optimum binary interaction parameters that minimize the deviations between the experimental data and the calculation values, respectively, and can be written as equations (3) and (4): (3) (4) In equation (3), T refers to an absolute temperature. The NRTL model has the following three interaction parameters, u ij, u ji,andα ij. The binary interaction parameters for the isobaric binary vapor-liquid equilibrium data were optimized by regressing the experimental bubble point temperatures and compositions, and were determined using equation (2). The pattern search optimization algorithm suggested by Nelder and Mead [11] was used to minimize the objective functions in equation (5). Based on this optimization algorithm, the iteration was carried out to minimize the objective function F(Obj), equation (5). For three variables of NRTL model, a simplex is a regular tetrahedron, and the method is the pattern search that compares objective function values at the four vertices of a regular tetrahedron. The worst vertex, where the objective function is largest, is rejected and replaced with a new vertex. A new regular tetrahedron is formed and the search is continued. The process generates a sequence of regular tetrahedron, which might have different shapes, for which the objective function values at each vertices get smaller and smaller. The size of the regular tetrahedron is reduced and the coordinates of the minimum point are found. (5) exp exp In the above equation (5), T j and y j are experimental bubble point temperature and composition for

3 714 Jungho Cho, So-Jin Park, Myung-Jae Choi, Seong-Bo Kim, Hai-Song Bae, and Jeong-Sik Han (a) (b) Figure 1. Isobaric vapor-liquid equilibrium data for the system of exo- and endo-thdcp at kpa with predicted values by NRTL liquid activity coefficient model. Table 3. Isobaric Vapor-Liquid Equilibria Data for exo- THDCP (1) + endo-thdcp (2) at kpa model u 12 u 21 α 12 Δy NRTL T/K x 1 y 1 T/K x 1 y j th data, respectively. Superscript cal means calculated (or regressed) values for vapor and liquid phase compositions. Table 3 shows the NRTL binary interaction parameters regressed from binary vapor-liquid equilibria at kpa with standard deviation of correlation results using NRTL equation. Figure 1 shows x-y and p-x-y diagram for exo- and endo-thdcp mixture at kpa. Process Simulation Results The simulation and optimization for the separation of exo-thdcp from endo-thdcp can be classified into four major parts: (1) determination of the column operating pressure; (2) determination of the minimum number of stages and minimum reflux ratio for separation; (3) simulation of the rigorous distillation column; and, (4) optimization of the distillation column. Determination of the Column Operating Pressure Determination of the distillation column operating pressure depends on the type of condenser and the type of refrigerant available. We assumed that cooling water was used for the cold utility and 3.0 Kg/cm 2 G of low-pressure saturated steam was used for hot utility. Cooling water was assumed to be supplied at K and to be returned at K. We used sub-cooled type of condenser and assumed an overhead reflux drum temperature operating at K. Since the 3.0 Kg/cm 2 Gof low-pressure saturated steam temperature is about K, column bottom temperature should be operated around K considering the temperature difference between column bottom and the steam. So, we calculated the bubble point pressure of the bottom liquid product having a composition of 1.0 wt% of exo-thdcp and 99.0 wt% of endo-thdcp. Bubble pressure calculation result showed that the bubble point pressure is about kpa. Determination of the Minimum Number of Stages and Minimum Reflux Ratio for Separation Next step is to determine the minimum number of stages based on the column operating pressure, kpa. Table 4 shows feedstock stream information. According to Table 4, feedstock flow rate is 1,000 kg/h and 50 wt% of exo-thdcp and 50 wt% of endo-thdcp. Feed stream is fed to the column at saturated liquid state. According to PRO/II SHORTCUT module, minimum number of stages is and the corresponding minimum reflux ratio is Case studies for the relation of theoretical number of stages and reflux ratio were per-

4 Simulation and Optimization Study on the Separation of Exo-Tetrahydrodicyclopentadiene from Endo-Tetrahydrodicylcopentadiene Through Distillation 715 Table 4. Feedstock Stream Information Component exo-thdcp endo-thdcp Total flow rate (Kg/h) Temperature (K) Pressure (kpa) Flow rate (Kg/h) , Figure 3. A schematic diagram of conventional distillation column for the separation of exo- and endo-thdcp. Figure 2. Plot of theoretical number of stages versus reflux ratio. formed to determine the optimum reflux ratio and the corresponding theoretical number of stages. Figure 2 shows a plot of theoretical number of stages versus reflux ratio. In general, for the higher reflux region, utility consumptions are very large even though initial equipment costs are relatively low, while for the low reflux region, initial investment costs are very large even if operating costs are low. Therefore, optimum reflux ratio that minimizes the total investment costs will be located at the very point that the curvature is most sharply changing. Figure 2 shows us that the optimum reflux ratio is slightly higher than 14 and the corresponding theoretical number of stage is 60. Simulation of the Rigorous Distillation Column For the rigorous simulation for the separation of exoand endo-thdcp using conventional distillation column, we used the distillation configuration illustrated in Figure 3. In Figure 3, tray number was counted from top to bottom. So, overhead condenser corresponds to tray number 1, column top tray is tray number 2, column bottom tray is 59, and the bottom reboiler is counted to tray number of 60. Feed tray location is assumed to be fed into the middle stage number of 31, which will be optimized to minimize the reboiler heat duty. Overhead reflux drum operating pressure was set to kpa and condenser or column pressure drop was neglected. Overhead reflux drum operating temperature was set to K in order to be sub-cooled using cooling water. Table 4 reveals the heat and material balance around the distillation column. According to the material balance furnished in Table 5, exo- and endo-thdcp purities are all 99.0 wt% at column top and bottom product, respectively. Table 6 shows input design data, product specifications and output summaries for the simulated distillation column. According to Table 6, the heat duties of condenser and reboiler are and Kcal/h, respectively. Column reflux ratio to obtain a desired purity both at column top and bottom product is , which is slightly smaller than shortcut case of study results. Optimization of the Distillation Column In most distillation columns, the major operating cost will be steam consumption in reboiler. Of course, if the cryogenic refrigerant used in the overhead condenser, this cold utility cost would also be quite large. For our exo- and endo-thdcp separation problem, the column top pressure was set so that cooling water could be used in the overhead condenser. Therefore, reboiler heat duty is objective function that should be minimized. The simulation has been run using different feed stages. The purities of both top and bottom product were kept constant. The feed stage that minimizes the reboiler heat duty could be the optimum stage. Figure 4 gives the results of these calculations. Feeding on stage 30 gives the minimum reboiler heat duty, Kcal/h. Conclusion This study was modeled and demonstrated to optimize the process for the separation of exo- and endo-thdcp through conventional distillation column using experi-

5 716 Jungho Cho, So-Jin Park, Myung-Jae Choi, Seong-Bo Kim, Hai-Song Bae, and Jeong-Sik Han Table 5. Heat and Material Balance Around Distillation Column Stream name Feed Stream Top Product Bottom Product Component Kg/h Weight% Kg/h Weight% Kg/h Weight% exo-thdcp endo-thdcp Total Rate (Kg/h) 1, Temperature (K) Pressure (kpa) Enthalpy (10 6 Kcal/h) Molecular Weight Heat Capacity (Kcal/kg o C) Table 6. Input Data, Product Specificationsand Simulation Results for Columns Input, specifications & output Values Tray number 60 Condenser type Sub-cooled Condenser temperature (K) Cooling medium Cooling water ( K/ K) Column top temperature (K) Condenser duty (10 6 Kcal/h) Reflux ratio Reboiler type Kettle Heating medium 3.0 Kg/cm 2 G saturated steam Column bottom temperature (K) Reboiler temperature (K) Reboiler duty (10 6 Kcal/h) Feed stage 31 By using pure component vapor pressure data and binary vapor-liquid equilibrium data, we could perform shortcut modeling to obtain minimum number of stages and reflux ratio, rigorous simulation for the reflux ratio, condenser and reboiler heat duty calculation. The optimal feed stage location that minimized the reboiler heat duty could be determined using this approach. Nomenclature A, B, C, D : coefficients in vapor pressure correlation R : gas constant T : absolute temperature (K) x : liquid phase mole fraction y : vapor phase mole fraction u, G : binary interaction parameter in NRTL model Greek Letters α : interaction parameter in equation (4) γ : activity coefficient in equation (2) τ : interaction parameter in equation (2) Superscripts exp : experimental value in equations (5) cal : calculated value in equations (5) Subscripts i, j, k : component i, j, and k Figure 4. Plot of reboiler heat duty versus feed tray location. mental binary isobaric vapor-liquid equilibrium data. Phase-equilibrium calculation data was decided by regression that used NRTL liquid activity coefficient for better prediction of experimental isobaric vapor-liquid equilibrium data. The absolute average deviation between the simulated and experimental data was only %. References 1. K.-J. Han, I.-C. Hwang, S.-J. Park, M.-J. Choi, S.-B. Lee, and J.-S. Han, Fluid Phase Equilibr., 249, 187 (2006). 2. H, Renon and J. M. Prausnitz, AIChE, 14, 135 (1968). 3. Simulation Science Inc., PRO/II user guide, Sim-

6 Simulation and Optimization Study on the Separation of Exo-Tetrahydrodicyclopentadiene from Endo-Tetrahydrodicylcopentadiene Through Distillation 717 ulation Science Inc., SouthLake Forest (2001). 4. Simulation Science Inc., PRO/II input manual, Simulation Science Inc., SouthLake Forest (2005). 5. J. H. Cho, T. H Lee, and J. K. Park, Korean Chem. Eng. Res., 43, 467 (2005). 6. J. H. Cho and J. K. Jeon, Korean Chem. Eng. Res., 43, 474 (2005). 7. J. H. Cho, Korean Chem. Eng. Res., 44, 129 (2006). 8. J. H. Cho, J. K. Park, and J. K. Jeon, J. Ind. Eng. Chem., 12, 206 (2006). 9. A, Fredenslund, R. L. Jones, and J. M. Prausnitz, AIChE, 27, 1086 (1975). 10. J. K. Park, N. H. Lee, S. J. Park, and J. H. Cho, J. Ind. Eng. Chem., 12, 516 (2006). 11. J. A. Nelder and R. A. Mead, Comput. J, 7, 303 (1965).

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