Evaluating the ionic liquids, commercial solvents, and pressure-swing for efficient azeotropic separation
-
Ammar Abbas Ali Saif
, Aqeel Ahmad Taimoor
, Saad Al-Shahrani , Usman Saeed , Sami-Ullah Rather and Majed A. Alamoudi
Abstract
Techniques like extractive distillation and pressure swing distillation (PSD) have been commercially developed to separate azeotropic mixtures. Extractive distillation using conventional solvents offers advantages in achieving high purity levels, but challenges include difficulty in solvent recovery, increased energy consumption, higher costs, and potential negative environmental impact. Selecting appropriate solvents is a challenging task with potential compromises. PSD manipulates pressure to overcome azeotropic points without an entrainer, offering solvent-free operation. Ionic liquids may provide an alternative to conventional solvents in extractive distillation. Five imidazolium, ammonium and pyridinium based ILs have been chosen to investigate their impact on the separation of the selected azeotropic mixtures. The three techniques are employed for seven different (model) azeotropic mixtures to evaluate the commercial feasibility of each process by comparing energy requirements and Total Annual Cost (TAC). Aspen Plus software has been employed to perform a comparison simulation among the processes. This benchmark analysis and process simulation can aid in evaluating the efficacy and feasibility of the possible optimum commercial process in separation. There is no one-size-fits-all technique that provides the best cost-effective and energy-efficient process for every azeotropic separation.
-
Research ethics: Not applicable.
-
Informed consent: Not applicable.
-
Author contributions: The authors have accepted responsibility for the entire content of this manuscript and approved its submission.
-
Use of Large Language Models, AI and Machine Learning Tools: None declared.
-
Conflict of interests: The authors state no conflict of interest.
-
Research funding: None declared.
-
Data availability: The raw data can be obtained on request from the corresponding author.
References
1. Elliott, JR, Rainwater, JC. The Bancroft point and vapor-liquid equilibria in the system benzene + isopropanol. Fluid Phase Equilib 2000;175:229–36. https://doi.org/10.1016/S0378-3812(00)00449-0.Search in Google Scholar
2. Zhang, Z, Lv, M, Chen, L, Li, W. Organic solvents for separating ethyl acetate-ethanol by extractive distillation. Adv Mater Res 2012;550–553:699–703. https://doi.org/10.4028/www.scientific.net/AMR.550-553.699.Search in Google Scholar
3. Elisia, I, Nakamura, H, Lam, V, Hofs, E, Cederberg, R, Cait, J, et al.. DMSO represses inflammatory cytokine production from human blood cells and reduces autoimmune arthritis. PLoS One 2016;11:e0152538. https://doi.org/10.1371/JOURNAL.PONE.0152538.Search in Google Scholar PubMed PubMed Central
4. Cushnie, TPT, Cushnie, B, Echeverría, J, Fowsantear, W, Thammawat, S, Dodgson, JL, et al.. Bioprospecting for antibacterial drugs: a multidisciplinary perspective on natural product source material, bioassay selection and avoidable pitfalls. Pharm Res 2020;37:125. https://doi.org/10.1007/S11095-020-02849-1.Search in Google Scholar PubMed
5. Zhang, X, Liu, H, Liu, Y, Jian, C, Wang, W. Experimental isobaric vapor-liquid equilibrium for the binary and ternary systems with methanol, methyl acetate and dimethyl sulfoxide at 101.3 kPa. Fluid Phase Equilib 2016;408:52–7. https://doi.org/10.1016/j.fluid.2015.08.014.Search in Google Scholar
6. Liang, J-H, Sun, C, Bai, P, Zang, L. Separation of cyclohexane-1-propanol by batch extractive distillation. Xiandai Huagong/Mod Chem Ind 2013;33:108–11.Search in Google Scholar
7. Li, G, Yu, Y, Bai, P. Batch extractive distillation of mixture methanol-acetonitrile using aniline as a asolvent. Pol J Chem Technol 2012;14:48–53. https://doi.org/10.2478/v10026-012-0083-4.Search in Google Scholar
8. Xian, C, Jin, Z, Bin, Z, Tian, F, Zhi, Y. Separation of acetonitrile-toluene mixture by batch extractive distillation, no. 022, 1994. Available from: http://www.cnki.net.Search in Google Scholar
9. Aquilon, AF, Cargullo, DM, Onayan, J, Sarno, J, Molino, VM, Lopez, ECR. Recent advances in extractive distillation. Eng Proc 2023;56:11. https://doi.org/10.3390/ASEC2023-15261.Search in Google Scholar
10. Kanse, NG, Matondkar, D, Bane, S, Matondkar, P, Student, BE. Overview of pressure-swing distillation process for separation of azeotropic mixture. Int J Res Anal Rev 2019;6:674–8.Search in Google Scholar
11. Wang, Y, Cui, P, Ma, Y, Zhang, Z. Extractive distillation and pressure-swing distillation for THF/ethanol separation. J Chem Technol Biotechnol 2015;90:1463–72. https://doi.org/10.1002/JCTB.4452.Search in Google Scholar
12. Muñoz, R, Montón, JB, Burguet, MC, de la Torre, J. Separation of isobutyl alcohol and isobutyl acetate by extractive distillation and pressure-swing distillation: simulation and optimization. Sep Purif Technol 2006;50:175–83. https://doi.org/10.1016/J.SEPPUR.2005.11.022.Search in Google Scholar
13. Phimister, JR, Seider, WD. Semicontinuous, pressure-swing distillation. Ind. Eng. Chem. Res 2000;39:122–30. https://doi.org/10.1021/ie9904302.Search in Google Scholar
14. Liang, S, Cao, Y, Liu, X, Li, X, Zhao, Y, Wang, Y, et al.. Insight into pressure-swing distillation from azeotropic phenomenon to dynamic control. Chem Eng Res Des 2017;117:318–35. https://doi.org/10.1016/j.cherd.2016.10.040.Search in Google Scholar
15. Zhai, J, Chen, X, Sun, X, Xie, H. Economically and thermodynamically efficient pressure-swing distillation with heat integration and heat pump techniques. Appl Therm Eng 2023;218:119389. https://doi.org/10.1016/j.applthermaleng.2022.119389.Search in Google Scholar
16. Cui, C, Zhang, Q, Zhang, X, Sun, J, Chien, I-L. Dynamics and control of thermal-versus electrical-driven pressure-swing distillation to separate a minimum-boiling azeotrope. Sep Purif Technol 2022;280:119839. https://doi.org/10.1016/j.seppur.2021.119839.Search in Google Scholar
17. Zhang, Z, Wang, Y, Zhang, M, Guang, C, Li, M, Gao, J. Energy-saving investigation of pressure-swing distillation strengthening configurations for benzene/isobutanol binary azeotrope. Sep Purif Technol 2022;296:121381. https://doi.org/10.1016/j.seppur.2022.121381.Search in Google Scholar
18. Luyben, WL. Pressure-swing distillation for minimum-and maximum-boiling homogeneous azeotropes. Ind Eng Chem Res 2012;15:10881–6. https://doi.org/10.1021/ie3002414.Search in Google Scholar
19. Qin, Y, Zhuang, Y, Wang, C, Zhang, L, Liu, L, Du, J. Multi-objective optimization and comparison of the entrainer-assisted pressure-swing distillation and extractive distillation separation sequences for separating a pressure-insensitive binary azeotrope. Comput Chem Eng 2022;165:107959. https://doi.org/10.1016/j.compchemeng.2022.107959.Search in Google Scholar
20. Zhang, F, Sun, D, Li, Y, Shan, B, Ma, Y, Wang, Y, et al.. Heat integration and dynamic control for separating the ternary azeotrope of butanone/isopropanol/n-heptane via pressure-swing distillation. J Chem Technol Biotechnol 2022;97:2557–71. https://doi.org/10.1002/jctb.7128.Search in Google Scholar
21. Yang, A, Kong, ZY, Sunarso, J, Shen, W. Towards energy saving and carbon reduction of pressure-swing distillation for separating the ternary azeotropic mixtures by thermodynamic insights and process intensification. Sep Purif Technol 2022;301:121983. https://doi.org/10.1016/j.seppur.2022.121983.Search in Google Scholar
22. Zhang, Y-R, Wu, T-W, Chien, I-L. Energy-efficient heterogeneous azeotropic distillation coupling with pressure swing distillation for the separation of IPA/DIPE/water mixture. J Taiwan Inst Chem Eng 2022;130:103843. https://doi.org/10.1016/j.jtice.2021.04.059.Search in Google Scholar
23. Li, Q, Zhang, J, Lei, Z, Zhu, J, Zhu, J, Huang, X. Selection of ionic liquids as entrainers for the separation of ethyl acetate and ethanol. Ind Eng Chem Res 2009;48:9006–12. https://doi.org/10.1021/ie8017127.Search in Google Scholar
24. Lei, Z, Chen, B, Koo, YM, Macfarlane, DR. Introduction: ionic liquids. Chem Rev 2017;117:6633–5. https://doi.org/10.1021/acs.chemrev.7b00246.Search in Google Scholar PubMed
25. Hwang, JH, Park, H, Choi, DW, Nam, KT, Lim, KM. Investigation of dermal toxicity of ionic liquids in monolayer-cultured skin cells and 3D reconstructed human skin models. Toxicol In Vitro 2018;46:194–202. https://doi.org/10.1016/J.TIV.2017.09.025.Search in Google Scholar
26. Song, J. Research progress of ionic liquids as lubricants. ACS Omega 2021;6:29345–9. https://doi.org/10.1021/ACSOMEGA.1C04512/ASSET/IMAGES/LARGE/AO1C04512_0001.JPEG.Search in Google Scholar
27. Freemantle, M. Ionic liquids in organic synthesis. Chem Eng News 2004;82:44–7. https://doi.org/10.1021/cen-v082n045.p044.Search in Google Scholar
28. Canales, RI, Brennecke, JF. Comparison of ionic liquids to conventional organic solvents for extraction of aromatics from aliphatics. J Chem Eng Data 2016;61:1685–99. https://doi.org/10.1021/acs.jced.6b00077.Search in Google Scholar
29. Zhao, H. Innovative applications OF IONIC liquids as ‘green’ engineering liquids. Chem Eng Commun 2006;193:1660–77. https://doi.org/10.1080/00986440600586537.Search in Google Scholar
30. Kalb, RS. Toward industrialization of ionic liquids. In: Commercial applications of ionic liquids; 2020:261–82 pp.10.1007/978-3-030-35245-5_11Search in Google Scholar
31. Ge, X, Zhang, R, Liu, P, Liu, B, Liu, B. Optimization and control of extractive distillation for formic acid-water separation with maximum-boiling azeotrope. Comput Chem Eng 2023;169:108075. https://doi.org/10.1016/J.COMPCHEMENG.2022.108075.Search in Google Scholar
32. Graczová, E, Dobcsányi, D, Steltenpohl, P. Separation of methyl acetate-methanol azeotropic mixture using 1-ethyl-3-methylimidazolium trifluoromethanesulfonate. Chem Eng Trans 2017;61:1183–8. https://doi.org/10.3303/CET1761195.Search in Google Scholar
33. Lee, LS, Shen, HC. Azeotropic behavior of a water + n-propanol + cyclohexane mixture using cyclohexane as an entrainer for separating the water + n-proponal mixture at 760 mmHg. Ind Eng Chem Res 2003;42:5905–14. https://doi.org/10.1021/IE0208220/ASSET/IMAGES/LARGE/IE0208220F00009.JPEG.Search in Google Scholar
34. Lazutkina, YS, Kleymenova, MN, Komarova, LF. Thermodynamic-topological analysis of butanol-toluene mixture. Fine Chem Technol 2015;3:50–5.Search in Google Scholar
35. Szabados, RJ. The separation of azeotropes by extractive distillation. Montana State University – Bozeman, College of Engineering; 1988. https://scholarworks.montana.edu/xmlui/handle/1/7035 [Accessed 16 Jan 2024].Search in Google Scholar
36. Li, GB, Song, BQ, Wang, SQ, Pei, LM, Liu, SG, Song, JL, et al.. Selective adsorption of water, methanol, and ethanol by naphthalene diimide-based coordination polymers with constructed open Cu2+ metal sites and separation of ethanol/acetonitrile. ACS Omega 2019;4:1995–2000. https://doi.org/10.1021/acsomega.8b03229.Search in Google Scholar PubMed PubMed Central
37. Berg, L, Yeh, A-I. Separation of methyl acetate from methanol by extractive distillation. US Patent 4597834, 1986.Search in Google Scholar
38. Merenov, AS, Abraham, MA. Catalyzing the carbonylation of methanol using a heterogeneous vapor phase catalyst. Catal Today 1998;40:397–404. https://doi.org/10.1016/S0920-5861(98)00068-6.Search in Google Scholar
39. Lee, L, Shen, H. Water + n-proponal mixture at 760 mmHg azeotropic behavior. USA: Industrial and Engineering Chemistry Research; 2003, vol. XLII:5905–14 pp.10.1021/ie0208220Search in Google Scholar
40. Лазуткина, ЮС, Клейменова, МН, Комарова, ЛФ, Lazutkina, YS, Kleymenova, MN, Komarova, LF. Термодинамико-топологический анализ бутанольно-толуольной смеси Thermodynamic-topological analysis of butanol-toluene mixture. Fine Chem Technol 2015;10:50–5.Search in Google Scholar
41. McConvey, IF, Woods, D, Lewis, M, Gan, Q, Nancarrow, P. The importance of acetonitrile in the pharmaceutical industry and opportunities for its recovery from waste. Org Process Res Dev 2012;16:612–24. https://doi.org/10.1021/op2003503.Search in Google Scholar
42. Batch extractive distillation separating method of acetonitrile-methylbenzene azeotropic mixture 2005.Search in Google Scholar
43. Berg, L, Szabados, RJ. Separation of acetic acid from dioxane by extractive distillation. 4801358-United States, 1988.Search in Google Scholar
44. Berg, L, Yeh, AI. The separation of methyl acetate from methanol by extractive distillation 2007;30:113–17. https://doi.org/10.1080/00986448408911119.Search in Google Scholar
45. Lloyd, B, An-I, Y. Dehydration of formic acid by extractive distillation. 4642166-United States, 1986.Search in Google Scholar
46. Gai, H, Lin, K, Feng, Y, Xiao, M, Guo, K, Song, H. Conceptual design of an extractive distillation process for the separation of azeotropic mixture of n-butanol-isobutanol-water. Chin J Chem Eng 2018;26:2040–7. https://doi.org/10.1016/J.CJCHE.2018.05.003.Search in Google Scholar
47. 1-Ethyl-3-methylimidazolium trifluoromethanesulfonate | C7H11F3N2O3S | CID 2758874 – PubChem. https://pubchem.ncbi.nlm.nih.gov/compound/2758874#section=Chemical-and-Physical-Properties (Accessed 16 Jan 2024).Search in Google Scholar
48. 1-Butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide | C10H15F6N3O4S2 | CID 11258643 – PubChem. https://pubchem.ncbi.nlm.nih.gov/compound/11258643#section=Computed-Properties (Accessed 16 Jan 2024).Search in Google Scholar
49. Methyltrioctylammonium trifluoromethanesulfonate | C26H54F3NO3S | CID 22678982 – PubChem. https://pubchem.ncbi.nlm.nih.gov/compound/22678982 (Accessed 16 Jan 2024).Search in Google Scholar
50. 1-Butyl-3-methylimidazolium methanesulfonate | C9H18N2O3S | CID 11492381 – PubChem. https://pubchem.ncbi.nlm.nih.gov/compound/1-Butyl-3-methylimidazolium-methanesulfonate#section=Crystal-Structures (Accessed 16 Jan 2024).Search in Google Scholar
51. 1-Butyl-4-methylpyridinium bis(trifluoromethylsulfonyl)imide | C12H16F6N2O4S2 | CID 121235094 – PubChem. https://pubchem.ncbi.nlm.nih.gov/compound/121235094 (Accessed 16 Jan 2024).Search in Google Scholar
52. Singh, SK, Savoy, AW. Ionic liquids synthesis and applications: an overview. J Mol Liq 2020;297:112038. https://doi.org/10.1016/j.molliq.2019.112038.Search in Google Scholar
53. Abushammala, H, Mao, J. A review on the partial and complete dissolution and fractionation of wood and lignocelluloses using imidazolium ionic liquids. Polymers 2020;12:195. https://doi.org/10.3390/POLYM12010195.Search in Google Scholar
54. Ngo, HL, LeCompte, K, Hargens, L, McEwen, AB. Thermal properties of imidazolium ionic liquids. Thermochim Acta 2000;357:97–102. https://doi.org/10.1016/s0040-6031(00)00373-7.Search in Google Scholar
55. Sosa, JE, Araújo, JMM, Amado-González, E, Pereiro, AB. Separation of azeotropic mixtures using protic ionic liquids as extraction solvents. J Mol Liq 2020;297:111733. https://doi.org/10.1016/j.molliq.2019.111733.Search in Google Scholar
56. Pereiro, AB, Araújo, JMM, Esperança, J, Marrucho, IM, Rebelo, LPN. Ionic liquids in separations of azeotropic systems – a review. J Chem Thermodyn 2012;46:2–28. https://doi.org/10.1016/j.jct.2011.05.026.Search in Google Scholar
57. Wu, C, De Visscher, A, Gates, ID. Comparison of electronic and physicochemical properties between imidazolium-based and pyridinium-based ionic liquids. J Phys Chem B 2018;122:6771–80. https://doi.org/10.1021/ACS.JPCB.8B00764/ASSET/IMAGES/LARGE/JP-2018-00764G_0011.JPEG.Search in Google Scholar
58. Ogbodo, R, Karunaratne, WV, Acharya, GR, Emerson, MS, Mughal, M, Yuen, HM, et al.. Structural origins of viscosity in imidazolium and pyrrolidinium ionic liquids coupled with the NTf2- anion. J Phys Chem B 2023;127:6342–53. https://doi.org/10.1021/acs.jpcb.3c02604.Search in Google Scholar PubMed PubMed Central
59. Philippi, F, Welton, T. Targeted modifications in ionic liquids – from understanding to design. Phys Chem Chem Phys 2021;23:6993–7021. https://doi.org/10.1039/d1cp00216c.Search in Google Scholar PubMed
60. Towler, G, Sinnott, R. Chemical engineering design: principles, practice and economics of plant and process design. UK: Elsevier; 2021.Search in Google Scholar
61. Seader, JD, Henley, EJ, Roper, DK. Separation process principles: chemical and biochemical operations. Hoboken, NJ: Wiley; 2011.Search in Google Scholar
62. Smith, JM. Introduction to chemical engineering thermodynamics. J Chem Educ 1950;27:584. https://doi.org/10.1021/ed027p584.3.Search in Google Scholar
63. Gebreyohannes, S, Neely, BJ, Gasem, KAM. Generalized nonrandom two-liquid (NRTL) interaction model parameters for predicting liquid-liquid equilibrium behavior. Ind Eng Chem Res 2014;53:12445–54. https://doi.org/10.1021/IE501699A/SUPPL_FILE/IE501699A_SI_001.XLS.Search in Google Scholar
64. Gmehling, J, Kleiber, M, Kolbe, B, Rarey, J. Chemical thermodynamics for process simulation. Hoboken, NJ, USA: Wiley; 2019.10.1002/9783527809479Search in Google Scholar
65. Maurer, G, Prausnitz, JM. On the derivation and extension of the uniquac equation. Fluid Phase Equilib 1978;2:91–9. https://doi.org/10.1016/0378-3812(78)85002-X.Search in Google Scholar
66. Fredenslund, A, Jones, RL, Prausnitz, JM. Group-contribution estimation of activity coefficients in nonideal liquid mixtures. AIChE J 1975;21:1086–99. https://doi.org/10.1002/AIC.690210607.Search in Google Scholar
67. Ghosh, SK, Chopra, SJ. Activity coefficients from the Wilson equation. Ind Eng Chem Process Des Dev 1975;14:304–8. https://doi.org/10.1021/I260055A019/ASSET/I260055A019.FP.PNG_V03.Search in Google Scholar
68. George Hayden, J, O’Connell, JP. A generalized method for predicting second virial coefficients. Ind Eng Chem Process Des Dev 1975;14:209–16. https://doi.org/10.1021/I260055A003/SUPPL_FILE/I260055A003_SI_001.PDF.Search in Google Scholar
69. Engel, E, Dreizler, RM. Density functional theory: an advanced course. Theor Math Phys 2011;2011:499–515.10.1007/978-3-642-14090-7Search in Google Scholar
70. Chermette, H. Density functional theory: a powerful tool for theoretical studies in coordination chemistry. Coord Chem Rev 1998;178–180:699–721. https://doi.org/10.1016/S0010-8545(98)00179-9.Search in Google Scholar
71. Klamt, A, Schüürmann, G. COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. J Chem Soc Perkin Trans 1993;2:799–805. https://doi.org/10.1039/p29930000799.Search in Google Scholar
72. Mullins, E, Oldland, R, Liu, YA, Wang, S, Sandler, SI, Chen, CC, et al.. Sigma-profile database for using COSMO-based thermodynamic methods. Ind Eng Chem Res 2006;45:4389–415. https://doi.org/10.1021/IE060370H.Search in Google Scholar
73. Rather, SU, Bamufleh, HS, Alhumade, H, Saeed, U, Taimoor, AA, Sulaimon, AA, et al.. Theoretical and experimental studies of 1-Butyl-3-methylimidazolium methanesulfonate ionic liquid. Int J Energy Res 2023;2023:1–10. https://doi.org/10.1155/2023/3971296.Search in Google Scholar
74. Gerber, RP, Soares, RDP. Prediction of infinite-dilution activity coefficients using UNIFAC and COSMO-SAC variants. Ind Eng Chem Res 2010;49:7488–96. https://doi.org/10.1021/IE901947M/SUPPL_FILE/IE901947M_SI_001.PDF.Search in Google Scholar
75. Lin, ST, Sandler, SI. A priori phase equilibrium prediction from a segment contribution solvation model. Ind Eng Chem Res 2002;41:899–913. https://doi.org/10.1021/ie001047w.Search in Google Scholar
76. Bairagya, P, Kundu, D, Banerjee, T. Simplified COSMO-SAC-based phase equilibria predictions for extractive distillation of toluene–heptane mixtures using ionic liquids. Asia Pac J Chem Eng 2020;15:e2513. https://doi.org/10.1002/APJ.2513.Search in Google Scholar
77. Yu, G, Wei, Z, Chen, K, Guo, R, Lei, Z. Predictive molecular thermodynamic models for ionic liquids. AIChE J 2022;68:e17575. https://doi.org/10.1002/AIC.17575.Search in Google Scholar
78. Xu, S, Cui, X, Xing, Y, Di, J, Zhang, X, He, J, et al.. Computer-aided molecular design of double-salt ionic liquid solvents for extractive distillation with the COSMO-SAC and genetic algorithm. Ind Eng Chem Res 2021;60:18086–93. https://doi.org/10.1021/ACS.IECR.1C03545/ASSET/IMAGES/LARGE/IE1C03545_0010.JPEG.Search in Google Scholar
79. Papaioannou, V, Lafitte, T, Adjiman, CS, Galindo, A, Jackson, G. Simultaneous prediction of phase behaviour and second derivative properties with a group contribution approach (SAFT-γ Mie). Comput Aided Chem Eng 2011;29:1593–7. https://doi.org/10.1016/B978-0-444-54298-4.50097-0.Search in Google Scholar
80. Valderrama, JO, Robles, PA. Critical properties, normal boiling temperatures, and acentric factors of fifty ionic liquids. Ind Eng Chem Res 2007;46:1338–44. https://doi.org/10.1021/IE0603058/ASSET/IMAGES/MEDIUM/IE0603058E00015.GIF.Search in Google Scholar
81. Reid, RC, Prausnitz, JM, Poling, BE. The properties of gases & liquids, 4th ed. New York, USA: Mc-Graw-Hill, Inc.; 1987.Search in Google Scholar
82. ullah Rather, S, Taimoor, AA, Saeed, U, Siddiqui, ME, Bamufleh, HS. Carbon dioxide capturing in temperature/pressure swing-commercial processes using ionic liquids. Chem Eng Technol 2024;47:1097–113. https://doi.org/10.1002/CEAT.202300497.Search in Google Scholar
83. Dong, K, Liu, X, Dong, H, Zhang, X, Zhang, S. Multiscale studies on ionic liquids. Chem Rev 2017;117:6636–95. https://doi.org/10.1021/ACS.CHEMREV.6B00776/ASSET/IMAGES/CR-2016-007763_M047.GIF.Search in Google Scholar
84. Orchillés, AV, Miguel, PJ, Vercher, E, Martínez-Andreu, A. Isobaric vapor-liquid equilibria for ethyl acetate + ethanol + 1-ethyl-3-methylimidazolium trifluoromethanesulfonate at 100 kPa. J Chem Eng Data 2007;52:2325–30. https://doi.org/10.1021/JE700322P/ASSET/IMAGES/LARGE/JE700322PF00004.JPEG.Search in Google Scholar
85. Nagahama, K, Mitsuho, H. Binary vapor-liquid pressures – methyl acetate-methanol and methyl acetate-water. J Chem Eng Jpn 1971;4:1–6.10.1252/jcej.4.205Search in Google Scholar
86. Brouwer, T, Crespo, EA, ten Kate, A, Coutinho, JAP, Kersten, SRA, Bargeman, G, et al.. Isobaric vapor-liquid equilibrium prediction from excess molar enthalpy using cubic equations of state and PC-SAFT. Ind Eng Chem Res 2023;62:12329–44. https://doi.org/10.1021/acs.iecr.3c00804.Search in Google Scholar
87. Kumarkrishna Rao, VN, Swami, DR, Narasinga Rao, M. High-pressure vapor–liquid equilibriums of nonideal solutions. IV. cyclohexane–propanol. J Sci Ind Res 1957;16:294–9.Search in Google Scholar
88. Zhang, WTH, Zheng, X, Zhao, Y. Measurement and correlation of vapor-liquid equilibrium data for benzene-cyclohexanemethyl-cyclohexane-DMF systems. Nat Gas Chem Ind 1997;22:52–5.Search in Google Scholar
89. Nagata, I. Vapor-liquid equilibrium in ternary mixtures formed by ethanol, acetonitrile and benzene. Fluid Phase Equilib 1985;19:13–20. https://doi.org/10.1016/0378-3812(85)85032-9.Search in Google Scholar
90. Chen, G, Yan, X, Han, S, Ma, Z, Wang, Q. Phase equilibria under superatmospheric pressures for binary systems of cyclohexane 1-butanol and toluene. Huagong Xuebao/J Chem Ind Eng 1994;45:94–101 [Accessed 23 Jan 2024].Search in Google Scholar
91. Tao, H, Guan, GF, Chang, WX, Wan, H. Study on isobaric vapor-liquid equilibrium of formic acid-water-n-pentyl formate systems. Gao Xiao Hua Xue Gong Cheng Xue Bao/J Chem Eng Chin Univ 2007;21:924–8.Search in Google Scholar
92. Di Cave, S, Mazzarotta, B. Isobaric vapor-liquid equilibria for the binary systems formed by acetonitrile and aromatic hydrocarbons. J Chem Eng Data 2023;36:293–7. https://doi.org/10.1021/JE00003A011.Search in Google Scholar
Supplementary Material
This article contains supplementary material (https://doi.org/10.1515/cppm-2024-0064).
© 2025 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- Research Articles
- An improvement of level control of non-linear horizontal tank process using sliding mode controller
- Numerical investigation of inlet pressure effects on condensation flow regime in a supersonic nozzle
- Effects of tapered helical obstacles on heat transfer in tubes
- Gasification process prediction using a novel and reliable metaheuristic algorithm coupled with the K-nearest neighbors
- Evaluating the ionic liquids, commercial solvents, and pressure-swing for efficient azeotropic separation
- A synergistic approach to CO2 sequestration: evaluating trapping mechanisms in saline aquifers
- Diffusion modeling and optimization of drying dynamics of ogbono seed (Irvingea gabonensis): empirical insights into energy indices and process conditions
- Production of polyphenol extracts with antioxidant activity from olive pomace: process modeling and optimization
Articles in the same Issue
- Frontmatter
- Research Articles
- An improvement of level control of non-linear horizontal tank process using sliding mode controller
- Numerical investigation of inlet pressure effects on condensation flow regime in a supersonic nozzle
- Effects of tapered helical obstacles on heat transfer in tubes
- Gasification process prediction using a novel and reliable metaheuristic algorithm coupled with the K-nearest neighbors
- Evaluating the ionic liquids, commercial solvents, and pressure-swing for efficient azeotropic separation
- A synergistic approach to CO2 sequestration: evaluating trapping mechanisms in saline aquifers
- Diffusion modeling and optimization of drying dynamics of ogbono seed (Irvingea gabonensis): empirical insights into energy indices and process conditions
- Production of polyphenol extracts with antioxidant activity from olive pomace: process modeling and optimization