Solubility modeling of supercritical fluid extraction in a wide range compounds: comparison between fuzzy-genetic and new empirical models

References

• Adachi, Y., and B. C. Y. Lu. 1983. Supercritical fluid extraction with carbon dioxide and ethylene. Fluid Phase Equilibria 14:147–56. doi:10.1016/0378-3812(83)80120-4.
   Web of Science ®Google Scholar
• Anitescu, G., and L. Tavlarides. 1997. Solubilities of solids in supercritical fluids—I. New quasistatic experimental method for polycyclic aromatic hydrocarbons (PAHs)+ pure fluids. The Journal of Supercritical Fluids 10:175–89. doi:10.1016/S0896-8446(97)00024-7.
   Web of Science ®Google Scholar
• Asghari-Khiavi, M., Y. Yamini, and M. A. Farajzadeh. 2004. Solubilities of two steroid drugs and their mixtures in supercritical carbon dioxide. The Journal of Supercritical Fluids 30:111–17. doi:10.1016/j.supflu.2003.07.002.
   Web of Science ®Google Scholar
• Azevedo, Á. B. A. D., T. G. Kieckbusch, A. K. Tashima, R. S. Mohamed, P. Mazzafera, and S. A. B. V. D. Melo. 2008. Supercritical CO2 recovery of caffeine from green coffee oil: New experimental solubility data and modeling. Química Nova 31:1319–23. doi:10.1590/S0100-40422008000600009.
   Web of Science ®Google Scholar
• Bai, Y., H.-J. Yang, C. Quan, and C.-Y. Guo. 2007. Solubilities of 2, 2ʹ-bipyridine and 4, 4ʹ-dimethyl-2, 2ʹ-bipyridine in supercritical carbon dioxide. Journal of Chemical & Engineering Data 52:2074–76. doi:10.1021/je700269m.
   Web of Science ®Google Scholar
• Bao, Z. B., Z. J. Wei, B. G. Su, and Q. L. Ren. 2006. Solubility of racemic paroxetine intermediate in supercritical carbon dioxide. Journal of Chemical & Engineering Data 51:1731–34. doi:10.1021/je0601558.
   Web of Science ®Google Scholar
• Bartle, K. D., A. Clifford, S. Jafar, and G. Shilstone. 1991. Solubilities of solids and liquids of low volatility in supercritical carbon dioxide. Journal of Physical and Chemical Reference Data 20:713–56. doi:10.1063/1.555893.
   Web of Science ®Google Scholar
• Ch, R., and G. Madras. 2010. An association model for the solubilities of pharmaceuticals in supercritical carbon dioxide. Thermochimica Acta 507:99–105. doi:10.1016/j.tca.2010.05.006.
   Web of Science ®Google Scholar
• Chen, Y. P., Y. M. Chen, and M. Tang. 2009. Solubilities of cinnamic acid, phenoxyacetic acid and 4-methoxyphenylacetic acid in supercritical carbon dioxide. Fluid Phase Equilibria 275:33–38. doi:10.1016/j.fluid.2008.09.009.
   Web of Science ®Google Scholar
• Cheng, S. H., F. C. Yang, Y. H. Yang, C. C. Hu, and W. T. Chang. 2013. Measurements and modeling of the solubility of ergosterol in supercritical carbon dioxide. Journal of the Taiwan Institute of Chemical Engineers 44:19–26. doi:10.1016/j.jtice.2012.09.001.
   Web of Science ®Google Scholar
• Choi, E. S., H. Y. Shin, S. S. You, and K. P. Yoo. 1997. Measurement and correlation of solubilities ofo-, m-andp-Coumaric Acid isomers in supercritical Carbon Dioxide. Korean Journal of Chemical Engineering 14:292–96. doi:10.1007/BF02706826.
   Web of Science ®Google Scholar
• Chrastil, J. 1982. Solubility of solids and liquids in supercritical gases. The Journal of Physical Chemistry A 86:3016–21. doi:10.1021/j100212a041.
   Web of Science ®Google Scholar
• Coelho, J. P., and R. P. Stateva. 2011. Solubility of red 153 and blue 1 in supercritical carbon dioxide. Journal of Chemical & Engineering Data 56:4686–90. doi:10.1021/je200652j.
   Google Scholar
• Coimbra, P., M. R. Blanco, H. S. Costa Silva, M. H. Gil, and H. C. de Sousa. 2006. Experimental determination and correlation of artemisinin’s solubility in supercritical carbon dioxide. Journal of Chemical & Engineering Data 51:1097–104. doi:10.1021/je060015y.
   Web of Science ®Google Scholar
• Coimbra, P., D. Fernandes, M. H. Gil, and H. C. D. Sousa. 2008. Solubility of diflunisal in supercritical carbon dioxide. Journal of Chemical & Engineering Data 53:1990–95. doi:10.1021/je800384h.
   Web of Science ®Google Scholar
• Del Valle, J. M., and J. M. Aguilera. 1988. An improved equation for predicting the solubility of vegetable oils in supercritical carbon dioxide. Industrial & Engineering Chemistry Research 27:1551–53. doi:10.1021/ie00080a036.
   Web of Science ®Google Scholar
• Duarte, A. R. C., P. Coimbra, H. C. de Sousa, and C. M. Duarte. 2004. Solubility of flurbiprofen in supercritical carbon dioxide. Journal of Chemical & Engineering Data 49:449–52. doi:10.1016/j.supflu.2003.07.002.
   Web of Science ®Google Scholar
• Elizalde-Solis, O., and L. A. Galicia-Luna. 2005. Solubility of thiophene+ pentane and thiophene+ octane binary mixtures in supercritical carbon dioxide at temperatures from 333 to 383 K. Industrial & Engineering Chemistry Research 44:5757–60. doi:10.1021/ie048780y.
   Web of Science ®Google Scholar
• Garcı́a-González, J., M. A. J. Molina, F. Rodrı́guez, and F. Mirada. 2002. Solubilities of hydroquinone and p-quinone in supercritical carbon dioxide. Fluid Phase Equilibria 200:31–39. doi:10.1016/S0378-3812(02)00010-9.
   Web of Science ®Google Scholar
• García-González, J., M. J. Molina, F. Rodríguez, and F. Mirada. 2001. Solubilities of phenol and pyrocatechol in supercritical carbon dioxide. Journal of Chemical & Engineering Data 46:918–21. doi:10.1021/je0003795.
   Web of Science ®Google Scholar
• Garlapati, C., and G. Madras. 2009. Solubilities of solids in supercritical fluids using dimensionally consistent modified solvate complex models. Fluid Phase Equilibria 283:97–101. doi:10.1016/j.fluid.2009.05.013.
   Web of Science ®Google Scholar
• Garlapati, C., and G. Madras. 2010. New empirical expressions to correlate solubilities of solids in supercritical carbon dioxide. Thermochimica Acta 500:123–27. doi:10.1016/j.tca.2009.12.004.
   Web of Science ®Google Scholar
• Garmroodi, A., J. Hassan, and Y. Yamini. 2004. Solubilities of the drugs benzocaine, metronidazole benzoate, and naproxen in supercritical carbon dioxide. Journal of Chemical & Engineering Data 49:709–12. doi:10.1021/je020218w.
   Web of Science ®Google Scholar
• Ghaziaskar, H. S., and M. Kaboudvand. 2008. Solubility of trioctylamine in supercritical carbon dioxide. The Journal of Supercritical Fluids 44:148–54. doi:10.1016/j.supflu.2007.10.006.
   Web of Science ®Google Scholar
• Ghiasvand, A. R., M. Hosseini, H. Sharghi, Y. Yamini, and M. Shamsipur. 1999. Solubilities of some hydroxyxanthone derivatives in supercritical carbon dioxide. Journal of Chemical & Engineering Data 44:1135–38. doi:10.1021/je9900068.
   Web of Science ®Google Scholar
• Gordillo, M., M. Blanco, A. Molero, and E. M. De La Ossa. 1999. Solubility of the antibiotic Penicillin G in supercritical carbon dioxide. The Journal of Supercritical Fluids 15:183–190. doi: 10.1016/S0896-8446(99)00008-X.
   Web of Science ®Google Scholar
• Gurdial, G. S., and N. R. Foster. 1991. Solubility of o-hydroxybenzoic acid in supercritical carbon dioxide. Industrial & Engineering Chemistry Research 30:575–80. doi:10.1021/ie00051a020.
   Web of Science ®Google Scholar
• Hampson, J. W., R. J. Maxwell, S. Li, and R. J. Shadwell. 1999. Solubility of three veterinary sulfonamides in supercritical carbon dioxide by a recirculating equilibrium method. Journal of Chemical & Engineering Data 44:1222–25. doi:10.1021/je990075m.
   Web of Science ®Google Scholar
• Heryanto, R., E. C. Abdullah, and M. Hasan. 2010. Solubility of isoniazid in supercritical carbon dioxide. Journal of Chemical & Engineering Data 55:2306–09. doi:10.1021/je900622h.
   Web of Science ®Google Scholar
• Hojjati, M., Y. Yamini, M. Khajeh, and A. Vatanara. 2007. Solubility of some statin drugs in supercritical carbon dioxide and representing the solute solubility data with several density-based correlations. The Journal of Supercritical Fluids 41:187–94. doi:10.1016/j.supflu.2006.10.006.
   Web of Science ®Google Scholar
• Hosseini, M., H. N. Alizadeh, and A. R. Khanchi. 2010. Solubility analysis of clozapine and lamotrigine in supercritical carbon dioxide using static system. The Journal of Supercritical Fluids 52:30–35. doi:10.1016/j.supflu.2009.11.006.
   Web of Science ®Google Scholar
• Hozhabr, S. B., S. H. Mazloumi, and J. Sargolzaei. 2014. Correlation of solute solubility in supercritical carbon dioxide using a new empirical equation. Chemical Engineering Research and Design 92:2734–39. doi:10.1016/j.cherd.2014.01.026.
   Web of Science ®Google Scholar
• Huang, S. Y., M. Tang, S. L. Ho, and Y. P. Chen. 2007. Solubilities of N-phenylacetamide, 2-methyl-N-phenylacetamide and 4-methyl-N-phenylacetamide in supercritical carbon dioxide. The Journal of Supercritical Fluids 42:165–71. doi:10.1016/j.supflu.2007.04.001.
   Web of Science ®Google Scholar
• Huang, Z., M. Feng, Y. Guo, J. Su, L. Teng, T. Liu, and Y. C. Chiew. 2008. Ternary solubility of mixed cholesteryl esters in supercritical carbon dioxide. Fluid Phase Equilibria 272:8–17. doi:10.1016/j.fluid.2008.07.012.
   Web of Science ®Google Scholar
• Huang, Z., Y. H. Guo, H. Miao, and L. J. Teng. 2014. Solubility of progesterone in supercritical carbon dioxide and its micronization through RESS. Powder Technology 258:66–77. doi:10.1016/j.powtec.2014.03.009.
   Web of Science ®Google Scholar
• Huang, Z., W. D. Lu, S. Kawi, and Y. C. Chiew. 2004. Solubility of aspirin in supercritical carbon dioxide with and without acetone. Journal of Chemical & Engineering Data 49:1323–27. doi:10.1021/je0499465.
   Web of Science ®Google Scholar
• Huang, Z., X. W. Yang, G. B. Sun, S.-W. Song, and S. Kawi. 2005. The solubilities of xanthone and xanthene in supercritical carbon dioxide: Structure effect. The Journal of Supercritical Fluids 36:91–97. doi:10.1016/j.supflu.2005.04.002.
   Web of Science ®Google Scholar
• Ismadji, S. 2008. Solubility of methyl salicylate in supercritical carbon dioxide at several temperatures. Journal of Chemical & Engineering Data 53:2207–10. doi:10.1021/je800476n.
   Web of Science ®Google Scholar
• Ismadji, S., Y. H. Ju, F. E. Soetaredjo, and A. Ayucitra. 2011. Solubility of azadirachtin in supercritical carbon dioxide at several temperatures. Journal of Chemical & Engineering Data 56:4396–99. doi:10.1021/je200239p.
   Web of Science ®Google Scholar
• Jin, J. S., Y. W. Wang, H. F. Zhang, X. Fan, and H. Wu. 2014. Solubility of 4-Hydroxybenzaldehyde in supercritical carbon dioxide with and without cosolvents. Journal of Chemical & Engineering Data 59:1521–27. doi:10.1021/je401082x.
   Web of Science ®Google Scholar
• Jouyban, A., H. K. Chan, and N. R. Foster. 2002. Mathematical representation of solute solubility in supercritical carbon dioxide using empirical expressions. The Journal of Supercritical Fluids 24:19–35. doi: 10.1016/S0896-8446(02)00015-3.
   Web of Science ®Google Scholar
• Kazemi, S., V. Belandria, N. Janssen, D. Richon, C. J. Peters, and M. C. Kroon. 2012. Solubilities of ferrocene and acetylferrocene in supercritical carbon dioxide. The Journal of Supercritical Fluids 72:320–25. doi:10.1016/j.supflu.2012.10.009.
   Web of Science ®Google Scholar
• Khansary, M. A., F. Amiri, A. Hosseini, A. H. Sani, and H. Shahbeig. 2015. Representing solute solubility in supercritical carbon dioxide: A novel empirical model. Chemical Engineering Research and Design 93:355–65. doi:10.1016/j.cherd.2014.05.004.
   Web of Science ®Google Scholar
• Khansary, M. A., and A. H. Sani. 2014. Using genetic algorithm (GA) and particle swarm optimization (PSO) methods for determination of interaction parameters in multicomponent systems of liquid–Liquid equilibria. Fluid Phase Equilibria 365:141–45. doi:10.1016/j.fluid.2014.01.016.
   Web of Science ®Google Scholar
• Kostrzewa, D., A. Dobrzyńska-Inger, and E. Rój. 2013. Experimental data on xanthohumol solubility in supercritical carbon dioxide. Fluid Phase Equilibria 360:445–50. doi:10.1016/j.fluid.2013.10.001.
   Web of Science ®Google Scholar
• Kumar, S. K., and K. P. Johnston. 1988. Modelling the solubility of solids in supercritical fluids with density as the independent variable. The Journal of Supercritical Fluids 1:15–22. doi: 10.1016/0896-8446(88)90005-8.
   Google Scholar
• Kumoro, A., H. Singh, and M. Hasan. 2009. Solubility of piperine in supercritical and near critical carbon dioxide. Chinese Journal of Chemical Engineering 17:1014–20. doi:10.1016/S1004-9541(08)60310-9.
   Web of Science ®Google Scholar
• Laitinen, A., and M. Jäntti. 1996. Solubility of 6-caprolactam in supercritical carbon dioxide. Journal of Chemical & Engineering Data 41:1418–20. doi:10.1021/je9600313.
   Web of Science ®Google Scholar
• Lee, C. A., M. Tang, and Y. P. Chen. 2014. Measurement and correlation for the solubilities of cinnarizine, pentoxifylline, and piracetam in supercritical carbon dioxide. Fluid Phase Equilibria 367:182–87. doi:10.1016/j.fluid.2014.01.041.
   Web of Science ®Google Scholar
• Lee, C. A., M. Tang, S. L. Ho, and Y. P. Chen. 2014. Solubilities of chlormezanone, metaxalone and methocarbamol in supercritical carbon dioxide. The Journal of Supercritical Fluids 85:11–16. doi:10.1016/j.supflu.2013.10.006.
   Web of Science ®Google Scholar
• Lee, L. S., J. H. Fu, and H. L. Hsu. 2000. Solubility of solid 1, 4-dimethoxybenzene in supercritical carbon dioxide. Journal of Chemical & Engineering Data 45:358–61. doi:10.1021/je9902591.
   Web of Science ®Google Scholar
• Li, Y., Y. Ning, J. Jin, and Z. Zhang. 2013. Solubility of 3-aminobenzoic acid in supercritical carbon dioxide modified by ethanol. Journal of Chemical & Engineering Data 58:2176–80. doi:10.1021/je4000845.
   Web of Science ®Google Scholar
• Lim, J., H. Kim, H. K. Cho, and M. S. Shin. 2011. Solubility of hinokitiol in supercritical fluids; measurement and correlation. Korean Journal of Chemical Engineering 28:2319–23. doi:10.1007/s11814-011-0112-7.
   Web of Science ®Google Scholar
• Liu, T., S. Li, R. Zhou, D. Jia, and S. Tian. 2009. Solubility of triphenylmethyl chloride and triphenyltin chloride in supercritical carbon dioxide. Journal of Chemical & Engineering Data 54:1913–15. doi:10.1021/je9000944.
   Web of Science ®Google Scholar
• Maheshwari, P., Z. Nikolov, T. White, and R. Hartel. 1992. Solubility of fatty acids in supercritical carbon dioxide. Journal of the American Oil Chemists’ Society 69:1069–76. doi:10.1007/BF02541039.
   Web of Science ®Google Scholar
• McHugh, M., and M. E. Paulaitis. 1980. Solid solubilities of naphthalene and biphenyl in supercritical carbon dioxide. Journal of Chemical & Engineering Data 25:326–29. doi:10.1021/je60087a018.
   Web of Science ®Google Scholar
• Medina, I., and J. L. Bueno. 2001. Solubilities of zopiclone and nimodipine in supercritical carbon dioxide. Journal of Chemical & Engineering Data 46:1211–14. doi:10.1021/je010025t.
   Web of Science ®Google Scholar
• Mendez-Santiago, J., and A. S. Teja. 2000. Solubility of solids in supercritical fluids: Consistency of data and a new model for cosolvent systems. Industrial & Engineering Chemistry Research 39:4767–71. doi:10.1021/ie000339u.
   Web of Science ®Google Scholar
• Murga, R., M. T. Sanz, S. Beltrán, and J. L. Cabezas. 2004. Solubility of syringic and vanillic acids in supercritical carbon dioxide. Journal of Chemical & Engineering Data 49:779–82. doi:10.1021/je034129a.
   Web of Science ®Google Scholar
• Nejad, S. J., H. Abolghasemi, M. Moosavian, and M. Maragheh. 2010. Prediction of solute solubility in supercritical carbon dioxide: A novel semi-empirical model. Chemical Engineering Research and Design 88:893–98. doi:10.1016/j.cherd.2009.12.006.
   Web of Science ®Google Scholar
• Ren, J., S. Zhan, J. Zhou, and M. Zhang. 2012. New equilibrium autoclave for determining solubility and melting point of solid solute in supercritical fluids. 1. Determination of solubility of levonorgestrel in supercritical carbon dioxide. Industrial & Engineering Chemistry Research 51:2451–55. doi:10.1021/ie201785w.
   Web of Science ®Google Scholar
• Shamsipur, M., M. R. Fat’hi, Y. Yamini, and A. R. Ghiasvand. 2002. Solubility determination of nitrophenol derivatives in supercritical carbon dioxide. The Journal of Supercritical Fluids 23:225–31. doi:10.1016/S0896-8446(01)00143-7.
   Web of Science ®Google Scholar
• Shamsipur, M., A. R. Ghiasvand, and Y. Yamini. 2004. Solubilities of chelating ligands dibenzoylmethane, 1, 10-phenanthroline, and 8-hydroxyquinoline in supercritical carbon dioxide. Journal of Chemical & Engineering Data 49:1483–86. doi:10.1021/je034098j.
   Web of Science ®Google Scholar
• Sovova, H. 2001. Solubility of ferulic acid in supercritical carbon dioxide with ethanol as cosolvent. Journal of Chemical & Engineering Data 46:1255–57. doi:10.1021/je0101146.
   Web of Science ®Google Scholar
• Sovova, H., and J. Jez. 1994. Solubility of menthol in supercritical carbon dioxide. Journal of Chemical & Engineering Data 39:840–41. doi:10.1021/je00016a045.
   Web of Science ®Google Scholar
• Su, B., H. Xing, Y. Yang, and Q. Ren. 2008. Solubility of oxymatrine in supercritical carbon dioxide. Journal of Chemical & Engineering Data 53:1672–74. doi:10.1021/je800179c.
   Web of Science ®Google Scholar
• Sung, H. D., and J. J. Shim. 1999. Solubility of CI disperse red 60 and CI disperse blue 60 in supercritical carbon dioxide. Journal of Chemical & Engineering Data 44:985–89. doi:10.1021/je990018t.
   Web of Science ®Google Scholar
• Tayyebi, S., and S. Soltanali. 2017. A new approach of GA-based type reduction of interval type-2 fuzzy model for nonlinear MIMO system: Application in methane oxidation process. Chemometrics and Intelligent Laboratory Systems 167:152–60. doi:10.1016/j.chemolab.2017.06.004.
   Web of Science ®Google Scholar
• Tsai, C. C., H. M. Lin, and M. J. Lee. 2008a. Solubility of 1, 5-Diaminobromo-4, 8-dihydroxyanthraquinone in supercritical carbon dioxide with or without cosolvent. Journal of Chemical & Engineering Data 54:1442–46. doi:10.1021/je800646h.
   Web of Science ®Google Scholar
• Tsai, C. C., H. M. Lin, and M. J. Lee. 2008b. Solubility of CI Disperse Violet 1 in supercritical carbon dioxide with or without cosolvent. Journal of Chemical & Engineering Data 53:2163–69. doi:10.1021/je8003673.
   Web of Science ®Google Scholar
• Wang, L. H., and -Y.-Y. Cheng. 2005. Solubility of puerarin in ethanol+ supercritical carbon dioxide. Journal of Chemical & Engineering Data 50:1747–49. doi:10.1021/je050192j.
   Web of Science ®Google Scholar
• Wang, T. C., and P. Y. Lee. 2014. Measurement and correlation for the solid solubility of antioxidants d-isoascorbic acid and calcium l-ascorbate dihydrate in supercritical carbon dioxide. Journal of Chemical & Engineering Data 59:613–17. doi:10.1021/je400369n.
   Web of Science ®Google Scholar
• Weinstein, R. D., K. R. Muske, J. Moriarty, and E. K. Schmidt. 2004. The solubility of benzocaine, lidocaine, and procaine in liquid and supercritical carbon dioxide. Journal of Chemical & Engineering Data 49:547–52. doi:10.1021/je034163p.
   Web of Science ®Google Scholar
• Wu, X., J. M. Yi, Y. J. Liu, Y. B. Liu, and P. L. Zhang. 2013. Solubility and micronisation of phenacetin in supercritical carbon dioxide. Chemical Papers 67:517–25. doi:10.2478/s11696-013-0328-6.
   Web of Science ®Google Scholar
• Yamini, Y., J. Arab, and M. Asghari-Khiavi. 2003. Solubilities of phenazopyridine, propranolol, and methimazole in supercritical carbon dioxide. Journal of Pharmaceutical and Biomedical Analysis 32:181–87. doi:10.1016/S0731-7085(03)00016-5.
   PubMed Web of Science ®Google Scholar
• Yamini, Y., and N. Bahramifar. 2000. Solubility of polycyclic aromatic hydrocarbons in supercritical carbon dioxide. Journal of Chemical & Engineering Data 45:53–56. doi:10.1021/je990129s.
   Web of Science ®Google Scholar
• Yamini, Y., J. Hassan, and S. Haghgo. 2001. Solubilities of some nitrogen-containing drugs in supercritical carbon dioxide. Journal of Chemical & Engineering Data 46:451–55. doi:10.1021/je000286n.
   Web of Science ®Google Scholar
• Youn, H. S., M. K. Roh, A. Weber, G. T. Wilkinson, and B. S. Chun. 2007. Solubility of astaxanthin in supercritical carbon dioxide. Korean Journal of Chemical Engineering 24:831–34. doi:10.1007/s11814-007-0049-z.
   Web of Science ®Google Scholar
• Yu, Z. R., B. Singh, S. S. Rizvi, and J. A. Zollweg. 1994. Solubilities of fatty acids, fatty acid esters, triglycerides, and fats and oils in supercritical carbon dioxide. The Journal of Supercritical Fluids 7:51–59. doi:10.1016/0896-8446(94)90006-X.
   Web of Science ®Google Scholar
• Yun, S. J., K. K. Liong, G. S. Gurdial, and N. R. Foster. 1991. Solubility of cholesterol in supercritical carbon dioxide. Industrial & Engineering Chemistry Research 30:2476–82. doi:10.1021/ie00059a018.
   Web of Science ®Google Scholar
• Zeinolabedini Hezave, A., and F. Esmaeilzadeh. 2012. Solubility measurement of diclofenac acid in the supercritical CO2. Journal of Chemical & Engineering Data 57:1659–64. doi:10.1021/je200012x.
   Web of Science ®Google Scholar
• Zhou, R., S. Li, and T. Liu. 2008. Measurement and Correlation of Solubility of Uracil in Supercritical Carbon Dioxide. Journal of Chemical & Engineering Data 53:2679–82. doi:10.1021/je800614u.
   Web of Science ®Google Scholar