Improving understanding of solvent effects on intermolecular interactions in reactive liquid.liquid extraction with Isothermal Titration Calorimetry and molecular modeling

Lisette M.J. Sprakel; Boelo Schuur

Journal of Industrial and Engineering Chemistry, Vol.72, 364-373, April, 2019

DOI10.1016/j.jiec.2018.12.038 Export Citation

Improving understanding of solvent effects on intermolecular interactions in reactive liquid.liquid extraction with Isothermal Titration Calorimetry and molecular modeling

Lisette M.J. Sprakel, and Boelo Schuur^†

Faculty of Science and Technology, Sustainable Process Technology Group, University of Twente, The Netherlands

E-mail:

Isothermal Titration Calorimetry (ITC) and molecular modeling (MM) were combined with liquid-liquid equilibrium data to obtain better understanding of solvent effects on complexation in reactive liquid-liquid extraction. Two examples with ample extraction literature available were studied, acetic acid extraction and phenol extraction. Interactions with binary solvents were studied. Based on the insight and quantification of complexation with MM and ITC, models describing the liquid-liquid equilibrium (LLE) were formulated and validated with experiments, showing that ITC can predict LLE. ITC together with MM indeed can yield additional insight in complexation behavior in reactive liquid-liquid extraction and may guide solvent selection procedures.

Keywords:Liquid-liquid extraction;Crboxylic acids;Phenol;Isothermal titration calorimetry;Molecular modeling

[References]

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Verkuijl BJV, Schuur B, Minnaard AJ, de Vries JG, Feringa BL, Org. Biomol. Chem., 8, 3045 (2010)
Schuur B, Verkuijl BJV, Minnaard AJ, de Vries JG, Heeres HJ, Feringa BL, Org. Biomol. Chem., 9, 36 (2011)
Rowley D, Steiner H, Zimmen E, J. Soc. Chem. Ind. London, 65, 237 (1946)
van Delden ML, Kuipers NJM, de Haan AB, Sep. Purif. Technol., 51(2), 219 (2006)
Kiezyk PR, Mackay D, Can. J. Chem. Eng., 49, 747 (1971)
Krzyzaniak A, Leeman M, Vossebeld F, Visser TJ, Schuur B, de Haan AB, Sep. Purif. Technol., 111, 82 (2013)
Li QZ, Jiang XL, Feng XJ, Wang JM, Sun C, Zhang HB, Xian M, Liu HZ, J. Microbiol. Biotechnol., 26, 1 (2016)
Hartl J, Marr R, Sep. Sci. Technol., 28, 805 (1993)
Blahusiak M, Kiss AA, Kersten SRA, Schuur B, Energy, 116, 20 (2016)
Kiss AA, Lange JP, Schuur B, Brilman DWF, van der Ham AGJ, Kersten SRA, Biomass Bioenergy, 95, 296 (2016)
Bradley JC, Abraham MH, Acree WE, Lang AS, Chem. Cent. J., 9, 12 (2015)
Eckert F, Klamt A, AlChE J., 48, 369 (2002)
Jongmans MTG, Londono A, Mamilla SB, Pragt HJ, Aaldering KTJ, Bargeman G, Nieuwhof MR, ten Kate A, Verwer P, Kiss AA, van Strien CJG, Schuur B, de Haan AB, Sep. Purif. Technol., 98, 206 (2012)
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Sprakel LMJ, Schuur B, Sep. Purif. Technol., 211, 935 (2019)
Girisuta B, Janssen LPBM, Heeres HJ, Ind. Eng. Chem. Res., 46(6), 1696 (2007)
Cuypers B, Burghoff ATM, Sudholter EJR, de Haan AB, Zuilhof H, J. Phys. Chem. A, 112, 11714 (2008)
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Cai W, Zhu S, Piao X, J. Chem. Eng. Data, 46, 1472 (2001)
Wasewar KL, Shende DZ, J. Chem. Eng. Data, 56(2), 288 (2011)
Brouwer T, Blahusiak M, Babic K, Schuur B, Sep. Purif. Technol., 185, 186 (2017)
Wisniewski M, Pierzchalska M, J. Chem. Technol. Biotechnol., 80(12), 1425 (2005)
Yang YZ, Yang YH, Sun GX, Meng XJ, Wang ZQ, Sun SX, Chem. J. Chin. Univ., 17, 515 (1996)
Tamada JA, King CJ, Ind. Eng. Chem. Res., 29, 1327 (1990)
Barrow GM, Yerger EA, J. Am. Chem. Soc., 76, 5211 (1954)
Masaru N, Tatsuya S, Bull. Chem. Soc. Jpn., 51, 705 (1978)
Sprakel LMJ, Schuur B, Ind. Eng. Chem. Res., 12574 (2018).
Wang K, Chang ZD, Ma YC, Lei C, Jin SC, Wu Y, Mahmood I, Hua C, Liu HZ, Fluid Phase Equilib., 278(1-2), 103 (2009)
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Cichy W, Schlosser S, Szymanowski J, J. Chem. Technol. Biotechnol., 80(2), 189 (2005)
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Krishtalik LI, BBA-Bioenergetics, 1458, 6 (2000)

[Referenced By]

[1] Meyers RA, Handbook of Petroleum Refining Processes, 3rd edn., McGraw-Hill, New York, 2004.

[2] Verkuijl BJV, Schuur B, Minnaard AJ, de Vries JG, Feringa BL, Org. Biomol. Chem., 8, 3045 (2010)

[3] Schuur B, Verkuijl BJV, Minnaard AJ, de Vries JG, Heeres HJ, Feringa BL, Org. Biomol. Chem., 9, 36 (2011)

[4] Rowley D, Steiner H, Zimmen E, J. Soc. Chem. Ind. London, 65, 237 (1946)

[5] van Delden ML, Kuipers NJM, de Haan AB, Sep. Purif. Technol., 51(2), 219 (2006)

[6] Kiezyk PR, Mackay D, Can. J. Chem. Eng., 49, 747 (1971)

[7] Krzyzaniak A, Leeman M, Vossebeld F, Visser TJ, Schuur B, de Haan AB, Sep. Purif. Technol., 111, 82 (2013)

[8] Li QZ, Jiang XL, Feng XJ, Wang JM, Sun C, Zhang HB, Xian M, Liu HZ, J. Microbiol. Biotechnol., 26, 1 (2016)

[9] Hartl J, Marr R, Sep. Sci. Technol., 28, 805 (1993)

[10] Blahusiak M, Kiss AA, Kersten SRA, Schuur B, Energy, 116, 20 (2016)

[11] Kiss AA, Lange JP, Schuur B, Brilman DWF, van der Ham AGJ, Kersten SRA, Biomass Bioenergy, 95, 296 (2016)

[12] Bradley JC, Abraham MH, Acree WE, Lang AS, Chem. Cent. J., 9, 12 (2015)

[13] Eckert F, Klamt A, AlChE J., 48, 369 (2002)

[14] Jongmans MTG, Londono A, Mamilla SB, Pragt HJ, Aaldering KTJ, Bargeman G, Nieuwhof MR, ten Kate A, Verwer P, Kiss AA, van Strien CJG, Schuur B, de Haan AB, Sep. Purif. Technol., 98, 206 (2012)

[15] Laurence C, Gal JF, Lewis Basicity and Affinity Scales, John Wiley & Sons, Ltd., 2009.

[16] Sprakel LMJ, Schuur B, Sep. Purif. Technol., 211, 935 (2019)

[17] Girisuta B, Janssen LPBM, Heeres HJ, Ind. Eng. Chem. Res., 46(6), 1696 (2007)

[18] Cuypers B, Burghoff ATM, Sudholter EJR, de Haan AB, Zuilhof H, J. Phys. Chem. A, 112, 11714 (2008)

[19] Uslu H, Datta D, Bamufleh HS, J. Mol. Liq., 212, 430 (2015)

[20] Marti ME, Sep. Sci. Technol., 1 (2016).

[21] Rasrendra CB, Girisuta B, van de Bovenkamp HH, Winkelman JGM, Leijenhorst EJ, Venderbosch RH, Windt M, Meier D, Heeres HJ, Chem. Eng. J., 176-177, 244 (2011)

[22] Hano T, Matsumoto M, Ohtake T, Sasaki K, Hori F, Kawano Y, J. Chem. Eng. Jpn., 23, 734 (1990)

[23] Cai W, Zhu S, Piao X, J. Chem. Eng. Data, 46, 1472 (2001)

[24] Wasewar KL, Shende DZ, J. Chem. Eng. Data, 56(2), 288 (2011)

[25] Brouwer T, Blahusiak M, Babic K, Schuur B, Sep. Purif. Technol., 185, 186 (2017)

[26] Wisniewski M, Pierzchalska M, J. Chem. Technol. Biotechnol., 80(12), 1425 (2005)

[27] Yang YZ, Yang YH, Sun GX, Meng XJ, Wang ZQ, Sun SX, Chem. J. Chin. Univ., 17, 515 (1996)

[28] Tamada JA, King CJ, Ind. Eng. Chem. Res., 29, 1327 (1990)

[29] Barrow GM, Yerger EA, J. Am. Chem. Soc., 76, 5211 (1954)

[30] Masaru N, Tatsuya S, Bull. Chem. Soc. Jpn., 51, 705 (1978)

[31] Sprakel LMJ, Schuur B, Ind. Eng. Chem. Res., 12574 (2018).

[32] Wang K, Chang ZD, Ma YC, Lei C, Jin SC, Wu Y, Mahmood I, Hua C, Liu HZ, Fluid Phase Equilib., 278(1-2), 103 (2009)

[33] Hong YK, Hong WH, Bioprocess. Eng., 22, 281 (2000)

[34] Falconer RJ, Penkova A, Jelesarov I, Collins BM, J. Mol. Recognit., 23, 395 (2010)

[35] Boyce SE, Tellinghuisen J, Chodera JD, bioRxiv (2015) 23796/23791-23796/23797.

[36] Qin W, Li ZY, Dai YY, Ind. Eng. Chem. Res., 42(24), 6196 (2003)

[37] Aono S, Kato S, J. Comput. Chem., 31, 2924 (2010)

[38] Lide DR, CRC Handbook of Chemistry and Physics, 74th edn., CRC Press, Boca Raton, 1993.

[39] Zidi C, Tayeb R, Dhahbi M, J. Hazard. Mater., 194, 62 (2011)

[40] Zidi C, Tayeb R, Ali MB, Dhahbi M, J. Membr. Sci., 360(1-2), 334 (2010)

[41] Cichy W, Schlosser S, Szymanowski J, J. Chem. Technol. Biotechnol., 80(2), 189 (2005)

[42] Gutierrez R, Urtiaga A, Ortiz I, J. Chem. Technol. Biotechnol., 85(9), 1215 (2010)

[43] Gilli P, Pretto L, Bertolasi V, Gilli G, Accounts Chem. Res., 42, 33 (2009)

[44] Krishtalik LI, BBA-Bioenergetics, 1458, 6 (2000)