β-Diketones at Water/Supercritical CO2 Interface:A Molecular Dynamics Simulation

Abstract

Abstract: The structural and dynamical properties of hexafluoroacetylacetone(HFA) and acetylacetone(AA) at the water/supercritical CO₂(Sc-CO₂) interface at 20 MPa and 318.15 K are investigated by molecular dynamics simulations.The TIP3P potential is used for water and the EPM2 model is for CO₂.The water phase and SC-CO₂ phase form a distinct immiscible liquid-liquid interface.The two chelating molecules show interfacial preference.Comparatively,the AA molecules show somewhat more preference for interfacial region,whereas the HFA molecules are preferably near the Sc-CO₂ phase.The orientational distribution of the β-diketone molecules and the radial distribution functions between β-diketones and solvents are obtained in order to study the microscopic structural properties of the β-diketones at the water-SC-CO₂ interface.It is found that the translational diffusion and rotational diffusion of HFA and AA are obviously anisotropic and decrease as the β-diketone molecules approach the interface.The anisotropic dynamic behavior for the solute molecules is related to the corresponding structural properties.

Key words: molecular dynamics simulation, liquid/liquid interface, supercritical carbon dioxide, β-diketone

摘要： The structural and dynamical properties of hexafluoroacetylacetone(HFA) and acetylacetone(AA) at the water/supercritical CO₂(Sc-CO₂) interface at 20 MPa and 318.15 K are investigated by molecular dynamics simulations.The TIP3P potential is used for water and the EPM2 model is for CO₂.The water phase and SC-CO₂ phase form a distinct immiscible liquid-liquid interface.The two chelating molecules show interfacial preference.Comparatively,the AA molecules show somewhat more preference for interfacial region,whereas the HFA molecules are preferably near the Sc-CO₂ phase.The orientational distribution of the β-diketone molecules and the radial distribution functions between β-diketones and solvents are obtained in order to study the microscopic structural properties of the β-diketones at the water-SC-CO₂ interface.It is found that the translational diffusion and rotational diffusion of HFA and AA are obviously anisotropic and decrease as the β-diketone molecules approach the interface.The anisotropic dynamic behavior for the solute molecules is related to the corresponding structural properties.

关键词: molecular dynamics simulation, liquid/liquid interface, supercritical carbon dioxide, β-diketone

LIU Shuyan, CHAI Jingchun, YANG Xiaoning. β-Diketones at Water/Supercritical CO₂ Interface:A Molecular Dynamics Simulation[J]. , 2009, 17(6): 990-998.

刘淑延, 柴景春, 杨晓宁. β-Diketones at Water/Supercritical CO₂ Interface:A Molecular Dynamics Simulation[J]. CIESC Journal, 2009, 17(6): 990-998.

References

1 Clifford, Y.T., You, G.S., “Fractional of metal ions from water using supercritical carbon dioxide”, AIChE J., 50(7), 1627-1630(2004).
2 Iwao, S., El-Fatah, S.A., Furukawa, K., Seki, T., Sasaki, M., Goto, M., “Recovery of palladium from spent catalyst with supercritical CO₂ and chelating agent”, J. Supercrit. Fluids, 42, 200-204(2007).
3 Chou, W.L., Yang, K.C., “Effect of various chelating agents on supercritical carbon dioxide extraction of indium(III) ions from acidic aqueous solution”, J. Hazard. Mater., 154, 498-505(2008).
4 Chen, J.L., Liu, C.Y., “Chelating resin sorption followed by supercritical fluid extraction and liquid chromatographic determination of aluminum in liquid samples”, Anal. Chim. Acta, 494, 125-132(2003).
5 Shamsipur, M., Ghiasvand, A.R., Yamini, Y., “Extraction of uranium from solid matrices using modified supercritical fluid CO₂”, J. Supercrit. Fluids, 20, 163-169(2001).
6 Ozel, M.Z., Burford, M.D., Clifford, A.A., Bartle, K.D., Shadrin, A., Smart, N.G., Tinker, N.D., “Supercritical fluid extraction of cobalt with fluorinated and non-fluorinated β-diketones”, Anal. Chim. Acta, 346, 73-80(1997).
7 Lalntz, K.E., Tachlkawa, E., “Extraction of lanthanides from acidic solution using tributyl phosphate modified supercritical carbon dioxide”, Anal. Chem., 66, 2190-2193(1994).
8 Murphy, J.M., Erkey, C., “Thermodynamics of extraction of copper(II) from aqueous solutions by chelation in supercritical carbon dioxide”, Environ. Sci. Technol., 31, 1674-1679(1997).
9 Erkey, C., “Supercritical carbon dioxide extraction of metals from aqueous solutions:A review”, J. of Supercrit. Fluids, 17, 259-287(2000).
10 Murphy, J.M., Erkey, C., “Copper(II) removal from aqueous solutions by chelation in supercritical carbon dioxide using fluorinated beta-diketones”, Ind. Eng. Chem. Res., 36, 5371-5376(1997).
11 Mitrinovic, D.M., Zhang, Z., Williams, S.M., Huang, Z., Schlossman, M.L., “X-ray reflectivity study of the water-hexane interface”, J. Phys. Chem. B, 103, 1779-1782(1999).
12 Zarbakhsh, A., Querol, A., Bowers, J., Yaseen, M., Lu, J.R., Webster, J.R.P., “Neutron reflection from the liquid-liquid interface:Adsorption of hexadecylphosphorylcholine to the hexadecane-aqueous solution interface”, Langmuir, 21, 11704-11709(2005).
13 Ohe, C., Ida, Y., Matsumoto, S., Sasaki, T., Goto, Y., Noi, M., Tsurumaru, T., Itoh, K., “Investigations of polymyxin B-phospholipid interactions by vibrational sum frequency generation spectroscopy”, J. Phys. Chem. B, 108, 18081-18087(2004).
14 Nochi, K., Yamaguchi, A., Hayashita, T., Uchida, T., Teramae, N., “Direct observation of alkali metal ion recognition processes at the heptane/water interface by second harmonic generation spectroscopy”, J. Phys. Chem. B, 106, 9906-9911(2002).
15 Takechi, H., Adachi, K., Monjushiro, H., Watarai, H., “Linear dichroism of Zn(II)-tetrapyridylporphine aggregates formed at the toluene/water interface”, Langmuir, 24, 4722-4728(2008).
16 Timgren, A., Tragardh, G., Tragardh, C., “Application of the PIV technique to measurements around and inside a forming drop in a liquid-liquid system”, Exp. Fluids, 44, 565-575(2008).
17 Chang, T.M., Dang, L.X., “Molecular dynamics simulations of CCl₄-H₂O liquid-liquid interface with polarizable potential models”, J. Chem. Phys., 104, 6772-6783(1996).
18 Benjamin, I., “Theoretical study of the water/l,2-dichloroethane interface:Structure, dynamics, and conformational equilibria at the liquid-liquid interface”, J. Chem. Phys., 97, 1432-1445(1992).
19 Fernandes, P.A., Cordeiro, M.N.D.S., Gomes, J.A.N.F., “Molecular dynamics simulation of the water/2-heptanone liquid-liquid interface”, J. Phys. Chem. B, 103, 6290-6299(1999).
20 Jedlovszky, P., Vincze, A., Horvai, G., “Full description of the orientational statistics of molecules near to interfaces. Water at the interface with CCl₄”, Phys. Chem. Chem. Phys., 6, 1874-1879(2004).
21 Jorge, M., Natalia, M., Cordeiro, D.S., “Intrinsic structure and dynamics of the water/nitrobenzene interface”, J. Phys. Chem. C, 111, 17612-17626(2007).
22 Buhn, J.B., Bopp, P.A., Hampe, M.J., “Structural and dynamical properties of liquid-liquid interfaces:A systematic molecular dynamics study”, J. Mol. Liq., 125, 187-196(2006).
23 da Rocha, S.R.P., Johnston, K.P., Westacott, R.E., Rossky, P.J., “Molecular structure of the water/supercritical CO₂ interface”, J. Phys. Chem. B, 105, 12092-12104(2001).
24 Vayssiere, P., Wipff, G., “Ethers, crown ethers and 18-crown-6 K + complexes at a water/SC-CO₂ interface:A molecular dynamics study”, Phys. Chem. Chem. Phys., 5, 127-135(2003).
25 Schurhammer, R., Berny, F., Wipff, G., “Importance of interfacial phenomena in assisted ion extraction by supercritical a molecular dynamics investigation”, Phys. Chem. Chem. Phys., 3, 647-656(2001).
26 Galand, N., Wipff, G., “Uranyl extraction by β-diketonate ligands to SC-CO₂:Theoretical studies on the effect of ligand fluorination and on the synergistic effect of TBP”, J. Phys. Chem. B, 109, 277-287(2005).
27 da Rocha, S.R.P., Johnston, K.P., Rossky, P.J., “Surfactant-modified CO₂-water interface:A molecular view”, J. Phys. Chem. B, 106, 13250-13261(2002).
28 Chaumont, A., Galand, N., Schurhammer, R., Vayssiere, P., Wipff, G., “Accumulation of host-guest ion complexes with different counterions at the water/supercritical CO₂ interface:A molecular dynamics study”, Russ. Chem. Bull., 53, 1459-1565(2004).
29 Guo, J.X., Sun, S.X., Yuan, S.L., Ran, X.K., Xu, G.Y., “Computer simulations of extractant primary amine N1923 and N1923 hydrochloride salt at water/chloroform interface”, Mol. Simul., 32, 451-455(2006).
30 Lu, L.Y., Berkowitz, M.L., “The effect of the rigidity of perfluoropolyether surfactant on its behavior at the water/supercritical carbon dioxide interface”, J. Phys. Chem. B, 109, 21725-21731(2005).
31 Jorgensen, W.L., Chandrasekhar, J., Madura, J.D., Impey, R.W., Klein, M.L., “Comparison of simple potential functions for simulating liquid water”, J. Chem. Phys., 79, 926-935(1983).
32 Harris, J.G., Yung, K.H., “Carbon dioxide's liquid-vapor coexistence curve and critical properties as predicted by a simple molecular model”, J. Phys. Chem., 99, 12021-12024(1995).
33 Perdew, J.P., Chevary, J.A., Vosko, S.H., Jackson, K.A., Pederson, M.R., Singh, D.J., Fiolhais, C., “Atoms, molecules, solids, and surfaces:Applications of the generalized gradient approximation for exchange and correlation”, Phys. Rev. B, 46, 6671-6687(1992).
34 Collazo, N., Shin, S., Rice, S.A., “Molecular-dynamics studies of the structure and properties of monolayers of perfluorinated amphiphiles”, J. Chem. Phys., 96, 4735-4742(1992).
35 Jorgensen, W.L., Briggs, J.M., Contreras, M.L., “Relative partition coefficients for organic solutes from fluid simulations”, J. Phys. Chem., 94, 1683-1686(1990).
36 Yang, X.N., Matthews, M.A., “Diffusion of chelating agents in supercritical CO₂ and a predictive approach for diffusion coefficients”, J. Chem. Eng. Data, 46, 588-595(2001).
37 Lagalante, A.F., Hansen, B.N., Bruno, T.J., Sievers, R.E., “Solubilities of copper(II) and chromium(III) beta-diketonates in supercritical carbon-dioxide”, Inorg. Chem., 34, 5781-5785(1995).
38 Ozel, M.Z., Bartle, K.D., Clifford, A.A., Burford, M.D., “Extraction, solubility and stability of metal complexes using stainless steel supercritical fluid extraction system”, Anal. Chim. Acta, 417, 177-184(2000).
39 Galand, N., Wipff, G., “Solvation of benzene derivatives in SC-CO₂:A molecular dynamics study of fluorination effects”, New J. Chem., 27, 1319-1325(2003).
40 Guardia, E., Marti, J., Padro, J.A., Saiz, L., Komolkin, A.V., “Dynamics in hydrogen bonded liquids:Water and alcohols”, J. Mol. Liq., 96-97, 3-17(2002).
41 Higashi, H., Iwai, Y., Miyazaki, K., Arai, Y., “Molecular dynamics simulation of fluorination effect for solvation of trifluoromethylbenzoic acid isomers in supercritical carbon dioxide”, Mol. Simul., 31, 725-730(2005).
42 Meredith, J.C., Johnston, K.P., Seminario, J.M., Kazarian, S.G., Eckert, C.A., “Quantitative equilibrium constants between CO₂ and lewis bases from FTIR spectroscopy”, J. Phys. Chem., 100, 10837-10848(1996).
43 Wang, H., Carlson, E., Henderson, D., Rowley, R.L., “Molecular dynamics simulation of the liquid-liquid interface for immiscible and partially miscible mixtures”, Mol. Simul., 29, 777-785(2003).
44 Michael, D., Benjamin, I., “Solute orientational dynamics and surface roughness of water/hydrocarbon interfaces”, J. Phys. Chem., 99, 1530-1536(1995).
45 Inomata, H., Saito, S., Debenedetti, P.G., “Molecular dynamics simulation of infinitely dilute solutions of benzene in supercritical CO₂”, Fluid Phase Equilib., 116, 282-288(1996).
46 Smirnov, K.S., Bougeard, D., “A molecular dynamics study of structure and short-time dynamics of water in kaolinite”, J. Phys. Chem. B, 103, 5266-5273(1999).
47 Siavosh-Haghighi, A., Adams, J.E., “Rotational relaxation in a nondipolar supercritical fluid:Toluene in CO₂”, J. Phys. Chem. A, 105, 2680-2686(2001).
48 Nicolas, J.P., “Molecular dynamics simulation of surfactin molecules at the water-hexane interface”, Biophys. J., 85, 1377-1391(2003).

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β-Diketones at Water/Supercritical CO₂ Interface:A Molecular Dynamics Simulation

β-Diketones at Water/Supercritical CO₂ Interface:A Molecular Dynamics Simulation

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