Selective adsorption of L-TA/D-TA by β-cyclodextrin derivative modified with L-tryptophan: Isotherm, kinetic and thermodynamics studies

Kaichen He; Fengxian Qiu; Jiao Qin; Jie Yan; Dongya Yang

Journal of Industrial and Engineering Chemistry, Vol.20, No.4, 1293-1300, July, 2014

DOI10.1016/j.jiec.2013.07.008 Export Citation

Selective adsorption of L-TA/D-TA by β-cyclodextrin derivative modified with L-tryptophan: Isotherm, kinetic and thermodynamics studies

Kaichen He, Fengxian Qiu^†, Jiao Qin, Jie Yan, and Dongya Yang

School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, China

E-mail:

β-Cyclodextrin derivative modified with L-tryptophan (L-Trp-CD) was prepared for recognitive chiral separation of tartaric acid enantiomers from ethanol solution. Kinetic properties were successfully investigated by pseudo-first-order model and pseudo-second-order model. Equilibrium data were described by the Langmuir and Freundlich isotherm models. The thermodynamics parameters (positive values of △H° and △S°, negative values of △G°) indicated that binding system for L-Trp-CD was endothermic, entropy gained and spontaneous. Selective adsorption result of L-tartaric acid (L-TA)/D-tartaric acid (D-TA) by L-Trp-CD indicated that L-Trp-CD has significantly higher adsorption capacity for L-TA compared with D-TA, and the selectivity coefficient is 3.36.

Keywords:β-Cyclodextrin;Tartaric acid;Adsorption isotherm;Kinetic model;Thermodynamics parameters

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[Referenced By]

[1] Zhou JW, Ritte H, Polymer, 1, 1552 (2010)

[2] Cooper G, Sant M, Asiyo C, J. Chromatogr. A, 1216, 6838 (2009)

[3] Campos-Candel A, Llobat-Estelles M, Mauri-Aucejo A, Talanta, 78, 1286 (2009)

[4] Tran CD, Kang JX, J. Chromatogr. A, 978, 221 (2002)

[5] Han CP, Li HB, Small, 4, 1344 (2008)

[6] Yokoyama T, Tanaka Y, Sato M, Kan-No N, Nakano T, Yamaguchi T, Nagahisa E, Fish Sci., 71, 924 (2005)

[7] Chen YX, Gao BJ, Jiang GM, Zhang RX, Acta Chim. Sin., 69, 1705 (2011)

[8] Chen Y, Li F, Liu BW, Jiang BP, Zhang HY, Wang LH, Liu Y, J. Phys. Chem. B, 114(49), 16147 (2010)

[9] Lenn AY, Fortier CA, Jack IV, Zhu XF, Warner IM, J. Incl. Phenom. Macrocycl. Chem., 51, 87 (2005)

[10] Ghosh S, Badruddoza AZM, Uddin MS, Hidajat K, J. Colloid Interface Sci., 354(2), 483 (2011)

[11] Ravoo BJ, Jacquier JC, Macromolecules, 35(16), 6412 (2002)

[12] Kano K, Nishiyabu R, Yamazaki T, Yamazaki I, J. Am. Chem. Soc., 125(35), 10625 (2003)

[13] Kano K, Nishiyabu R, Asada T, Kuroda Y, J. Am. Chem. Soc., 124(33), 9937 (2002)

[14] Sasaki K, Nakagawa H, Zhang XY, Sakurai S, Kano K, Kuroda Y, Chem. Commun., 4, 408 (2004)

[15] Donze C, Rizzarelli E, Vecchio G, J. Incl. Phenom. Macrocycl. Chem., 31, 27 (1998)

[16] Liu Y, Han BH, Li B, Zhang YM, Zhao P, Chen YT, Wada T, Inoue Y, J. Org. Chem., 63, 1444 (1998)

[17] Liu Y, Han BH, Sun SX, Wada T, Inoue Y, J. Org. Chem., 64, 1487 (1999)

[18] Liu Y, Shi J, Guo DS, J. Org. Chem., 72, 8227 (2007)

[19] Wang H, Cao R, Ke CF, Liu Y, Wada T, Inoue Y, J. Org. Chem., 70, 8703 (2005)

[20] Hishiya T, Shibata M, Kakazu M, Asanuma H, Komiyama M, Macromolecules, 32(7), 2265 (1999)

[21] Kyzas GZ, Lazaridis NK, Bikiaris DN, Carbohydr. Polym., 91, 198 (2013)

[22] Nie JJ, Xu DJ, Wu JY, Chiang MY, Acta Crystallogr. Sect. E, 57, 0428 (2001)

[23] Stouten PFW, Kroon-Batenburg LMJ, Kroon J, J. Mol. Struct., 200, 169 (1989)

[24] Debrus S, Marchewka MK, Baran J, Drozd M, Czopnik R, Pietraszko A, Ratajczak H, J. Solid State Chem., 178, 2880 (2005)

[25] Kaveh A, Behdad GA, Amirhossein HAK, J. Inorg. Mater., 27, 660 (2012)

[26] Wang SB, Ng CW, Wang WT, Li Q, Li LQ, J. Chem. Eng. Data, 57, 1963 (2012)

[27] Petter RC, Salek JS, Sikorski CT, Kumaravel G, Lin FT, J. Am. Chem. Soc., 112, 3860 (1990)

[28] Ersoz A, Ball JC, Grimes CA, Bachas LG, Anal. Chem., 74, 4050 (2002)

[29] Lagergren S, Kungliga Svenska Vetenskapsakademiens Handlingar 24 (1898) 1.39.

[30] Ho YS, McKay G, Chem. Eng. J., 70(2), 115 (1998)

[31] Casado C, Castan J, Gracia I, Yus M, Mayoral A, Sebastian V, Lopez-Ram-de-Viu P, Uriel S, Coronas J, Langmuir, 28(16), 6638 (2012)

[32] Langmuir I, J. Am. Chem. Soc., 38, 2221 (1916)

[33] Hall K, Eagleton L, Acrivos A, Vermeulen T, Ind. Eng. Chem. Fundam., 5, 212 (1966)

[34] Webi WT, Chakravort RK, AIChE J., 20, 228 (1974)

[35] Fytianos K, Voudrias E, Kokkalis E, Chemosphere, 40, 3 (2000)

[36] Smith JM, Van Ness HC (Eds.), Introduction to Chemical Engineering Thermodynamics, McGraw-Hill, New York, U.S.A, 1987.