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http://dx.doi.org/10.12989/amr.2013.2.1.051

Synthesis of solid enantioselective macromer of trimesic acid for the enantiomeric separation of chiral alcohols  

Ingole, Pravin G. (Greenhouse Gas Research Center, Korea Institute of Energy Research (KIER))
Bajaj, Hari C. (Central Salt & Marine Chemicals Research Institute, Council of Scientific and Industrial Research (CSIR-CSMCRI))
Singh, Kripal (Central Salt & Marine Chemicals Research Institute, Council of Scientific and Industrial Research (CSIR-CSMCRI))
Publication Information
Advances in materials Research / v.2, no.1, 2013 , pp. 51-64 More about this Journal
Abstract
Enantioselective macromer of trimesic acid was prepared using S(-) menthol with trimesoyl chloride on polyimide (PI) ultrafiltration membrane. The chemical composition of macromer as well as polyimide ultrafiltration membrane was determined by ATR-FTIR Spectroscopy. The optical resolution of chiral alcohols was performed in pressure driven process. The effect of monomer solutions concentration, effect of air-drying time of S(-) menthol solution, effect of reaction time, effect of operating pressure, effect of feed concentration of racemate on the performance of macromer was studied. The synthesised material exhibits separation of chiral alcohols (menthol ~23% and sobrelol ~21%).
Keywords
chiral alcohols; enantioselective membrane; polyimide; optical resolution;
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1 Ahuja, S. (1991), Chiral separation by liquid chromatography, American Chemical Society, Washington.
2 Aoki, T. (1999), "Macromolecular design of permselective membranes", Prog. Polym. Sci., 24(7), 951-993.   DOI   ScienceOn
3 Aoki, T., Kobayashi, Y., Kaneko, T., Oikawa, E., Yamamura, Y., Fujita, Y., Teraguchi, M., Nomura, R. and Masuda, T. (1999), "Synthesis and properties of polymers from disubstituted acetylenes with chiral pinanyl groups", Macromolecules, 32(1), 79-85.   DOI   ScienceOn
4 Aoki, T., Ohshima, M., Shinohara, K., Kaneko, T. and Oikawa, E. (1997), "Enantioselective permeation of racemates through a solid (+)-poly{2-[dimethyl(10-pinanyl)silyl]norbornadiene} membrane", Polymer, 38(1), 235-238.   DOI   ScienceOn
5 Aoki, T., Shinohara, K., Kaneko, T. and Oikawa, E. (1996), "Enantioselective permeation of various racemates through an optically-active poly(1-(dimethyl(10-pinanyl)silyl)-1-propyne) membrane", Macromolecules, 29(12), 4192-4198.   DOI   ScienceOn
6 Aoki, T., Tomizawa, S. and Oikawa, E. (1995), "Enantioselective permeation through poly[$\gamma$-[3- (pentamethyldisiloxanyl)propyl]-l-glutamate] membranes", J. Membrane. Sci., 99(2), 117-125.   DOI   ScienceOn
7 Asztemborska, M., Sybilska, D., Nowakowski, R. and Perez, G. (2003), "Chiral recognition ability of acyclodextrin with regard to some monoterpenoids under gas-liquid chromatographic conditions", J. Chromatogr. A, 1010(2), 233-242.   DOI   ScienceOn
8 Baker, R.W. (2002), "Future directions of membrane gas separation technology", Ind. Eng. Chem. Res., 41(6), 1393-1411.   DOI   ScienceOn
9 Jacques, J. and Collet, A. (1981), Enantiomers, racemates and resolutions, Wiley Interscience, New York.
10 Keurentjes, J.T.F., Nabuurs, L.J.W.M. and Vegter, E.A. (1996), "Liquid membrane technology for the separation of racemic mixtures", J. Membrane. Sci., 113(2), 351-360.   DOI   ScienceOn
11 Kim, K.J. and Fane, A.G. (1994), "Low voltage scanning electron microscopy in membrane research", J. Membrane. Sci., 88(1), 103-114.   DOI   ScienceOn
12 Kim, W.G. and Jhon, M.S. (1985), "The transport phenomena of some solute through the copolymer membranes of 2-hydroxyethylmethacrylate (HEMA) with selected hydrophobic monomers", B. K. Chem. Soc., 6, 128.
13 Koros, W.J. and Fleming, G.K. (1993), "Membrane-based gas separation", J. Membrane. Sci., 83(1), 1-80.   DOI   ScienceOn
14 Koros, W.J. and Mahajan, R. (2000), "Pushing the limits on possibilities for large scale gas separation: which strategies?", J. Membrane. Sci., 175(2), 181-196.   DOI   ScienceOn
15 Lough, W.J. (1989), Chiral liquid chromatography, Chapman and Hall, New York.
16 Lee, N.H. and Frank, C.W. (2002), "Separation of chiral molecules using polypeptide-modified poly(vinylidene fluoride) membranes", Polymer, 43(23), 6255-6262.   DOI   ScienceOn
17 Lin, D.J., Chang, C.L., Chen, T.C. and Cheng, L.P. (2002), "Microporous PVDF membrane formation by immersion precipitation from water/TEP/PVDF system", Desalination, 145(1-3), 25-29.   DOI   ScienceOn
18 Manabu, I., Hironobu, O. and Kiyoshi, M. (2005), "Specific permeation of hydrophobic solutes across a hydrophobic polymer membrane", B. Chem. Soc. Jpn., 78(9), 1702-1703.   DOI   ScienceOn
19 Maruyama, A., Adachi, N., Takatsuki, T., Torii, M., Sanui, K. and Ogata, N. (1990), "Enantioselective permeation of $\alpha$-amino acid isomers through poly(amino acid)-derived membranes", Macromolecules, 23(10), 2748-2752.   DOI
20 Nakamura, M., Kiyohara, S., Saito, K., Sugita, K. and Sugo, T. (1999), "High resolution of DL-tryptophan at high flow rates using a bovine serum albumin-multilayered porous hollow-fiber membrane", Anal. Chem., 71(7), 1323-1325.   DOI   ScienceOn
21 Newcomb, M., Helgeson, R.C. and Cram, D.J. (1974), "Enantiomer differentiation in transport through bulk liquid membranes", J. Am. Chem. Soc., 96(23), 7367-7369.   DOI
22 Noble, R.D. (1992), "Generalized microscopic mechanism of facilitated transport in fixed site carrier membranes", J. Membrane. Sci., 75(1-2), 121-129.   DOI   ScienceOn
23 Randon, J., Garnier, F., Rocca, J.L. and Maisterrena, B. (2000), "Optimization of the enantiomeric separation of tryptophan analogs by membrane processes", J. Membrane. Sci., 175(1), 111-117.   DOI   ScienceOn
24 Nohira, H., Watanabe, K. and Kurokawa, M. (1976), "Optical resolution of N-benzyl-NNcis-2- aminocyclohexanecarboxylic acid by preferential crystallization", Chem. Lett., 5, 299-300.   DOI
25 Palacio, L., Pradanos, P., Calvo, J.I. and Hernandez, A. (1999), "Porosity measurements by a gas penetration method and other techniques applied to membrane characterization", Thin Solid Films, 348(1), 22-29.   DOI   ScienceOn
26 Ramdeehul, S., Dierkes, P., Aguado, R., Kamer, P.C.J., Van Leeuwen, P.W.N.M. and Osborn, J.A. (1998), "Mechanistic implications of the observation of kinetic resolution in a palladium-catalyzed enantioselective allylic alkylation", Angew. Chem. Int. Ed., 37(22), 3118-3121.   DOI
27 Schurig, V. (2001), "Separation of enantiomers by gas chromatography", J. Chromatogr. A, 906(1-2), 275-299.   DOI   ScienceOn
28 Shinohara, K. Aoki, T. and Oikawa, E. (1995), "Optical resolution by vapour permeation of 1,3-butanediol and 2-butanol through (+)-poly{1-[dimethyl(10-pinanyl)silyl]-1-propyne} membrane", Polymer, 36(12), 2403-2405.   DOI   ScienceOn
29 Singh, K. and Bhattacharya, A. (2006), "Porometric study of Polysulfone membranes and their co-relation with the Performance", J. Indian Chem. Soc., 83, 201-204.
30 Stern, S.A. (1994), "Polymers for gas separation: the next decade", J. Membrane. Sci., 94(1), 1-65.   DOI   ScienceOn
31 Stevenson, D. and Wilson, I.D. (1990), Recent advances in chiral separation, Plenum Press, New York.
32 Teraguchi, M. and Masuda, T. (2002), "Poly(diphenylacetylene) membranes with high gas permeability and remarkable chiral memory", Macromolecules, 35(4), 1149-1151.   DOI   ScienceOn
33 Teraguchi, M., Mottate, K., Kim, S.Y., Aoki, T., Kaneko, T., Hadano, S. and Masuda, T. (2005), "Synthesis of chiral helical poly(hydroxyl-containing phenylacetylene) membranes by in-situ depinanylsilylation and their enantioselective permeabilities", Macromolecules, 38(15), 6367-6373.   DOI   ScienceOn
34 Wang, D.L., Li, K. and Teo, W.K. (1999), "Preparation and characterization of polyvinylidene fluoride (PVDF) hollow fiber membranes", J. Membrane. Sci., 163(2), 211-220.   DOI   ScienceOn
35 Teraguchi, M., Suzuki, J., Kaneko, T., Aoki, T. and Masuda, T. (2003), "Enantioselective permeation through membranes of chiral helical polymers prepared by depinanylsilylation of poly(diphenylacetylene) with a high content of the pinanylsilyl group", Macromolecules, 36(26), 9694-9697.   DOI   ScienceOn
36 Twist, J.N. and Zatz, J.L. (1988), "Membrane-solvent-solute interaction in a model permeation system", J. Pharmacol. Sci., 77(6), 536-540.   DOI
37 Ulbricht, M. (2006), "Advanced functional polymer membranes", Polymer, 47(7), 2217-2262.   DOI   ScienceOn
38 Williams, M.E. (2003), A review of reverse osmosis theory, EET Corporation and Williams Engineering Services Company, Inc.
39 Xiong, W.W., Wang, W.F., Zhao, L., Song, Q. and Yuan, L.M. (2009), "Chiral separation of (R,S)-2- phenyl-1-propanol through glutaraldehyde-crosslinked chitosan membranes", J. Membrane. Sci., 328(1-2), 268-272.   DOI   ScienceOn
40 Xu, H.W., Wang, Q.W., Zhu, J., Deng, J.G., Cun, L.F., Cui, X., Wu, J., Xu, X.L. and Wu, Y.L. (2005), "Copper(II)-mediated resolution of $\alpha$-halo carboxylic acids with chiral O,O'-dibenzoyltartaric acid: spontaneous racemization and crystallization-induced dynamic resolution", Org. Biomol. Chem., 3, 4227-4232.   DOI   ScienceOn