The discrimination of enantiomers is a challenging task in separation technology, and using a membrane is most promising for separating enantiomers from racemic mixture. The optical resolution of chiral compounds is of interest to researchers working in a variety of fields from analytical, organic and medicinal chemistry, to pharmaceutics and materials, to process engineering for fabricating pharmaceuticals, agrochemicals, fragrances and foods, and so on. There is considerable demand for separation techniques appropriate for the large-scale resolution of chiral molecules. The separation of chiral compounds using chiral or achiral/non-chiral polymeric membranes with or without chiral selector represents a promising system for future commercial applications. This review focuses on an active field of chiral separation, membrane-based enantioseparation technique, which has potential for large-scale production of singleenantiomers. Enantiomeric separation by membrane processes has been studied using various configurations of liquid and solid polymer membranes. Selectivity and permeability of liquid-membranes is reasonably good because the rate of diffusion of solute molecules is high in liquids but has inferior durability and stability. Solid polymer membranes have inferior permeability because diffusion of solute through solids is slow but quite stable and durable; however, commercial application of membrane technology for optical resolution is yet to be realized. Several chiral separation membranes were prepared from chiral polymers where enantioselectivity was generated from chiral carbons in the main chain. However, it is rather tricky to generate excellent chiral separation membranes from chiral polymers alone, because_x000D_ racemic penetrants mainly encounter the flexible side chains of the membrane polymers.

Chiral Separation Optical Resolution Enantioselective Polymeric Membranes Pharmaceutical

Ingole PG, Thakare NR, Kim KH, Bajaj HC, Singh K, Lee HK, New J. Chem., 37, 4018 (2013)
Maier NM, Franco P, Linder W, J. Chromatogr. A, 906, 3 (2001)
Daniels JM, Nestmann ER, Kerr A, J. Drug Inf., 31, 639 (1997)
Ghanem A, Aboul-Enein HY, Tetrahedron: Asym., 15, 3331 (2004)
Ghanem A, Aboul-Enein HY, Chirality, 17, 1 (2005)
Keith JM, Larrow JF, Jacobsen EN, Adv. Synth. Catal., 343, 5 (2001)
Schoemaker HE, Mink D, Wubbolts MG, Science, 299, 1694 (2003)
Bornscheuer UT, Angew. Chem. Int. Ed., 42, 3336 (2003)
Pellissier H, Tetrahedron, 59, 8291 (2003)
Strauss UT, Felfer U, Faber K, Tetrahedron: Asym., 10, 107 (1999)
Strauss UT, Faber K, Tetrahedron: Asym., 10, 4079 (1999)
Rikken GLJA, Raupach E, Nature, 405, 932 (2000)
Maggiora GM, Mao B, Chou KC, New Developments in Molecular Chirality, Ed. P. G. Mezey, Kluwer Academic Publishers, Dordrecht., 5, 93 (1991)
Foye WO, Lemke TL, Williams DA, Foye’s principles of medicinal chemistry, Lippincott Williams & Wilkins (2007)
Aranaz I, Mengibar M, Harris R, Panos I, Miralles B, Acosta N, Galed G, Heras A, Current Chem. Biolo., 3, 203 (2009)
Hewala II, Moneeb MS, Elmongy HA, Wahbi AAM, Talanta, 130, 506 (2014)
Caner H, Groner E, Levy L, Drug Discovery Today, 9, 105 (2004)
Anon, FDA’s Policy statement for the development of new stereoisomeric drugs, Chirality, 4, 338 (1992)
Tobis J, Boch L, Thomann Y, Tiller JC, J. Membr. Sci., 372(1-2), 219 (2011)
Food & Drug Administration, Policy Statement for the Development of New Stereoisomeric Drugs, 57 Fed. Reg., 22, 249 (1992)
Maier NM, Franco P, Lindner W, J. Chromatogr. A, 906, 3 (2001)
Afonso CAM, Crespo JG, Angew. Chem., Int. Ed., 43, 5293 (2004)
Jirage KB, Martin CR, Trends Biotechnol., 17, 197 (1999)
Masters PM, Forensic Sci. Int., 32, 179 (1986)
Cronin JR, Pizzarello S, Science, 275(5302), 951 (1997)
Breuer M, Ditrich K, Habicher T, Hauer B, Kesseler M, Sturmer R, Zelinski T, Angew. Chem., Int. Ed., 43, 788 (2004)
Fassihi AR, Int. J. Pharm., 92, 1 (1993)
Sabia R, Ciogli A, Pierini M, Gasparrini F, Villani C, J. Chromatogr. A, DOI:10.1016/j.chroma.2014.07.097. (2014)
Brode WR, J. Opt. Soc. Am., 41, 987 (1951)
Ward TJ, Oswald TM, Encyclopaedia of Analytical Chemistry (2006)
Kraml CM, Zhou D, Byrne N, McConnell O, J. Chromatogr. A, 1100, 108 (2005)
Nohira H, Watanabe K, Kurokawa M, Chem. Lett., 5, 299 (1976)
Jacques J, Collet A, Wiley Interscience, New York (1981)
Sekhon BS, Int. J. Chem. Technol. Res., 2, 1584 (2010)
Bommarius AS, Riebel-Bommarius BR, Biocatalysis: Fundamentals and Applications, Wiley (2007)
Lee E, Park MB, Kim JM, Kim WS, Kim IH, Korean J. Chem. Eng., 27(1), 231 (2010)
Noble RD, J. Membr. Sci., 75, 121 (1992)
Ulbricht M, Polymer, 7, 2217 (2006)
Nakamura M, Kiyohara S, Saito K, Sugita K, Sugo T, Anal. Chem., 71, 1323 (1999)
Lee NH, Frank CW, Polymer, 43(23), 6255 (2002)
Newcomb M, Helgeson RC, Cram DJ, J. Am. Chem. Soc., 96, 7367 (1974)
Maruyama A, Adachi N, Takatsuki T, Torii M, Sanui K, Ogata N, Macromolecules, 23, 2748 (1990)
Aoki T, Shinohara K, Kaneko T, Oikawa E, Macromolecules, 29(12), 4192 (1996)
Aoki T, Kobayashi Y, Kaneko T, Oikawa E, Yamamura Y, Fujita Y, Teraguchi M, Nomura R, Masuda T, Macromolecules, 32(1), 79 (1999)
Aoki T, Prog. Polym. Sci., 24, 951 (1999)
Aoki T, Ohshima M, Shinohara KI, Kaneko T, Oikawa E, Polymer, 38(1), 235 (1997)
Teraguchi M, Masuda T, Macromolecules, 35(4), 1149 (2002)
Teraguchi M, Suzuki J, Kaneko T, Aoki T, Masuda T, Macromolecules, 36(26), 9694 (2003)
Teraguchi M, Mottate K, Kim SY, Aoki T, Kaneko T, Hadano S, Masuda T, Macromolecules, 38(15), 6367 (2005)
Masakazu Y, Akon H, Enantioselective Membranes, DOI: 10.1002/9781118522318.emst131 John Wiley & Sons, Inc. All (2013)
Lonsdale HK, J. Membr. Sci., 10, 81 (1982)
Madihally SV, Principles of Biomedical Engineering, Artech House, Boston London (2010)
Villaluenga JPG, Tabe-Mohammadi A, J. Membr. Sci., 169(2), 159 (2000)
Cadotte JE, Cobian KE, Forester RH, Petersen RJ, NTIS Report No. PB-253193 (1976)
Altinkaya SA, Desalination, 199(1-3), 459 (2006)
Singh K, Ingole PG, Bajaj HC, Bhattacharya A, Brahmbhatt HR, Sep. Sci. Technol., 45(10), 1374 (2010)
Vedejs E, Jure M, Angew. Chem., Int. Ed., 44, 3974 (2005)
Cook GR, Curr. Org. Chem., 4, 869 (2000)
Keith JM, Larrow JF, Jacobsen EN, Adv. Synth. Catal., 343, 5 (2001)
Tokunaga M, Larrow JF, Kakiuchi F, Jacobsen EN, Science, 277(5328), 936 (1997)
Ramdeehul S, Dierkes P, Aguado R, Kamer PCJ, Van Leeuwen PWNM, Osborn JA, Angew. Chem., Int. Ed., 37, 3118 (1998)
Pellissier H, Tetrahedron, 59, 8291 (2003)
Schurig V, J. Chromatogr. A, 906, 275 (2001)
Fanali S, Catarcini P, Blaschke G, Chankvetadze B, Electrophoresis, 22(15), 3131 (2001)
Nagata Y, Iida T, Sakai M, J. Mol. Catal. B: Enzym., 12, 105 (2001)
Peacock SS, Walba DM, Gaeta FCA, Helgeson RC, Cram DJ, J. Am. Chem. Soc., 102, 2043 (1980)
Dietrich B, Lehn JM, Sauvage JP, Tetrahedron, 29, 1647 (1973)
Dietrich B, Lehn JM, Tetrahedron Lett., 15, 1225 (1973)
Kyba EP, Timko JM, Kaplan LJ, de Jong F, Gokel GW, Cram DJ, J. Am. Chem. Soc., 100, 4555 (1978)
Cram DJ, Cram JH, ACC. Chem. Res., 11, 8 (1978)
Sousa LR, Hoffman DH, Kaplan L, Cram DJ, J. Am. Chem. Soc., 96, 7100 (1974)
Sousa LR, Sogah GDY, Hoffmann DH, Cram DJ, J. Am. Chem. Soc., 100, 4569 (1978)
Sogah GDY, Cram DJ, J. Am. Chem. Soc., 101, 3035 (1979)
Sough GDY, Cram DJ, J. Am. Chem. Soc., 97, 1259 (1975)
Pirkle WH, US Patent, 5,080,795 (1992)
Pirkle WH, WO 9,117,816 (1992)
Pirkle WH, Bowen WE, Tetrahedron: Asymmetry, 5, 773 (1994)
Pirkle WH, Doherty EM, J. Am. Chem. Soc., 111, 4113 (1989)
Thoelen C, De bruyn M, Theunissen E, Kondo Y, Vankelecom IFJ, Grobet P, Yoshikawa M, Jacobs PA, J. Membr. Sci., 186(2), 153 (2001)
Aoki T, Tomizawa S, Oikawa E, J. Membr. Sci., 99(2), 117 (1995)
Yashima E, Noguchi J, Okamoto Y, J. Appl. Polym. Sci., 54(8), 1087 (1994)
Kakuchi T, Takaoka T, Yokota K, Polym. J., 22, 199 (1990)
Xiao Y, Lim HM, Chung TS, Rajagopalan R, Langmuir, 23(26), 12990 (2007)
Zhou ZZ, Xiao YC, Hatton TA, Chung TS, J. Membr. Sci., 339(1-2), 21 (2009)
Zhang Y, Yu H, Wu Y, Zhao W, Yang M, Jing H, Chen A, Ana. Biochem., 462, 13 (2014)
He K, Qiu F, Qin J, Yan J, Yang D, Korean J. Chem. Eng., 30(11), 2078 (2013)
Liu X, Meng L, Korean J. Chem. Eng., 30(4), 918 (2013)
Kim JH, Kim JH, Jegal J, Lee KH, J. Membr. Sci., 213(1-2), 273 (2003)
Li W, Li Y, Fu Y, Zhang J, Korean J. Chem. Eng., 30(7), 1448 (2013)
Chen L, He X, Zhao B, Liu Y, Anal. Chim. Acta, 417, 51 (2000)
Sunsandee N, Leepipatpiboon N, Ramakul P, Wongsawa T, Pancharoen U, Sep. Purif. Technol., 102, 50 (2013)
Sunsandee N, Leepipatpiboon N, Ramakul P, Korean J. Chem. Eng., 30(6), 1312 (2013)
Higuchi A, Hara M, Horiuchi T, Nakagawa T, J. Membr. Sci., 93(2), 157 (1994)
Shinohara K, Aoki T, Oikawa E, Polymer, 36(12), 2403 (1995)
Sakaki K, Hara S, Itoh N, Desalination, 149(1-3), 247 (2002)
Wang YJ, Hu Y, Xu H, Luo GS, Dai YY, J. Membr. Sci., 293(1-2), 133 (2007)
Bodalo A, Gomez JL, Gomez E, Maximo MF, Montiel MC, Enzyme Microb. Technol., 35(2-3), 261 (2004)
Liese A, Kragl U, Kierkels H, Schulze B, Enzyme Microb. Technol., 30(5), 673 (2002)
Long WS, Bhatia S, Kamaruddin A, J. Membr. Sci., 219(1-2), 69 (2003)
Miyako E, Maruyama T, Kamiya N, Goto M, Chem. Eur. J., 11, 1163 (2005)
Robeson LM, Freeman BD, Paul DR, Rowe BW, J. Membr. Sci., 341(1-2), 178 (2009)
Robeson LM, J. Membr. Sci., 320(1-2), 390 (2008)
Freeman BD, Macromolecules, 32(2), 375 (1999)
Long WS, Kamaruddin A, Bhatia S, J. Membr. Sci., 247(1-2), 185 (2005)
Papra A, Hicke HG, Paul D, J. Appl. Polym. Sci., 74(7), 1669 (1999)
Ito Y, Ochiai Y, Park YS, Imanishi Y, J. Am. Chem. Soc., 119(7), 1619 (1997)
Yang J, Hage DS, J. Chromatogr., 645, 241 (1993)
Kimura T, Nakanishi K, Nakagawa T, Shibukawa A, Matsuzaki K, Pharm. Res., 22, 667 (2005)
Su CL, Dai RJ, Tong B, Deng YL, Chinese Chem. Lett., 17, 649 (2006)
Bowen WR, Nigmatullin RR, Sep. Sci. Technol., 37(14), 3227 (2002)
Gumi T, Minguillon C, Palet C, Polymer, 46(26), 12306 (2005)
Higuchi A, Yomogita H, Yoon BO, Kojima T, Hara M, Maniwa S, Saitoh M, J. Membr. Sci., 205(1-2), 203 (2002)
Wagenknecht HA, Stemp EDA, Barton JK, J. Am. Chem. Soc., 122(1), 1 (2000)
Higuchi A, Ishida Y, Nakagawa T, Desalination, 90, 127 (1993)
Garnier F, Randon J, Rocca JL, Sep. Purif. Technol., 116, 243 (1999)
Edmondson S, Osborne VL, Huck WTS, Chem. Soc. Rev., 1, 14 (2004)
Tone S, Masawaki T, Hamada T, J. Membr. Sci., 103(1-2), 57 (1995)
Tone S, Masawaki T, Eguchi K, J. Membr. Sci., 118(1), 31 (1996)
Aoki T, Fukuda T, Shinohara KI, Kaneko T, Teraguchi M, Yagi M, J. Polym. Sci. A: Polym. Chem., 42(18), 4502 (2004)
Higuchi A, Hayashi A, Kanda N, Sanui K, Kitamura H, J. Mol. Str., 739, 145 (2005)
Matsuoka Y, Kanda N, Lee YM, Higuchi A, J. Membr. Sci., 280(1-2), 116 (2006)
Higuchi A, Higuchi Y, Furuta K, Yoon BO, Hara M, Maniwa S, Saitoh M, Sanui K, J. Membr. Sci., 221(1-2), 207 (2003)
Kim IC, Jegal J, Lee KH, J. Polym. Sci. B: Polym. Phys., 40(19), 2151 (2002)
Gumi T, Valiente A, Palet C, J. Membr. Sci., 256(1-2), 150 (2005)
Randon J, Garnier F, Rocca JL, Maisterrena B, J. Membr. Sci., 175(1), 111 (2000)
Lee SB, Mitchell DT, Tron L, Nevanen TK, Soderlund H, Martin CR, Science, 296, 2198 (2002)
Aoki T, Shinohara K, Oikawa E, Makromol. Chem. Rapid Commun., 13, 565 (1992)
Teraguchi M, Masuda T, Macromolecules, 35(4), 1149 (2002)
Paris J, Molina-Jouve C, Nuel D, Moulin P, Charbit F, J. Membr. Sci., 237(1-2), 9 (2004)
Yoshikawa M, Murakoshi K, Kogita T, Hanaoka K, Guiver MD, Robertson GP, Europ. Polym. J., 42, 2532 (2006)
Nakagawa M, Ikeuchi Y, Yoshikawa M, Polymer, 49(21), 4612 (2008)
Yoshikawa M, Kondo Y, Morita Y, Bioseparation, 10, 323 (2001)
Ingole PG, Singh K, Bajaj HC, Arab. J. Chem., DOI:10.1016/j.arabjc.2011.10.011. (2011)
Yoshikawa M, Ooi T, Izumi JI, Eur. Polym. J., 37, 335 (2001)
Keurentjes JT, Nabuurs LJ, Vegter EA, J. Membr. Sci., 113(2), 351 (1996)
Ulbricht M, J. Chromatogr. B: Anal. Technol. Biomed. Life Sci., 804, 113 (2004)
van der Ent EM, van't Riet K, Keurentjes JTF, van der Padt A, J. Membr. Sci., 185(2), 207 (2001)
Lakshmi BB, Martin CR, Nature, 388(6644), 758 (1997)
Jirage KB, Martin CR, Trends Biotechnol., 17, 197 (1999)
Ingole PG, Choi W, Kim KH, Jo HD, Choi WK, Park JS, Lee HK, Desalination, 345, 136 (2014)
Ingole PG, Choi W, Kim KH, Park CH, Choi WK, Lee HK, Chem. Eng. J., 243, 137 (2014)
Rao AP, Joshi SV, Trivedi JJ, Devmurari CV, Shah VJ, J. Membr. Sci., 211(1), 13 (2003)
Leob S, Sourirajan S, Reverse Osmosis, National Research Council of Canada, Ottawa, Canada (1985)
Yun SH, Ingole PG, Kim KH, Choi WK, Kim JH, Lee HK, Chem. Eng. J., 258, 348 (2014)
Cadotte JE, Petersen RJ, Larson RE, Erickson EE, Desalination, 32, 25 (1980)
Singh K, Bajaj HC, Ingole P, Bhattacharya A, Sep. Sci. Technol., 45(3), 346 (2010)
Singh K, Bajaj HC, Ingole PG, Patent Number(s): WO2010109490-A1; IN200900629-I1 (2010)
Ingole PG, Singh K, Bajaj HC, Sep. Sci. Technol., 46(12), 1898 (2011)
Singh K, Ingole PG, Chaudhari J, Bhrambhatt H, Bhattacharya A, Bajaj HC, J. Membr. Sci., 378(1-2), 531 (2011)
Ingole PG, Bajaj HC, Singh K, Indian J. Chem. Technol., 18(3), 197 (2011)
Ingole PG, Singh K, Bajaj HC, J. Trends Chem., 1, 1 (2010)
Singh K, Ingole PG, Bhrambhatt H, Bhattachayra A, Bajaj HC, Sep. Purif. Technol., 78(2), 138 (2011)
Ingole PG, Singh K, Bajaj HC, Desalination, 281, 413 (2011)
Ingole PG, Bajaj HC, Singh K, Desalination, 305, 54 (2012)
Ingole PG, Bajaj HC, Singh K, Desalination, 343, 75 (2014)
Ingole PG, Bajaj HC, Singh K, Procedia Engineering, 44, 358 (2012)
Ingole PG, Bajaj HC, Singh K, RSC Advances, 3, 3667 (2013)
Singh K, Ingole PG, Bajaj HC, Gupta H, Desalination, 298, 13 (2012)
Ingole PG, Bajaj HC, Srivastava DN, Rebary B, Singh K, Sep. Sci. Technol., 48(12), 1777 (2013)
Ingole PG, Singh K, Bajaj HC, Adv. Mater. Res., 2, 1 (2013)
Singh K, Bajaj HC, Ingole PG, Patent Number(s): WO2013118148-A1; PCT/IN2013/000081 (2010)