Issue
Korean Journal of Chemical Engineering,
Vol.31, No.12, 2109-2123, 2014
Methods for separation of organic and pharmaceutical compounds by different polymer materials
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 racemic penetrants mainly encounter the flexible side chains of the membrane polymers.
[References]
  1. Ingole PG, Thakare NR, Kim KH, Bajaj HC, Singh K, Lee HK, New J. Chem., 37, 4018, 2013
  2. Maier NM, Franco P, Linder W, J. Chromatogr. A, 906, 3, 2001
  3. Daniels JM, Nestmann ER, Kerr A, J. Drug Inf., 31, 639, 1997
  4. Ghanem A, Aboul-Enein HY, Tetrahedron: Asym., 15, 3331, 2004
  5. Ghanem A, Aboul-Enein HY, Chirality, 17, 1, 2005
  6. Keith JM, Larrow JF, Jacobsen EN, Adv. Synth. Catal., 343, 5, 2001
  7. Schoemaker HE, Mink D, Wubbolts MG, Science, 299, 1694, 2003
  8. Bornscheuer UT, Angew. Chem. Int. Ed., 42, 3336, 2003
  9. Pellissier H, Tetrahedron, 59, 8291, 2003
  10. Strauss UT, Felfer U, Faber K, Tetrahedron: Asym., 10, 107, 1999
  11. Strauss UT, Faber K, Tetrahedron: Asym., 10, 4079, 1999
  12. Rikken GLJA, Raupach E, Nature, 405, 932, 2000
  13. Maggiora GM, Mao B, Chou KC, New Developments in Molecular Chirality, Ed. P. G. Mezey, Kluwer Academic Publishers, Dordrecht., 5, 93, 1991
  14. Foye WO, Lemke TL, Williams DA, Foye’s principles of medicinal chemistry, Lippincott Williams & Wilkins, 2007
  15. Aranaz I, Mengibar M, Harris R, Panos I, Miralles B, Acosta N, Galed G, Heras A, Current Chem. Biolo., 3, 203, 2009
  16. Hewala II, Moneeb MS, Elmongy HA, Wahbi AAM, Talanta, 130, 506, 2014
  17. Caner H, Groner E, Levy L, Drug Discovery Today, 9, 105, 2004
  18. Anon, FDA’s Policy statement for the development of new stereoisomeric drugs, Chirality, 4, 338, 1992
  19. Tobis J, Boch L, Thomann Y, Tiller JC, J. Membr. Sci., 372(1-2), 219, 2011
  20. Food & Drug Administration, Policy Statement for the Development of New Stereoisomeric Drugs, 57 Fed. Reg., 22, 249, 1992
  21. Maier NM, Franco P, Lindner W, J. Chromatogr. A, 906, 3, 2001
  22. Afonso CAM, Crespo JG, Angew. Chem., Int. Ed., 43, 5293, 2004
  23. Jirage KB, Martin CR, Trends Biotechnol., 17, 197, 1999
  24. Masters PM, Forensic Sci. Int., 32, 179, 1986
  25. Cronin JR, Pizzarello S, Science, 275(5302), 951, 1997
  26. Breuer M, Ditrich K, Habicher T, Hauer B, Kesseler M, Sturmer R, Zelinski T, Angew. Chem., Int. Ed., 43, 788, 2004
  27. Fassihi AR, Int. J. Pharm., 92, 1, 1993
  28. Sabia R, Ciogli A, Pierini M, Gasparrini F, Villani C, J. Chromatogr. A, DOI:10.1016/j.chroma.2014.07.097., 2014
  29. Brode WR, J. Opt. Soc. Am., 41, 987, 1951
  30. Ward TJ, Oswald TM, Encyclopaedia of Analytical Chemistry, 2006
  31. Kraml CM, Zhou D, Byrne N, McConnell O, J. Chromatogr. A, 1100, 108, 2005
  32. Nohira H, Watanabe K, Kurokawa M, Chem. Lett., 5, 299, 1976
  33. Jacques J, Collet A, Wiley Interscience, New York, 1981
  34. Sekhon BS, Int. J. Chem. Technol. Res., 2, 1584, 2010
  35. Bommarius AS, Riebel-Bommarius BR, Biocatalysis: Fundamentals and Applications, Wiley, 2007
  36. Lee E, Park MB, Kim JM, Kim WS, Kim IH, Korean J. Chem. Eng., 27(1), 231, 2010
  37. Noble RD, J. Membr. Sci., 75, 121, 1992
  38. Ulbricht M, Polymer, 7, 2217, 2006
  39. Nakamura M, Kiyohara S, Saito K, Sugita K, Sugo T, Anal. Chem., 71, 1323, 1999
  40. Lee NH, Frank CW, Polymer, 43(23), 6255, 2002
  41. Newcomb M, Helgeson RC, Cram DJ, J. Am. Chem. Soc., 96, 7367, 1974
  42. Maruyama A, Adachi N, Takatsuki T, Torii M, Sanui K, Ogata N, Macromolecules, 23, 2748, 1990
  43. Aoki T, Shinohara K, Kaneko T, Oikawa E, Macromolecules, 29(12), 4192, 1996
  44. Aoki T, Kobayashi Y, Kaneko T, Oikawa E, Yamamura Y, Fujita Y, Teraguchi M, Nomura R, Masuda T, Macromolecules, 32(1), 79, 1999
  45. Aoki T, Prog. Polym. Sci., 24, 951, 1999
  46. Aoki T, Ohshima M, Shinohara KI, Kaneko T, Oikawa E, Polymer, 38(1), 235, 1997
  47. Teraguchi M, Masuda T, Macromolecules, 35(4), 1149, 2002
  48. Teraguchi M, Suzuki J, Kaneko T, Aoki T, Masuda T, Macromolecules, 36(26), 9694, 2003
  49. Teraguchi M, Mottate K, Kim SY, Aoki T, Kaneko T, Hadano S, Masuda T, Macromolecules, 38(15), 6367, 2005
  50. Masakazu Y, Akon H, Enantioselective Membranes, DOI: 10.1002/9781118522318.emst131 John Wiley & Sons, Inc. All, 2013
  51. Lonsdale HK, J. Membr. Sci., 10, 81, 1982
  52. Madihally SV, Principles of Biomedical Engineering, Artech House, Boston London, 2010
  53. Villaluenga JPG, Tabe-Mohammadi A, J. Membr. Sci., 169(2), 159, 2000
  54. Cadotte JE, Cobian KE, Forester RH, Petersen RJ, NTIS Report No. PB-253193, 1976
  55. Altinkaya SA, Desalination, 199(1-3), 459, 2006
  56. Singh K, Ingole PG, Bajaj HC, Bhattacharya A, Brahmbhatt HR, Sep. Sci. Technol., 45(10), 1374, 2010
  57. Vedejs E, Jure M, Angew. Chem., Int. Ed., 44, 3974, 2005
  58. Cook GR, Curr. Org. Chem., 4, 869, 2000
  59. Keith JM, Larrow JF, Jacobsen EN, Adv. Synth. Catal., 343, 5, 2001
  60. Tokunaga M, Larrow JF, Kakiuchi F, Jacobsen EN, Science, 277(5328), 936, 1997
  61. Ramdeehul S, Dierkes P, Aguado R, Kamer PCJ, Van Leeuwen PWNM, Osborn JA, Angew. Chem., Int. Ed., 37, 3118, 1998
  62. Pellissier H, Tetrahedron, 59, 8291, 2003
  63. Schurig V, J. Chromatogr. A, 906, 275, 2001
  64. Fanali S, Catarcini P, Blaschke G, Chankvetadze B, Electrophoresis, 22(15), 3131, 2001
  65. Nagata Y, Iida T, Sakai M, J. Mol. Catal. B: Enzym., 12, 105, 2001
  66. Peacock SS, Walba DM, Gaeta FCA, Helgeson RC, Cram DJ, J. Am. Chem. Soc., 102, 2043, 1980
  67. Dietrich B, Lehn JM, Sauvage JP, Tetrahedron, 29, 1647, 1973
  68. Dietrich B, Lehn JM, Tetrahedron Lett., 15, 1225, 1973
  69. Kyba EP, Timko JM, Kaplan LJ, de Jong F, Gokel GW, Cram DJ, J. Am. Chem. Soc., 100, 4555, 1978
  70. Cram DJ, Cram JH, ACC. Chem. Res., 11, 8, 1978
  71. Sousa LR, Hoffman DH, Kaplan L, Cram DJ, J. Am. Chem. Soc., 96, 7100, 1974
  72. Sousa LR, Sogah GDY, Hoffmann DH, Cram DJ, J. Am. Chem. Soc., 100, 4569, 1978
  73. Sogah GDY, Cram DJ, J. Am. Chem. Soc., 101, 3035, 1979
  74. Sough GDY, Cram DJ, J. Am. Chem. Soc., 97, 1259, 1975
  75. Pirkle WH, US Patent, 5,080,795, 1992
  76. Pirkle WH, WO 9,117,816, 1992
  77. Pirkle WH, Bowen WE, Tetrahedron: Asymmetry, 5, 773, 1994
  78. Pirkle WH, Doherty EM, J. Am. Chem. Soc., 111, 4113, 1989
  79. Thoelen C, De bruyn M, Theunissen E, Kondo Y, Vankelecom IFJ, Grobet P, Yoshikawa M, Jacobs PA, J. Membr. Sci., 186(2), 153, 2001
  80. Aoki T, Tomizawa S, Oikawa E, J. Membr. Sci., 99(2), 117, 1995
  81. Yashima E, Noguchi J, Okamoto Y, J. Appl. Polym. Sci., 54(8), 1087, 1994
  82. Kakuchi T, Takaoka T, Yokota K, Polym. J., 22, 199, 1990
  83. Xiao Y, Lim HM, Chung TS, Rajagopalan R, Langmuir, 23(26), 12990, 2007
  84. Zhou ZZ, Xiao YC, Hatton TA, Chung TS, J. Membr. Sci., 339(1-2), 21, 2009
  85. Zhang Y, Yu H, Wu Y, Zhao W, Yang M, Jing H, Chen A, Ana. Biochem., 462, 13, 2014
  86. He K, Qiu F, Qin J, Yan J, Yang D, Korean J. Chem. Eng., 30(11), 2078, 2013
  87. Liu X, Meng L, Korean J. Chem. Eng., 30(4), 918, 2013
  88. Kim JH, Kim JH, Jegal J, Lee KH, J. Membr. Sci., 213(1-2), 273, 2003
  89. Li W, Li Y, Fu Y, Zhang J, Korean J. Chem. Eng., 30(7), 1448, 2013
  90. Chen L, He X, Zhao B, Liu Y, Anal. Chim. Acta, 417, 51, 2000
  91. Sunsandee N, Leepipatpiboon N, Ramakul P, Wongsawa T, Pancharoen U, Sep. Purif. Technol., 102, 50, 2013
  92. Sunsandee N, Leepipatpiboon N, Ramakul P, Korean J. Chem. Eng., 30(6), 1312, 2013
  93. Higuchi A, Hara M, Horiuchi T, Nakagawa T, J. Membr. Sci., 93(2), 157, 1994
  94. Shinohara K, Aoki T, Oikawa E, Polymer, 36(12), 2403, 1995
  95. Sakaki K, Hara S, Itoh N, Desalination, 149(1-3), 247, 2002
  96. Wang YJ, Hu Y, Xu H, Luo GS, Dai YY, J. Membr. Sci., 293(1-2), 133, 2007
  97. Bodalo A, Gomez JL, Gomez E, Maximo MF, Montiel MC, Enzyme Microb. Technol., 35(2-3), 261, 2004
  98. Liese A, Kragl U, Kierkels H, Schulze B, Enzyme Microb. Technol., 30(5), 673, 2002
  99. Long WS, Bhatia S, Kamaruddin A, J. Membr. Sci., 219(1-2), 69, 2003
  100. Miyako E, Maruyama T, Kamiya N, Goto M, Chem. Eur. J., 11, 1163, 2005
  101. Robeson LM, Freeman BD, Paul DR, Rowe BW, J. Membr. Sci., 341(1-2), 178, 2009
  102. Robeson LM, J. Membr. Sci., 320(1-2), 390, 2008
  103. Freeman BD, Macromolecules, 32(2), 375, 1999
  104. Long WS, Kamaruddin A, Bhatia S, J. Membr. Sci., 247(1-2), 185, 2005
  105. Papra A, Hicke HG, Paul D, J. Appl. Polym. Sci., 74(7), 1669, 1999
  106. Ito Y, Ochiai Y, Park YS, Imanishi Y, J. Am. Chem. Soc., 119(7), 1619, 1997
  107. Yang J, Hage DS, J. Chromatogr., 645, 241, 1993
  108. Kimura T, Nakanishi K, Nakagawa T, Shibukawa A, Matsuzaki K, Pharm. Res., 22, 667, 2005
  109. Su CL, Dai RJ, Tong B, Deng YL, Chinese Chem. Lett., 17, 649, 2006
  110. Bowen WR, Nigmatullin RR, Sep. Sci. Technol., 37(14), 3227, 2002
  111. Gumi T, Minguillon C, Palet C, Polymer, 46(26), 12306, 2005
  112. Higuchi A, Yomogita H, Yoon BO, Kojima T, Hara M, Maniwa S, Saitoh M, J. Membr. Sci., 205(1-2), 203, 2002
  113. Wagenknecht HA, Stemp EDA, Barton JK, J. Am. Chem. Soc., 122(1), 1, 2000
  114. Higuchi A, Ishida Y, Nakagawa T, Desalination, 90, 127, 1993
  115. Garnier F, Randon J, Rocca JL, Sep. Purif. Technol., 116, 243, 1999
  116. Edmondson S, Osborne VL, Huck WTS, Chem. Soc. Rev., 1, 14, 2004
  117. Tone S, Masawaki T, Hamada T, J. Membr. Sci., 103(1-2), 57, 1995
  118. Tone S, Masawaki T, Eguchi K, J. Membr. Sci., 118(1), 31, 1996
  119. Aoki T, Fukuda T, Shinohara KI, Kaneko T, Teraguchi M, Yagi M, J. Polym. Sci. A: Polym. Chem., 42(18), 4502, 2004
  120. Higuchi A, Hayashi A, Kanda N, Sanui K, Kitamura H, J. Mol. Str., 739, 145, 2005
  121. Matsuoka Y, Kanda N, Lee YM, Higuchi A, J. Membr. Sci., 280(1-2), 116, 2006
  122. Higuchi A, Higuchi Y, Furuta K, Yoon BO, Hara M, Maniwa S, Saitoh M, Sanui K, J. Membr. Sci., 221(1-2), 207, 2003
  123. Kim IC, Jegal J, Lee KH, J. Polym. Sci. B: Polym. Phys., 40(19), 2151, 2002
  124. Gumi T, Valiente A, Palet C, J. Membr. Sci., 256(1-2), 150, 2005
  125. Randon J, Garnier F, Rocca JL, Maisterrena B, J. Membr. Sci., 175(1), 111, 2000
  126. Lee SB, Mitchell DT, Tron L, Nevanen TK, Soderlund H, Martin CR, Science, 296, 2198, 2002
  127. Aoki T, Shinohara K, Oikawa E, Makromol. Chem. Rapid Commun., 13, 565, 1992
  128. Teraguchi M, Masuda T, Macromolecules, 35(4), 1149, 2002
  129. Paris J, Molina-Jouve C, Nuel D, Moulin P, Charbit F, J. Membr. Sci., 237(1-2), 9, 2004
  130. Yoshikawa M, Murakoshi K, Kogita T, Hanaoka K, Guiver MD, Robertson GP, Europ. Polym. J., 42, 2532, 2006
  131. Nakagawa M, Ikeuchi Y, Yoshikawa M, Polymer, 49(21), 4612, 2008
  132. Yoshikawa M, Kondo Y, Morita Y, Bioseparation, 10, 323, 2001
  133. Ingole PG, Singh K, Bajaj HC, Arab. J. Chem., DOI:10.1016/j.arabjc.2011.10.011., 2011
  134. Yoshikawa M, Ooi T, Izumi JI, Eur. Polym. J., 37, 335, 2001
  135. Keurentjes JT, Nabuurs LJ, Vegter EA, J. Membr. Sci., 113(2), 351, 1996
  136. Ulbricht M, J. Chromatogr. B: Anal. Technol. Biomed. Life Sci., 804, 113, 2004
  137. van der Ent EM, van't Riet K, Keurentjes JTF, van der Padt A, J. Membr. Sci., 185(2), 207, 2001
  138. Lakshmi BB, Martin CR, Nature, 388(6644), 758, 1997
  139. Jirage KB, Martin CR, Trends Biotechnol., 17, 197, 1999
  140. Ingole PG, Choi W, Kim KH, Jo HD, Choi WK, Park JS, Lee HK, Desalination, 345, 136, 2014
  141. Ingole PG, Choi W, Kim KH, Park CH, Choi WK, Lee HK, Chem. Eng. J., 243, 137, 2014
  142. Rao AP, Joshi SV, Trivedi JJ, Devmurari CV, Shah VJ, J. Membr. Sci., 211(1), 13, 2003
  143. Leob S, Sourirajan S, Reverse Osmosis, National Research Council of Canada, Ottawa, Canada, 1985
  144. Yun SH, Ingole PG, Kim KH, Choi WK, Kim JH, Lee HK, Chem. Eng. J., 258, 348, 2014
  145. Cadotte JE, Petersen RJ, Larson RE, Erickson EE, Desalination, 32, 25, 1980
  146. Singh K, Bajaj HC, Ingole P, Bhattacharya A, Sep. Sci. Technol., 45(3), 346, 2010
  147. Singh K, Bajaj HC, Ingole PG, Patent Number(s): WO2010109490-A1; IN200900629-I1, 2010
  148. Ingole PG, Singh K, Bajaj HC, Sep. Sci. Technol., 46(12), 1898, 2011
  149. Singh K, Ingole PG, Chaudhari J, Bhrambhatt H, Bhattacharya A, Bajaj HC, J. Membr. Sci., 378(1-2), 531, 2011
  150. Ingole PG, Bajaj HC, Singh K, Indian J. Chem. Technol., 18(3), 197, 2011
  151. Ingole PG, Singh K, Bajaj HC, J. Trends Chem., 1, 1, 2010
  152. Singh K, Ingole PG, Bhrambhatt H, Bhattachayra A, Bajaj HC, Sep. Purif. Technol., 78(2), 138, 2011
  153. Ingole PG, Singh K, Bajaj HC, Desalination, 281, 413, 2011
  154. Ingole PG, Bajaj HC, Singh K, Desalination, 305, 54, 2012
  155. Ingole PG, Bajaj HC, Singh K, Desalination, 343, 75, 2014
  156. Ingole PG, Bajaj HC, Singh K, Procedia Engineering, 44, 358, 2012
  157. Ingole PG, Bajaj HC, Singh K, RSC Advances, 3, 3667, 2013
  158. Singh K, Ingole PG, Bajaj HC, Gupta H, Desalination, 298, 13, 2012
  159. Ingole PG, Bajaj HC, Srivastava DN, Rebary B, Singh K, Sep. Sci. Technol., 48(12), 1777, 2013
  160. Ingole PG, Singh K, Bajaj HC, Adv. Mater. Res., 2, 1, 2013
  161. Singh K, Bajaj HC, Ingole PG, Patent Number(s): WO2013118148-A1; PCT/IN2013/000081, 2010