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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Ionic Liquid–Liquid Separations Using Countercurrent Chromatography: A New General-Purpose Separation Methodology

Leslie Brown A , Martyn J. Earle B C , Manuela A. Gîlea B , Natalia V. Plechkova B and Kenneth R. Seddon B
+ Author Affiliations
- Author Affiliations

A AECS-QuikPrep Ltd, 55 Gower Street, London, WC1 6HQ, UK.

B The QUILL Research Centre, School of Chemistry, The Queen’s University of Belfast, Belfast, BT9 5AG, Northern Ireland, UK.

C Corresponding author. Email: quill@qub.ac.uk

Australian Journal of Chemistry 70(8) 923-932 https://doi.org/10.1071/CH17004
Submitted: 13 January 2017  Accepted: 1 April 2017   Published: 25 May 2017

Abstract

Liquid–liquid separations based on countercurrent chromatography, in which at least one phase contains an ionic liquid, represent a new empirical approach for the separation of organic, inorganic, or bio-based materials. A custom-designed instrument has been developed and constructed specifically to perform separations (including transition metal salts, arenes, alkenes, alkanes, and sugars) with ionic liquids, and has been demonstrated for use on the 0.1 to 10 g scale.


References

[1]  L. R. Snyder, J. J. Kirkland, Introduction to Modern Liquid Chromatography 1979 (John Wiley & Sons Inc.: New York, NY).

[2]  A. Vailaya, in Encyclopedia of Chromatography, 3rd edn (Ed. J. Cazes) 2009, pp. 1414–1417 (Taylor & Francis: Boca Raton, FL).

[3]  Modern Countercurrent Chromatography (Eds W. D. Conway, R. J. Petroski) 1995 (American Chemical Society: Washington, DC).

[4]  F. Oka, H. Oka, Y. Ito, J. Chromatogr. A 1991, 538, 99.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXhtlSgtrg%3D&md5=1a1390b99fb2764115b5f86907982f48CAS |

[5]  L. Brown, T. A. Luu, J. Sep. Sci. 2010, 33, 999.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXlt1Cgu7k%3D&md5=bea470d106e5a47a20bd3cf9597dc0f8CAS |

[6]  I. J. Garrard, J. Liq. Chromatogr. Relat. Technol. 2005, 28, 1923.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXps1Gqsrg%3D&md5=20b2dc8bcaf5c63a0427aa450a2ecc22CAS |

[7]  Z. M. Chao, Y. Shibusawa, H. Shindo, Y. Ito, J. Liq. Chromatogr. Relat. Technol. 2003, 26, 1895.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXlslaht74%3D&md5=7a4597d408c5611ff9c864e500ba15a4CAS |

[8]  K. Ishii, Y. Tanaka, K. Hata, M. Goto, K. Saitoh, H. Minamisawa, M. Shibukawa, Bunseki Kagaku 2004, 53, 911.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXnvVagu7s%3D&md5=0101d788d4e15191f191ced789e3a835CAS |

[9]  I. A. Sutherland, L. Brown, S. Forbes, G. Games, D. Hawes, K. Hostettmann, E. H. McKerrell, A. Marston, D. Wheatley, P. Wood, J. Liq. Chromatogr. Relat. Technol. 1998, 21, 279.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXhs1ejtrs%3D&md5=d5c648c6af1abceb4f8e26db655950e4CAS |

[10]  H. J. Rafson, Odor and VOC Control Handbook 1998 (McGraw-Hill: New York, NY).

[11]  I. Sutherland, S. Ignatova, P. Hewitson, L. Janaway, P. Wood, N. Edwards, G. Harris, H. Guzlek, D. Keay, K. Freebairn, D. Johns, N. Douillet, C. Thickitt, E. Vilminot, B. Mathews, J. Chromatogr. A 2011, 1218, 6114.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtVKlt7bI&md5=f60e2ed2b5fc3a15cea0c4db347ab1a1CAS |

[12]  I. A. Sutherland, in Encyclopedia of Chromatography (Ed. J. Cazes) 2010, pp. 2116–2119 (Taylor & Francis: Boca Raton, FL).

[13]  Ionic Liquids in Synthesis (Eds P. Wasserscheid, T. Welton) 2008 (Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim).

[14]  Y. Ito, W. D. Conway, Crit. Rev. Anal. Chem. 1986, 17, 65.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28XmtVantL8%3D&md5=c429cda4db4be0f2df1caf0ce1dbff07CAS |

[15]  Encyclopedia of Chromatography, 3rd edn (Ed. J. Cazes) 2009 (Taylor & Francis: Boca Raton, FL).

[16]  H. Guzlek, P. L. Wood, L. Janaway, J. Chromatogr. A 2009, 1216, 4181.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXkvVWjtLo%3D&md5=e92ba963687ed5f07eaee050e2a10a2eCAS |

[17]  A. Berthod, in Countercurrent Chromatography: The Support-Free Liquid Stationary Phase (Comprehensive Analytical Chemistry Series) (Ed. A. Berthod) 2002, pp. 1–20 (Elsevier Science: Amsterdam).

[18]  N. Rubio, S. Ignatova, C. Minguillon, I. A. Sutherland, J. Chromatogr. A 2009, 1216, 8505.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtlyqtbjN&md5=7479ba174f483cc0f3f6e5c90ff6ef0fCAS |

[19]  A. Berthod, M. J. Ruiz-Angel, S. Carda-Broch, J. Chromatogr. A 2008, 1184, 6.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXivVyntrY%3D&md5=821dd6b0d1f1ac5a68af0fed55bbaecdCAS |

[20]  Y. Ito, in Chemical Analysis (Eds Y. Ito, W. D. Conway) 1996, pp. 3–44 (John Wiley & Sons: New York, NY).

[21]  S. Ignatova, D. Hawes, R. van den Heuvel, P. Hewitson, I. A. Sutherland, J. Chromatogr. A 2010, 1217, 34.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsFyktbjJ&md5=d6ab500ddfa35d20cc8f31d3f174c54eCAS |

[22]  I. A. Sutherland, D. Heywood-Waddington, Y. Ito, J. Chromatogr. A 1987, 384, 197.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2sXpvVKrtg%3D%3D&md5=1098592f7da52123eb3fd59890e11cb5CAS |

[23]  Y. Ito, J. Sandlin, W. G. Bowers, J. Chromatogr. A 1982, 244, 247.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL38XkvFCltLs%3D&md5=feb2ae7efa396fda246b59d019fa95a6CAS |

[24]  M. Freemantle, An Introduction to Ionic Liquids 2009 (The Royal Society of Chemistry: Cambridge).

[25]  M. J. Earle, J. Esperança, M. A. Gîlea, J. N. C. Lopes, L. P. N. Rebelo, J. W. Magee, K. R. Seddon, J. A. Widegren, Nature 2006, 439, 831.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhsVSkurk%3D&md5=3291977fca9908ffbbd8b542015b1d65CAS |

[26]  M. Freemantle, Chemistry World, 7 October 2016. Available at https://www.chemistryworld.com/feature/ionic-liquids-revisted/1017383.article (accessed 23 April 2017).

[27]  N. V. Plechkova, K. R. Seddon, Chem. Soc. Rev. 2008, 37, 123.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXmtVWhsQ%3D%3D&md5=3288e9be22f58f40caed15fd6f3b706bCAS |

[28]  K. R. Seddon, in The International George Papatheodorou Symposium: Proceedings (Eds S. Boghosian, V. Dracopoulos, C. G. Kontoyannis, G. A. Voyiatzis) 1999, pp. 131–135 (Patras, Greece).

[29]  J. L. Anderson, D. W. Armstrong, G. T. Wei, Anal. Chem. 2006, 78, 2892.
         | Crossref | GoogleScholarGoogle Scholar |

[30]  A. Arce, M. J. Earle, H. Rodriguez, K. R. Seddon, A. Soto, Green Chem. 2009, 11, 365.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXivVOltLc%3D&md5=89d03fe0e9e16f173bbef993cb569261CAS |

[31]  M. C. García-Alvarez-Coque, M. J. Ruiz-Angel, A. Berthod, S. Carda-Broch, Anal. Chim. Acta 2015, 883, 1.
         | Crossref | GoogleScholarGoogle Scholar |

[32]  M. L. Zhang, A. K. Mallik, M. Takafuji, H. Ihara, H. D. Qiu, Anal. Chim. Acta 2015, 887, 1.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXmvV2jt74%3D&md5=0c687951ca026cd67c7974498623411aCAS |

[33]  A. Berthod, S. Carda-Broch, Anal. Bioanal. Chem. 2004, 380, 168.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXntlCisr8%3D&md5=267868cebb75848c3a56b5f05022b979CAS |

[34]  A. Berthod, M.-J. Ruiz-Angel, S. Carda-Broch, in Ionic Liquids in Chemical Analysis (Ed. M. Koel) 2009, pp. 211–227 (CRC Press: Boca Raton, FL).

[35]  A. Berthod, S. Carda-Broch, J. Liq. Chromatogr. Relat. Technol. 2003, 26, 1493.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXlsV2quro%3D&md5=598f106b45ce3061d9624c86741eed15CAS |

[36]  L. L. Xu, A. F. Li, A. L. Sun, R. M. Liu, J. Sep. Sci. 2010, 33, 31.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtFakurc%3D&md5=8467b01ef7d3dccc2f2ce65215bda342CAS |

[37]  C. Fan, N. Li, X. L. Cao, J. Sep. Sci. 2015, 38, 2109.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXosFKitL8%3D&md5=740e9be7363e287fc424eb08602ebc28CAS |

[38]  C. Fan, X. L. Cao, M. Liu, W. Wang, J. Chromatogr. A 2016, 1436, 133.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC28XhvFShsb0%3D&md5=4fff7292d04bbf4f5a76a7ec75001504CAS |

[39]  M. J. Ruiz-Angel, V. Pino, S. Carda-Broch, A. Berthod, J. Chromatogr. A 2007, 1151, 65.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXkvF2iurs%3D&md5=018f4f2d0f5494fa9ebfbb46bed5d1dcCAS |

[40]  W. D. Conway, Y. Ito, J. Liq. Chromatogr. 1984, 7, 275.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2cXhsVGmtL8%3D&md5=32ad53570ac6b0aa390cf69e4028f78dCAS |

[41]  T. P. Abbott, R. Kleiman, J. Chromatogr. A 1991, 538, 109.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXhtlSgtrk%3D&md5=7d7d73c0fad7652e615732214044c972CAS |

[42]  F. das Neves Costa, G. G. Leitao, J. Sep. Sci. 2010, 33, 336.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXisVaisb4%3D&md5=3e932ab550e0397b89da63a4525e34fcCAS |

[43]  A. Berthod, S. Carda-Broch, Actual. Chim. 2004, 271, 24.

[44]  J. Lu, A. He, S. Y. Li, L. R. Nie, W. Zhang, S. Yao, Mini Rev. Org. Chem. 2015, 12, 435.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXitVagu7nE&md5=6f14163fb2a250e3147c0aac166b5ce0CAS |

[45]  Y. Chauvin, A. Hirschauer, H. Olivier, J. Mol. Catal. 1994, 92, 155.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXmtVOqtb0%3D&md5=45467d931d45dec2fc775736acb5ac8aCAS |

[46]  A. Arce, M. J. Earle, S. P. Katdare, H. Rodriguez, K. R. Seddon, Fluid Phase Equilib. 2007, 261, 427.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtFyksL%2FE&md5=aa329f69086e82b77d58050c053c08ddCAS |

[47]  M. Kosmulski, J. Gustafsson, J. B. Rosenholm, Thermochim. Acta 2004, 412, 47.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhvV2nsbg%3D&md5=b042d1a5c71f6d039868429951c1c19fCAS |

[48]  P. L. Wood, D. Hawes, L. Janaway, I. A. Sutherland, J. Liq. Chromatogr. Relat. Technol. 2003, 26, 1373.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXlsV2qtbc%3D&md5=6530001f582c3998d77f8e3969d576e9CAS |

[49]  C. H. He, C. X. Zhao, AIChE J. 2007, 53, 1460.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXmtVWmsr0%3D&md5=3b4e053621fb230499e6948501cd40dbCAS |

[50]  M. J. Earle, K. R. Seddon, R. Self, L. Brown, World Patent WO2013121218A1 2013.

[51]  P. L. Wood, J. Chromatogr. A 2010, 1217, 1283.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtlCkt7k%3D&md5=320fa2f71693b686ffcaed0f79f0f499CAS |

[52]  A. Berthod, M. Hassoun, G. Harris, J. Liq. Chromatogr. Relat. Technol. 2005, 28, 1851.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXps1Gqsr4%3D&md5=ce565f0fc7ab6a0550e343f011b2ad9fCAS |

[53]  S. J. Zhang, N. Sun, X. Z. He, X. M. Lu, X. P. Zhang, J. Phys. Chem. Ref. Data 2006, 35, 1475.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXptF2guw%3D%3D&md5=c8c95e2ef69b437ce069b237c11f5a03CAS |

[54]  W. Liu, L. Cheng, Y. Zhang, H. Wang, M. Yu, J. Mol. Liq. 2008, 140, 68.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXktl2ltb0%3D&md5=b5a3417c4165b0438908570d84cafe2bCAS |

[55]  T. Zhou, L. Chen, Y. Ye, L. Chen, Z. Qi, H. Freund, K. Sundmacher, Ind. Eng. Chem. Res. 2012, 51, 6256.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xls1Sju70%3D&md5=cb09f2a97f254ec5f72b489414135c68CAS |

[56]  A. B. Pereiro, J. M. M. Araujo, F. S. Teixeira, I. M. Marrucho, M. M. Pineiro, L. P. N. Rebelo, Langmuir 2015, 31, 1283.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXmvVyrtQ%3D%3D&md5=dedcf9caa8890b7b208dd65c84e11c56CAS |

[57]  NIST Standard Reference Database #147, 2016. Available at: http://ilthermo.boulder.nist.gov/index.html (accessed 19 December 2016).

[58]  U. Domańska, M. Wlazlo, J. Chem. Thermodyn. 2016, 103, 76.
         | Crossref | GoogleScholarGoogle Scholar |

[59]  M. T. Clough, C. R. Crick, J. Grasvik, P. A. Hunt, H. Niedermeyer, T. Welton, O. P. Whitaker, Chem. Sci. 2015, 6, 1101.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhvVKltbbO&md5=d3c234d8fb66babcc1136425bdc2c708CAS |

[60]  M. Tariq, K. Shimizu, J. M. S. S. Esperança, J. N. C. Lopes, L. P. N. Rebelo, Phys. Chem. Chem. Phys. 2015, 17, 13480.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXmslGhtL4%3D&md5=5b2839a32c3ad0e65ab979e3c773ca53CAS |

[61]  A. Arce, M. J. Earle, H. Rodriguez, K. R. Seddon, J. Phys. Chem. B 2007, 111, 4732.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXpvFymtw%3D%3D&md5=9c7c7c5b561b0a7a5c818bf8efb85697CAS |

[62]  K. R. Seddon, A. Stark, M. J. Torres, Pure Appl. Chem. 2000, 72, 2275.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXisVCgtb4%3D&md5=737061bb97773effd55a9885fe9fbc52CAS |

[63]  S. Atashrouz, M. Zarghampour, S. Abdolrahimi, G. Pazuki, B. Nasernejad, J. Chem. Eng. Data 2014, 59, 3691.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhvVGlsbrM&md5=abfff9071cd1a07fd398d9650c9a7d08CAS |

[64]  A. Arce, M. J. Earle, S. P. Katdare, H. Rodriguez, K. R. Seddon, Chem. Commun. 2006, 2548.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XlvV2gur8%3D&md5=b2539baedffc236e4ebbfccfaccef414CAS |

[65]  A. Arce, M. J. Earle, H. Rodriguez, K. R. Seddon, Green Chem. 2007, 9, 70.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhtVegsQ%3D%3D&md5=32100d175051b0b65dd61a5dea05263cCAS |

[66]  A. Arce, M. J. Earle, S. P. Katdare, H. Rodríguez, K. R. Seddon, Phys. Chem. Chem. Phys. 2008, 10, 2538.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXlt1aisro%3D&md5=b8b5285e57c2b0028439035d68cb7566CAS |

[67]  A. Arce, M. J. Earle, H. Rodriguez, K. R. Seddon, A. Soto, Green Chem. 2008, 10, 1294.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhsVWhsbbP&md5=2d9d9c0be6210eb72375b828477d8d8cCAS |

[68]  M. J. Earle, M. A. Gilea, World Patent WO2013140185A1 2013.

[69]  J. M. Lopes, A. B. Paninho, M. F. Môlho, A. V. M. Nunes, A. Rocha, N. M. T. Lourenço, V. Najdanovic-Visak, J. Chem. Thermodyn. 2013, 67, 99.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhsFCjsrbE&md5=d23a0665d079b713fbbea3da0622ee61CAS |

[70]  M. Klähn, C. Stuber, A. Seduraman, P. Wu, J. Phys. Chem. B 2010, 114, 2856.
         | Crossref | GoogleScholarGoogle Scholar |

[71]  S. Carda-Broch, A. Berthod, D. W. Armstrong, Anal. Bioanal. Chem. 2003, 375, 191.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXosVOgsQ%3D%3D&md5=daf3cce701c7a77c560aca0b77a6afdfCAS |

[72]  P. S. Kulkarni, L. C. Branco, J. G. Crespo, M. C. Nunes, A. Raymundo, C. A. M. Afonso, Chem. – Eur. J. 2007, 13, 8478.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXht1ansLvN&md5=56a1cfe05b455b5342babeadfabca193CAS |

[73]  E. J. González, N. Calvar, E. A. Macedo, J. Chem. Thermodyn. 2014, 69, 93.
         | Crossref | GoogleScholarGoogle Scholar |

[74]  M. M. S. Abullah, H. A. Al-Lohedan, A. M. Attah, J. Mol. Liq. 2016, 219, 54.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC28Xkt1Ggu7s%3D&md5=22a9ad5419f56844d5bd618e49464a2bCAS |

[75]  A. Z. Hezave, S. Dorostkar, S. Ayatollahi, M. Nabipour, B. Hemmateenejad, Colloids Surf. A 2013, 421, 63.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXktFaitr4%3D&md5=f47a6ed09abe323c98a0913a541ee58fCAS |

[76]  P. S. Fedotov, R. V. Khachaturov, J. Liq. Chromatogr. Relat. Technol. 2000, 23, 655.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXitVWlt74%3D&md5=a713e4c42947800d4542b7dd2513f1beCAS |

[77]  Z. Zhu, W. Zhang, Y. Pranolo, C. Y. Cheng, Hydrometallurgy 2012, 127–128, 1.
         | Crossref | GoogleScholarGoogle Scholar |

[78]  S. Wellens, R. Goovaerts, C. Moeller, J. Luyten, B. Thijs, K. Binnemans, Green Chem. 2013, 15, 3160.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhs1Cmu7zO&md5=5ec1a2c691d863260d09970c8b7ce5b7CAS |

[79]  G. B. Kauffman, M. L. Adams, J. Chem. Educ. 1989, 66, 166.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXhsFegt7g%3D&md5=478bc7f8bbd00650bf2175f31f097c09CAS |

[80]  N. S. Bhave, S. R. Dhudey, R. B. Kharat, Sep. Sci. Technol. 1978, 13, 193.
         | Crossref | GoogleScholarGoogle Scholar |

[81]  A. Mohammad, E. Iraqi, Y. H. Sirwal, Sep. Sci. Technol. 2003, 38, 2255.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXlsFakt74%3D&md5=073c76f036ea6542a403360cb8bf2b0aCAS |

[82]  M. Y. Khuhawar, A. K. Talpur, J. Chem. Soc. Pak. 1992, 14, 102.
         | 1:CAS:528:DyaK3sXhvVahtL4%3D&md5=70c69f1f31542c3273bbbf7f4b04644fCAS |

[83]  E. Toyota, K. Itoh, H. Sekizaki, K. Tanizawa, Bioorg. Chem. 1996, 24, 150.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28Xks1Kgu78%3D&md5=eb026825cb130d6bc5b4e3199f2982ceCAS |

[84]  M. A. Mirza, M. Y. Khuhawar, R. Arain, M. A. Choudhary, A. J. Kandhro, T. M. Jahangir, Asian J. Chem. 2013, 25, 3719.
         | 1:CAS:528:DC%2BC3sXlslGntrw%3D&md5=d009a26b8f1940620d28d9079bea75a2CAS |

[85]  S. Loonker, J. K. Sethia, Izv. Him. 2009, 41, 19.
         | 1:CAS:528:DC%2BD1MXptVaisb0%3D&md5=4cbdeddccac444b775dc31235fbbc0beCAS |

[86]  F. Vláčil, H. D. Khanh, Fresenius Z. Anal. Chem. 1980, 302, 36.
         | Crossref | GoogleScholarGoogle Scholar |

[87]  K. Anderson, H. Rodriguez, K. R. Seddon, Green Chem. 2009, 11, 780.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXmvV2qt7c%3D&md5=002e734e7a8f623180dcb9262c7f129eCAS |

[88]  D. Cholico-Gonzalez, M. Avila-Rodriguez, J. A. Reyes-Aguilera, G. Cote, A. Chagnes, J. Mol. Liq. 2012, 169, 27.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XlvV2rs7Y%3D&md5=b2372c0ade85bd851a51500ccb11c737CAS |

[89]  C. Neves, P. J. Carvalho, M. G. Freire, J. A. P. Coutinho, J. Chem. Thermodyn. 2011, 43, 948.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXjsVKktLY%3D&md5=3fa76a84b122090a4f0ce22bb9dff6eaCAS |

[90]  G. M. Zhong, T. Fornstedt, G. Guiochon, J. Chromatogr. A 1996, 734, 63.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XjtlSrur8%3D&md5=37bbdace590e9ca9d4572736319ed276CAS |

[91]  P. Deckert, W. Arlt, Chem. Ing. Tech. 1994, 66, 1334.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXitFalt7c%3D&md5=7fcf944cfde5731cf07459316ddcc507CAS |

[92]  R. C. R. Rodrigues, R. J. S. Silva, J. P. B. Mota, J. Chromatogr. A 2010, 1217, 3382.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXlt1Gjsrw%3D&md5=93694a7eff7f6c455b371caff7dd22fbCAS |

[93]  M. Verzele, G. Simoens, F. Vandamme, Chromatographia 1987, 23, 292.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2sXks12qtL8%3D&md5=403a236bf75786fd48e31fdec7b14bdcCAS |

[94]  E. Nitsch, US Patent 3812010 1974.

[95]  P. E. Shaw, C. W. Wilson, J. Sci. Food Agric. 1983, 34, 109.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3sXhsF2hsrk%3D&md5=0c38c3e33fb6a951bd17b59f9e97e135CAS |

[96]  M. Filip, M. Vlassa, V. Coman, A. Halmagyi, Food Chem. 2016, 199, 653.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXitVyksr%2FF&md5=1c1b8775934d52397e23ac7626b46873CAS |

[97]  T. Schmid, B. Baumann, M. Himmelsbach, C. W. Klampfl, W. Buchberger, Anal. Bioanal. Chem. 2016, 408, 1871.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC28Xps1Wquw%3D%3D&md5=58f8eea14b1204dabc103bbf713ca337CAS |

[98]  J. González, G. Remaud, E. Jamin, N. Naulet, G. G. Martin, J. Agric. Food Chem. 1999, 47, 2316.
         | Crossref | GoogleScholarGoogle Scholar |

[99]  T. Véronèse, A. Bouchu, P. Perlot, Biotechnol. Tech. 1999, 13, 43.
         | Crossref | GoogleScholarGoogle Scholar |

[100]  K. Shinomiya, Y. Ito, J. Liq. Chromatogr. Relat. Technol. 2006, 29, 733.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhsleksL4%3D&md5=fa8527557dce6826bcadf036255686b3CAS |

[101]  K. E. Gutowski, G. A. Broker, H. D. Willauer, J. G. Huddleston, R. P. Swatloski, J. D. Holbrey, R. D. Rogers, J. Am. Chem. Soc. 2003, 125, 6632.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXjs12ks7k%3D&md5=136eee3621d498134328d7cfd07ac89eCAS |

[102]  R. H. Doremus, J. Colloid Interface Sci. 1985, 104, 114.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2MXhsFWiur8%3D&md5=39f49f5ebaf732b6c995845b407c8561CAS |