Efficient separation of phenolic compounds from model oil by the formation of choline derivative-based deep eutectic solvents

Separation and Purification Technology

Volumn 163, Issue , 2016, Pages 310-318

  Zhang, Yue ^a   Li, Zhiyong ^a   Wang, Huiyong ^a   Xuan, Xiaopeng ^a   Wang, Jianji ^a  

^a HENAN NORMAL UNIVERSITY   (China)

Author keywords

Deep eutectic solvents; Far infrared spectroscopy; Hydrogen bond; Phenolic compounds; Separation

Indexed keywords

CHEMICAL BONDS; CHEMICAL COMPOUNDS; CHEMICAL INDUSTRY; CHLORINE COMPOUNDS; DENSITY FUNCTIONAL THEORY; EFFICIENCY; EUTECTICS; HYDROGEN BONDS; INFRARED SPECTROSCOPY; ORGANIC CHEMICALS; ORGANIC SOLVENTS; PHENOLS; REMOVAL; SALTS; SEPARATION; SOLVENTS; TOLUENE;

DEEP EUTECTIC SOLVENTS; DRIVING FORCES; ENVIRONMENTAL PROBLEMS; FAR-INFRARED SPECTROSCOPY; PHENOLIC COMPOUNDS; PRODUCTION PROCESS; REMOVAL EFFICIENCIES; STRONG ACIDS;

COMPLEXATION;

EID: 84960384731     PISSN: 13835866     EISSN: 18733794     Source Type: Journal    
DOI: 10.1016/j.seppur.2016.03.014     Document Type: Article

References (56)

1. M. Weber, M. Weber, and M. Kleine-Boymann Phenol Ullmann's Encyclopedia of Industrial Chemistry 2000 Wiley VCH Verlag GmbH & Co. KGaA
2. 13C NMR and pyrolysis-GC-MS studies of structure and liquefaction reactions of Montana subbituminous coal Fuel Process. Technol. 34 1993 249 276
3. A. Matsumura, S. Sato, Y. Kodera, I. Saito, and K. Ukegawa Methanol-mediated extraction for coal liquid (2)-the effect of phase separation caused by methanol on naphtha fraction derived from Wyoming coal Fuel Process. Technol. 68 2000 13 21
4. S. Sato, A. Matsumura, I. Saito, and K. Ukegawa Methanol-mediated extraction of coal liquid (5). Conceptual design and mass balance of a continuous methanol-mediated extraction process Energy Fuels 16 2002 1337 1342
5. A.P. Abbott, G. Capper, D.L. Davies, R.K. Rasheed, and V. Tambyrajah Novel solvent properties of choline chloride/urea mixtures Chem. Commun. 2003 70 71
6. E.L. Smith, A.P. Abbott, and K.S. Ryder Deep eutectic solvents (dess) and their applications Chem. Rev. 114 2014 11060 11082
7. Y. Dai, J. van Spronsen, G.-J. Witkamp, R. Verpoorte, and Y.H. Choi Natural deep eutectic solvents as new potential media for green technology Anal. Chim. Acta 766 2013 61 68
8. A. Paiva, R. Craveiro, I. Aroso, M. Martins, R.L. Reis, and A.R.C. Duarte Natural deep eutectic solvents-solvents for the 21st century ACS Sust. Chem. Eng. 2 2014 1063 1071
9. A.P. Abbott, D. Boothby, G. Capper, D.L. Davies, and R.K. Rasheed Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids J. Am. Chem. Soc. 126 2004 9142 9147
10. Y. Gu, and F. Jerome Bio-based solvents: an emerging generation of fluids for the design of eco-efficient processes in catalysis and organic chemistry Chem. Soc. Rev. 42 2013 9550 9570
11. Q. Zhang, K. De Oliveira Vigier, S. Royer, and F. Jerome Deep eutectic solvents: syntheses, properties and applications Chem. Soc. Rev. 41 2012 7108 7146
12. M. Francisco, A. van den Bruinhorst, and M.C. Kroon Low-transition-temperature mixtures (LTTMS): a new generation of designer solvents Angew. Chem. Int. Ed. 52 2013 3074 3085
13. K.D.O. Vigier, A. Benguerba, J. Barrault, and F. Jerome Conversion of fructose and inulin to 5-hydroxymethylfurfural in sustainable betaine hydrochloride-based media Green Chem. 14 2012 285 289
14. A.P. Abbott, J.C. Barron, G. Frisch, S. Gurman, K.S. Ryder, and A. Fernando Silva Double layer effects on metal nucleation in deep eutectic solvents Phys. Chem. Chem. Phys. 13 2011 10224 10231
15. Z.-H. Zhang, X.-N. Zhang, L.-P. Mo, Y.-X. Li, and F.-P. Ma Catalyst-free synthesis of quinazoline derivatives using low melting sugar-urea-salt mixture as a solvent Green Chem. 14 2012 1502 1506
16. A. Zhu, L. Li, J. Wang, and K. Zhuo Direct nucleophilic substitution reaction of alcohols mediated by a zinc-based ionic liquid Green Chem. 13 2011 1244 1250
17. S. Hu, Z. Zhang, Y. Zhou, J. Song, H. Fan, and B. Han Direct conversion of inulin to 5-hydroxymethylfurfural in biorenewable ionic liquids Green Chem. 11 2009 873 877
18. K. Shahbaz, F.S. Mjalli, M.A. Hashim, and I.M. AlNashef Eutectic solvents for the removal of residual palm oil-based biodiesel catalyst Sep. Purif. Technol. 81 2011 216 222
19. E.R. Cooper, C.D. Andrews, P.S. Wheatley, P.B. Webb, P. Wormald, and R.E. Morris Ionic liquids and eutectic mixtures as solvent and template in synthesis of zeolite analogues Nature 430 2004 1012 1016
20. E.A. Drylie, D.S. Wragg, E.R. Parnham, P.S. Wheatley, A.M.Z. Slawin, J.E. Warren, and R.E. Morris Ionothermal synthesis of unusual choline-templated cobalt aluminophosphates Angew. Chem. Int. Ed. 46 2007 7839 7843
21. J. Zhang, J.T. Bu, S. Chen, T. Wu, S. Zheng, Y. Chen, R.A. Nieto, P. Feng, and X. Bu Urothermal synthesis of crystalline porous materials Angew. Chem. Int. Ed. 49 2010 8876 8879
22. 4 gas mixtures Energy Environ. Sci. 5 2012 8699 8707
23. M.C. Gutierrez, M.L. Ferrer, L. Yuste, F. Rojo, and F. del Monte Bacteria incorporation in deep-eutectic solvents through freeze-drying Angew. Chem. Int. Ed. 49 2010 2158 2162
24. A.P. Abbott, G. Capper, D.L. Davies, K.J. McKenzie, and S.U. Obi Solubility of metal oxides in deep eutectic solvents based on choline chloride J. Chem. Eng. Data 51 2006 1280 1282
25. 2 Green Chem. 10 2008 1142 1145
26. 2 by ionic liquid/polyethylene glycol mixture and the thermodynamic parameters Green Chem. 10 2008 879 884
27. 2 in a choline chloride plus urea eutectic mixture J. Chem. Eng. Data 53 2008 548 550
28. C.-M. Lin, R.B. Leron, A.R. Caparanga, and M.-H. Li Henry's constant of carbon dioxide-aqueous deep eutectic solvent (choline chloride/ethylene glycol, choline chloride/glycerol, choline chloride/malonic acid) systems J. Chem. Thermodyn. 68 2014 216 220
29. F.S. Oliveira, A.B. Pereiro, L.P.N. Rebelo, and I.M. Marrucho Deep eutectic solvents as extraction media for azeotropic mixtures Green Chem. 15 2013 1326 1330
30. S. Mulyono, H.F. Hizaddin, I.M. Alnashef, M.A. Hashim, A.H. Fakeeha, and M.K. Hadj-Kali Separation of BTEX aromatics from n-octane using a (tetrabutylammonium bromide+ sulfolane) deep eutectic solvent-experiments and COSMO-RS prediction Rsc Adv. 4 2014 17597 17606
31. Y. Dai, G.-J. Witkamp, R. Verpoorte, and Y.H. Choi Natural deep eutectic solvents as a new extraction media for phenolic metabolites in Carthamus tinctorius L Anal. Chem. 85 2013 6272 6278
32. W. Bi, M. Tian, and K.H. Row Evaluation of alcohol-based deep eutectic solvent in extraction and determination of flavonoids with response surface methodology optimization J. Chromatogr. A 1285 2013 22 30
33. Q. Cui, X. Peng, X.-H. Yao, Z.-F. Wei, M. Luo, W. Wang, C.-J. Zhao, Y.-J. Fu, and Y.-G. Zu Deep eutectic solvent-based microwave-assisted extraction of genistin, genistein and apigenin from pigeon pea roots Sep. Purif. Technol. 150 2015 63 72
34. Z. Wei, X. Qi, T. Li, M. Luo, W. Wang, Y. Zu, and Y. Fu Application of natural deep eutectic solvents for extraction and determination of phenolics in Cajanus cajan leaves by ultra performance liquid chromatography Sep. Purif. Technol. 149 2015 237 244
35. X.-H. Yao, D.-Y. Zhang, M.-H. Duan, Q. Cui, W.-J. Xu, M. Luo, C.-Y. Li, Y.-G. Zu, and Y.-J. Fu Preparation and determination of phenolic compounds from Pyrola incarnata Fisch with a green polyols based-deep eutectic solvent Sep. Purif. Technol. 149 2015 116 123
36. Q. Zeng, Y. Wang, Y. Huang, X. Ding, J. Chen, and K. Xu Deep eutectic solvents as novel extraction media for protein partitioning Analyst 139 2014 2565 2573
37. Y. Hou, J. Li, S. Ren, M. Niu, and W. Wu Separation of the isomers of benzene poly (carboxylic acid)s by quaternary ammonium salt via formation of deep eutectic solvents J. Phys. Chem. B 118 2014 13646 13650
38. A.P. Abbott, P.M. Cullis, M.J. Gibson, R.C. Harris, and E. Raven Extraction of glycerol from biodiesel into a eutectic based ionic liquid Green Chem. 9 2007 868 872
39. K. Shahbaz, F.S. Mjalli, M.A. Hashim, and I.M. AlNashef Using deep eutectic solvents based on methyl triphenyl phosphunium bromide for the removal of glycerol from palm-oil-based biodiesel Energy Fuels 25 2011 2671 2678
40. C. Li, D. Li, S. Zou, Z. Li, J. Yin, A. Wang, Y. Cui, Z. Yao, and Q. Zhao Extraction desulfurization process of fuels with ammonium-based deep eutectic solvents Green Chem. 15 2013 2793 2799
41. X.-D. Tang, Y.-F. Zhang, J.-J. Li, Y.-Q. Zhu, D.-Y. Qing, and Y.-X. Deng Deep extractive desulfurization with arenium ion deep eutectic solvents Ind. Eng. Chem. Res. 54 2015 4625 4632
42. J. Yin, J. Wang, Z. Li, D. Li, G. Yang, Y. Cui, A. Wang, and C. Li Deep desulfurization of fuels based on an oxidation/extraction process with acidic deep eutectic solvents Green Chem. 17 2015 4552 4559
43. T. Jiao, C. Li, X. Zhuang, S. Cao, H. Chen, and S. Zhang The new liquid-liquid extraction method for separation of phenolic compounds from coal tar Chem. Eng. J. 266 2015 148 155
44. T. Gu, M. Zhang, T. Tan, J. Chen, Z. Li, Q. Zhang, and H. Qiu Deep eutectic solvents as novel extraction media for phenolic compounds from model oil Chem. Commun. 50 2014 11749 11752
45. K. Pang, Y. Hou, W. Wu, W. Guo, W. Peng, and K.N. Marsh Efficient separation of phenols from oils via forming deep eutectic solvents Green Chem. 14 2012 2398 2401
46. W. Guo, Y. Hou, W. Wu, S. Ren, S. Tian, and K.N. Marsh Separation of phenol from model oils with quaternary ammonium salts via forming deep eutectic solvents Green Chem. 15 2013 226 229
47. J.K. Blusztajn Choline, a vital amine Science 281 1998 794 795
48. J. Pernak, A. Syguda, I. Mirska, A. Pernak, J. Nawrot, A. Pradzynska, S.T. Griffin, and R.D. Rogers Choline-derivative-based ionic liquids Chem. Eu. J. 13 2007 6817 6827
49. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. P eralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox Gaussian 09, Revision C.01 2010 Gaussian, Inc. Wallingford, CT
50. S.F. Boys, and F. Bernardi The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors Mol. Phys. 19 1970 553 566
51. A. Wulf, K. Fumino, and R. Ludwig Spectroscopic evidence for an enhanced anion-cation interaction from hydrogen bonding in pure imidazolium ionic liquids Angew. Chem. Int. Ed. 49 2010 449 453
52. K. Fumino, T. Peppel, M. Geppert-Rybczynska, D.H. Zaitsau, J.K. Lehmann, S.P. Verevkin, M. Koeckerling, and R. Ludwig The influence of hydrogen bonding on the physical properties of ionic liquids Phys. Chem. Chem. Phys. 13 2011 14064 14075
53. B.P. Dailey, and J.N. Shoolery The electron withdrawal power of substituent groups J. Am. Chem. Soc. 77 1955 3977 3981
54. W. Zierkiewicz, D. Michalska, B. Czarnik-Matusewicz, and M. Rospenk Molecular structure and infrared spectra of 4-fluorophenol: a combined theoretical and spectroscopic study J. Phys. Chem. A 107 2003 4547 4554
55. 35Cl NQR on hydrogen bonding and temperature in dichlorophenol-aniline charge transfer complexes Magn. Reson. Chem. 45 2007 860 864
56. N.T. Hunt, A.R. Turner, and K. Wynne Inter- and intramolecular hydrogen bonding in phenol derivatives: a model system for poly-l-tyrosine J. Phys. Chem. B 109 2005 19008 19017