Selective extraction of 1-hexene against n -hexane in ionic liquids with or without silver salt

Industrial and Engineering Chemistry Research

Volumn 51, Issue 25, 2012, Pages 8588-8597

  Li, Rulong ^a   Xing, Huabin ^a   Yang, Qiwei ^a   Zhao, Xu ^a   Su, Baogen ^a   Bao, Zongbi ^a   Yang, Yiwen ^a   Ren, Qilong ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1-HEXENE; ALKYL CHAIN LENGTHS; CARBON-CARBON DOUBLE BONDS; EXTRACTANTS; EXTRACTION CAPACITY; EXTRACTION EFFICIENCIES; EXTRACTION SELECTIVITY; EXTRACTIVE SEPARATION; HIGH SELECTIVITY; INITIAL FEED CONCENTRATION; N-HEXANE; REACTION MEDIA; SELECTIVE EXTRACTION; SILVER SALTS;

AMIDES; CYANIDES; FUNCTIONAL GROUPS; IONIC LIQUIDS; MATHEMATICAL MODELS; POSITIVE IONS; SALTS; SEPARATION; STOICHIOMETRY;

HEXANE;

EID: 84863210687     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie3001452     Document Type: Article

References (56)

1. Tullo, A. H. Plastics Additives? Steady Evolution Chem. Eng. News. 2000, 49, 21
2. Sadrameli, S. M.; Green, A. E. S. Systematics and Modeling Representations of Naphtha Thermal Cracking for Olefin Production J. Anal. Appl. Pyrolysis 2005, 73, 305
3. Li, X. M.; Song, F. R. Advances in Olefin Production Technology by Catalytic Cracking Petrochem. Technol. 2002, 31, 569
4. Eldridge, R. B. Olefin/paraffin Separation Technology: a Review Ind. Eng. Chem. Res. 1993, 32, 2208
5. Liao, B.; Lei, Z.; Xu, Z.; Zhou, R. Q.; Duan, Z. T. New Process for Separating Propylene and Propane by Extractive Distillation with Aqueous Acetonitrile Chem. Eng. J. 2001, 84, 581
6. Wentink, A. E.; Kuipers, N. J. M.; de Haan, A. B.; Scholtz, J.; Mulder, H. Olefin Isomer Separation by Reactive Extractive Distillation: Modelling of Vapor-Liquid Equilibria and Conceptual Design for 1-Hexene Purification Chem. Eng. Process. 2007, 46, 800
7. Safarik, D. J.; Eldridge, R. B. Olefin/Paraffin Separations by Reactive Absorption:A Review Ind. Eng. Chem. Res. 1998, 37, 2571
8. Reine, T. A.; Eldridge, R. B. Absorption Equilibrium and Kinetics for Ethylene-Ethane Separation with a Novel Solvent Ind. Eng. Chem. Res. 2005, 44, 7505
9. Chen, J.; Eldridge, R. B.; Rosen, E. L.; Bielawski, C. W. A Study of Cu(I)-Ethylene Complexation for Olefin-Paraffin Separation AIChE J. 2011, 57, 630
10. Li, K.; Olson, D. H.; Seidel, J.; Emge, T. J.; Gong, H. W.; Zeng, H. P.; Li, J. Zeolitic Imidazolate Frameworks for Kinetic Separation of Propane and Propene J. Am. Chem. Soc. 2009, 131, 10368
11. Grande, C. A.; Rodrigues, A. E. Propane/propylene Separation by Pressure Swing Adsorption Using Zeolite 4A Ind. Eng. Chem. Res. 2005, 44, 8815
12. Grande, C. A.; Araujo, J. D. P.; Cavenati, S.; Firpo, N.; Basaldella, E.; Rodrigues, A. E. New ? -Complexation Adsorbents for Propane-propylene Separation Langmuir 2004, 20, 5291
13. Grande, C. A.; Silva, V. M. T. M.; Gigola, C.; Rodrigues, A. E. Adsorption of Propane and Propylene onto Carbon Molecular Sieve Carbon 2003, 41, 2533
14. Ruthven, D. M.; Reyes, S. C. Adsorptive Separation of Light Olefins from Paraffns Microporous Mesoporous Mater. 2007, 104, 59
15. Bao, Z. B.; Alnemrat, S.; Yu, L.; Vasiliev, I.; Ren, Q. L.; Lu, X. Y.; Deng, S. G. Adsorption of Ethane, Ethylene, Propane, and Propylene on a Magnesium-Based Metal-Organic Framework Langmuir 2011, 27, 13554
16. Miltenburg, A. V.; Zhu, W.; Kapteijn, F.; Moulijn, J. A. Adsorptive Separation of Light Olefin/Paraffin Mixtures Chem. Eng. Res. Des. 2006, 84, 350
17. Uchida, S.; Kawamoto, R.; Tagami, H.; Nakagawa, Y.; Mizuno, N. Highly Selective Sorption of Small Unsaturated Hydrocarbons by Nonporous Flexible Framework with Silver Ion J. Am. Chem. Soc. 2008, 130, 12370
18. Ferreira, A. F. P.; Santos, J. C.; Plaza, M. G.; Lamia, N.; Loureiro, J. M.; Rodrigues, A. E. Suitability of Cu-BTC Extrudates for Propane-Propylene Separation by Adsorption Processes Chem. Eng. J. 2011, 167, 1
19. Chng, M. L.; Xiao, Y.; Chung, T. S.; Toriida, M.; Tamai, S. Enhanced Propylene/Propane Separation by Carbonaceous Membrane Derived from Poly(aryl ether ketone)/2,6-bis(4-azidobenzylidene)-4-methyl-cyclohexanone Interpenetrating Network Carbon 2009, 47, 1857
20. Das, M.; Koros, W. J. Performance of 6FDA-6FpDA Polyimide for Propylene/Propane Separations J. Membr. Sci. 2010, 365, 399
21. Xu, L.; Rungta, M.; Koros, W. J. Matrimid Derived Carbon Molecular Sieve Hollow Fiber Membranes for Ethylene/Ethane Separation J. Membr. Sci. 2011, 380, 138
22. Nymeijer, K.; Visser, T.; Assen, R.; Wessling, M. Olefin-Selective Membranes in Gas-Liquid Membrane Contactors for Olefin/Paraffin Separation Ind. Eng. Chem. Res. 2004, 43, 720
23. Azhin, M.; Kaghazchi, T.; Rahmani, M. A Review on Olefin/Paraffin Separation Using Reversible Chemical Complexation Technology J. Ind. Eng. Chem. 2008, 14, 622
24. Bessarabov, D. G.; Theron, J. P.; Sanderson, R. D.; Schwarz, H.-H.; Schossig-Tiedemann, M.; Paul, D. Separation of 1-Hexene/ n -Hexane Mixtures Using a Hybrid Membrane/Extraction System Sep. Purif. Technol. 1999, 16, 167
25. Yang, Q. W.; Xing, H. B.; Cao, Y. F.; Su, B. G.; Yang, Y. W.; Ren, Q. L. Selective Separation of Tocopherol Homologues by Liquid-Liquid Extraction Using Ionic Liquids Ind. Eng. Chem. Res. 2009, 48, 6417
26. Palgunadi, J.; Kim, H. S.; Lee, J. M.; Jung, S. Ionic Liquids for Acetylene and Ethylene Separation: Material Selection and Solubility Investigation Chem. Eng. Process. 2010, 49, 192
27. Bara, J. E.; Gabriel, C. J.; Carlisle, T. K.; Camper, D. E.; Finotello, A.; Gin, D. L.; Noble, R. D. Gas Separations in Fluoroalkyl-functionalized Room-Temperature Ionic Liquids Using Supported Liquid Membranes Chem. Eng. J. 2009, 147, 43
28. Matsumoto, M.; Mochiduki, K.; Fukunishi, K.; Kondo, K. Extraction of Organic Acids Using Imidazolium-Based Ionic Liquids and Their Toxicity to Lactobacillus rhamnosus Sep. Purif. Technol. 2004, 40, 97
29. Zhu, J. Q.; Chen, J.; Li, C. Y.; Fei, W. Y. Centrifugal Extraction for Separation of Ethylbenzene and Octane Using 1-Butyl-3-methylimidazolium Hexafluorophosphate Ionic Liquid as Extractant Sep. Purif. Technol. 2007, 56, 237
30. Mokrushin, V.; Assenbaum, D.; Paape, N.; Gerhard, D.; Mokrushina, L.; Wasserscheid, P.; Arlt, W.; Kistenmacher, H.; Neuendorf, S.; Göke, V. Ionic Liquids for Propene-Propane Separation Chem. Eng. Technol. 2010, 33, 63
31. Lei, Z. G.; Wolf, G. A.; Wasserscheid, P. Separation of 1-Hexene and n -Hexane with Ionic Liquids Fluid Phase Equilib. 2006, 241, 290-299
32. Lei, Z. G.; Arlt, W. G.; Wasserscheid, P. Selection of Entrainers in the 1-Hexene/ n -hexane System with a Limited Solubility Fluid Phase Equilib. 2007, 260, 29
33. Domańska, U.; Laskowska, M. Measurements of Activity Coefficients at Infinite Dilution of Aliphatic and Aromatic Hydrocarbons, Alcohols, Thiophene, Tetrahydrofuran, MTBE, and Water in Ionic Liquid [BMIM][SCN] Using GLC J. Chem. Thermodyn. 2009, 41, 645
34. Blahut, A.; Sobota, M.; Dohnal, V.; Vrbka, P. Activity Coefficients at Infinite Dilution of Organic Solutes in the Ionic Liquid 1-Ethyl-3- methylimidazolium Methanesulfonate Fluid Phase Equilib. 2010, 299, 198
35. Krummen, M.; Wasserscheid, P.; Gmehling, J. Measurement of Activity Coefficients at Infinite Dilution in Ionic Liquids Using the Dilutor Technique J. Chem. Eng. Data 2002, 47, 1411
36. Ortiz, A.; Ruiz, A.; Gorri, D.; Ortiz, I. Room Temperature Ionic Liquid with Silver Salt as Efficient Reaction Media for Propylene/Propane Separation: Absorption Equilibrium Sep. Purif. Technol. 2008, 63, 311
37. Ortiz, A.; Galán, L. M.; Gorri, D.; Haan, A. B.; Ortiz, I. Reactive Ionic Liquid Media for the Separation of Propylene/Propane Gaseous Mixtures Ind. Eng. Chem. Res. 2010, 49, 7227
38. Gorri, D.; Ruiz, A.; Ortiz, A.; Ortiz, I. The Use of Ionic Liquids as Efficient Extraction Medium in the Reactive Separation of Cycloolefins from Cyclohexane Chem. Eng. J. 2009, 254, 241
39. Galán, L. M.; Meindersma, G. W.; Haan, A. B. Potential of Silver-Based Room-Temperature Ionic Liquids for Ethylene/Ethane Separation Ind. Eng. Chem. Res. 2009, 48, 10650
40. 3 by a Semi-continuous Process Chem. Eng. J. 2010, 158, 384
41. Ohno, H.; Fukumoto, K. Amino Acid Ionic Liquids J. Acc. Chem. Res. 2007, 40, 1122
42. Harlow, K. J.; Hill, A. F.; Welton, T. Convenient and General Synthesis of Symmetrical N, N -disubstituted Imidazolium Halides J. Synth. 1996, 6, 697
43. Mutelet, F.; Jaubert, J. N.; Rogalski, M.; Harmand, J.; Sindt, M.; Mieloszynski, J. L. Activity Coefficients at Infinite Dilution of Organic Compounds in 1-(Meth)acryloyloxyalkyl-3-methylimidazolium Bromide Using Inverse Gas Chromatography J. Phys. Chem. B 2008, 112, 3773
44. Chen, S. C.; Hsueh, H. H.; Chen, C. H.; Lee, C. S.; Liu, F. C.; Lin, I. J. B.; Lee, G. H.; Peng, S. M. Synthesis and Structures of Polymeric Silver and Mercury Complexes with Amido-functionalized N -heterocyclic Carbenes Inorg. Chim. Acta 2009, 362, 3343
45. Hardacre, C.; Holbrey, J. D.; Katdare, S. P.; Seddon, K. R. Alternating Copolymerization of Styrene and Carbon Monoxide in Ionic Liquids Green Chem. 2002, 4, 143
46. Mutelet, F.; Revelli, A.-L.; Jaubert, J.-N.; Sprunger, L. M.; Acree, W. E., Jr.; Baker, G. A. Partition Coefficients of Organic Compounds in New Imidazolium and Tetralkylammonium Based Ionic Liquids Using Inverse Gas Chromatography J. Chem. Eng. Data 2010, 55, 234
47. Kato, R.; Gmehling, J. Systems with Ionic Liquids: Measurement of VLE and γ Data and Prediction of Their Thermodynamic Behavior Using Original UNIFAC, mod. UNIFAC(Do) and COSMO-RS(Ol) J. Chem. Thermodyn. 2005, 37, 603
48. Olivier, E.; Letcher, T. M.; Naidoo, P.; Ramjugernath, D. Activity Coefficients at Infinite Dilution of Organic Solutes in the Ionic Liquid 1-Ethyl-3-methylimidazolium Trifluoromethanesulfonate Using Gas-liquid Chromatography at T = 313.15, 323.15, and 333.15 K J. Chem. Thermodyn. 2010, 42, 78
49. Lee, J. M. Solvent Properties of Piperidinium Ionic Liquids Chem. Eng. J. 2011, 172, 1066
50. Marciniak, A. Influence of Cation and Anion Structure of the Ionic Liquid on Extraction Processes Based on Activity Coefficients at Infinite Dilution. A Review Fluid Phase Equilib. 2010, 284, 213
51. Prausnitz, J. M.; Anderson, R. Thermodynamics of Solvent Selectivity in Extractive Distillation of Hydrocarbons AIChE J. 1961, 7, 96
52. Hartmann, M.; Wetmore, S. D.; Radom, L. C-H···X Hydrogen Bonds of Acetylene, Ethylene, and Ethane with First- and Second-Row Hydrides J. Phys. Chem. A 2001, 105, 4470
53. Wentink, A. E.; Kockmann, D.; Kuipers, N. J. M.; de Haan, A. B.; Scholtz, J.; Mulder, H. Effect of C6-olefin Isomers on ? -Complexation for Purification of 1-Hexene by Reactive Extractive Distillation Sep. Purif. Technol. 2005, 43, 149
54. Sunderrajan, S.; Freeman, B. D.; Hall, C. K. Fourier Transform Infrared Spectroscopic Characterization of Olefin Complexation by Silver Salts in Solution Ind. Eng. Chem. Res. 1999, 38, 4051
55. Hu, X.; Yu, J.; Liu, H. Liquid-Liquid Equilibria of the System 1-(2-Hydroxyethyl)-3-methyl-imidozolium Tetrafluoroborate or 1-(2-Hydroxyethyl)-2,3-dimethylimidozolium Tetrafluoroborate + Water + 1-Butanol at 293.15 K J. Chem. Eng. Data 2006, 51, 691
56. Meindersma, G. W.; Podt, A.; de Haan, A. B. Ternary Liquid-Liquid Equilibria for Mixtures of an Aromatic + an Aliphatic Hydrocarbon + 4-Methyl-N-butylpyridinium Tetrafluoroborate J. Chem. Eng. Data 2006, 51, 1814