Deterpenation of citrus essential oil by liquid-liquid extraction with 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)amide ionic liquids

Journal of Chemical and Engineering Data

Volumn 56, Issue 4, 2011, Pages 1273-1281

  Lago, Sara ^a   Rodríguez, Héctor ^a   Soto, Ana ^a   Arce, Alberto ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL SIDE CHAINS; ALKYL SUBSTITUENT; ANALOGOUS SYSTEMS; DETERPENATION; EXPERIMENTAL DATA; IMIDAZOLIUM CATION; LIQUID LIQUID EQUILIBRIUM; LIQUID-LIQUID EXTRACTION; NON RANDOM TWO LIQUIDS; SOLUTE DISTRIBUTION; THERMODYNAMIC MODEL; UNIQUAC; UNIVERSAL QUASI CHEMICALS;

ALKYLATION; AMIDES; ESSENTIAL OILS; IONS; OLEFINS; PHASE EQUILIBRIA; SOLVENT EXTRACTION; TERNARY SYSTEMS;

IONIC LIQUIDS;

EID: 79954626524     PISSN: 00219568     EISSN: 15205134     Source Type: Journal    
DOI: 10.1021/je1011339     Document Type: Article

References (43)

1. Verzera, A.; Trozzi, A.; Dugo, G.; Di Bella, G.; Cotroneo, A. Biological lemon and sweet orange essential oil composition Flavour Fragrance J. 2004, 19, 544-548 (Pubitemid 39534829)
2. Arce, A.; Soto, A. In Tree and Forestry Science and Biotechnology; Benkeblia, N.; Tennant, P., Eds.; Global Sciences Books: London, 2009; Special Issue 1, Vol. 2.
3. Owusu-Yaw, J.; Matthews, R. F.; West, P. F. Alcohol Deterpenation of Orange Oil J. Food Sci. 1986, 51, 1180-1182
4. Kondo, M.; Goto, M.; Kodama, A.; Hirose, T. Fractional Extraction by Supercritical Carbon Dioxide for the Deterpenation of Bergamot Oil Ind. Eng. Chem. Res. 2000, 39, 4745-4748 (Pubitemid 32075066)
5. Stuart, G. R.; Lopes, D.; Oliveira, J. V. Deterpenation of Brazilian Orange Peel Oil by Vacuum Distillation J. Am. Oil Chem. Soc. 2001, 78, 1041-1044 (Pubitemid 34043660)
6. Arce, A.; Marchiaro, A.; Rodríguez, O.; Soto, A. Liquid-liquid Equilibria of Limonene + Linalool + Diethylene glycol System at Different Temperatures Chem. Eng. J. 2002, 89, 223-227 (Pubitemid 35372005)
7. Gramajo de Oz, M. B.; Cases, A. M.; Sólimo, H. N. (Liquid + liquid) equilibria of (water + linalool + limonene) ternary system at T = (298.15, 308.15 and 318.15) K J. Chem. Thermodyn. 2008, 40, 1575-1579
8. Brose, D. J.; Chidlaw, M. B.; Friesen, D. T.; LaChapelle, E. D.; van Eikeren, P. Fractionation of Citrus Oils Using a Membrane-Based Extraction Process Biotechnol. Prog. 1995, 11, 214-220
9. Diaz, S.; Espinosa, S.; Brignole, E. A. Citrus peel oil deterpenation with supercritical fluids: Optimal process and solvent cycle design J. Supercrit. Fluids 2005, 35, 49-61 (Pubitemid 40902608)
10. Plechkova, N. V.; Seddon, K. R. Applications of Ionic Liquids in the Chemical Industry Chem. Soc. Rev. 2008, 1, 123-150
11. Stark, A.; Seddon, K. R. Ionic Liquids. In Kirk-Othmer Encyclopedia of Chemical Technology, 5 th ed.; Wiley-VCH: New York, 2007; Vol. 26.
12. Werner, S.; Haumann, M.; Wasserscheid, P. Ionic Liquids in Chemical Engineering Annu. Rev. Chem. Biomol. Eng. 2010, 1, 203-230
13. Arce, A.; Marchiaro, A.; Rodríguez, O.; Soto, A. Essential Oil Terpenless by Extraction Using Organic Solvents or Ionic Liquids AIChE J. 2006, 52, 2089-2097 (Pubitemid 43837610)
14. Arce, A.; Pobudkowska, A.; Rodríguez, O.; Soto, A. Citrus essential oil terpenless by extraction using 1-ethyl-3-methylimidazolium ethylsulfate ionic liquid: Effect of the temperature Chem. Eng. J. 2007, 133, 213-218 (Pubitemid 46935545)
15. Francisco, M.; Lago, S.; Soto, A.; Arce, A. Essential oil deterpenation by solvent extraction using 1-ethyl-3-methylimidazolium 2-(2-methoxyethoxy) ethylsulfate ionic liquid Fluid Phase Equilib. 2010, 296, 149-153
16. Holbrey, J. D.; Rogers, R. D. In Ionic Liquids in Synthesis; Wasserscheid, P.; Welton, T., Eds.; 2 nd ed.; Wiley-VCH: Weinheim, 2008; Vol. 1.
17. Mantz, R. A.; Trulove, P. C. In Ionic Liquids in Synthesis; Wasserscheid, P.; Welton, T., Eds.; 2 nd ed.; Wiley-VCH: Weinheim, 2008; Vol. 1.
18. Arce, A.; Earle, M. J.; Rodríguez, H.; Seddon, K. R. Separation of Benzene and Hexane by Solvent Extraction with 1-Alkyl-3-methylimidazolium Bis{(trifluoromethyl)sulfonyl}amide Ionic Liquids: Effect of the Alkyl-Substituent Length J. Phys. Chem. B 2007, 111, 4732-4736 (Pubitemid 46826378)
19. Renon, H.; Prausnitz, J. M. Local Compositions in Thermodynamic Excess Functions for Liquid Mixtures AIChE J. 1968, 14, 135-144
20. Abrams, D. S.; Prausnitz, J. M. Statistical Thermodynamics of Liquid Mixtures: a New Expression for the Excess Gibbs Energy of Partly or Completely Miscible Systems AIChE J. 1975, 21, 116-128
21. Bonhôte, P.; Dias, A.-P.; Armand, M.; Papageorgiou, N.; Kalyanasundaram, K.; Grätzel, M. Hydrophobic, Highly Conductive Ambient-Temperature Molten Salts. Inorg. Chem. 1996, 35, 1168 - 1178 [Erratum: Inorg. Chem. 1998, 37, 166].
22. Seddon, K. R.; Stark, A.; Torres, M. J. Influence of chloride, water, and organic solvents on the physical properties of ionic liquids Pure Appl. Chem. 2000, 72, 2275-2287
23. Riddick, J. A.; Bunger, W. B.; Sakano, T. K. Organic Solvents-Physical Properties and Methods of Purification, 4 th ed.; Wiley: New York, 1986.
24. Comelli, F.; Ottani, S. Densities, Viscosities, and Refractive Indices of Binary Mixtures Containing n -Hexane + Components of Pine Resins and Essential Oils at 298.15 K J. Chem. Eng. Data 2002, 47, 93-97 (Pubitemid 35410087)
25. Francesconi, R.; Castellari, C. Densities, Viscosities, Refractive Indices, and Excess Molar Enthalpies of Methyl tert- Butyl Ether + Components of Pine Resins and Essential Oils at 298.15 K J. Chem. Eng. Data 2001, 46, 1520-1525 (Pubitemid 33073924)
26. 2] in Dependence on Temperature at Atmospheric Pressure J. Phys. Chem. B 2008, 112, 12420-12430
27. Muhammad, A.; Mutalib, M. I. A.; Wilfred, C. D.; Murugesan, T.; Shafeeq, A. Thermophysical properties of 1-hexyl-3-methyl imidazolium based ionic liquids with tetrafluoroborate, hexafluorophosphate and bis(trifluoromethylsulfonyl) imide anions J. Chem. Thermodyn. 2008, 40, 1433-1438
28. Shimizu, K.; Tariq, M.; Costa Gomes, M. F.; Rebelo, L. P. N.; Canongia Lopes, J. N. Assessing the Dispersive and Electrostatic Components of the Cohesive Energy of Ionic Liquids Using Molecular Dynamics Simulations and Molar Refraction Data J. Phys. Chem. B 2010, 114, 5831-5834
29. Arce, A.; Rodríguez, H.; Soto, A. Effect of anion fluorination in 1-ethyl-3-methylimidazolium as solvent for the liquid extraction of ethanol from ethyl tert-butyl ether Fluid Phase Equilib. 2006, 242, 164-168
30. Arce, A.; Earle, M. J.; Rodríguez, H.; Seddon, K. R. Separation of aromatic hydrocarbons from alkanes using the ionic liquid 1-ethyl-3- methylimidazolium bis{(trifluoromethyl) sulfonyl}amide Green Chem. 2007, 9, 70-74
31. Domańska, U.; Zołek-Tryznowska, Z.; Pobudkowska, A. Separation of Hexane/Ethanol Mixtures. LLE of Ternary Systems (Ionic Liquid or Hyperbranched Polymer + Ethanol + Hexane) at T = 298.15 K J. Chem. Eng. Data 2009, 54, 972-976
32. Treybal, R. E. Mass-Transfer Operations, 3 rd ed.; McGraw-Hill: New York, 1981.
33. Muñoz, M. A.; Galán, M.; Carmona, C.; Balón, M. Hydrogen-bonding interactions between 1-methylindole and alcohols Chem. Phys. Lett. 2005, 401, 109-114
34. Novák, J. P.; Matous, J.; Pick, J. Liquid-liquid equilibria; Elsevier: Amsterdam, 1987.
35. Wang, Y. A.; Voth, G. A. Unique Spatial Heterogeneity in Ionic Liquids J. Am. Chem. Soc. 2005, 127, 12192-12193 (Pubitemid 41279221)
36. Canongia Lopes, J. N. A.; Pádua, A. A. H. Nanostructural Organization in Ionic Liquids J. Phys. Chem. B 2006, 110, 3330-3335
37. Canongia Lopes, J. N.; Costa Gomes, M. F.; Pádua, A. A. H. Nonpolar, Polar, and Associating Solutes in Ionic Liquids J. Phys. Chem. B 2006, 110, 16816-16818 (Pubitemid 44412302)
38. Hyun, B. R.; Dzyuba, S. V.; Bartsch, R. A.; Quitevis, E. L. Intermolecular Dynamics of Room-Temperature Ionic Liquids: Femtosecond Optical Kerr Effect Measurements on 1-Alkyl-3-methylimidazolium Bis((trifluoromethyl) sulfonyl)imides J. Phys. Chem. A 2002, 106, 7579-7585 (Pubitemid 35382558)
39. http://www.merck-chemicals.com/spain/1-etil-3-metil-imidazol-metano- sulfonato/MDA-CHEM-490286/p-KQeb.s1L.8AAAAEWqeEfVhTl (accessed Mar 1, 2011).
40. Bondi, A. Physical Properties of Molecular Crystals, Liquids and Glasses; Wiley: New York, 1968.
41. ∞ data and prediction of their thermodynamic behavior using original UNIFAC, mod. UNIFAC(Do) and COSMO-RS(Ol) J. Chem. Thermodyn. 2005, 37, 603-619
42. Lei, Z.; Zhang, J.; Li, Q.; Chen, B. UNIFAC model for ionic liquids Ind. Eng. Chem. Res. 2009, 48, 2697-2704
43. Sørensen, J. M.; Arlt, W. Liquid-Liquid Equilibrium Data Collection; DECHEMA Chemistry Data Series: Frankfurt, 1980.