Lipidic protic ionic liquid crystals

ACS Sustainable Chemistry and Engineering

Volumn 2, Issue 4, 2014, Pages 672-682

  Maximo, Guilherme J ^a   Santos, Ricardo J B N ^b   Lopes Da Silva, José A ^c   Costa, Mariana C ^a   Meirelles, Antonio J A ^a   Coutinho, João A P ^b  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b UNIVERSITY OF AVEIRO   (Portugal)

^c UNIVERSITY OF AVEIRO   (Portugal)

Author keywords

Ethanolamine; Fatty acid; Ionic liquid; Liquid crystal; Rheology; Solid liquid equilibrium

Indexed keywords

CARBOXYLATION; ELASTICITY; ETHANOLAMINES; FATTY ACIDS; INDUSTRIAL APPLICATIONS; LIQUID CRYSTALS; MIXTURES; RHEOLOGY; SYNTHESIS (CHEMICAL);

ETHANOLAMINE; HYDROPHOBIC/HYDROPHILIC; LIQUID CRYSTAL MESOPHASE; LYOTROPIC MESOPHASES; NON-NEWTONIAN BEHAVIORS; PROTIC IONIC LIQUIDS; SELF-ASSEMBLING ABILITY; SOLID LIQUID EQUILIBRIUM;

IONIC LIQUIDS;

EID: 84898008608     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc400365h     Document Type: Article

References (60)

1. Brennecke, J. F.; Maginn, E. J. Ionic liquids: Innovative fluids for chemical processing Aiche J. 2001, 47 (11) 2384-2389
2. Plechkova, N. V.; Seddon, K. R. Applications of ionic liquids in the chemical industry Chem. Soc. Rev. 2008, 37 (1) 123-150
3. Rogers, R. D.; Seddon, K. R. Ionic liquids-Solvents of the future? Science 2003, 302 (5646) 792-793
4. Greaves, T. L.; Weerawardena, A.; Krodkiewska, I.; Drummond, C. J. Protic ionic liquids: Physicochemical properties and behavior as amphiphile self-assembly solvents J. Phys. Chem. B 2008, 112 (3) 896-905
5. Greaves, T. L.; Weerawardena, A.; Fong, C.; Krodkiewska, I.; Drummond, C. J. Protic ionic liquids: Solvents with tunable phase behavior and physicochemical properties J. Phys. Chem. B 2006, 110 (45) 22479-22487
6. Belieres, J. P.; Angell, C. A. Protic ionic liquids: Preparation, characterization, and proton free energy level representation J. Phys. Chem. B 2007, 111 (18) 4926-4937
7. Ventura, S. P. M.; Gurbisz, M.; Ghavre, M.; Ferreira, F. M. M.; Gonçalves, F.; Beadham, I.; Quilty, B.; Coutinho, J. A. P.; Gathergood, N. Imidazolium and pyridinium ionic liquids from mandelic acid derivatives: Synthesis and bacteria and algae toxicity evaluation ACS Sustainable Chem. Eng. 2013, 1 (4) 393-402
8. Handy, S. T. Greener solvents: Room temperature ionic liquids from biorenewable sources Chem.-Eur. J. 2003, 9 (13) 2938-2944
9. Hou, X.-D.; Li, N.; Zong, M.-H. Facile and simple pretreatment of sugar cane bagasse without size reduction using renewable ionic liquids-water mixtures ACS Sustainable Chem. Eng. 2013, 1 (5) 519-526
10. FAO Agricultural Outlook, 2013. FAO OECD. http://www.fao.org.
11. Chu, Z.; Feng, Y. Vegetable-derived long-chain surfactants synthesized via a "green" route ACS Sustainable Chem. Eng. 2012, 1 (1) 75-79
12. Alvarez, V. H.; Mattedi, S.; Martin-Pastor, M.; Aznar, M.; Iglesias, M. Synthesis and thermophysical properties of two new protic long-chain ionic liquids with the oleate anion Fluid Phase Equilib. 2010, 299 (1) 42-50
13. Reinish, M. D. Soaps from fatty acids J. Am. Oil Chem. Soc. 1952, 29 (11) 506-510
14. Maag, H. Fatty-acid derivatives: Important surfactants for household, cosmetic and industrial purposes J. Am. Oil Chem. Soc. 1984, 61 (2) 259-267
15. de Souza, R. L.; de Faria, E. L. P.; Figueiredo, R. T.; Freitas, L.; Iglesias, M.; Mattedi, S.; Zanin, G. M.; dos Santos, O. A. A.; Coutinho, J. A. P.; Lima, á. S.; Soares, C. M. F. Protic ionic liquid as additive on lipase immobilization using silica sol-gel Enzyme Microb. Technol. 2013, 52 (3) 141-150
16. Trusler, R. B. Ethanolamine soaps Ind. Eng. Chem. 1929, 21, 685-687
17. Zhu, S.; Heppenstall-Butler, M.; Butler, M. F.; Pudney, P. D. A.; Ferdinando, D.; Mutch, K. J. Acid soap and phase behavior of stearic acid and triethanolamine stearate J. Phys. Chem. B 2005, 109 (23) 11753-11761
18. Zhu, S.; Pudney, P. D. A.; Heppenstall-Butler, M.; Butler, M. F.; Ferdinando, D.; Kirkland, M. Interaction of the acid soap of triethanolamine stearate and stearic acid with water J. Phys. Chem. B 2007, 111 (5) 1016-1024
19. Pudney, P. D. A.; Mutch, K. J.; Zhu, S. P. Characterising the phase behaviour of stearic acid and its triethanolamine soap and acid-soap by infrared spectroscopy Phys. Chem. Chem. Phys. 2009, 11 (25) 5010-5018
20. Meyer, N. E. Monoethanolamine oleate: A new chemical for the obliteration of varicose veins Am. J. Surg. 1938, 40 (3) 628-629
21. Yamamoto, K.; Sakaguchi, H.; Anai, H.; Tanaka, T.; Morimoto, K.; Kichikawa, K.; Uchida, H. Sclerotherapy for simple cysts with use of ethanolamine oleate: Preliminary experience Cardiovasc. Inter. Rad. 2005, 28 (6) 751-755
22. Kiripolsky, M. G. Commentary: More on ethanolamine oleate as a vascular sclerosant Dermatol. Surg. 2010, 36 (7) 1153-1154
23. Gomes, C. C.; Gomez, R. S.; do Carmo, M. A.; Castro, W. H.; Gala-Garcia, A.; Mesquita, R. A. Mucosal varicosities: Case report treated with monoethanolamine oleate Med. Oral Patol. Oral Cir. Bucal. 2006, 11 (1) E44-E46
24. Hough, W. L.; Smiglak, M.; Rodriguez, H.; Swatloski, R. P.; Spear, S. K.; Daly, D. T.; Pernak, J.; Grisel, J. E.; Carliss, R. D.; Soutullo, M. D.; Davis, J. J. H.; Rogers, R. D. The third evolution of ionic liquids: Active pharmaceutical ingredients New J. Chem. 2007, 31 (8) 1429-1436
25. Greaves, T. L.; Weerawardena, A.; Fong, C.; Drummond, C. J. Formation of amphiphile self-assembly phases in protic ionic liquids J. Phys. Chem. B 2007, 111 (16) 4082-4088
26. Lawrence, M. J. Surfactant systems: Their use in drug-delivery Chem. Soc. Rev. 1994, 23 (6) 417-424
27. Sagar, G. H.; Arunagirinathan, M. A.; Bellare, J. R. Self-assembled surfactant nano-structures important in drug delivery: A review Indian J. Exp. Biol. 2007, 45 (2) 133-159
28. Muller-Goymann, C. C. Physicochernical characterization of colloidal drug delivery systems such as reverse micelles, vesicles, liquid crystals and nanoparticles for topical administration Eur. J. Pharm. Biopharm. 2004, 58 (2) 343-356
29. Bowlas, C. J.; Bruce, D. W.; Seddon, K. R. Liquid-crystalline ionic liquids Chem. Commun. 1996, 14, 1625-1626
30. Holbrey, J. D.; Seddon, K. R. The phase behaviour of 1-alkyl-3- methylimidazolium tetrafluoroborates; ionic liquids and ionic liquid crystals J. Chem. Soc., Dalton Trans. 1999, 13, 2133-2139
31. Li, X.-W.; Zhang, J.; Dong, B.; Zheng, L.-Q.; Tung, C.-H. Characterization of lyotropic liquid crystals formed in the mixtures of 1-alkyl-3-methylimidazolium bromide/p-xylene/water Colloids Surf., A 2009, 335 (1-3) 80-87
32. Burrell, G. L.; Dunlop, N. F.; Separovic, F. Non-Newtonian viscous shear thinning in ionic liquids Soft Matter 2010, 6 (9) 2080-2086
33. Amann, T.; Dold, C.; Kailer, A. Rheological characterization of ionic liquids and ionic liquid crystals with promising tribological performance Soft Matter 2012, 8 (38) 9840-9846
34. Mukherjee, I.; Manna, K.; Dinda, G.; Ghosh, S.; Moulik, S. P. Shear- and temperature-dependent viscosity behavior of two phosphonium-based ionic liquids and surfactant Triton X-100 and their biocidal activities J. Chem. Eng. Data 2012, 57 (5) 1376-1386
35. Binnemans, K. Ionic liquid crystals Chem. Rev. 2005, 105 (11) 4148-4204
36. Gin, D. L.; Pecinovsky, C. S.; Bara, J. E.; Kerr, R. L. Functional lyotropic liquid crystal materials Struct. Bonding (Berlin) 2008, 128, 181-222
37. Costa, M. C.; Rolemberg, M. P.; Boros, L. A. D.; Krahenbuhl, M. A.; de Oliveira, M. G.; Meirelles, A. J. A. Solid-liquid equilibrium of binary fatty acid mixtures J. Chem. Eng. Data 2007, 52 (1) 30-36
38. Maximo, G. J.; Costa, M. C.; Meirelles, A. J. A. Solid-liquid equilibrium of triolein with fatty alcohols Braz. J. Chem. Eng. 2013, 30 (1) 33-43
39. Carvalho, P. J.; Regueira, T.; Santos, L. M. N. B. F.; Fernandez, J.; Coutinho, J. A. P. Effect of water on the viscosities and densities of 1-butyl-3-methylimidazolium dicyanamide and 1-butyl-3-methylimidazolium tricyanomethane at atmospheric pressure J. Chem. Eng. Data 2010, 55 (2) 645-652
40. Chernik, G. G. Phase-equilibria in phospholipid water-systems Adv. Colloid Interface Sci. 1995, 61, 65-129
41. Greaves, T. L.; Weerawardena, A.; Fong, C.; Drummond, C. J. Many protic ionic liquids mediate hydrocarbon-solvent interactions and promote amphiphile self-assembly Langmuir 2007, 23 (2) 402-404
42. Dierking, I. Textures of Liquid Crystals; Wiley-VCH: Weinheim, 2003.
43. Novales, B.; Navailles, L.; Axelos, M.; Nallet, F.; Douliez, J.-P. Self-assembly of fatty acids and hydroxyl derivative salts Langmuir 2008, 24 (1) 62-68
44. Sagnella, S. M.; Conn, C. E.; Krodkiewska, I.; Moghaddam, M.; Drummond, C. J. Endogenous nonionic saturated monoethanolamide lipids: Solid state, lyotropic liquid crystalline, and solid lipid nanoparticle dispersion behavior J. Phys. Chem. B 2010, 114 (4) 1729-1737
45. Sagnella, S. M.; Conn, C. E.; Krodkiewska, I.; Drummond, C. J. Nonionic diethanolamide amphiphiles with saturated hydrocarbon chains: Neat crystalline and lyotropic liquid crystalline phase behavior J. Colloid Interface Sci. 2012, 385 (1) 87-95
46. Sagnella, S. M.; Conn, C. E.; Krodkiewska, I.; Drummond, C. J. Nonionic diethanolamide amphiphiles with unsaturated C18 hydrocarbon chains: Thermotropic and lyotropic liquid crystalline phase behavior Phys. Chem. Chem. Phys. 2011, 13 (29) 13370-13381
47. Fay, H.; Meeker, S.; Cayer-Barrioz, J.; Mazuyer, D.; Ly, I.; Nallet, F.; Desbat, B.; Douliez, J.-P.; Ponsinet, V.; Mondain-Monval, O. Polymorphism of natural fatty acid liquid crystalline phases Langmuir 2011, 28 (1) 272-282
48. Zheng, M.; Wang, Z.; Liu, F.; Mi, Q.; Wu, J. Study on the microstructure and rheological property of fish oil lyotropic liquid crystal Colloids Surf., A 2011, 385 (1-3) 47-54
49. Reid, R. C.; Prausnitz, J. M.; Pouling, B. E. The Properties of Gases and Liquids; McGraw-Hill: New York, 1987.
50. Laughlin, R. G. The Aqueous Phase Behavior of Surfactants; Academic Press: London, 1994.
51. Chernik, G. G. A differential scanning calorimetry study of a binary-system 0.1. Interpretation of DSC curves for isothermal and nonisothermal phase-transitions in binary-systems J. Colloid Interface Sci. 1991, 141 (2) 400-408
52. Figueira-Gonzalez, M.; Francisco, V.; Garcia-Rio, L.; Marques, E. F.; Parajo, M.; Rodriguez-Dafonte, P. Self-aggregation properties of ionic liquid 1,3-didecyl-2-methylimidazolium chloride in aqueous solution: From spheres to cylinders to bilayers J. Phys. Chem. B 2013, 117 (10) 2926-2937
53. Hyde, S.; Andersson, S.; Larsson, K.; Blum, Z.; Landh, T.; Lidin, S.; Ninham, B. W. The Language of Shape-The Role of Curvature in Condensed Matter: Physics, Chemistry and Biology; Elsevier Science B.V.: Amsterdam, 1997.
54. Kucharski, S. Surface properties and micelle formation of n,n-di-(2-hydroxy-3-alkoxypropyl)ethanolamine and n-(2-hydroxy-3-alkoxypropyl) diethanolamine surfactants J. Colloid Interface Sci. 1978, 64 (2) 300-310
55. Malik, W. U.; Chand, P. Critical micelle concentration of lauric acid-diethanolamine condensate by polarographic and spectrophotometric methods: A comparative study J. Am. Oil Chem. Soc. 1966, 43 (7) 446.
56. Mukherjee, P.; Dash, S.; Patel, S.; Mishra, B. K. Self-organized assemblies of surfactants derived from ethanolamines J. Dispersion Sci. Technol. 2012, 33 (6) 881-886
57. Weiss, R. G. Thermotropic liquid crystals as reaction media for mechanistic investigations1 Tetrahedron 1988, 44 (12) 3413-3475
58. Rao, M. A. Rheology of Fluid and Semisolid Foods; Springer: New York, 2007.
59. Vocadlo, J. J.; MooYoung, M. Rheological properties os some commercially available fats Can. Inst. Food Technol. J. 1969, 2, 137-140
60. Rao, M. A. Rheology of liquid foods: A review J. Texture Stud. 1977, 8 (2) 135-168 de Pessoal de Nível Superior