Formation and Solubilization Property of Water-in-Oil Microemulsions of Alkyl Glucosides

Hidetaka Noritomi, Yuki Ishida, Tomokazu Yamada, Hiroaki Saito, Satoru Kato

Department of Applied Chemistry, Tokyo Metropolitan University, Tokyo, Japan.
GUN EI Chemical Industry CO., LTD., Takasaki-shi, Japan.

DOI: 10.4236/anp.2013.24050                

Abstract

The dependence of solubilization properties on the alkyl chain length of alkyl glucosides (AG) in AG/isooctane/ n-butanol/water system was investigated. The stable Winsor II system consisting of a water-in-oil (w/o) microemulsion phase and an aqueous phase was formed in AG/isooctane/n-butanol/water system. The apparent critical micelle concentration of AG reverse micelles in organic phases was markedly dependent upon the alkyl chain length of AG. The limiting amount of solubilized water increased with an increase in the alkyl chain length of AG. The solubilization capacity of methyl orange (MO) was superior to that of methylene blue (MB), and the solubilization capacities of MO and MB tended to increase with increasing the alkyl chain length of AG. Reverse micelles of dodecyl glucoside (AG12) exhibited the significant solubilization capacities of cytochrome c and lysozyme, while ribonuclease A was not solubilized by AG12 reverse micelles.

Keywords

Microemulsion; Reverse Micelle; Winsor II; Alkyl Glucoside; Solubilization; Organic Dye; Protein

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	P. Kumar and K. L. Mittal, “Handbook of Microemulsion Science and Technology,” CRC Press, New York, 1999.
[2]	K. Tonova and Z. Lazarova, “Reversed Micelle Solvents as Tools of Enzyme Purification and Enzyme-Catalyzed Conversion,” Biotechnology Advances, Vol. 26, No. 6, 2008, pp. 516-532. http://dx.doi.org/10.1016/j.biotechadv.2008.06.002
[3]	P. Barnickel and A. Wokaun, “Synthesis of Metal Colloids in Inverse Microemulsions,” Molecular Physics, Vol. 69, No. 1, 1990, pp. 1-9. http://dx.doi.org/10.1080/00268979000100011
[4]	A. Taleb, C. Petit and M. P. Pileni, “Synthesis of Highly Monodisperse Silver Nanoparticles from AOT Reverse Micelles: A Way to 2D and 3D Self-Organization,” Chemistry of Materials, Vol. 9, No. 4, 1997, pp. 950-959. http://dx.doi.org/10.1021/cm960513y
[5]	R. P. Bagwe and K. C. Khilar, “Effects of Intermicellar Exchange Rate on the Formation of Silver Nanoparticles in Reverse Microemulsions of AOT,” Langmuir, Vol. 16, No. 3, 2000, pp. 905-910. http://dx.doi.org/10.1021/la980248q
[6]	W. Zhang, X. Qiao, J. Chen and H. Wang, “Preparation of Silver Nanoparticles in Water-in-Oil AOT Reverse Micelles,” Journal of Colloid and Interface Science, Vol. 302, No. 1, 2006, pp. 370-373. http://dx.doi.org/10.1016/j.jcis.2006.06.035
[7]	Y. Okumura, “Organic Solvents and Surfactants for Toxicity Test Using Aquatic Organisms and Their Acceptable Concentrations,” Bulletin of the National Research Institute of Fisheries Science, Vol. 11, No. 11, 1998, pp. 113-134.
[8]	P. D. Abel, “Toxicity of Synthetic Detergents to Fish and Aquatic Invertebrates,” Journal of Fish Biology, Vol. 6, No. 3, 1974, pp. 279-298. http://dx.doi.org/10.1111/j.1095-8649.1974.tb04545.x
[9]	H. Noritomi, S. Ito, N. Kojima, S. Kato and K. Nagahama, “Forward and Backward Extractions of Cytochrome c Using Reverse Micellar System of Sucrose Fatty Acid Ester,” Colloid and Polymer Science, Vol. 284, No. 6, 2006, pp. 604-610. http://dx.doi.org/10.1007/s00396-005-1398-y
[10]	H. Noritomi, H. Kowata, N. Kojima, S. Kato and K. Nagahama, “Application of Sucrose Fatty Acid Ester to Reverse Micellar Extraction of Lysozyme,” Colloid and Polymer Science, Vol. 284, No. 6, 2006, pp. 677-682. http://dx.doi.org/10.1007/s00396-005-1419-x
[11]	H. Noritomi, N. Kojima, S. Kato and K. Nagahama, “How Can Temperature Affect Reverse Micellar Extraction Using Sucrose Fatty Acid Ester?” Colloid and Polymer Science, Vol. 284, No. 6, 2006, pp. 683-687. http://dx.doi.org/10.1007/s00396-005-1452-9
[12]	H. Noritomi, T. Takasugi and S. Kato, “Refolding of Denatured Lysozyme by Water-in-Oil Microemulsions of Sucrose Fatty Acid Esters,” Biotechnology Letters, Vol. 30, No. 4, 2008, pp. 689-693. http://dx.doi.org/10.1007/s10529-007-9587-z
[13]	H. Noritomi, K. Kagitani, Y. Muratsubaki and S. Kato, “Effect of Composition of Sucrose Fatty Acid Esters on Formation of Palladium Nanoparticles in Reverse Micelles,” Colloid and Polymer Science, Vol. 287, No. 7, 2009, pp. 795-799. http://dx.doi.org/10.1007/s00396-009-2031-2
[14]	H. Noritomi, N. Igari, K. Kagitani, Y. Umezawa, Y. Muratsubaki and S. Kato, “Synthesis and Size Control of Silver Nanoparticles Using Reverse Micelles of Sucrose Fatty Acid Esters,” Colloid and Polymer Science, Vol. 288, No. 8, 2010, pp. 887-891. http://dx.doi.org/10.1007/s00396-010-2214-x
[15]	H. Noritomi, Y. Umezawa, S. Miyagawa and S. Kato, “Preparation of Highly Concentrated Silver Nanoparticles in Reverse Micelles of Sucrose Fatty Acid Esters through Solid-Liquid Extraction Method,” Advances in Chemical Engineering and Science, Vol. 1, No. 4, 2011, pp. 299-304. http://dx.doi.org/10.4236/aces.2011.14041
[16]	H. Noritomi, “Preparation of Highly Concentrated Silver Nanoparticles: Method Using Solid-Liquid Extraction by Reverse Micelles,” LAP LAMBERT Academic Publishing, Saarbrücken, 2012.
[17]	N. Otomo, “Self-Organized Structures of Food Emulsifiers and Their Applications,” Japan Journal of Food Engineering, Vol. 4, No. 1, 2003, pp. 1-9.
[18]	H. Noritomi, S. Tamai, H. Saito and S. Kato, “Extraction of Water Miscible Organic Dyes by Reverse Micelles of Alkyl Glucosides,” Colloid and Polymer Science, Vol. 287, No. 4, 2009, pp. 455-459. http://dx.doi.org/10.1007/s00396-008-1988-6
[19]	H. Noritomi, S. Miyagawa, N. Igari, H. Saito and S. Kato, “Application of Reverse Micelles of Alkyl Glucosides to Synthesis of Silver Nanoparticles,” Advances in Nanoparticles, accepted.
[20]	D. J. Shaw, “Introduction to Colloid and Surface Chemistry,” Butterworth-Heinemann, Oxford, 1992.
[21]	J. N. Israelachvili, “Intermolecular and Surface Forces,” Academic Press Ltd., London, 1985.
[22]	D. J. Mitchell and B. W. Ninham, “Micelles, Vesicles, and Microemulsions,” Journal of the Chemical Society, Faraday Transactions 2, Vol. 77, No. 4, 1981, pp. 601629. http://dx.doi.org/10.1039/f29817700601
[23]	T. Kawai, K. Hamada, N. Shindo and K. Kon-no, “Formation of AOT Reversed Micelles and W/O Microemulsions,” Bulletin of the Chemical Society of Japan, Vol. 65, No. 10, 1992, pp. 2715-2719. http://dx.doi.org/10.1246/bcsj.65.2715
[24]	K. Kon-no, K. Morita, H. Nagasawa and T. Kawai, “Solubilized States of Water and Formation of Reverse Micelles of Homogeneous Dodecyl Polyethylene Glycol Ethers in Cyclohexane,” Journal of Japan Oil Chemist’s Society, Vol. 43, No. 6, 1994, pp. 490-494. http://dx.doi.org/10.5650/jos1956.43.490
[25]	W. F. Waugh, “Protein-Protein Interactions,” Advances in Protein Chemistry, Vol. 9, 1954, pp. 325-437. http://dx.doi.org/10.1016/S0065-3233(08)60210-7
[26]	P. Brochette, C. Petit and M. P. Pileni, “Cytochrome c in Sodium Bis(2-ethylhexyl) Sulfosuccinate Reverse Micelles: Structure and Reactivity,” The Journal of Physical Chemistry, Vol. 92, No. 12, 1988, pp. 3505-3511. http://dx.doi.org/10.1021/j100323a037
[27]	M. Adachi and M. Harada, “Solubilization Mechanism of Cytochrome c in Sodium Bis(2-ethylhexyl) Sulfosuccinate Water/Oil Microemulsion,” The Journal of Physical Chemistry, Vol. 97, No. 14, 1993, pp. 3631-3640. http://dx.doi.org/10.1021/j100116a031