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International Journal of Science and Research (IJSR) ISSN (Online): 2319-7064

Impact Factor (2012): 3.358

Volume 3 Issue 10, October 2014 www.ijsr.net

Licensed Under Creative Commons Attribution CC BY

Synthesis, Characterization and Some Properties of Glycerol Ester Based Non-Ionic Gemini Surfactant

with 1, 2, 7, 8 -Diepoxideoctane as Spacer

*Ishwar T. Gawali1, Ghayas. A. Usmani2

Department of Oil Technology, University Institute of Chemical Technology, North Maharashtra University, Jalgaon-425001, MS, India

Abstract: The synthesis of novel glycerol based non-ionic gemini surfactant was carried out in two stages in the present research work. Initially glycerol was esterified using cotton seed oil at higher temperature followed by reaction with 1, 2, 7, 8-Diepoxideoctane to form the non-ionic gemini surfactant. The new gemini surfactant was characterized by FTIR, 1H-NMR, 13C-NMR spectroscopy and Scanning electron microscopy (SEM). The effect of surfactant on Solubilization of polar and non-polar solute was studied. Contact angles with respect to different solid probes were measured. It can be concluded that the new glycerol-based non-ionic gemini surfactant exhibit generally good solubilizing and wetting behaviour. Keywords: Gemini Surfactant, Characterization, SEM, Solubilization Behaviour, Contact angle. 1. Introduction Surfactants are well known materials generally described as compounds bearing a hydrophobic and hydrophilic group per molecule. They are well known to have numerous uses such as emulsifier, detergents, dispersants and solubilizing agents in the field of cosmetic, textile treatment, industrial and personal cleaning operation. As consequence of hydrophobic effect, the surfactants within the aggregated assemblies are oriented with their polar head groups to the aqueous phase and their hydrophobic tail away from the aqueous phase [1]. Today, new surfactants should be milder, safer, and efficient with a minimal impact on the environment. Environmental awareness and protection have led to the development of more environmentally benign surfactant. There is trend toward replacing petrochemicals by renewable raw materials [2]. Gemini surfactants are newer type of surfactants capable of forming self assemblies having two amphiphiles in molecules, chemically bonded through a spacer group. They are more surface active by order of magnitude than conventional surfactants. They have good water solubility and their ability to form micelles and lowering surface tension characteristics are fairly good as compared to conventional surfactants [1], [3]-[4]. Gemini surfactants have a very high potential for practical applications because of their excellent ability to reduce surface tension of water and low Krafft temperatures. Due to their high molecular weight, skin penetration of gemini surfactant is expected to be low, which is one of the desirable properties of a surfactant to be used in body care products such as soaps, shampoos and cosmetics. However, the main factor that has prevented the use of Gemini surfactants in practical applications is their higher cost [5], [4]. There are several research publications on Gemini surfactants and their potential applications. Aratani et al have synthesized Gemini surfactants from tartaric acid and

studied properties. Anno Wagennaar et al synthesized non-ionic reduced-sugar based bola amphiphiles and gemini surfactants with an α, ω-diamino-(oxa) alkyl spacer. Wenjian Zhang et al synthesized non-ionic gemini surfactant Di-Glycerol 2, 9-Dihexyldecanedioate and studied the physico-chemical and performance properties [1], [6]-[7]. In order to make the use of gemini surfactant cost effective, efficient and economically viable in wide variety of applications, gemini surfactant are expected to be produced via a low cost synthetic mechanism. One of the keys of achieving this is by use of cheap and readily available feed stock and simple reaction mechanism. In the present research work, a new Gemini surfactant using glycerol as hydrophilic head group and cotton seed oil as source of hydrophobic tail has been synthesized. There is industrial important for the use of glycerol due to its low cost factor. Cotton seed oil contains linoleic acid as a major component. Pure linoleic acid is not cost effective and may not be economic for the industrial use. Synthesis involved initial esterification of glycerol to form glycerol ester which was dimerised using 1, 2,7, 8-Diepoxide. The prepared non-ionic Gemini surfactant was thoroughly characterized. Solubilization behaviour and contact angle measurement were studied in detail. 2. Experimental Procedure 2.1 Materials and Equipment Setup The cotton seed oil was procured from local market. Glycerol with purity > 99%, Calcium oxide, 1, 2 7, 8-diepoxideoctane, Methanol, Sodium hydroxide were purchased from Merck. The Infrared (IR) spectrum was obtained by SHIMADZU FTIR 8400 in the 400-4000 cm-1

range using KBr pellets. Proton nuclear magnetic resonance (1H –NMR) and 13C nuclear magnetic resonance (13C–NMR) spectra were obtained with Bruker advanced 400 MHz spectroscopy.

Paper ID: SEP14701 580

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Paper ID: SEP14701 581

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Paper ID: SEP14701 582

International Journal of Science and Research (IJSR) ISSN (Online): 2319-7064

Impact Factor (2012): 3.358

Volume 3 Issue 10, October 2014 www.ijsr.net

Licensed Under Creative Commons Attribution CC BY

Smaller the contact angle better is the wetting power. These value shows that synthesized gemini surfactant has good wetting property for steel and Teflon but not for glass at concentration (1mMol/L).

Table 1: Contact angle measurement of synthesized (1mMol/L) non-ionic Gemini surfactant with respect to

different solid probes.

Sr. No.

Solid probes

Contact angle With respect to

Distilled water

Surfactant sol (1mMol/L )

1 Glass 300 430 2 Steel 750 650 3 Teflon 980 850

4. Conclusion In the present study a new protocol for the synthesis of novel glycerol based non-ionic Gemini surfactant through an environmental friendly process has been described. Non-ionic Gemini surfactants have wide applications because of their high surface activity and low critical micelle concentration. They can be used as emulsifier, dispersants, hydrophobic agent and also act as mild surfactant. Glycerol based nonionic Gemini surfactant was successfully synthesized by using, 1, 2 7, 8-Diepoxideoctane as spacer. The various functional groups present in the surfactant are determined by FTIR spectroscopy. The number of hydrogen atom and carbon atom of synthesized non-ionic gemini surfactant is also assigned by 1H-NMR and 13C-NMR spectroscopy. SEM analysis shows surface morphology of synthesized surfactant in aqueous solution is somewhat spherical in shape. The performance properties like solubilizing behaviour, Contact angle were studied. It can be concluded that the new glycerol-based non-ionic Gemini surfactant exhibit generally good solubilizing and wetting behaviour. Acknowledgment Authors are thankful to the UGC (University Grants Commission of India), for providing the research grant for this research work [Project F.No.41-373/2012 (SR)]. References [1] Wenjian Zhang, Liguo Zhou, and Zhaoyun Ding,

“Synthesis and Performance of Nonionic Gemini Surfactant Di-Glycerol 2, 9-Dihexyldecanedioate”, Journal of Dispersion Science and Technology, vol. 30(9), pp. 1161-1166, 2009.

[2] Brita M. Folmer, Krister Holmeberg, Eva Gottberg klingskog and Karin bergstrom, “Fatty amide ethoxylates: synthesis and self assembly”, Journal of surfactant and detergent, vol. 4, pp. 175-183, 2001.

[3] R. Janardhan, V. Vijayabaskar & B. S. R. Redd, “Synthesis and Characterization of Sulfonated Dimeric Malenised Soya Fatty Acid: A Novel Gemini Surfactant”, Journal Surface Sci. Technol., vol. 28 (3-4), pp. 163-178, 2012.

[4] S. K. Hait and S. P. Moulik, “Gemini surfactants: A distinct class of self-assembling molecules”, Current Science, vol. 82(9), pp. 1101-1111, 2012.

[5] Adewale Adewuy, Andrea Gopfert, Thomas Wolff, “Properties of sodium phosphate-hydroxy ethanolamide gemini surfactant synthesized from the seed oil of Luffa cylindrical”, Central Europian Journal of chemistry, vol. 11(8), pp. 1368-1380, 2013.

[6] Aratani K., Oida T., Shimizu T., and Hayashu Y., “Preparation and Properties of gemini surfactant from tartaric acid”, Communications presented as a las Jornadas del Comite Espanol de la Detergencia, vol. 28, pp. 45-46, 1998.

[7] Anno Wagenaar & Jan B. F. N. Engberts, “Synthesis of nonionic reduced-sugar bola amphiphiles and surfactants with an α,ω-diamin-(oxa) alkyl spacer”, Science Direct Tetrahedron vol. 63, pp. 10622-10629, 2007.

[8] Wim D. Bossaert, Dirk E. De Vos, Wim M. Van Rhijn, Joren Bullen, Piet J. Grobet and Pierre A. Jacob, “Mesoporous Sulfonic Acids as Selective Heterogeneous Catalysts for the synthesis of Monoglyceride”, Journal of Catalysis, vol. 182(1), pp. 156-164,1999.

[9] Thomas M. Schmitt, second edition, “Analysis of surfactant”, BASF Corporation New York, Detergent, vol. 96 (2), 2001.

[10] B. S. Furniss, A. J. Hannaford , P. W. G. Smith, Austin R. Tatchell, “ Vogel’s Text book of practical organic chemistry, “Addision Wesley Longman, Inc. 1989.

[11] L. M. Harwood, C. J. Moody and J. M. Percy, second edition, “Experimental Organic Chemistry, Standard and micro scale”, Wiley Pvt. Ltd , India 2011.

[12] A. S. Mohamed, M. Z. Mohamad & D. A. Ismail, “Alinine-Based Surfactants: Synthesis and Some Surface Properties”, Journal of Surfactant, vol. 7 (4), pp. 415-419, 2004.

[13] Erwin A. Vogler, “Practical Use of Concentration-Dependent Contact Angles as a Measure of Solid-Liquid Adsorption. 1. Theoretical Aspects”, American Chemical Society, vol. 8 (8), pp. 2005-2012, 1992.

[14] E. M. Kandeel “Synthesis and Performance of Glycerol Ester-Based Non-ionic Surfactant”, Der Chemical Sinica, vol. 2 (3), pp. 88-98, 2011

Author Profile

Ishwar T. Gawali was born on 25 Feb. 1986 at Gondi Mohagaon, District Nagpur (M. S.), India. He has got his master degree M. Sc. (Organic Chemistry) in 2010 from Nabira

Mahavidyalaya, katol, R. T. M. University, Nagpur. He has also got master degree M. Tech. (Oleochemical and Surfactant Technology) in 2014 from University Institute of Chemical Technology North Maharashtra University Jalgaon. He is currently working on his Ph. D. degree in the field of surfactant chemistry from University Institute of Chemical Technology, North Maharashtra University, Jalgaon, India.

Ghayas Usmani was born on 12 March, 1964. He has got his bachelor degree B. Tech. (Chem. Engg.),master degree M. Tech (Oil Tech) and Ph.D. (Oil Tech) from HBTI,

Kanpur India He is currently. Working as professor at

Paper ID: SEP14701 583

International Journal of Science and Research (IJSR) ISSN (Online): 2319-7064

Impact Factor (2012): 3.358

Volume 3 Issue 10, October 2014 www.ijsr.net

Licensed Under Creative Commons Attribution CC BY

university Institute of Chemical Technology, North Maharashtra University, Jalgaon, India. He had completed several research project funded by University Grand Comission, New Delhi, India, All India council of technical education, New Delhi, India. He had presented and published his research papers in several seminars and journals.

Paper ID: SEP14701 584