شیمى کاربردى روز

شیمى کاربردى روز

سنتز و شناسایی سورفکتانت نوین غیر یونی گلوکزآمینی و مقایسه آن با سورفکتانت متیل‌گلوکامین

نوع مقاله : مقاله علمی پژوهشی

نویسندگان
1 گروه شیمی، واحد اراک، دانشگاه آزاد اسلامی، اراک، ایران
2 گروه شیمی آلی، مرکز تحقیقات شیمی و مهندسی شیمی ایران، ایران، تهران، 14335-186
چکیده
در این مطالعه، سنتز و ارزیابی خواص سطحی و ترمودینامیکی یک سورفکتانت نوین غیر یونی مبتنی بر گلوکزامین (2-(دودسیلوکسی)-N-((2R,3R,4R,5S,6R)-2,4,5-تری هیدروکسی -6-(هیدروکسی متیل)تتراهیدرو-2H-پیران-3-ایل)استامید (NGAS) انجام شد و نتایج با سورفکتانت N-متیل گلوکامین مقایسه شد. NGAS از طریق واکنش آسان و مستقیم گلوکزامین با 2-(دودسیلوکسی)استیل کلرید در حضور تری اتیل آمین سنتز شد. کشش سطحی NGAS با روش تانسیومتری تعیین شد. خواص سطحی شامل غلظت بحرانی میسل (CMC)، راندمان جذب (pC20)، مازاد سطح (Γmax) و سطح اشغال شده توسط هر یک از مولکول های سورفکتانت (Amin) در دمای 15/۲۹۸ کلوین در آب دیونیزه بررسی شد و کشش سطحی آب با استفاده از سورفکتانت در سطح غلظت۳-۱۰×۰۶/۲ مول بر لیتربه حدود 41 میلی نیوتن بر متر کاهش یافت. پارامترهای ترمودینامیکی میسل سازی (ΔG°mic) و جذب سطحی (ΔG°ads) از داده های CMC محاسبه شد. پارامتر تعادل آب دوستی و چربی دوستی (HLB) از معادله گریفین به دست آمد. با توجه به نتایج، میسل‌سازی و جذب سطحی این سورفکتانت یک فرآیندی خود به خودی در محلول آبی است. علاوه بر این، این نتایج نشان می دهد که NGAS می تواند به عنوان یک امولسیفایر در امولسیون های روغن در آب استفاده شود.
کلیدواژه‌ها
موضوعات

عنوان مقاله English

Synthesis and Characterization of a Novel Nonionic Glucosamine-Based Surfactant and its Comparison with N-Methylglucamine Surfactant

نویسندگان English

Syedeh Enciyeh Rastegar Fatemi 1
Hadi Shafiei 1
Mohammad Majid Mojtahedi 2
1 Department of Chemistry, Arak Branch, Islamic Azad University, Arak, Iran
2 Organic Chemistry Department, Chemistry and Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
چکیده English

In this study, the synthesis and evaluation of surface and thermodynamics properties a novel non-ionic glucosamine-based surfactant (2-(dodecyloxy)-N-((2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide (NGAS) is carried out and the comparison of the results with N-methylglucamine surfactant is reported. NGAS was synthesized via the facile and straightforward reaction of glucosamine with 2-(dodecyloxy)acetyl chloride in the presence of triethylamine. The surface tension of NGAS was determined by tensiometric methods. The surface properties including Critical Micelle Concentration (CMC), the efficiency of adsorption (pC20), the surface excess (Γmax) and the area occupied by each of the surfactant molecules (Amin) were investigated at 298.15 K in deionized water. The surface tension of water was reduced to about 41 mN.m-1 by using the surfactant at the concentration level of 2.06×10-3 molL-1. The thermodynamic parameters of micellization (ΔG°mic) and surface adsorption (ΔG°ads) were calculated from CMC data. The hydrophilicity and lipophilicity balance parameter (HLB) were obtained from the Griffin equation. According to the results, micellization and surface adsorption of this surfactant is a spontaneous process in aqueous solution. In addition, these results show that NGAS can be used as an emulsifier in oil-in-water emulsions.

کلیدواژه‌ها English

Non-ionic surfactant
Surface tension
Glucosamine
Emulsifier
Hydrophilicity-lipophilicity balance
[1] Kandasamy, R., Rajasekaran, M., Venkatesan, S. K., & Uddin, M. (2019). New trends in the biomanufacturing of green surfactants: biobased surfactants and biosurfactants. American Chemical Society.
[2] Taheri, E., & Bagheri, A. (2018). Analysis of surface and micellar phases in binary mixture of surfactant and ionic liquid by surface tension measurement. Applied Chemistry Today, 13(48), 167-180.
[3] Abdous, B., Sajjadi, S.M., & Bagheri, A. (2022). Determining the aggregation number of anionic surfactants based on conductivity method: employing QSAR-ANN modelling techniques for predicting the aggregation number of surfactants. Applied Chemistry Today, 17(63), 87-108.
[4] Bagheri, A. (2021). Interfacial. micellization properties of pure surfactants with similar hydrocarbon chain length (C16H33) and different polar head in aqueous medium. Applied Chemistry Today, 15(57), 55-64.
[5] Rajabi, M., Arab, A., & Bagheri, A. (2021). The inhibition effect of CTAB and Triton X-100 surfactants on the corrosion of nickel in alkaline solution. Applied Chemistry Today, 16(59), 63-72.
[6] Rosen, M. J.; Kunjappu, J. T. (2012). Surfactants and interfacial phenomena, 4th Ed., John Wiley & Sons, Inc., New York USA.
[7] Maleki, S., Mennati, A., & Salehi Sadaghiani, A. R. (2011). Determine and compare the cmc point of SDS, Triton x-100 and CTAB surfactants using conductometery method. Applied Chemistry Today, 6(20), 47-52.
[8] Bagheri, A., & Rafati, A. A. (2014). Thermodynamic investigation of inclusion complex formation between cetyltrimethyl ammonium bromide (CTAB) and β-cyclodextrin at various temperatures. Journal of Molecular Liquids, 195, 145-149.
[9] Kovensky J., & Grand E. (2016). Recent advances in the synthesis of sugar-based surfactants. RSC Green Chemistry, London UK, p. 159-204.
[10] Bazito, R. C., & El Seoud, O. A. (2002). Sugar-based surfactants: adsorption and micelle formation of sodium methyl 2-acylamido-2-deoxy-6-O-sulfo-D-glucopyranosides. Langmuir, 18(11), 4362-4366.
[11] Teng, Y., Stewart, S. G., Hai, Y. W., Li, X., Banwell, M. G., & Lan, P. (2020). Sucrose fatty acid esters: synthesis, emulsifying capacities, biological activities and structure-property profiles. Critical Reviews in Food Science and Nutrition, 61(19), 3297-3317.
[12] Maugard, T., Remaud-Simeon, M., Petre, D., & Monsan, P. (1997). Lipase-catalysed synthesis of biosurfactants by transacylation of N-methyl-glucamine and fatty-acid methyl esters. Tetrahedron, 53(22), 7629-7634.
[13] Cristobal, C. R. (2008). Sugar-based surfactants: fundamentals and applications. Marcel Dekker: New York.
[14] Holmberg, K. (2003). Novel surfactants: preparation, applications, and biodegradability. 2nd edn. Marcel Dekker: New York.
[15] Plat, T., & Linhardt, R. (2001). Syntheses and applications of sucrose-based esters. Journal of Surfactants and Detergents, 4(4), 415-421.
[16] Satge, C., Granet, R., Verneuil, B., Champavier, Y., & Krausz, P. (2004). Synthesis and properties of new bolaform and macrocyclic galactose-based surfactants obtained by olefin metathesis. Carbohydrate Research, 339(7), 1243-1254.
[17] Hill, K., & Rhode, O. (1999). Sugar-based surfactants for consumer products and technical applications. Lipid – Fett, 101(1), 25-33.
[18] Zhi, L., Li, J., Li, X., Chen, Y., Song, Y.,Yu, J.,& Zhang, Q.(2019). Enhancing water solubility of N-dodecyl-d-gluconamide surfactant using borax. Chemical Physics Letters, 725, 87-91.
[19] Kida, T., Yurugi, K., Masuyama, A., Nakatsuji, Y., Ono, D., & Takeda, T. (1995). Preparation and properties of new surfactants containingd-glucosamine as the building block. Journal of the American Oil Chemists Society, 72(7), 773-780.
[20] Burczyk, B., Wilk, K. A., Sokolowski, A., & Syper, L. (2001). Synthesis and surface properties of N-alkyl-N-methylgluconamides and N-alkyl-N-methyl lactobionamides. Journal of Colloid and Interface Science, 240(2), 552-558.
[21] Laughlin, R. G., Fu, Y.-C., Wireko, F. C., Scheibel, J. J., & Munyon, R. L. (2003). N-Alkanoyl-N-alkyl-1-glycamines in: novel surfactants: preparation, applications, and biodegradability. Marcel Dekker: New York.
[22] Han, F., & Zhang, G. (2004). New family of gemini surfactants with glucosamide-based trisiloxane. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 237(1-3), 79-85.
[23] Han, F., & Zhang, G. Synthesis and characterization of glucosamide-based trisiloxane gemini surfactants. (2004). Journal of Surfactants and Detergents, 7(2), 175-180.
[24] Gaber, Y., Tornvall, U., Orellana-Coca, C., Amin, M. A., & Hatti-Kaul, R. (2010). Enzymatic synthesis of N-alkanoyl-N-methylglucamide surfactants: solvent-free production and environmental assessment. Green Chemistry, 12(10), 1817-1825.
[25] Han, F., Deng, Y., Wang, P., Song, J., Zhou, Y., & Xu, B. (2012). Synthesis and characterization of glucosamide surfactant. Journal of Surfactants and Detergents, 16(2), 155-159.
[26] Zhang, H., Lu, Y.,Wang, Y., Zhang, X., & Wang, T. (2018). D-Glucosamine production from chitosan hydrolyzation over a glucose-derived solid acid catalyst. RSC Advances, 8(10), 5608-5613.
[27] Ji, S., Shen, W., Chen, L., Zhang, Y., Wu, X., Fan, Y., Fu, F., & Chen, G. (2019). Synthesis and properties of sugar-based surfactants alkoxyethyl β-D-glucopyranoside. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 564, 59-68.
[28] Michocka, K., Staszak, K., Gwiazdowska, D., & Wieczorek, D. (2019). Synthesis, surface and antimicrobial activity of new lactose-based surfactants. Molecules, 24(21), 4010-4023.
[29] Haghighi, O. M., Zargar, G., Manshad, A. K., Ali, M., Takassi, M. A., Ali, J. A., & Keshavarz, A. (2020). Effect of environment-friendly non-ionic surfactant on interfacial tension reduction and wettability alteration; implications for enhanced oil recovery. Energies, 13(15), 3988-4004.
[30] Wang, L., & Queneau, Y. (2019). Carbohydrate-based amphiphiles: resource for bio-based surfactants. Green Chemistry and Chemical Engineering; Springer p. 349-383.
[31] Moldes, A. B., Rodríguez-López, L., Rincón-Fontán, M., López-Prieto, A., Vecino, X., & Cruz, J. M. (2021).  Synthetic and bio-derived surfactants versus microbial biosurfactants in the cosmetic industry: an overview. International Journal of Molecular Sciences, 22(5), 2371-2393.
[32] Lubberink, M., Finnigan, W., Schnepel, C., Baldwin, C. R., Turner, N. J., & Flitsch, S. L. (2022). One‐step biocatalytic synthesis of sustainable surfactants by selective amide bond formation. Angewandte Chemie International Edition, 61(30), e202205054.
[33] Rastegar Fatemi, S. E., Shafiei, H., & Mojtahedi, M. M. (2023). Theoretical and experimental investigation of eco-friendly nonionic surfactant based on glucosamine and extraction of relevant constants. Letters in Organic Chemistry, 2(21), 163-191.
[34] Jaeeun, K., Jaemin, L., Hyuk, D.,Hyun, D. S., Kwon, K. S., & Jung, P. S.(2023). Acid addition salts of indene derivative prodrug and its preparation mehods. US2023399298A1.
[35] Hato, M., Shinoda, K., & Miyagawa, T. (1976). Physico-chemical properties of aqueous solutions of Cn−1H2n−1OCH2CO2Na. Bulletin of the Chemical Society of Japan, 49(5), 1257-1259.
[36] Zhu, Y. P., Rosen, M. J., Vinson, P. K., & Morral, S. W. (1999). Surface properties of N-alkanoyl-N-metylglucamines and related materials. Journal of Surfactants and Detergents, 2, 357-362.
[37] Gao, S., Song, Z., Zhu, D., Lan, F., & Jiang, Q. (2018).  Synthesis, surface activities, and aggregation behavior of phenyl-containing carboxybetaine Surfactants. RSC Advances, 8(58), 33256-33268.
[38] Abdel-Raouf, M. E.-S.,Abdul-Raheim, A.-R. M., & Abdel-Azim, A.-A. A. (2011). Surface properties and thermodynamic parameters of some sugar-based ethoxylated aminesurfactants: 1-synthesis, characterization, and demulsification efficiency. Journal of Surfactants and Detergents, 14(1), 113-121.
[39] Sameer, H. K., & Bahar, S. (2015). Adsorption properties for aqueous solution of binary mixture of cocamidopropyl betaine-sodiumdodecyl sulfate surfactants on air-liquid interface. International Journal of Sciences: Basic and Applied Research, 24(3), 50-58.
[40] Wang, L., Zhang, Y., Ding, L.; Liu, J., Zhao, B.; Deng, Q., & Yan, T. (2015). Synthesis and physiochemical properties of novel gemini surfactants with phenyl-1,4-bis(carbamoylmethyl) Spacer. RSC Advances, 5(91), 74764-74773.
[41] Vafakish, B., & Wilson, L. D. (2021). A review on recent progress of glycan-based surfactant micelles as nanoreactor systems for chemical synthesis applications. Polysaccharides, 2(1), 168-186.
[42] Shah, S. K., & Bhattarai, A. (2020). Interfacial and micellization behavior of cetyltrimethylammonium bromide (CTAB) in water and methanol-water mixture at 298.15 to 323.15 K. Journal of Chemistry, 2020, 1-13.
[43] Rokhati, N., Kusworo, T. D., Prasetyaningrum, A., Hamada, N. A., Utomo, D. P., & Riyanto, T. (2022). Effect of surfactant HLB value on enzymatic hydrolysis of chitosan. Chemical Engineering, 6(1), 17-28.
[44] Griffin, W. C. (1954). Calculation of HLB values of non-ionic surfactants. Journal of the Society of Cosmetic Chemists, 5(4), 249-256.