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Amide-Based Surfactants from Methyl Glucoside as Potential Emulsifiers

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Journal of Surfactants and Detergents

Abstract

A series of amide-linked surfactants from methyl glucoside was synthesized and investigated for their potential use as water-in-oil emulsifiers. The synthetic concept combined a nucleophilic substitution approach with a Staudinger coupling of the intermediate azide. Both straight and Guerbet-type branched fatty acids ranging from C8 to C16 were applied. All surfactants exhibited very high Krafft temperatures, which were related to the amide linkage and exclusively formed the hexagonal H1-phase. The Guerbet C16 surfactant enabled the formation of a stable water-in-oil gel at ambient temperature, which, however, required heating to form the corresponding fluid emulsion.

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References

  1. Knepper TP, Berna JL (2003) Chapter 1 surfactants: properties, production and environmental aspects. Compr Anal Chem 40:1–49

  2. Hepworth P (2006) Non-ionic surfactants. Chem Tech Surfactants 133–152

  3. von Rybinski W (1996) Alkyl glycosides and polyglycosides. Curr Opin Colloid Interface Sci 1:587–597

    Article  Google Scholar 

  4. Luders H (2000) Synthesis of alkyl glucosides and alkyl polyglucosides. Surfactant Sci Ser 91:19–75

    CAS  Google Scholar 

  5. Allen DK, Tao BY (1999) Carbohydrate-alkyl ester derivatives as biosurfactants. J Surf Det 2:383–390

    Article  CAS  Google Scholar 

  6. Hill K, Rhode O (1999) Sugar-based surfactants for consumer products and technical applications. Lipid 101:25–33

    Article  CAS  Google Scholar 

  7. Chang SW, Shaw JF (2009) Biocatalysis for the production of carbohydrate esters. New Biotech 26:109–116

    Article  CAS  Google Scholar 

  8. Gumel AM, Annuar MSM, Heidelberg T, Christi Y (2011) Lipase mediated synthesis of sugar fatty acid esters. Proc Biochem 46:2079–2090

    Article  CAS  Google Scholar 

  9. Albericio F, Chinchilla R, Dodsworth DJ, Najera C (2001) New trends in peptide coupling reagents. Org Prep Proced Int 33:203–263

    Article  CAS  Google Scholar 

  10. Lloyd-Williams P, Albericio F, Giralt E (1993) Convergent solid-phase peptide synthesis. Tetrahedron 49:11065–11133

    Article  CAS  Google Scholar 

  11. Salatov VG (2011) Method for preparing an emulsion, system and apparatus for carrying out said method. PCT Int. Appl. WO 2011016742A2

  12. Bols M (1996) Carbohydrate Building Blocks. Wiley, New York

    Google Scholar 

  13. Fieser M, Fieser LF, Toromanoff E, Hirata Y, Heymann H, Tefft M, Bhattacharya S (1956) Synthetic emulsifying agents. J Am Chem Soc 78:2825–2832

    Article  CAS  Google Scholar 

  14. Maunier V, Boullanger P, Lafont D, Chevalier Y (1997) Synthesis and surface-active properties of amphiphilic 6-aminocarbonyl derivatives of d-glucose. Carbohydr Res 299:49–57

    Article  CAS  Google Scholar 

  15. Hanessian S, Ducharme D, Capmau ML (1978) A one-flask preparation of methyl 6-azido-6-deoxy-α-d-hexopyranosides. Carbohydr Res 63:265–269

    Article  CAS  Google Scholar 

  16. Hanessian S, Ponpipom MM, Lavellee L (1972) Procedures for the direct replacement of primary hydroxyl groups in carbohydrates by halogen. Carbohydr Res 24:45–56

    Article  CAS  Google Scholar 

  17. Blanco JLJ, Fernandez JMG, Gadelle A, Defaya J (1997) A mild one-step selective conversion of primary hydroxyl groups into azides in mono- and oligo-saccharides. Carbohydr Res 303:367–372

    Article  Google Scholar 

  18. Staudinger H, Hauser E (1921) Über neue organische Phosphorverbindungen IV: phosphinimine. Helv Chim Acta 4:861–886

    Article  CAS  Google Scholar 

  19. Gololobov YG, Zhmurova IN, Kasukhin LF (1981) Sixty years of Staudinger reaction. Tetrahedron 37:437–472

    Article  CAS  Google Scholar 

  20. Gololobov YG, Kasukhin LF (1992) Recent advances in the Staudinger reaction. Tetrahedron 48:1353–1406

    Article  CAS  Google Scholar 

  21. Czifrák K, Hadady Z, Docsa T, Gergely P, Schmidt J, Wessjohann L, Somsák L (2006) Synthesis of N-(β-d-glucopyranosyl) monoamides of dicarboxylic acids as potential inhibitors of glycogen phosphorylase. Carbohydr Res 341:947–956

    Article  Google Scholar 

  22. Boullanger P, Maunier V, Lafont D (2000) Synthesis pf amphiphilic glycosyl amides from glycosyl azides without reduction to glycosyl amines. Carbohydr Res 324:97–106

    Article  CAS  Google Scholar 

  23. Daubert BF, Fricke HH, Longenecker HE (1943) Unsaturated synthetic glycerides I: unsymmetrical monooleo-disaturated triglycerides. J Am Chem Soc 65:2142–2144

    Article  CAS  Google Scholar 

  24. Zemplen G, Gerecs A, Hadacsy I (1936) Über die Verseifung acetylierter Kohlenhydrate. Ber Dt Chem Ges 69B:1827–1829

    Article  CAS  Google Scholar 

  25. Rendall K, Tiddy GJT, Trevathan MA (1983) Optical microscopy and nuclear magnetic resonance studies of mesophases formed at compositions between hexagonal and lamellar phases in sodium n-alkanoate + water mixtures and related surfactant systems. J Chem Soc Faraday Trans 1(79):637–649

    Article  Google Scholar 

  26. Laughlin RG (1992) The role of swelling methods in surfactant phase science: past, present and future. Adv Colloid Interface Sci 41:57–79

    Article  CAS  Google Scholar 

  27. Nielson F, Södermann O, Johanson I (1998) Four different C8 alkylglucosides. Anomeric effects and the influence of straight vs. branched hydrocarbon chains. Colloid Interface Sci 203:131–139

    Article  Google Scholar 

  28. Heidelberg T, Chuan R, Chie NC, Anwar SA, Hashim R (eds) (2009) Synthesis and surfactant study on isomeric octyl glucosides. Mal J Sci 28:105–113.

  29. López O, Cócera M, Parra JL, de la Maza A (2001) Influence of the alkyl chain length of alkyl glucosides on their ability to solubilize phosphatidylcholine liposomes. Colloids Surf A 193:221–229

    Article  Google Scholar 

  30. Ariffin MFK, Annuar MSM, Heidelberg T (2013) Surfactant synthesis via lipase esterification of methyl a-D-glucopyranoside with selected aliphatic carboxylic acids. J Surfact Deterg. doi:10.1007/s11743-013-1529-2 (in print)

  31. Brooks NJ, Hamid HAA, Hashim R, Heidelberg T, Seddon JM, Conn CE, Husseini SMM, Zahid NIM, Hussen RSD (2011) Thermotropic and lyotropic liquid crystalline phases of Guerbet branched-chain D-glucosides. Liq Cryst 38:1725–1734

    Article  CAS  Google Scholar 

  32. Israelachvili JN, Mitchel DJ, Ninham BW (1976) Theory of self-assembly of hydrocarbon amphiphiles into micelles and bilayers. J Chem Soc Faraday Trans II 72:1525–1568

    Article  Google Scholar 

  33. Matsumara S, Imai K, Yoshokawa S, Kawada K, Uchibori T (1990) Surface activities, biodegradability and antimicrobial properties of n-alkyl glucosides, mannosides and galactosides. J Am Oil Chem Soc 67:996–1001

    Article  Google Scholar 

  34. Kjellin URM, Claesson PM, Vulfson EN (2001) Studies of N-dodecyllactobionamide, maltose 6′-O-dodecanoate and octyl β-glucoside with surface tension, surface force and wetting techniques. Langmuir 17:1941–1949

    Article  CAS  Google Scholar 

  35. Sakya P, Seddon JM, Vill V (1997) Thermotropic and lyotropic phase behavior of monoalkyl glycosides. Liq Cryst 23:409–424

    Article  CAS  Google Scholar 

  36. Nguan HS, Heidelberg T, Hashim R, Tiddy GJT (2010) Quantitative analysis of the packing of alkyl glycosides: a comparison of linear and branched alkyl chains. Liq Cryst 37:1205–1213

    Article  CAS  Google Scholar 

  37. Kurita H, Yamagushi T, Onta T (1995) Acylaminosaccharide derivative and process for preparing the same, European patent EP 650974A1

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Acknowledgments

This work was supported by the University of Malaya under research grants PS382-2010B, RP024-2012B and RG264-13AFR.

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Authors and Affiliations

  1. Faculty of Science, Chemistry Department, University of Malaya, Lembah Pantai, 50603, Kuala Lumpur, Malaysia

    Salih Mahdi Salman, Thorsten Heidelberg, Rusnah Syahila Duali Hussen & Hairul Anuar Bin Tajuddin

  2. Faculty of Medicine, Chemistry Department, University of Diyala, Diyala Governorate, Republic of Iraq

    Salih Mahdi Salman

Authors
  1. Salih Mahdi Salman
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  2. Thorsten Heidelberg
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  3. Rusnah Syahila Duali Hussen
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  4. Hairul Anuar Bin Tajuddin
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Corresponding author

Correspondence to Thorsten Heidelberg.

Electronic Supplementary material

Detailed synthetic procedures and spectroscopic data on the prepared surfactants are provided as supplementary material, which can be accessed from the journal home page. The supplementary information also contains exemplary 1H-NMR spectra to demonstrate the compound purity as well as additional molecular modeling data and images

Supplementary material 1 (DOC 458 kb)

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Salman, S.M., Heidelberg, T., Hussen, R.S.D. et al. Amide-Based Surfactants from Methyl Glucoside as Potential Emulsifiers. J Surfact Deterg 17, 1141–1149 (2014). https://doi.org/10.1007/s11743-014-1628-8

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  • DOI: https://doi.org/10.1007/s11743-014-1628-8

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