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The Use of a Eutectic Mixture of Olive Pomace Oil Fatty Amides to Easily Prepare Sulfated Amides Applied as Lime Soap Dispersants

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Journal of the American Oil Chemists' Society

Abstract

Sulfated diethanolamides of fatty acids are known to be effective lime soap dispersing agents. However, their preparation from fatty acids via fatty amides requires the use of organic solvents due to the high viscosity of both fatty amides and sulfated fatty amides. This study shows that the preparation of sulfated fatty amides is relatively easy when using olive pomace oil as the raw material. The latter, is converted into sulfated fatty amides by performing the following steps: saponification, hydrolysis, esterification, amidation, and sulfation. In the final step, the mixture obtained has sufficient fluidity, due to its high linoleic acid amide content, to obviate the use of organic solvents, as usually suggested in the literature. Characterization of the product was carried out by chemical analyses, FTIR, 13C NMR, GC, and HPLC. It was shown that the yield of the amidation reaction is about 80%, and that of the sulfation reaction can exceed 100% against the pure amide (more than one sulfate group could be linked to one amide molecule). On the other hand, the Borghetty test showed that the product is an effective dispersant with a lime soap dispersing power equal to five.

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References

  1. Hellsten KME, Klingberg AW (1974) Soap compositions capable of dispersing lime soaps. US Patent 3,850,834

  2. Borland JE, Sauer JD, Smith KR (1992) Lime soap dispersant comprising sodium cocoyl glyceryl sulfonate and N-alkyl-N,N-dimethylamine oxide. US Patent 5,102,572

  3. Schonfeldt N (1968) The action of various lime soap dispersants. J Am Oil Chem Soc 45(2):80–82

    Article  CAS  Google Scholar 

  4. Hewitt GT (1976) Soap crud dispersant. US Patent 3,951,596

  5. Smith FD, Weil JK, Linfield WM (1974) Soap-based detergent formulations: IX. α-Sulfo fatty alkanolamides as lime soap dispersing agents. J Am Oil Chem Soc 51:435–438

    Article  CAS  Google Scholar 

  6. Bistline RG, Noble WR, Smith FD, Linfield WM (1977) Cosulfation of fatty acid alkanolamides and lower molecular weight alcohols. J Am Oil Chem Soc 54:371–374

    Article  CAS  Google Scholar 

  7. Duccini Y, Keenan AC, Shulman JE (1998) Cleaning compositions containing lime-soap dispersant and method of preparation. US Patent 5,854,197

  8. Shukla D, Tyagi VK (2006) Anionic gemini surfactants: a distinct class of surfactants. J Oleo Sci 55:215–226

    CAS  Google Scholar 

  9. Determination de la teneur en matière active anionique (methode par titratrage direct dans deux phases) NF T 73–258 April 1972

  10. Arida VP, Binlayo DL, Chua S (1979) Preparation of coconut monoethanolamide (CMA). Philippine J coconut studies 4(3): 17–24

    Google Scholar 

  11. Borghetty HC, Bergman CA (1950) Synthetic detergents in the soap industry. J Am Oil Chem Soc 27:88–90

    Article  CAS  Google Scholar 

  12. Linfield M (1978) Soap and lime soap dispersants. J Am Oil Chem Soc 55:87–92

    Article  CAS  Google Scholar 

  13. Lohr JW (1962) Method of making fatty alkanolamides. US Patent 3,040,075

  14. Bistline RGJ, Linfield WM (1980) Thermal rearrangement of sulfated tallow alkanolamides. J Am Oil Chem Soc 57(5):167–169

    Article  CAS  Google Scholar 

  15. Ben-Bassat AA, Wasserman T, Basch A (1984) Determination of the mono and diethanolamides of palmitic acid and soybean oil fatty acids by high performance liquid chromatography. J Liq Chromatogr 7(13):2545–2560

    Article  CAS  Google Scholar 

  16. Vedanayagam H, Rao BVSK, Rao S, Lakshminarayana G (1984) preparation, characterization and surfactant properties of fatty acid diethanolamides. J Oil Technol Assoc India 15(2):68–71

    CAS  Google Scholar 

  17. Konig H (1977) Anionic surfactants chemical analysis. Surf Sci series 8:141–192

    Google Scholar 

  18. Bistline RGJ, Linfield WM, Noble WR (1978) Process for sulfating fatty alkanolamides. US Patent 4,116,986

  19. Letton JC (1994) Synthesis of sulfated polyhydroxy fatty acid amide surfactants. US Patent 5,312,934

  20. Weil JK, Parris N, Stirton AJ (1970) Synthesis and properties of sulfated alkanolamides. J Am Oil Chem Soc 47(3):91–93

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors would like to thank: the Société d’Innovations Chimiques—Tunisia for its technical and financial support, the Tunisian Ministère de l’Enseignement et de la Recherche Scientifique et de la Technologie for its financial support and the Unité de service commun de RMN du Solide ENIS-Sfax-Tunisia for the 13C NMR analyses.

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Authors and Affiliations

  1. Laboratoire de Chimie Industrielle, Ecole Nationale d’Ingénieurs de Sfax, 3038, Sfax, Tunisia

    Faicel Rais, Rochdi Baati, Nesrin Damak & Amel Kamoun

  2. Société d’Innovations Chimiques, Pépinière d’entreprises, ENIS, Sfax, Tunisia

    Moncef Chaabouni

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  1. Faicel Rais
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  2. Rochdi Baati
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  3. Nesrin Damak
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  4. Amel Kamoun
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  5. Moncef Chaabouni
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Correspondence to Amel Kamoun.

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Rais, F., Baati, R., Damak, N. et al. The Use of a Eutectic Mixture of Olive Pomace Oil Fatty Amides to Easily Prepare Sulfated Amides Applied as Lime Soap Dispersants. J Am Oil Chem Soc 85, 869–877 (2008). https://doi.org/10.1007/s11746-008-1266-2

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  • DOI: https://doi.org/10.1007/s11746-008-1266-2

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