Skip to main content
SpringerLink
Log in

Synthesis and Evaluation of Surface and Biological Properties of Some Lactic Acid-Based Anionic Surfactants

  • Original Article
  • Published:
Journal of Surfactants and Detergents

Abstract

In the present study, 11 lactic acid-based anionic surfactants were synthesized and evaluated for their surface and biological activities. The synthesis involved the esterification of lactic acid with a range of fatty alcohols differing in chain length as well as in branching and unsaturation. The resultant ester was sulfonated by treatment with chlorosulfonic acid followed by salt formation with aqueous NaOH solution. The surface properties of all the synthesized surfactants were determined using surface tensiometry. Synthesized surfactants showed low critical micelle concentration (CMC) values and a decreasing trend with an increase in the alkyl chain length. Alkyl branching also led to a mild change in CMC values when compared with linear counterparts having the same number of carbon atoms, though such decreases or increases were observed to be dependent on the position and number of the branching. Some of the synthesized surfactants exhibited good antimicrobial and anti-cancer activities against the tested microbial strains and cell lines.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Anupam V, Mihir KP (2009) Synthesis, characterization and physical properties studies of anionic surfactants. Indian J Chem Technol 17:233–237

    Google Scholar 

  2. Karsa DR, Bailey RM, Shelmerdine B, McCann SA (1999) Overview: a decade of change in the surfactant industry. In: Karsa DR (ed) Industrial application of surfactants IV. The Royal Society of Chemistry, Cambridge, p 1

    Chapter  Google Scholar 

  3. CESIO (2001) Presentation to the Renewable Raw Materials Group (Working Group 5/Industry) under the European Climate Change Programme (ECCP), Brussels

  4. Veronika D, Iris L, Martin P (2003) Comparing the land requirements, energy savings, and greenhouse gas emissions reduction of biobased polymers and bioenergy. J Ind Ecol 7:93–116

    Google Scholar 

  5. Reznik GO, Vishwanath P, Pynn MA, Sitnik JM, Todd JJ, Wu J, Jiang Y, Keenan BG, Castle AB, Haskell RF, Smith TF, Somasundaran P, Jarrell KA (2010) Use of sustainable chemistry to produce an acyl amino acid surfactant. Appl Microbiol Biotechnol 86:1387–1397

    Article  CAS  Google Scholar 

  6. Magali D, Michel P (2004) From renewable vegetables resources to microorganisms: new trends in surfactants. C R Chim 7:641–646

    Article  Google Scholar 

  7. Joachim E (2002) Current situation and future prospects of EU industry using renewable raw materials. Environmental Aspects of Industry Policy, Brussels

    Google Scholar 

  8. Patrick F, Azadeh KP, Evan SB, Julie BZ (2012) Derivation and synthesis of renewable surfactants. Chem Soc Rev 41:1499–1518

    Article  Google Scholar 

  9. Frank DG, John LH, Fred BP (1997) Lipid Technologies and Applications. Marcel Dekker, New York

    Google Scholar 

  10. Perez L, Pinazo A, Garcia MT, Lozano M, Manresa A, Angelet M, Vinardell MP, Mitjans M, Pons R, Infante MR (2009) Cationic surfactants from lysine: Synthesis, micellization and biological evaluation. Eur J Med Chem 44:1884–1892

    Article  CAS  Google Scholar 

  11. Murguia MC, Vaillard VA, Sanchez VG, Conza JD, Grau RJ (2008) Synthesis, surface active properties and antimicrobial activities of new double-chain gemini surfactants. J Oleo Sci 57:301–308

    Article  CAS  Google Scholar 

  12. Amelia PR, Susana L, Tania A, Diana S, Veronica R, Jorge J, Ana N, Filipa VMS, Maria CO, Maria JF, Maria SS, Ester B (2005) Synthesis, surface active and antimicrobial properties of new alkyl 2,6-dideoxy-L-arabino-hexopyranosides. Carbohydr Res 340:191–201

    Article  Google Scholar 

  13. Naoual A, Moustapha N, Christian A, Serge P, Pierre L (2000) Synthesis and characterization of new cationic surfactants derived from lactic acid. J Surf Deter 3:381–386

    Article  Google Scholar 

  14. Avelino C, Sara I, Alexandra V (2007) Chemical routes for the transformation of biomass into chemicals. Chem Rev 107:2411–2502

    Article  Google Scholar 

  15. Bowmer CT, Hooftman RN, Hanstveit AO, Venderbosch PW, Vander HN (1998) The ecotoxicity and the biodegradability of lactic acid, alkyl lactate esters and lactate salts. Chemosphere 37:1317–1333

    Article  CAS  Google Scholar 

  16. Adkins H (1947) Organic synthesis, alkyl lactate, vol 26. Wiley, New York, pp 4–5

    Google Scholar 

  17. Mats F, Patrick A, Mattiasson B (1997) Lipase catalyzed esterification of lactic acid. Biotechnol Lett 19:315–317

    Article  Google Scholar 

  18. Torres C, Otero C (1999) Part I: enzymatic synthesis of lactate and gycolate esters of fatty alcohols. Enzyme Microb Technol 25:745–752

    Article  CAS  Google Scholar 

  19. Hyung CS (1993) Alkyl sulphooxyalkanoate compounds and compositions. Unilever NV [NL], Unilever PLC [GB], European Patent, EP0530866 (A1)

  20. Robert FN, Weldon GB (1947) Reaction of organic compounds by lithium aluminium hydride. I. Aldehydes, ketones, esters, acid chlorides and acid anhydrides. J Am Chem Soc 69:1197–1199

    Article  Google Scholar 

  21. Knothe G (2002) Synthesis, applications, and characterization of Guerbet compounds and their derivatives. Lipid Technol 14:101–104

    CAS  Google Scholar 

  22. Karuna MSL, Devi BLAP, Prasad PSS, Prasad RBN (2009) Synthesis of sulfated sodium salts of 1-alkylamino-3-alkyloxy-2-propanols and N, N-(2-hydroxy-3-alkyloxy propyl) alkylamines as potential surfactants. J Surf Detergents 12:117–123

    Article  CAS  Google Scholar 

  23. Mosmann T (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65:55–63

    Article  CAS  Google Scholar 

  24. Kumar CG, Mamidyala SK (2011) Extracellular synthesis of silver nanoparticles using culture supernatant of Pseudomonas aeruginosa. Colloid Surf B 84:462–466

    Article  CAS  Google Scholar 

  25. Saddula S, Paidimarla SR, Prasad RBN, Kanjilal S (2011) Synthesis and evaluation of new imidazolium-based aromatic ether functionalized cationic mono and gemini surfactants. Eur J Lipid Sci Technol 113:756–762

    Article  Google Scholar 

  26. Menger FM, Littau CA (1993) Gemini surfactants: a new class of self-assembling molecules. J Am Chem Soc 115:10083–10090

    Article  CAS  Google Scholar 

  27. Mukherjee P (1967) The nature of the association equilibria and hydrophobic bonding in aqueous solutions of association colloids. Adv Colloid Interface Sci 1:242–275

    Article  Google Scholar 

  28. Varadaraj R, Bock J, JrP Valint, Zushma S, Thomas R (1991) Fundamental interfacial properties of alkyl-branched sulfate and ethoxy sulfate surfactants derived from Guerbet alcohols. 1. Surface and instantaneous interfacial tensions. J Phys Chem 95:1671–1676

    Article  CAS  Google Scholar 

  29. Shoba J, Balasubramanian D (1986) Hairpin looping of terminally functionalized carboxylate surfactants. J Phys Chem 90:2800–2802

    Article  Google Scholar 

Download references

Acknowledgments

One of the authors, Y.S., gratefully acknowledges the Department of Biotechnology, New Delhi for the financial assistance under sponsored project and Director, CSIR-IICT for providing the facilities.

Author information

Authors and Affiliations

  1. Centre for Lipid Research, CSIR‐Indian Institute of Chemical Technology (CSIR‐IICT), Hyderabad, 500007, Telangana, India

    Yasa Sathyam Reddy, Sanjit Kanjilal & Penumarthy Vijayalakshmi

  2. Medicinal Chemistry and Pharmacology Division, CSIR‐Indian Institute of Chemical Technology (CSIR‐IICT), Hyderabad, 500007, Telangana, India

    Pombala Sujitha & Chityal Ganesh Kumar

Authors
  1. Yasa Sathyam Reddy
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Pombala Sujitha
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Chityal Ganesh Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Sanjit Kanjilal
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Penumarthy Vijayalakshmi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Penumarthy Vijayalakshmi.

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sathyam Reddy, Y., Sujitha, P., Kumar, C.G. et al. Synthesis and Evaluation of Surface and Biological Properties of Some Lactic Acid-Based Anionic Surfactants. J Surfact Deterg 19, 343–351 (2016). https://doi.org/10.1007/s11743-015-1774-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11743-015-1774-7

Keywords

Search

Navigation