Skip to main content
Log in

Novel Non-ionic Gemini Surfactants from Fatty Acid and Diethanolamine: Synthesis, Surface-Active Properties and Anticorrosion Study

  • Original Article
  • Published:
Chemistry Africa Aims and scope Submit manuscript

Abstract

Series of novel non-ionic Gemini surfactant was prepared in two steps. Initially diethanolamine was converted into amide by using fatty acids viz. lauric acid, palmitic acid, myristic acid and stearic acid and corresponding prepared amide reacted with 1,6-dibromohexane to form the non-ionic Gemini surfactants. The formation of the targeted molecule was monitored and confirmed using FTIR, 1H-NMR and 13C-NMR spectroscopy. The effect of alkyl chain length of synthesized surfactants on the basic characteristics such as surface tension, foaming, emulsifying capability, lime soap dispersing power and wetting were studied. These new surfactants were investigated for their anticorrosion and biological properties. They have capacity to reduce surface tension of water from 71.8 to 25.44 mN m−1. All the Gemini surfactants possessed good antimicrobial activity against gram positive Bacteria Bacillis subtilis and Staphylococcus aureus. The N,N-bis(hydroxyethyl)octadecanamide based Gemini surfactant have 94.11% corrosion inhibition efficiency against carbon steel. They have low biodegradability.

Graphic Abstract

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. El-Shamy OAA, Khid TT, Doheim MM (2011) Effect of ethoxylate chain length on the pour point depressant of middle distillate fuel oil. J Dispers Sci Technol 32:654–658

    CAS  Google Scholar 

  2. Schmitt MT (2001) Analysis of surfactants. Surfactant science series, 3rd edn. CRC Press, Boca Raton, p 96

    Google Scholar 

  3. Becher P (1990) In: Basel JMR (ed) A review of cationic surfactants: organic chemistry, surfactant science series, vol 34, 1st edn. Marcel Dekker Inc, New York

    Google Scholar 

  4. Gunstone FD (1999) Fatty acid and lipid chemistry, vol 1. Aspen Publisher Inc., Gaithersburg

    Google Scholar 

  5. Channouf RB, Souissi N, Zanna S, Ardelean H, Bellakhal N, Marcus P (2018) Surface characterization of the corrosion product layer formed on synthetic bronze in aqueous chloride solution and the effect of the adding of juniperus communis extract by X-ray photoelectron spectroscopy analysis. Chem Afr 1:167–174

    Google Scholar 

  6. Jan J, Margareta S, Britt-Marie L, Andreas A, Tore C, Bengt R (2003) A synthetic surfactant based on a poly-Leu SP-C analog and phospholipids: effects on tidal volumes and lung gas volumes in ventilated immature newborn rabbits. J Apply Physiol 95:2055–2063

    Google Scholar 

  7. Han L, Chen H, Luo P (2004) Viscosity behavior of cationic gemini surfactants with long alkyl chains. Surf Sci 564:141–148

    CAS  Google Scholar 

  8. Devinsky F, Lacko I, Bittererova F, Tomeckova LJ (1986) Relationship between structure, surface activity and micelle formation of some new bisquaternary isosteres of 1,5-pentanediammonium dibromides. J Colloid Interface Sci 114:314–322

    CAS  Google Scholar 

  9. Okahara M, Masuyama A, Sumida Y, Zhu YP (1988) Surface active properties of new types of amphipathic compounds with two hydrophilic ionic groups and two lipophilic alkyl chains. J Jpn Oil Chem Soc 37:746–748

    CAS  Google Scholar 

  10. Mangat CK, Kaur S (2014) Synthesis, characterization and surface properties of cationic gemini surfactant. J Dispers Sci Technol 35:1528–1556

    CAS  Google Scholar 

  11. Zang Y, Yongshen X, Shouji Q, Yang L (2013) Synthesis and properties of mono or double long-chain alkanolamine surfactants. J Surfact Deterg 16:841–848

    Google Scholar 

  12. Patil VK, Gawali IT, Usmani GA (2016) Synthesis and properties of novel cationic triazolium gemini surfactants. J Dispers Sci Technol 37:1630–1637

    CAS  Google Scholar 

  13. Gawali IT, Mali Punam, Usmani GA (2016) 4,5-Dihydroimidazoline based non-ionic gemini surfactants: synthesis, characterization, physicochemical properties and anticorrosion behaviour in 1 N H2SO4 aqueous medium. Res J Recent Sci 5:39–49

    CAS  Google Scholar 

  14. Gawali IT, Umani GA (2018) Monoethanolamide based non-ionic gemini surfactants from renewable sources: synthesis, characterization and anticorrosion study. Int Educ J Sci Eng 1:12–20

    Google Scholar 

  15. Gawali IT, Umani GA (2019) Synthesis, surface active properties and applications of cationic gemini surfactants from triethylenetetramine. J Dispers Sci Technol. https://doi.org/10.1080/01932691.2019.1584112

    Article  Google Scholar 

  16. Schwartz, Perry (1949) Surface active agents, their chemistry and technology. Interscience Publishers Inc, New York, pp 175–183

    Google Scholar 

  17. Dai Y et al (2017) Synthetic method of coconut diethanol amide. China patent CN107513025A

  18. Williamson AW (1852) On etherification. J Chem Soc 4:229–239

    Google Scholar 

  19. Baylis RL, Bevan TH, Malkin T (1958) The synthesis of cephalin (phosphatidylethanolamine) and batyl, chimyl, glycol, and alkyl analogues. J Chem Soc. https://doi.org/10.1039/JR9580002962

    Article  Google Scholar 

  20. Smith RG, Vanterpool A, Culak HJ (1969) Dimethyl sulfoxide as a solvent in Williamson ether synthesis. Can J Chem 47:2015–2019

    CAS  Google Scholar 

  21. Ahmad I, Patial P, Kaur C, Kaur S (2014) Cationic imidazolium monomeric surfactants: their synthesis and surface active properties. J Surfact Deterg 17:269–277

    CAS  Google Scholar 

  22. Hughes FA, Lew BW (1970) Physical and functional properties of some higher alkyl polyglucosides. J Am Oil Chem Soc 47:162–167

    CAS  PubMed  Google Scholar 

  23. Gawali IT, Usmani GA (2014) Study of physico-chemical properties of glycerol ester based non-ionic gemini surfactant. Int J Sci Res 3:580–584

    Google Scholar 

  24. McCutecheon JW (1950) Synthetic detergents. McNair-Dorland’s, New York

    Google Scholar 

  25. Zhu YP, Masuyama A, Okahara M (1990) Preparation and surface active properties amphipathic compounds with two sulfate groups and two lipophilic alkyl chains. J Am Oil Chem Soc 67:459–463

    CAS  Google Scholar 

  26. Wakasman SA, Lechevalver HA (1962) The actinomycetes antibiotic of actinomycetes, vol 430. Williams & WIkins Co., Baltimore

    Google Scholar 

  27. El-Sukkary MMA, Syed NA, Helmy SM, Ismail A, El-Azab WIM (2009) Aqueous solution properties, biodegradability and antimicrobial activity of some alkylpolyglycosides surfactants. Tenside Surf Det 46:311–316

    CAS  Google Scholar 

  28. Petre ET, Richard RE, David A, Gayle KM, Felix HO (1974) Degradable surfactants derived from corn starch. JAOCS 51:486–494

    Google Scholar 

  29. Fouda AS, Elewady YA, Abd El-Aziz HK (2012) Corrosion inhibition of carbon steel by cationic surfactants in 0.5 m HCl solution. J Chem Sci Technol 1:45–53

    Google Scholar 

  30. Lah J, Pohar C, Vesnaver G (2000) Calorimetric study of the micellization of alkylpyridinium and alkyltrimethylammonium bromides in water. J Phys Chem B 104:2522–2526

    CAS  Google Scholar 

  31. Ismayilov IT, Abd El-Lateef HM, Abbasov VM, Aliyeva LI, Qasimov EE, Efremenko EN, Ismayilov TA, Mamedxanova SA (2013) Inhibition effects of some novel surfactants based on corn oil and diethanolamine on mild steel corrosion in chloride solutions saturated with CO2. Int J Thin Film Sci Technol 2:91–105

    Google Scholar 

  32. Li ZX, Dong CC, Thomas RK (1999) Neutron reflectivity studies of the surface excess of gemini surfactants at the air–water interface. Langmuir 15:4392–4396

    CAS  Google Scholar 

  33. Varma SK, Gosh KK (2011) Micellar and surface properties of some monomeric surfactants and a gemini cationic surfactant. J Surfact Deterg 14:347–352

    Google Scholar 

  34. Yeshimua T, Bong M, Matsuoka K, Honda C, Endo K (2009) Surface properties and aggregate morphology of partially fluorinated carboxylate-type anionic gemini surfactants. J Colloid Interface Sci 339:230–235

    Google Scholar 

  35. Xin L, Zhiyong H, Hailin Z, Duanlin C (2010) Synthesis and properties of novel alkyl sulfonates gemini surfactants. J Surfact Deterg 13:353–359

    Google Scholar 

  36. Shahin M, Hady SA, Hammad MN (2011) Mortadadevelopment of stable O/W emulsions of three different oils. Int J Pharm Stud Res 2:45–51

    Google Scholar 

  37. Solans C, Izquierdo P, Nolla J, Azemar N, Garcia-Celma MJ (2005) Nano-emulsions. Curr Opin Colloid Interface Sci 10:102–110

    CAS  Google Scholar 

  38. Toliwal SD, Patel K (2007) Preparation and surfactant properties of diethanolamides of rice bran, soyabean and rapeseed protein. J Sci Ind Res 66:385–387

    CAS  Google Scholar 

  39. Ware AM, Waghmare JT, Momin SA (2007) Alkylpolyglycoside: carbohydrate based surfactant. J Dispers Sci Technol 28:437–444

    CAS  Google Scholar 

  40. Adewale A, Rotimi AO, Rao AVSK, Prasad RBN (2012) Synthesis of alkanolamide: nonionic surfactant from the oil of Gliricida sepium. J Surfact Deterg 15:89–96

    Google Scholar 

  41. Qun X, Liyan W, Fenglan X (2011) Synthesis and properties of dissymmetric gemini surfactants. J Surfact Deterg 14:85–90

    Google Scholar 

  42. Karsa DR, Porter MR (1995) Biodegradability of surfactants. Springer, Netherlands

    Google Scholar 

  43. Tundo PP, Anastas D, Black BJ, Collins T, Memoli S, Miyamoto J, Polyakoff M, Tumas W (2000) Synthetic pathways and processes in green chemistry. Introductory overview. Pure Apply Chem 72:1207–1228

    CAS  Google Scholar 

  44. Sheng Z, Lijing G, Linlin Z (2011) Synthesis and properties of a new piperazine-based bicaudate gemini surfactant. J Dispers Sci Technol 33:960–964

    Google Scholar 

  45. Adewale A, Rotomi AO, Adebobola OA (2013) Antimicrobial activity of non-ionic and anionic surfactants from Citrullus lantus seed oil. Jundishapur J Microbiol 6:205–209

    Google Scholar 

  46. Bradshaw LJ (1992) Laboratory microbiology. Saunders College, New York

    Google Scholar 

  47. Raja PB, Sethuraman MG (2008) Inhibition effect of pepper extract on the sulphuric acid corrosion of mild steel. Mater Lett 62:2977–2979

    Google Scholar 

  48. Tang LB, Mu GN, Liu GH (2003) The effect of neutral red on the corrosion inhibition of cold rolled steel in 1.0 m hydrochloric acid. Corros Sci 45:2251–2262

    CAS  Google Scholar 

  49. Farag AA, Noor El-Din MR (2012) The adsorption and corrosion inhibition of some nonionic surfactants on API X65 steel surface in hydrochloric acid. Corros Sci 64:174–183

    CAS  Google Scholar 

  50. Free ML (2002) Understanding the effect of surfactant aggregation on corrosion inhibition of mild steel in acidic medium. Corros Sci 44:2865–2870

    CAS  Google Scholar 

  51. Heakal FE, Deyab FMA, Osman MM, Nessimb MI, Elkholyb AE (2017) Synthesis and assessment of new cationic gemini surfactants as inhibitors for carbon steel corrosion in oilfield water. RSC Adv 7(75):47335–47352

    Google Scholar 

  52. Ozturk S, Mudaber S, Yıldırım A (2018) Synthesis of 2,3-dihydroxypropyl-sulfanyl derivative nonionic surfactants and their inhibition activities against carbon steel corrosion in acidic media. JOTCSA 5(2):333–346

    Google Scholar 

Download references

Acknowledgements

This work was supported by University Grants Commission (UGC), India [Project F. no. 41-373/2012 (SR)].

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ishwar T. Gawali.

Ethics declarations

Conflict of interest

There is no conflict of interest

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 698 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gawali, I.T., Usmani, G.A. Novel Non-ionic Gemini Surfactants from Fatty Acid and Diethanolamine: Synthesis, Surface-Active Properties and Anticorrosion Study. Chemistry Africa 3, 75–88 (2020). https://doi.org/10.1007/s42250-019-00107-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s42250-019-00107-5

Keywords

Navigation