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Licensed Unlicensed Requires Authentication Published by De Gruyter April 28, 2022

Study on the synthesis and performance of sodium 2-laurylamido isobutyrate

  • Ying Li

    Ying Li, Postgraduate, she is currently involved in researching various aspects of surfactant application and synthesis.

    , Jian Huang

    Jian Huang, Postgraduate, he is currently involved in researching various aspects of surfactant application and synthesis.

    , Liangliang Lin

    Liangliang Lin, Associate professor, he received his Ph.D. degree in 2018 from the Eindhoven University of Technology.

    and Hujun Xu

    Hujun Xu, Professor, he received his Ph.D. degree in 2005 from Nanjing University of Science and Technology, P.R. China. He has been involved in surfactants and detergents for over 30 years. He has published over 100 papers in the field of surfactants and detergents.

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Abstract

In the present work, sodium 2-laurylamido isobutyrate was synthesized from 2-aminoisobutyric acid, NaOH and lauroyl chloride by the Schotten-Baumann condensation. Fourier transform infrared spectroscopy, mass spectroscopy and nuclear magnetic resonance spectroscopy were used to characterize the products, and confirming the successful synthesis of sodium 2-laurylamido isobutyrate. The influence of temperature on the surface tension of sodium 2-laurylamido isobutyrate was studied, comparing the chemical properties of the surface with those of sodium N-lauroyl sarcosinate. The results indicate that both surfactants have a similar pC 20, while the critical micelle concentration (CMC) and the surface tension at the critical micelle concentration (γ CMC) of sodium 2-laurylamido isobutyrate are higher than those of sodium N-lauroyl sarcosinate. Further studies on the thermodynamic parameters of sodium 2-laurylamido isobutyrate and sodium N-lauroyl sarcosinate indicate that the formation of micelles is a spontaneous exothermic process mainly driven by entropy. According to the dynamic surface tension of sodium 2-laurylamido isobutyrate and sodium N-lauroyl sarcosinate, the molecular adsorption of the two components mixture change from the initial diffusion controlled adsorption to the later mixed dynamic controlled adsorption.


Corresponding author: Corresponding author: Hujun Xu, School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu, P. R. China, E-mail:

Award Identifier / Grant number: BK20190605

Funding source: Fundamental Research Funds for the Central Universities

Award Identifier / Grant number: JUSRP221018

Funding source: Key Laboratory of Cosmetic Safety Assessment

Funding source: National Medical Products Administration

About the authors

Ying Li

Ying Li, Postgraduate, she is currently involved in researching various aspects of surfactant application and synthesis.

Jian Huang

Jian Huang, Postgraduate, he is currently involved in researching various aspects of surfactant application and synthesis.

Liangliang Lin

Liangliang Lin, Associate professor, he received his Ph.D. degree in 2018 from the Eindhoven University of Technology.

Hujun Xu

Hujun Xu, Professor, he received his Ph.D. degree in 2005 from Nanjing University of Science and Technology, P.R. China. He has been involved in surfactants and detergents for over 30 years. He has published over 100 papers in the field of surfactants and detergents.

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: We would like to acknowledge the financial support from the Natural Science Foundation of Jiangsu Province (BK20190605), the Fundamental Research Funds for the Central Universities (JUSRP221018), and the Key Laboratory of Cosmetic Safety Assessment, National Medical Products Administration, Guangdong Institute for Drug Control (KF2021014).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. Pinazo, A., Pons, R., Perez, L., Infante, M. R. Amino acids as raw material for biocompatible surfactants. Ind. Eng. Chem. Res. 2011, 50, 4805–4817; https://doi.org/10.1021/ie1014348.Search in Google Scholar

2. Moran, M. C., Pinazo, A., Perez, L., Clapes, P., Angelet, M., Garcia, M. T., Vinardell, M. P., Infante, M. R. “Green” amino acid-based surfactants. Green Chem. 2004, 6, 233–240; https://doi.org/10.1039/b400293h.Search in Google Scholar

3. Takehara, M. Properties and applications of amino acid based surfactants. Colloid. Surface. 1989, 38, 149–167; https://doi.org/10.1016/0166-6622(89)80151-9.Search in Google Scholar

4. Infante, M. R., Pérez, L., Pinazo, A., Clapés, P., Morán, M. C., Angelet, M., García, M. T., Vinardell, M. P. Amino acid-based surfactants. Compt. Rendus Chem. 2004, 7, 583–592; https://doi.org/10.1016/j.crci.2004.02.009.Search in Google Scholar

5. Divya, B. T., Anuradha, M., James, C., Thomas, F. Synthesis, chemistry, physicochemical properties and industrial applications of amino acid surfactants: a review. Compt. Rendus Chem. 2018, 21, 112–130; https://doi.org/10.1016/j.crci.2017.11.005.Search in Google Scholar

6. Chandra, N., Tyagi, V. K. Synthesis, properties, and applications of amino acids based surfactants: a review. J. Dispersion Sci. Technol. 2013, 34, 800–808; https://doi.org/10.1080/01932691.2012.695967.Search in Google Scholar

7. Qiao, W. H., Zheng, Z. B., Peng, H., Shi, L. Synthesis and properties of three series amino acid surfactants. Tenside Surfactants Deterg. 2012, 49, 161–166; https://doi.org/10.3139/113.110179.Search in Google Scholar

8. Reznik, G. O., Vishwanath, P., Pynn, M. A., Sitnik, J. M., Todd, J. J., Wu, J., Jiang, Y., Keenan, B. G., Castle, A. B., Haskell, R. F., Smith, T. F., Somasundaran, P., Jarrell, K. A. Use of sustainable chemistry to produce an acyl amino acid surfactant. Appl. Microbiol. Biotechnol. 2010, 86, 1387–1397; https://doi.org/10.1007/s00253-009-2431-8.Search in Google Scholar

9. Soo, E. L., Salleh, A. B., Basri, M., Rahman, R. N. Z. A., Kamaruddin, K. Response surface methodological study on lipase-catalyzed synthesis of amino acid surfactants. Process Biochem. 2004, 39, 1511–1518; https://doi.org/10.1016/s0032-9592(03)00279-6.Search in Google Scholar

10. Nagao, A., Kito, M. Synthesis of O-acyl-L-homoserine by lipase. J. Am. Oil Chem. Soc. 1989, 66, 170–213; https://doi.org/10.1007/BF02669958.Search in Google Scholar

11. Yoshida, R., Shishido, T. Process for preparing N-higher aliphatic acyl derivatives of amino acids, peptides or proteins, U.S. Patent 3985722, 1976.Search in Google Scholar

12. Sreenu, M., Rao, B. V. S. K., Prasad, R. B. N., Sujitha, P., Chityala, G. K. Synthesis, surface and biological properties of sodium N-acyl isoleucines. Eur. J. Lipid Sci. Technol. 2014, 116, 193–206; https://doi.org/10.1002/ejlt.201300189.Search in Google Scholar

13. Meng, F. Synthesis and Properties of Fatty Acid Sulfoalkyl Amide and Sulfoalkyl Ester; Jiangnan University: Wuxi, 2019.Search in Google Scholar

14. Yu, F. Current status of synthesis technology of sodium N-acyl sarcosinate. China Surfactant Deterg. Cosmetics 2016, 46, 53–57; https://doi.org/10.13218/j.cnki.csdc.2016.01.011.Search in Google Scholar

15. Qiao, W. H., Qiao, Y. Y. The relationship between the structure and properties of amino acid surfactants based on glycine and serine. J. Surfactants Deterg. 2013, 16, 821–828; https://doi.org/10.1007/s11743-012-1432-2.Search in Google Scholar

16. Li, Y., Xu, H. J. Study on the synthesis and performance of sodium N-lauroyl methylalanine. China Surfactant Deterg. Cosmetics 2021, 51, 496–501; https://doi.org/10.3969/j.issn.1001-1803.2021.06.004.Search in Google Scholar

17. Miller, R., Fainerman, V. B., Aksenenko, E. V., Leser, M. E., Michel, M. Dynamic surface tension and adsorption kinetics of β-casein at the solution/air interface. Langmuir 2004, 20, 771–777; https://doi.org/10.1021/la030332s.Search in Google Scholar

18. Ward, A. F. H., Tordai, L. Time-dependence of boundary tensions of solutions I. the role of diffusion in time-effects. J. Chem. Phys. 1946, 14, 453–461; https://doi.org/10.1063/1.1724167.Search in Google Scholar

19. Eastoe, J., Dalton, J. S. Dynamic surface tension and adsorption mechanisms of surfactants at the air-water interface. Adv. Colloid Interface Sci. 2000, 85, 103–144; https://doi.org/10.1016/s0001-8686(99)00017-2.Search in Google Scholar

20. Fainerman, V. B., Makievski, A. V., Miller, R. The analysis of dynamic surface tension of sodium alkyl sulphate solutions, based on asymptotic equations of adsorption kinetic theory. Colloids Surf. A Physicochem. Eng. Asp. 1994, 87, 61–75; https://doi.org/10.1016/0927-7757(94)02747-1.Search in Google Scholar

21. Liggieri, L., Ravera, F., Passerone, A. A diffusion-based approach to mixed adsorption kinetics. Colloids Surf. A Physicochem. Eng. Asp. 1996, 114, 351–359; https://doi.org/10.1016/0927-7757(96)03650-3.Search in Google Scholar

22. Shaban, S. M., Kim, D. H. The influence of the gemini surfactants hydrocarbon tail on in-situ synthesis of silver nanoparticles: characterization, surface studies and biological performance. Kor. J. Chem. Eng. 2020, 37, 1008–1019; https://doi.org/10.1007/s11814-020-0542-1.Search in Google Scholar

23. Mohammedsiddiq, A., Thangam, R., Madhan, B., Sayemalam, M. Counterion coupled (COCO) gemini surfactant capped Ag/Au alloy and Ag@Au core–shell nanoparticles for cancer therapy. RSC Adv. 2019, 9, 37830–37845; https://doi.org/10.1039/c9ra06494j.Search in Google Scholar

24. Xu, H. J., Li, Y., Lin, L. L., Shen, J., Chen, X. Y. Study on the synthesis and compounding performance of C21 dibasic acid potassium. J. Surfactants Deterg. 2020, 23, 855–862; https://doi.org/10.1002/jsde.12417.Search in Google Scholar

25. Meng, F., Xu, H. J., Chen, X. Y. Study on the synergism of binary surfactant mixtures containing N-lauroyl-N-methyl taurine sodium. Tenside Surfactants Deterg. 2019, 56, 216–221; https://doi.org/10.3139/113.110625.Search in Google Scholar

26. Liu, J. J., Hu, M. J., Xie, Y. C., Xu, H. J. Study on a class of cationic Gemini surfactants. Tenside Surfactants Deterg. 2019, 56, 319–326; https://doi.org/10.3139/113.110628.Search in Google Scholar

27. Hirohito, H., Norikatsu, H., Makoto, I., Hirofumi, O., Michihiro, F., Raoul, Z. Small-angle neutron-scattering study of bis(quaternary ammonium bromide) surfactant micelles in water. Effect of the spacer chain length on micellar structure. J. Phys. Chem. 1995, 99, 17778–17784; https://doi.org/10.1021/j100050a017.Search in Google Scholar

Received: 2021-06-07
Accepted: 2021-10-12
Published Online: 2022-04-28
Published in Print: 2022-05-25

© 2022 Walter de Gruyter GmbH, Berlin/Boston

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