Synthesis and properties of alkyl glyceryl ether sulfonate

Jixiang Guo; Hujun Xu; Jingguo Yang; Liangliang Lin

doi:10.1515/tsd-2022-2457

Article

Synthesis and properties of alkyl glyceryl ether sulfonate

Jixiang Guo
Jixiang Guo, Postgraduate of the School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu, P.R. China.
, 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 200 papers in the field of surfactants and detergents.
, Jingguo Yang
Jingguo Yang, Engineer, graduated from Wuxi University of Light Industry in 1996, majoring in fine chemicals. Mainly direction is in the research of chemical technology and equipment.
and Liangliang Lin
Liangliang Lin, Associate professor, he has published several papers in internationally renowned chemical journals such as AlChE Journal, Chemical Engineering Science, and Chemical Engineering Journal.

Published/Copyright: March 21, 2023

Published by

Become an author with De Gruyter Brill

Author Information

From the journal Tenside Surfactants Detergents Volume 60 Issue 3

Abstract

In this work, alkyl glyceryl ether sulfonates with two alkyl chain lengths were synthesised by etherification and sulfonation. The structures of these sulfonates were characterised by FTIR, ¹H NMR and MS. Their characterisations were investigated for their surface properties and thermodynamic properties by surface tension, conductivity and fluorescence methods. The critical micelle concentration (CMC) of surfactants increases with increasing temperature and decreases with increasing alkyl chain length. The micellation process of alkyl glyceryl ether sulfonates is spontaneous and driven by entropy.

Keywords: alkyl glyceryl ether sulfonates; entropy driven; micellization process; surface properties; thermodynamic properties

Corresponding author: Liangliang Lin, School of Chemical & Material Engineering, Jiangnan University, Wuxi, China, E-mail: linliangliang@jiangnan.edu.cn

About the authors

Jixiang Guo

Jixiang Guo, Postgraduate of the School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu, P.R. China.

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 200 papers in the field of surfactants and detergents.

Jingguo Yang

Jingguo Yang, Engineer, graduated from Wuxi University of Light Industry in 1996, majoring in fine chemicals. Mainly direction is in the research of chemical technology and equipment.

Liangliang Lin

Liangliang Lin, Associate professor, he has published several papers in internationally renowned chemical journals such as AlChE Journal, Chemical Engineering Science, and Chemical Engineering Journal.

Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
Research funding: None declared.
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. Rebello, S., Asok, A. K., Mundayoor, S., Jisha, M. S. Surfactants: toxicity, remediation and green surfactants. Environ. Chem. Lett. 2014, 12, 275–287; https://doi.org/10.1007/s10311-014-0466-2.Search in Google Scholar

2. Wang, T. F., Chang, D. J., Huang, D., Liu, Z. T., Wu, Y. K., Liu, H. L., Yuan, H. B., Jiang, Y. Application of surfactants in papermaking industry and future development trend of green surfactants. Appl. Microbiol. Biotechnol. 2021, 105, 7619–7634; https://doi.org/10.1007/s00253-021-11602-6.Search in Google Scholar PubMed

3. Ananthapadmanabhan, K. P. Amino-acid surfactants in personal cleansing (review). Tenside, Surfactants, Deterg. 2019, 56, 378–386; https://doi.org/10.3139/113.110641.Search in Google Scholar

4. Cassidy, W. A., Schwartz, J. R., Farris, R. D. Ultra Mild Surfactant with Good Lather. US 5567359, 1996.Search in Google Scholar

5. Jianfeng, S., Donghong, G., Haochuan, X., Lijun, W., Yuling, S., Chunqin, L. Synthesis and property evaluation of JP series high temperature resistant foam agents. Oil Drill. Prod. Technol. 2011, 33, 117–119.Search in Google Scholar

6. Whyte, D. D. Method For Preparing Detergent Compositions. US 2989547, 1961.Search in Google Scholar

7. Hato, M., Shinoda, K. Krafft points of calcium and sodium dodecylpoly (oxyethylene) sulfates and their mixtures. J. Phys. Chem. 1973, 77, 378–381; https://doi.org/10.1021/j100622a015.Search in Google Scholar

8. Xie, Y. C., Li, J., Zhu, R. H., Sun, T., Qu, G. M. Synthesis, surface activity, thermodynamic parameters, and performance evaluation of branched carboxylate gemini surfactants. J. Surfactants Deterg. 2019, 22, 421–430; https://doi.org/10.1002/jsde.12268.Search in Google Scholar

9. Zheng, L. C., Tong, Q. X. Synthesis, surface adsorption, micellization behavior and antibacterial activity of novel gemini surfactants with morpholinium headgroup and benzene-based spacer. J. Mol. Liq. 2021, 331, 115781; https://doi.org/10.1016/j.molliq.2021.115781.Search in Google Scholar

10. Rosen, M. J., Cohen, A. W., Dahanayake, M., Hua, X. Y. Relationship of structure to properties in surfactants. 10. Surface and thermodynamic properties of 2-dodecyloxypoly(ethenoxyethanol)s, C12H25(OC2H4)xOH, in aqueous solution. J. Phys. Chem. 1982, 86, 541–545; https://doi.org/10.1021/j100393a025.Search in Google Scholar

11. Patra, T., Ghosh, S., Dey, J. Cationic vesicles of a carnitine-derived single-tailed surfactant: physicochemical characterization and evaluation of in vitro gene transfection efficiency. J. Colloid Interface Sci. 2014, 436, 138–145; https://doi.org/10.1016/j.jcis.2014.08.049.Search in Google Scholar PubMed

12. Alami, E., Beinert, G., Marie, P., Zana, R. Alkanediyl-α,ω-bis (dimethylalkylammoniumbromide)Surfactants. 3. Behavior at the air-water interface. Langmuir 1993, 9, 1465–1467; https://doi.org/10.1021/la00030a006.Search in Google Scholar

13. Mahajan, R. K., Mahajan, S., Bhadani, S., Singh, S. Physicochemical studies of pyridinium gemini surfactants with promethazine hydrochloride in aqueous solution. Phys. Chem. Chem. Phys. 2012, 14, 887–898; https://doi.org/10.1039/c1cp22448d.Search in Google Scholar PubMed

14. Zhou, M., Li, S. S., Zhang, Z., Luo, G., Zhao, J. Z. Synthesis of oligomer betaine surfactant (DDTPA) and rheological properties of wormlike micellar solution system. J. Taiwan Inst. Chem. Eng. 2016, 66, 1–11; https://doi.org/10.1016/j.jtice.2016.05.013.Search in Google Scholar

15. Aiad, I., El-Sukkary, M. M., Soliman, E. A., El-Awady, M. Y., Shaban, S. M. Characterization, surface properties and biological activity of new prepared cationic surfactants. J. Ind. Eng. Chem. 2014, 20, 1633–1640; https://doi.org/10.1016/j.jiec.2013.08.010.Search in Google Scholar

16. Negm, N. A., Mishrif, M. R., Mohamed, D. E. Vanillin based cationic surfactants mixed systems: micellization and interfacial interaction behaviors in presence of nonionic conventional surfactant. Colloids Surf. A Physicochem. Eng. Asp. 2015, 480, 122–129; https://doi.org/10.1016/j.colsurfa.2014.09.035.Search in Google Scholar

17. Zhou, L. M., Jiang X. H., Li Y. T., Chen Z., Hu X. Q. Synthesis and properties of a novel class of gemini pyridinium surfactants. Langmuir. 2007, 23, 11404–11408; https://doi.org/10.1021/la701154w.Search in Google Scholar PubMed

18. Dai, C. L., Fang, S. S., Hu, M., He, X. J., Zhao, M. W., Wu, X. P., Yang, S., Wu, Y. N. Synthesis, surface adsorption and micelle formation of a class of morpholinium gemini surfactants. J. Ind. Eng. Chem. 2017, 54, 226–233; https://doi.org/10.1016/j.jiec.2017.05.037.Search in Google Scholar

19. Asadov, Z. H., Ahmadova, G. A., Rahimov, R. A., Hashimzade, S. F., Ismailov, E. H., Asadova, N. Z., Suleymanova, S. A., Zubkov, F. I., Mammadov, A. M., Agamaliyeva, D. B. Micellization and adsorption properties of new cationic gemini surfactants having hydroxyisopropyl group. J. Chem. Eng. Data, 2019, 64, 952–962; https://doi.org/10.1021/acs.jced.8b00815.Search in Google Scholar

20. Zana, R. Critical micellization concentration of surfactants inaqueous solution and free energy of micellization. Langmuir 1996, 12, 1208–1211; https://doi.org/10.1021/la950691q.Search in Google Scholar

21. Azum, N., Rub, M. A., Asiri, A. M., Bawazeer, W. A. Micellar and interfacial properties of amphiphilic drug-non-ionic surfactants mixed systems: surface tension, fluorescence and UV-vis studies. Colloids Surf. A Physicochem. Eng. Asp. 2017, 522, 183–192; https://doi.org/10.1016/j.colsurfa.2017.02.093.Search in Google Scholar

22. Ao, M. Q., Huang, P. P., Xu, G. Y., Yang, X. D., Wang, Y. J. Aggregation and thermodynamic properties of ionic liquid-type gemini imidazolium surfactants with different spacer length. Colloid Polym. Sci. 2009, 287, 395–402; https://doi.org/10.1007/s00396-008-1976-x.Search in Google Scholar

23. Lyu, B., Yu, Y. J., Gao, D., Wang, Y. F., Ma, J. Z. Asymmetric sodium benzenesulfonate Gemini surfactant: synthesis, properties and application. J. Mol. Liq. 2019, 285, 500–507; https://doi.org/10.1016/j.molliq.2019.04.109.Search in Google Scholar

Received: 2022-05-04

Accepted: 2022-06-16

Published Online: 2023-03-21

Published in Print: 2023-05-25

You are currently not able to access this content.

Articles in the same Issue

https://doi.org/10.1515/tsd-2022-2457

Keywords for this article

alkyl glyceryl ether sulfonates; entropy driven; micellization process; surface properties; thermodynamic properties