Startseite Naturwissenschaften Synthesis and surface properties of branched-chain tertiary fatty alcohol sulfate surfactants
Artikel
Lizenziert
Nicht lizenziert Erfordert eine Authentifizierung

Synthesis and surface properties of branched-chain tertiary fatty alcohol sulfate surfactants

  • Qian Wang

    Qian Wang is a M.D. student at the Shanxi Key Laboratory of Chemical Product Engineering, College of Chemical Engineering and Technology, Taiyuan University of Technology, working on the synthesis and application of fine chemicals.

    , Xu Li

    Xu Li is a lecturer at the Shanxi Key Laboratory of Chemical Product Engineering, College of Chemical Engineering and Technology, Taiyuan University of Technology, and conducts research on the synthesis and application of fine chemicals.

    und Jinxiang Dong

    Jinxiang Dong is a professor at the Shanxi Key Laboratory of Chemical Product Engineering, College of Chemical Engineering and Technology at Taiyuan University of Technology. He has been awarded the National Science Fund for Distinguished Young Scholars. His research is on dailysparse washing processes.

    EMAIL logo
Veröffentlicht/Copyright: 28. September 2023
Veröffentlichen auch Sie bei De Gruyter Brill

Abstract

In this paper, anionic branched-chain tertiary fatty alcohol sulfate surfactants were synthesized from n-hexene and n-octene using selective olefin dimerization, hydration reaction (hydroxylation), and sulfur trioxide sulfation. The direct hydration reaction of the α-olefin dimer 2-butyl-1-octene with water as a model reaction was explored for the synthesis of branched-chain tertiary fatty alcohols. Two branched-chain tertiary fatty alcohol sulfate surfactants, namely C12-SBTAS and C16-SBTAS, with different carbon chain lengths, were synthesized by the sulfur trioxide sulfation method. Their structures were confirmed by various analytical techniques, including HPLC, FT-IR, HR-MS, and 1H NMR. Equilibrium and dynamic surface tension, foaming, wetting, and emulsifying properties were compared with those of Guerbet cetyl alcohol sulfate (C16-SGAS). C12-SBTAS and C16-SBTAS exhibited good surface activity with equilibrium surface tension (γ CMC) values of 27.41 mN m−1 and 26.69 mN m−1, respectively. They also had low foaming and rapid defoaming abilities, as well as good wetting and emulsifying properties, which match the application characteristics of typical branched-chain surfactants.


Corresponding author: Jinxiang Dong, Shanxi Key Laboratory of Chemical Product Engineering College of Chemical Engineering and Technology, Taiyuan University of Technology, Taiyuan 030024, Shanxi, China; and School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, Guangdong, China, E-mail:

About the authors

Qian Wang

Qian Wang is a M.D. student at the Shanxi Key Laboratory of Chemical Product Engineering, College of Chemical Engineering and Technology, Taiyuan University of Technology, working on the synthesis and application of fine chemicals.

Xu Li

Xu Li is a lecturer at the Shanxi Key Laboratory of Chemical Product Engineering, College of Chemical Engineering and Technology, Taiyuan University of Technology, and conducts research on the synthesis and application of fine chemicals.

Jinxiang Dong

Jinxiang Dong is a professor at the Shanxi Key Laboratory of Chemical Product Engineering, College of Chemical Engineering and Technology at Taiyuan University of Technology. He has been awarded the National Science Fund for Distinguished Young Scholars. His research is on dailysparse washing processes.

  1. Research ethics: Not applicable.

  2. Author contributions: The authors have accepted responsibility for the entire content of this manuscript and approved its submission.

  3. Competing interests: The authors state no conflict of interest.

  4. Research funding: We thankfully acknowledge the generous financial support from the National Natural Science Foundation of China (Grant numbers. U21A20315, 22078219) and the Fund for Shanxi “1331” Project.

  5. Data availability: The raw data can be obtained on request from the corresponding author.

References

1. Alexander, S., Smith, G. N., James, C., Rogers, S. E., Guittard, F., Sagisaka, M., Eastoe, J. Low-surface energy surfactants with branched hydrocarbon architectures. Langmuir 2014, 30, 3413–3421. https://doi.org/10.1021/la500332s.Suche in Google Scholar PubMed

2. Dong, Q., Li, X., Dong, J. Branched polyoxyethylene surfactants with different hydrophilic head groups from fatty acid derivatives. Colloids Surf., A 2022, 649, 129419. https://doi.org/10.1016/j.colsurfa.2022.129419.Suche in Google Scholar

3. Varadaraj, R., Bock, J., Zushma, S., Brons, N. Influence of hydrocarbon chain branching on interfacial properties of sodium dodecyl sulfate. Langmuir 1992, 8, 14–17. https://doi.org/10.1021/la00037a004.Suche in Google Scholar

4. Ramesh, V., Bock, J., Valant, P. J., Brons, N. Micropolarity and water penetration in micellar aggregates of linear and branched hydrocarbon surfactants. Langmuir 1990, 6, 1376–1378. https://doi.org/10.1021/la00098a010.Suche in Google Scholar

5. Tao, Y., Wu, X., Zhang, W., Wang, F. Study of the synthesis of branched chain alkyl polyglucosides from Guerbet alcohol in an acid/phase transfer catalyst system and their properties. Tenside Surfact. Det. 2020, 57, 420–426. https://doi.org/10.3139/113.110702.Suche in Google Scholar

6. Gabriëls, D., Hernández, W. Y., Sels, B., Van Der Voort, P., Verberckmoes, A. Review of catalytic systems and thermodynamics for the Guerbet condensation reaction and challenges for biomass valorization. Catal. Sci. Technol. 2015, 5, 3876–3902. https://doi.org/10.1039/C5CY00359H.Suche in Google Scholar

7. Di, Z., Zhao, T., Feng, X., Luo, M. A newly designed core-shell-like zeolite capsule catalyst for synthesis of light olefins from Syngas via Fischer–Tropsch synthesis reaction. Catal. Lett. 2019, 149, 441–448. https://doi.org/10.1007/s10562-018-2624-9.Suche in Google Scholar

8. Eldridge, R. B. Olefin/paraffin separation technology: a review. Ind. Eng. Chem. Res. 1993, 32, 2208–2212. https://doi.org/10.1021/ie00022a002.Suche in Google Scholar

9. Antunes, B. M., Rodrigues, A. E., Lin, Z., Portugal, I., Silva, C. M. Alkenes oligomerization with resin catalysts. Fuel Process. Technol. 2015, 138, 86–99. https://doi.org/10.1016/j.fuproc.2015.04.031.Suche in Google Scholar

10. Harvey, B. G., Meylemans, H. A. 1-Hexene: a renewable C6 platform for full-performance jet and diesel fuels. Green Chem. 2014, 16, 770–776. https://doi.org/10.1039/C3GC41554F.Suche in Google Scholar

11. Nifant’ev, I. E., Sevostyanova, N. T., Batashev, S. A., Vinogradov, A. A., Vinogradov, A. A., Churakov, A. V., Ivchenko, P. V. Synthesis of methyl β-alkylcarboxylates by Pd/diphosphine-catalyzed methoxycarbonylation of methylenealkanes RCH2CH2C(R)=CH2. Appl. Catal., A 2019, 581, 123–132. https://doi.org/10.1016/j.apcata.2019.05.030.Suche in Google Scholar

12. Kaminsky, W. Highly active metallocene catalysts for olefin polymerization. J. Chem. Soc., Dalton Trans. 1998, 17, 1413–1418. https://doi.org/10.1039/A800056E.Suche in Google Scholar

13. Pandey, S., Raj, K. V., Shinde, D. R., Vanka, K., Kashyap, V., Kurungot, S., Vinod, C. P., Chikkali, S. H. Iron catalyzed hydroformylation of alkenes under mild conditions: evidence of an Fe(ii) catalyzed process. J. Am. Chem. Soc. 2018, 140, 4430–4439. https://doi.org/10.1021/jacs.8b01286.Suche in Google Scholar PubMed

14. Usui, Y., Sato, K., Tanaka, M. Catalytic dihydroxylation of olefins with hydrogen peroxide: an organic-solvent- and metal-free system. Angew. Chem., Int. Ed. 2003, 42, 5623–5625. https://doi.org/10.1002/anie.200352568.Suche in Google Scholar PubMed

15. Harvey, B. G., Meylemans, H. A., Quintana, R. L. Synthesis of renewable plasticizer alcohols by formal anti-Markovnikov hydration of terminal branched chain alkenes via a borane-free oxidation/reduction sequence. Green Chem. 2012, 14, 2450–2456. https://doi.org/10.1039/C2GC35595G.Suche in Google Scholar

16. Jia, J., Li, J., Liang, Y., Peng, B. Molecular dynamics study on performance of olefin sulfonate at the decane–water interface: effect of molecular architecture. Fuel 2022, 308, 122013. https://doi.org/10.1016/j.fuel.2021.122013.Suche in Google Scholar

17. Li, X., Li, J., Wang, X., Yang, L., Xu, H., Dong, J. Novel branched-chain sulfonate surfactants based on α-olefins from Fischer–Tropsch synthesis via reaction-separation-utilization integrated process. Fuel 2023, 339, 126961. https://doi.org/10.1016/j.fuel.2022.126961.Suche in Google Scholar

18. Varadaraj, R., Bock, J., Valint, P.Jr., Zushma, S. Thermodynamics of adsorption and micellization in linear and Guerbet sulfate and ethoxy sulfate surfactants. J. Phys. Chem. 1991, 95, 1682–1684. https://doi.org/10.1021/j100157a036.Suche in Google Scholar

19. Dong, Q., Li, X., Dong, J. Synthesis and properties of ethoxylated vicinal diol nonionic surfactants with double hydrophilic head groups. Colloids Surf., A 2022, 634, 127971. https://doi.org/10.1016/j.colsurfa.2021.127971.Suche in Google Scholar

20. Davies, J. T. Interfacial Phenomena; Academic Press Inc.: New York, 2011.Suche in Google Scholar

21. Rosen, M. J., Kunjappu, J. T. Surfactants and Interfacial Phenomena; John Wiley & Sons: New York, 2012.10.1002/9781118228920Suche in Google Scholar

22. Schulman, J. H., Leja, J. Control of contact angles at the oil-water-solid interfaces. Emulsions stabilized by solid particles (BaSO4). Trans. Faraday Soc. 1954, 50, 598–605. https://doi.org/10.1039/TF9545000598.Suche in Google Scholar

23. Hattori, H., Ono, Y. Solid acid catalysis: from Fundamentals to applications. Focus Catalysts 2015, 395, 7. https://doi.org/10.1016/j.focat.2015.07.088.Suche in Google Scholar

24. Arnett, E. M., Mach, G. W. Solvent effects in organic chemistry. VIII. Acidity function failure in different aqueous acids. J. Am. Chem. Soc. 1966, 88, 1177–1183. https://doi.org/10.1021/ja00958a019.Suche in Google Scholar

25. Chakrabarti, A., Sharma, M. M. Cationic ion exchange resins as catalyst. React. Polym. 1993, 20, 1–45. https://doi.org/10.1016/0923-1137(93)90064-M.Suche in Google Scholar

26. Karam, A., De Oliveira Vigier, K., Marinkovic, S., Estrine, B., Oldani, C., Jérôme, F. High catalytic performance of Aquivion PFSA, a reusable solid perfluorosulfonic acid polymer, in the biphasic glycosylation of glucose with fatty alcohols. ACS Catal. 2017, 7, 2990–2997. https://doi.org/10.1021/acscatal.6b03561.Suche in Google Scholar

27. Zhang, S., Hong, B., Fan, Z., Lu, J., Xu, Y., Pera-Titus, M. Aquivion–carbon composites with tunable amphiphilicity for pickering interfacial catalysis. ACS Appl. Mater. Interfaces 2018, 10, 26795–26804. https://doi.org/10.1021/acsami.8b08649.Suche in Google Scholar PubMed

28. Dou, Y., Zhou, S., Oldani, C., Fang, W., Cao, Q. 5-Hydroxymethylfurfural production from dehydration of fructose catalyzed by Aquivion@silica solid acid. Fuel 2018, 214, 45–54. https://doi.org/10.1016/j.fuel.2017.10.124.Suche in Google Scholar

29. Fang, W., Wang, S., Liebens, A., De Campo, F., Xu, H., Shen, W., Pera-Titus, M., Clacens, J.-M. Silica-immobilized Aquivion PFSA superacid: application to heterogeneous direct etherification of glycerol with n-butanol. Catal. Sci. Technol. 2015, 5, 3980–3990. https://doi.org/10.1039/C5CY00534E.Suche in Google Scholar

30. Su, G. M., Cordova, I. A., Yandrasits, M. A., Lindell, M., Feng, J., Wang, C., Kusoglu, A. Chemical and morphological origins of improved ion conductivity in perfluoro ionene chain extended ionomers. J. Am. Chem. Soc. 2019, 141, 13547–13561. https://doi.org/10.1021/jacs.9b05322.Suche in Google Scholar PubMed

31. Glueckauf, E., Kitt, G. P., Bell, R. P. A theoretical treatment of cation exchangers – III. The hydration of cations in polystyrene sulphonates. Proc. R. Soc. Lond. A Math. Phys. Sci. 1955, 228, 322–341. https://doi.org/10.1098/rspa.1955.0051.Suche in Google Scholar

32. Cha, J. Morphological effect of side chain on H3O+ transfer inside polymer electrolyte membranes across polymeric chain via molecular dynamics simulation. Sci. Rep-Uk. 2020, 10, 22014. https://doi.org/10.1038/s41598-020-77971-6.Suche in Google Scholar PubMed PubMed Central

33. Harmer, M. A., Sun, Q. Solid acid catalysis using ion-exchange resins. Appl. Catal., A 2001, 221, 45–62. https://doi.org/10.1016/S0926-860X(01)00794-3.Suche in Google Scholar

34. Kusoglu, A., Dursch, T. J., Weber, A. Z. Nanostructure/swelling relationships of bulk and thin-film PFSA ionomers. Adv. Funct. Mater. 2016, 26, 4961–4975. https://doi.org/10.1002/adfm.201600861.Suche in Google Scholar

35. Mosely, R. B., Papadopoulos, M. N. Hydration of Olefins to Alcohols and Ethers Using Halogenated Alkanol Solvents US3299150[P]. 1967-01-17.Suche in Google Scholar

36. Chen, M., Lu, W., Zhu, H., Gong, L., Zhao, Z., Ding, Y. Dehydration of long-chain n-alcohols to linear α-olefins using sodium-modified γ-Al2O3. Ind. Eng. Chem. Res. 2020, 59, 4388–4396. https://doi.org/10.1021/acs.iecr.9b06951.Suche in Google Scholar

37. Miles, M. G., Doyle, G., Cooney, R. P., Tobias, R. S. Raman and infrared spectra and normal coordinates of the trifluoromethanesulfonate and trichloromethanesulfonate anions. Spectrochim. Acta A Mol. Biomol. Spectrosc. 1969, 25, 1515–1526. https://doi.org/10.1016/0584-8539(69)80135-2.Suche in Google Scholar

38. Buzzoni, R., Bordiga, S., Ricchiardi, G., Spoto, G., Zecchina, A. Interaction of H2O, CH3OH, (CH3)2O, CH3CN, and pyridine with the superacid perfluorosulfonic membrane Nafion: an IR and Raman study. J. Phys. Chem. 1995, 99, 11937–11951. https://doi.org/10.1021/j100031a023.Suche in Google Scholar

39. Lowry, S. R., Mauritz, K. A. An investigation of ionic hydration effects in perfluorosulfonate ionomers by Fourier transform infrared spectroscopy. J. Am. Chem. Soc. 1980, 102, 4665–4667. https://doi.org/10.1021/ja00534a017.Suche in Google Scholar

40. Harmer, M. A., Farneth, W. E., Sun, Q. High surface area Nafion resin/silica nanocomposites: a new class of solid acid catalyst. J. Am. Chem. Soc. 1996, 118, 7708–7715. https://doi.org/10.1021/ja9541950.Suche in Google Scholar

41. Paul, S., Choi, S.-J., Kim, H. J. Enhanced proton conductivity of a Zn(II)-based MOF/Aquivion composite membrane for PEMFC applications. Energ Fuel 2020, 34, 10067–10077. https://doi.org/10.1021/acs.energyfuels.0c01703.Suche in Google Scholar

42. Holler, F., Callis, J. B. Conformation of the hydrocarbon chains of sodium dodecyl sulfate molecules in micelles: an FTIR study. J. Phys. Chem. 1989, 93, 2053–2058. https://doi.org/10.1021/j100342a068.Suche in Google Scholar

43. Liu, X., Zhao, Y., Li, Q., Niu, J. Surface tension, interfacial tension and emulsification of sodium dodecyl sulfate extended surfactant. Colloids Surf. A Physicochem. Eng. Asp. 2016, 494, 201–208. https://doi.org/10.1016/j.colsurfa.2016.01.037.Suche in Google Scholar

44. Varadaraj, R., Bock, J., Valint, P.Jr., Zushma, S., Thomas, R. Fundamental interfacial properties of alkyl-branched sulfate and ethoxy sulfate surfactants derived from Guerbet alcohols. 1. Surface and instantaneous interfacial tensions. J. Phys. Chem. 1991, 95, 1671–1676. https://doi.org/10.1021/j100157a033.Suche in Google Scholar

45. Yang, L., Li, X., Dong, J. Renewable branched-chain sulfonate surfactants by addition of sodium hydrogensulfite to alkyl oleate. Colloids Surf. A Physicochem. Eng. Asp. 2022, 641, 128513. https://doi.org/10.1016/j.colsurfa.2022.128513.Suche in Google Scholar

46. Varadaraj, R., Bock, J., Valint, P., Zushma, S., Brons, N. Relationship between fundamental interfacial properties and foaming in linear and branched sulfate, ethoxysulfate, and ethoxylate surfactants. J. Colloid Interf. Sci. 1990, 140, 31–34. https://doi.org/10.1016/0021-9797(90)90317-H.Suche in Google Scholar

47. Zhang, Y., Li, Y., Song, Y., Li, J. Synthesis and aggregation behaviors of tail-branched surfactant Guerbet-cetyl trimethyl ammonium chloride. Colloid Polym. Sci. 2016, 294, 271–279. https://doi.org/10.1007/s00396-015-3771-9.Suche in Google Scholar

48. Zhang, Q., Li, Y., Song, Y., Li, J., Wang, Z. Properties of branched alcohol polyoxyethylene ether carboxylates. J. Mol. Liq. 2018, 258, 34–39. https://doi.org/10.1016/j.molliq.2018.02.107.Suche in Google Scholar

49. Kang, P., Xu, H. Synthesis and properties of dissymmetric Gemini surfactants. J. Surfactants Deterg. 2013, 16, 921–925. https://doi.org/10.1007/s11743-013-1499-4.Suche in Google Scholar

50. Rahaman, S. M., Bardhan, A., Mandal, T., Chakraborty, M., Karmakar, K., Dhibar, S., Sharma, S., Chakravarty, M., Ibrahim, S. M., Saha, B. Understanding the effect of surfactants’ hydrophobicity on the growth of lanthanum sulfide nanospheres in water-in-oil microemulsions: a detailed dynamic light scattering, small angle X-ray scattering, and microscopy study. New J. Chem. 2023, 47, 10309–10321. https://doi.org/10.1039/d3nj00935a.Suche in Google Scholar

51. Rahaman, S. M., Chakraborty, M., Mandal, T., Kundu, S., Dhibar, S., Kumar, D., Ibrahim, S. M., Chakravarty, M., Saha, B. Mechanically tuned lanthanum carbonate nanorods in water-in-oil microemulsion scaffolds. J. Mol. Liq. 2023, 372, 121204. https://doi.org/10.1016/j.molliq.2023.121204.Suche in Google Scholar

Received: 2023-06-01
Accepted: 2023-07-10
Published Online: 2023-09-28
Published in Print: 2023-11-27

© 2023 Walter de Gruyter GmbH, Berlin/Boston

Heruntergeladen am 20.12.2025 von https://www.degruyterbrill.com/document/doi/10.1515/tsd-2023-2534/html
Button zum nach oben scrollen