Abstract
A new family of anionic surfactants has been produced by the simultaneous sulfonation and alkylation of aromatic compounds using olefin sulfonic acid(s). This new process does not require the conventional alkylation unit and the strong acid catalysts, such as AlCl3 or HF, normally used for alkylation. The resulting alkylaryl sulfonic acids differ from existing prodeucts by having the sulfonate group attached to the alkyl chain rather than the aromatic ring. This allows for further derivatization of the aromatic compounds by leaving more positions open on the ring. Aromatic compounds that lend themselves to the new process include benzene, toluene, xylene, alkylbenzenes, phenol, alkylphenols, alkoxylated phenols, alkoxylated alkylphenols, alkoxylated alkylphenol/formaldehyde resins, naphthalene, and alkylnaphthalenes. Any type of olefin that can be sulfonated can be used as the starting material. These include internal and α-olefins, linear and branched olefins, polyolefins, and vinylidenes. Mono- and disulfonated compounds, as well as geminitype surfactants, are easily prepared.
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References
Berger, P.D., C.H. Berger, and S.J. Herron, Chemistry of Olefin Acids. 1. Alkylation of Aromatic Sulfonic Acid, in Proceedings of the 5th World Surfactants Congress, FEDERCHIMICA, Milan, Vol. 1, 2001, p. 291.
Berger, P.D., C.H. Berger, and I.K. Hsu, Anionic Surfactants Based on alkene Sulfonic Acid, U.S. Patent 6,043,391 (2000)
Suter, M.L., Process for Sulphonating and Sulfating Olefins, U.S. Patent 2,366,133 (1944).
Tokiwa, F., and K. Tsujii, NMR Study of the Interaction Between Anionic and Nonionic Surfactants in Their Mixed Micells II, Colloid Interface Sci. 41:343 (1972).
Weil, J.K., A.J. Stirton, and F.D. Smith, Sulfonation of Hexadecene-1 and Octadecene-1, J. Am. Oil Chem. Soc., 42:873 (1965).
Finke, G.W., Process for Sulphonation of Organic Compounds, U.S. Patent 2,572,605 (1951).
Nelson, W.D., Normal Alkenyl-1-sulfonate Detergents, U.S. Patent 3,444,191 (1969).
Rosen, M.J., Geminis: A New Generation of Surfactants, CHEMTECH 30:31, 1993.
Van Zon, A., J.T. Bouman, H.H. Deuling, S. Karaborni, J. Karthaeuser, H.T.G.A. Memsen, N.M. van Os, and K.H. Raney, The Synthesis and Performance of Anionic Gemini Surfactants, Tenside Surf. Det. 36:84 (1999).
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Berger, P.D., Lee, C.H. New anionic alkylaryl surfactants based on olefin sulfonic acids. J Surfact Deterg 5, 39–43 (2002). https://doi.org/10.1007/s11743-002-0203-3
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DOI: https://doi.org/10.1007/s11743-002-0203-3