Abstract
For the purpose of estimating the reaction mechanism of the direct ethoxylation of a fatty ester in the presence of an Al-Mg composite oxide catalyst, a labeled fatty methyl ester C11H23CO18OCH3 containing 18O isotope was synthesized and directly ethoxylated. The product was evaluated by gas chromatography-mass spectrometry (GC-MS). The GC-MS spectra showed that the 18O isotope label was present only in the methoxy group at the molecular end of the ethoxylated fatty methyl ester. This supports the reaction mechanism of coordination anionic polymerization where the bond between the acyl and methoxy groups of the fatty methyl ester molecule was broken, caused by the bifunctional effect of the acid-base active sites; an intermediate chemisorption species was formed; and then ethylene oxide was addition-polymerized sequentially, in parallel.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Hama, I., T. Okamoto, and H. Nakamura, Preparation and Properties of Ethoxylated Fatty Methyl Ester Nonionics, J. Am. Oil Chem. Soc. 72:781–784 (1995).
Schick, M.J., Nonionic Surfactants, Marcel Dekker, New York, 1966, pp. 8–43.
Bender, M.L., and R. J. Thomas, The Concurrent Alkaline Hydrolysis and Isotopic Oxygen Exchange of a Series of p-Substituted Methyl Benzoates, J. Am. Chem. Soc. 83:4193–4196 (1961).
Shain, S.A., and J.F. Kirsch, Absence of Carbonyl Oxygen Exchange Concurrent with the Alkaline Hydrolysis of Substituted Methyl Benzoates, Ibid.:5848–5854 (1968).
McClelland, R.A., Rate-Limiting Deprotonation in Tetrahedral Intermediate Breakdown, Ibid.:7579–7583 (1984).
Wiberg, K.B., The Thermal Rearrangement of Methyl Benzoate, Ibid.:2665–2666 (1953).
Bender, M.L., Oxygen Exchange as Evidence for the Existence of an Intermediate in Ester Hydrolysis, Ibid.:1626–1629 (1951).
Hama, I., T. Okamoto, H. Sasamoto, and H. Nakamura, Japanese Patent JP6-277016A (1994).
Author information
Authors and Affiliations
About this article
Cite this article
Hama, I., Okamoto, T., Hidai, E. et al. Direct ethoxylation of fatty methyl ester over Al-Mg composite oxide catalyst. J Amer Oil Chem Soc 74, 19–24 (1997). https://doi.org/10.1007/s11746-997-0113-1
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s11746-997-0113-1