Abstract
Simple economical syntheses in good yield of octa-, nona-, and undecaethylene glycols were developed based on a coupling methodology whereby monobenzyl trior tetraethylene glycols were chain-extended either by coupling them together in the presence of tosyl chloride or through reaction with α,ω-ditosyl triethylene glycol in dioxane in the presence of powdered KOH. The α,ω-O-benzyl-protecting groups were removed by catalytic hydrogenolysis.
Similar content being viewed by others
References
Vitali, C.A., and B. Masci, Template Effects 7. Large Unsubstituted Crown Ethers from Polyethelene Glycols, Tetrahedron 45: 2201 (1989).
Ouchi, M., Y. Inoue, T. Kanzaki, and T. Hakushi, Molecular Design of Crown Ethers, J. Org. Chem. 49:1408 (1984).
Goodlett, V.W., Use of in situ Reactions for Characterization of Alcohols and Glycols by Nuclear Magnetic Resonance, Anal. Chem. 37:431 (1965).
Mak, H.D., and M.G. Rogers, Determination of Chain Branching in Epoxy Resins by NMR Spectroscopy. Ibid. 44:837 (1972).
De Vos, R., and E.J. Goethals, End Group Analysis of Commercial Polyethylene Glycol Monomethyl Ethers, Polym. Bull. 15: 547 (1985).
Bömer, B., W. Weitz, and W. Kern, Preparation of Monodisperse Polyethylene Oxides by Gel Permeation Chromatography of Discontinuous Polymer-Homologous Series, J. Chromatogr. 53:51 (1970).
Marshall, A., R.H. Mobbs, and C. Booth, Preparation of Polyethylene Glycol Oligomers, Eur. Polym. J. 16:881 (1980).
Teo, H.H., R.H. Mobbs, and C. Booth, Preparation of Polyethylene Glycol Oligomers II, Ibid. 18:541 (1982).
Kinugasa, S., and S. Hattori, Preparation of Pure Octadecaethylene Glycol, Kagaku Gijutsu Kenkyusho Hokuku 85:129 (1990); Chem. Abstr. 113:212771d (1990).
Kinugasa, S., A. Takatsu, H. Nakanishi, N. Nakahara, and S. Hattori, Preparation and Characterization of Pure Oligo(ethylene glycols), Macromolecules 25:4848 (1992).
Yeates, S., H.H., Teo, R.H. Mobbs, and C. Booth, Ethylene Glycol Oligomers, Makromol. Chem. 185:1559 (1984).
Coudert, G., M. Mpassi, G. Gillaumet, and C. Selve, A Novel Unequivocal Synthesis of Polyethylene Glycols, Synthetic Commun. 16:19 (1986).
Achilefu, S., C. Selve, M.J. Stébé, J.C. Raven, and J.J. Delpuech, Monodisperse Perfluoroalkyl Oxyethylene Nonionic Surfactants with Methoxy Capping: Synthesis and Phase Behavior of Water/Surfactant Binary Systems, Langmuir 10:2131 (1994).
Selve, C., S. Achilefu, and L. Mansuy, A Novel Procedure for the Synthesis of Ether-Bridged Perfluoro Nonionic Surfactants, Syn. Commun. 20:799 (1990).
Selve, C., and A. Achilefu, Synthesis of Mono-Disperse Perfluoroalkyloxy Ethylene Surfactants with Methoxy Capping: Surfactants of High Chemical Inertness, J. Chem. Soc. Chem. Commun.: 911 (1990).
Nakatsuji, Y., N. Kameda, and M. Okahara, A Facile Synthesis of Hexa- and Octa-ethylene Glycols, Synthesis:280 (1987).
Keegstra, E.M.D., J.W. Zwikker, M.A. Roest, and L.W. Jenneskens, A Highly Selective Synthesis of Monodisperse Oligo (ethylene glycols), J. Org. Chem. 57:6678 (1992).
Dust, J.M., Z. Fang, and J.M. Harris, Proton NMR Characterization of Poly(ethylene glycols) and Derivatives, Macromolecules 23:3742 (1990).
Author information
Authors and Affiliations
About this article
Cite this article
Zada, A., Avny, Y. & Zilkha, A. Simplified synthesis of oligoethylene glycols. J Surfact Deterg 4, 163–166 (2001). https://doi.org/10.1007/s11743-001-0170-8
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s11743-001-0170-8