Abstract
A comparison of liquid-liquid and solid-liquid PTC for the selective synthesis of diglycidyl ether from protected pentaerythritol and epichlorohydrin is presented. Solid-liquid PTC was found to be more useful than liquid-liquid PTC because the use of water or other solvents can be avoided and higher yields and selectivity are achieved. It was proved that etherification takes place in the solid phase-organic phase system even in the absence of the phase-transfer catalyst. However, the use of tetrabutylammonium bisulfate as catalyst is essential due to its crucial effect on the enhancement of the rate of etherification and on the improvement of the selectivity to diglycidyl ether, which is higher than 98%.
Similar content being viewed by others
REFERENCES
F.M. Menger, J.S. Keiper: Angew. Chem. Int. Ed., 39, 1906 (2000).
F.M. Menger, B.N.A. Mbadugha: J. Am. Chem. Soc., 123, 875 (2001).
Y. Zhu, A. Masuyama, Y. Kirito, M. Okahara, M. Rosen: JAOCS, 69, 7, 626 (1992).
M.C. Murguía, R.J. Grau: Synlett, 8, 1229 (2001).
H.H. Freedman, R.A. Dubois: Tetrahedron Lett., 38, 3251 (1975).
K. Urata, S. Yano, A. Kawamata, N. Takaishi, Y. Inamoto: JAOCS, 65, 8, 1299 (1988).
X. Gu, I. Ikeda, M. Okahara: Synthesis, 649 (1985).
Y. Zhu, A. Masuyama, Y. Kirito, M. Okahara: JAOCS, 68, 7, 539 (1991).
H. Kang, B.M. Lee, J. Yoon, M. Yoon: JAOCS, 78, 4, 423 (2001).
M.C. Murguía, S. Vaillard, R.J. Grau: Synthesis, 7, 1093 (2001).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Murguía, M.C., Cabrera, M.I. & Grau, R.J. Selective preparation of key intermediates for the synthesis of key intermediates for the synthesis of gemini surfactants by phase-transfer catalysis. Reaction Kinetics and Catalysis Letters 75, 205–211 (2002). https://doi.org/10.1023/A:1015219825198
Issue Date:
DOI: https://doi.org/10.1023/A:1015219825198