Benzyl ether from phase transfer catalyzed strongly alkaline hydrolysis of benzyl chloride |
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| Affiliation: | 1. Institute of Inorganic Chemistry Siberian Branch of RAS, 630090 Novosibirsk, Russia;2. Novosibirsk National Research State University, 630090 Novosibirsk, Russia;3. Institute of Physical and Organic Chemistry, Southern Federal University, 344090 Rostov-on-Don, Russia;4. Federal Research Centre of Fundamental and Translational Medicine, Institute of Molecular Biology and Biophysics, 630117 Novosibirsk, Russia;1. Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt;2. Department of Physics and Chemistry, Faculty of Education, Alexandria University, Egypt;3. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Alexandria University, Alexandria 21521, Egypt;4. Department of Clinical Pharmacology, Faculty of Medicine, University of Alexandria, Alexandria, Egypt;5. Department of Applied Chemistry, Faculty of Applied Science, Taibah University, Saudi Arabia;6. Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia;1. School of Chemical Engineering and Resource Recycling, Wuzhou University, Wuzhou 543002, PR China;2. School of Chemistry and Biological Engineering, Hechi University, Hechi 546300, PR China;1. Chemistry Department, Faculty of Science, Helwan University, Ain Helwan, Cairo, Egypt;2. Chemical and Materials Engineering Department, Faculty of Engineering, King Abdulaziz University, P.O. Box 80204, Jeddah 21589, Saudi Arabia;3. Applied Organic Chemistry Department, National Research Centre, Dokki, 12622, Cairo, Egypt |
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| Abstract: | The overall rate equation for the production of benzyl ether by phase transfer catalyzed strongly alkaline hydrolysis of benzyl chloride in the pseudo-steady state was derived. The effects of the concentrations and the sizes of the alkyl substituents of the catalysts, the concentration of hydroxide ions in the aqueous phase, the volume-fraction of the organic phase, the reaction temperature and the stirring speed on the production rate of benzyl ether can be explained with the derived rate equation. Under the conditions of 0.842 mol benzyl chloride, 50% aq. NaOH (2.5 mol NaOH), 42.2 mmol Bz(C2H5)3NCl, 70 °C and 500 rpm, the reactions proceeded to nearly 100% benzyl ether within 2 h. The cocatalyst, NaI, is effective for improving the reaction rate, suitable amounts being ~ 5% of the substrate, benzyl chloride. The decomposition rate of the practical catalyst, Bz(C2H5)3NCl, in 30% aq. NaOH at 70 °C is only about 3% per day. The conditions for producing benzyl ether by phase transfer catalyzed hydrolysis of benzyl chloride can be obtained from the rate equation and the experimental data. |
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