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Ethyl vinyl ether is used in fragrances, lubricating oil additives and spices preparation. It acts as an intermediate for sulfadiazine. It finds application in pharmaceuticals as anesthetics and analgesics. Further, it is used as a solvent in organic synthesis.
Acid-catalyzed reaction with alcohols gives 1-ethoxyethyl (EE) ethers, useful as protected derivatives, e.g. in reactions with organometallics. Possible catalysts include: tosic acid: J. Am. Chem. Soc., 101, 7104 (1979); Org. Synth., 76, 199 (1998), PPTS: Tetrahedron Lett., 28, 4303 (1987), or dichloroacetic acid: J. Org. Chem., 37, 1947 (1972). Cleavage of this mixed acetal occurs in dilute acid, more readily than THP ether (see 3,4-Dihydro-2H-pyran, L02731). Protection of cyanohydrins allows use as acyl anion equivalents: Org. Synth. Coll., 7, 381 (1990):
Also used in the protection of phenols as EE ethers which can be cleaved by acid-catalyzed methanolysis: J. Am. Chem. Soc., 119, 8071 (1997).
In the presence of Montmorillonite K10, an addition reaction with diethyl acetals gives the ß-ethoxy acetal of the bis-homologated aldehyde, providing, on acid cleavage, an effective route to the corresponding ɑß-unsaturated aldehyde: Synthesis, 137 (1981).
Khavani, M.; Izadyar, M. A comprehensive study of the solvent effects on the cycloaddition reaction of diethyl azodicarboxylate and ethyl vinyl ether: Efficient implementation of QM and TD-DFT study. Int. J. Quantum Chem. 2015, 115 (6), 381-388.
Han, D.; Cao, H.; Li, M.; Li, X.; Zhang, S.; He, M.; Hu, J. Computational study on the mechanisms and rate constants of the OH-initiated oxidation of ethyl vinyl ether in atmosphere. J. Phys. Chem. A 2015, 119 (4), 719-727.
Gefahrenhinweise (EU): H224-H319-H335-H336
Extremely flammable liquid and vapour. Causes serious eye irritation. May cause respiratory irritation. May cause drowsiness or dizziness.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.