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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.
Hazard Statements: H225-H336
Highly flammable liquid and vapour. May cause drowsiness or dizziness.
Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P261-P271-P280-P303+P361+P353-P304+P340-P312-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Avoid breathing dust/fume/gas/mist/vapours/spray. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Call a POISON CENTER or doctor/physician if you feel unwell. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant