What Is C2H5-O-CH=CH2? - Chemistry Stack Exchange

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Learn more about Teams What is C2H5-O-CH=CH2? Ask Question Asked 10 years, 3 months ago Modified 8 years, 9 months ago Viewed 3k times 9 $\begingroup$

Someone painted an original graffiti:

source

I wonder what kind of reaction was depicted; what's that product substance?

The graffiti reads: $\ce{C2H2 + C2H5OH -> C_2H_5-O-CH=CH_2}$

Does it have any more or less common uses?

• organic-chemistry
• identification

Share Cite Improve this question Follow edited Mar 11, 2016 at 22:24 mhchem 3,31622 gold badges1717 silver badges3535 bronze badges asked Aug 21, 2014 at 8:33 SF.SF. 65111 gold badge55 silver badges1818 bronze badges $\endgroup$ Add a comment |

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The particular reaction is of acetylene ($\ce{C2H2}$) and ethanol ($\ce{C2H5OH}$) to yield ethyl vinyl ether (IUPAC name ethoxyethene). It's one example of Reppe chemistry, a fairly diverse set of reactions, often operating on alkenes and alkynes (though certainly not exclusively). The specific reaction in the question is a vinylization reaction, though it was Reppe's carbonylation reactions which were probably of greater practical (read: economic) import historically, as they were famously used in the Monsanto process and in production of various acrylates and other acrylic acid derivatives.

The vinylization reactions could still be synthetically useful, as they provide an extremely simple alternative route to vinyl ethers without having to proceed via elimination, substitution, coupling, olefination, or substrate-specific oxidation reactions.

I'm not aware of any specific uses for ethyl vinyl ether, however it could certainly be used as a building block in any number of organic syntheses.

Share Cite Improve this answer Follow answered Aug 21, 2014 at 11:24 Greg E.Greg E. 11.9k33 gold badges3636 silver badges5656 bronze badges $\endgroup$ 2

• 1 $\begingroup$ Both divinyl ether and diethyl ether are anasthetics. Wikipedia article on divinyl ether lists differences between the two. One can suspect ethyl vinyl ether's properties will sit squat in the middle between them. $\endgroup$ – SF. Commented Aug 21, 2014 at 22:32
• 1 $\begingroup$ @SF., yes, you're right. A targeted search immediately found the following article. I have to suspect it's been retired for that purpose, like most non-halogenated ethers. $\endgroup$ – Greg E. Commented Aug 21, 2014 at 22:49

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