Acetaldehyde

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−123.5 °C, 150 K, -190 °F

20.2 °C, 293 K, 68 °F

Acetaldehyde (systematically ethanal) is an organic chemical compound with the formula CH3CHO or MeCHO. It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale industrially. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants as part of their normal metabolism. It is also produced by oxidation of ethanol and is popularly believed to be a cause of hangovers.[2]

Contents

Production

In 2003, global production was about 106 tons/year.[3] The main production method is the oxidation of ethylene via the Wacker process:

Alternatively, hydration of acetylene, catalyzed by mercury salts gives ethenol, which tautomerizes to acetaldehyde. This industrial route was dominant prior to the Wacker process[4] It is also prepared at smaller levels by both the dehydrogenation and the oxidation of ethanol.

Reactions

Like many other carbonyl compounds, acetaldehyde tautomerizes to give the enol. The enol of acetaldehyde is vinyl alcohol (IUPAC name: ethenol):

The equilibrium constant is only 6 x 10−5 at room temperature, so that the amount of the enol in a sample of acetaldehyde is very small.[5]

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