Acetaldehyde | |
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IUPAC name | Acetaldehyde |
Systematic name | Ethanal |
Identifiers | |
CAS number | 75-07-0 |
EINECS number | |
RTECS number | AB1925000 |
SMILES |
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ChemSpider ID | |
Properties | |
Molecular formula | C2H4O |
Molar mass | 44.05 g mol−1 |
Appearance | Colorless liquid Pungent, fruity odor |
Density | 0.788 g cm−3 |
Melting point |
−123.5 °C |
Boiling point |
20.2 °C |
Solubility in water | soluble in all proportions |
Viscosity | ~0.215 at 20 °C |
Structure | |
Molecular shape | trigonal planar (sp²) at C1 tetrahedral (sp³) at C2 |
Dipole moment | 2.7 D |
Hazards | |
EU classification | Very flammable (F+) Harmful (Xn) Carc. Cat. 3 |
NFPA 704 |
4
2
0
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R-phrases | R12, R36/37, R40 |
S-phrases | (S2), S16, S33, S36/37 |
Flash point | −39 °C |
Autoignition temperature |
185 °C |
Related compounds | |
Related aldehydes | Formaldehyde Propionaldehyde Ethylene oxide |
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
Acetaldehyde, sometimes known as ethanal, is an organic chemical compound with the formula CH3CHO or MeCHO. It is a flammable liquid with a fruity smell. Acetaldehyde occurs naturally in ripe fruit, coffee, and fresh bread, and is produced by plants as part of their normal metabolism. It is popularly known as the chemical that causes hangovers.[1]
In the chemical industry, acetaldehyde is used as an intermediate in the production of acetic acid, certain esters, and a number of other chemicals. In 1989, US production stood at 740 million pounds (336,000 tonnes). An important production method for acetaldehyde is the Wacker process.
Contents |
In the liver, the enzyme alcohol dehydrogenase converts ethanol into acetaldehyde, which is then further converted into harmless acetic acid by acetaldehyde dehydrogenase. The last steps of alcoholic fermentation in bacteria, plants and yeast involve the conversion of pyruvate into acetaldehyde by the enzyme pyruvate decarboxylase, followed by the conversion of acetaldehyde into ethanol. The latter reaction is again catalyzed by an alcohol dehydrogenase, now operating in the opposite direction.
Most people of East Asian descent have a mutation in their alcohol dehydrogenase gene that makes this enzyme unusually effective at converting ethanol to acetaldehyde, and about half of such people also have a form of acetaldehyde dehydrogenase that is less effective at converting acetaldehyde to acetic acid.[2] This combination causes them to suffer from the alcohol flush reaction, in which acetaldehyde accumulates after drinking, leading to severe and immediate hangover symptoms. These people are therefore less likely to become alcoholics. The drug disulfiram (Antabuse) also prevents the oxidation of acetaldehyde to acetic acid, with the same unpleasant effects for drinkers. It is used in the treatment of alcoholism.
Acetaldehyde is a common 2-carbon building block in organic synthesis.[3] Because of its small size and its availability as the anhydrous monomer (unlike formaldehyde), it is a common electrophile. With respect to its condensation reactions, acetaldehyde is prochiral. It is mainly used as a source of the CH3C+H(OH) synthon in aldol and related condensation reactions.[4] Grignard reagents and organolithium compounds react with MeCHO to give hydroxyethyl derivatives.[5] In one of the more spectacular condensation reactions, three equivalents of formaldehyde add to MeCHO to give pentaerythritol, C(CH2OH)4.[6]
In a Strecker reaction, acetaldehyde condenses with cyanide and ammonia to give, after hydrolysis, the amino acid alanine.[7] Acetaldehyde can condense with amines to yield imines, such as the condensation with cyclohexylamine to give N-ethylidenecyclohexylamine. These imines can be used to direct subsequent reactions like an aldol condensation.[8]
It is also an important building block for the synthesis of heterocyclic compounds. A remarkable example is its conversion upon treatment with ammonia to 5-ethyl-2-methylpyridine ("aldehyde-collidine”).[9]
Three molecules of acetaldehyde condense to form “paraldehyde,” a cyclic trimer containing C-O single bonds; four condense to form the cyclic molecule called metaldehyde.
Acetaldehyde forms a stable acetal upon reaction with ethanol under conditions that favor dehydration. The product, CH3CH(OCH2CH3)2, is in fact called "acetal,"[10] although acetal is used more widely to describe other compounds with the formula RCH(OR')2.
Only a trace of acetaldehyde exists as the enol form, ethenol, with Keq = 6 x 10-5.[11]
Acetaldehyde is an air pollutant resulting from combustion, such as automotive exhaust and tobacco smoke. It is also created by thermal degradation of polymers in the plastics processing industry. [12]
Acetaldehyde is toxic when applied externally for prolonged periods, an irritant, and a probable carcinogen.[13] In addition, acetaldehyde is damaging to both DNA [14] and causes abnormal muscle development as it binds to proteins [15]