Acetaldehyde
From Wikipedia, the free encyclopedia
| Acetaldehyde | |
|---|---|
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| IUPAC name |
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| Systematic name | Ethanal |
| Identifiers | |
| CAS number | [] |
| EC 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, 150 K, -190 °F |
| Boiling point |
20.2 °C, 293 K, 68 °F |
| 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 | |
| MSDS | External MSDS |
| EU classification | Very flammable (F+) Harmful (Xn) Carc. Cat. 3 |
| R-phrases | R12 R36/37 R40 |
| S-phrases | (S2) S16 S33 S36/37 |
| NFPA 704 |
 4
2
0
|
| Flash point | −39 °C |
| Autoignition temperature |
185 °C |
| Related compounds | |
| Related aldehydes | Formaldehyde Propionaldehyde Ethylene oxide |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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Acetaldehyde (systematically: ethanal) is an organic chemical compound with the formula CH3CHO or MeCHO. It is a flammable liquid. Acetaldehyde occurs naturally in ripe fruit, coffee, and bread, and is produced by plants as part of their normal metabolism. It is popularly known as a chemical that causes hangovers.[1]
Contents |
[edit] Structure
Like other carbonyl compounds, acetaldehyde tautomerizes to give the enol, ethenol, with Keq = 6 x 10-5.[2]
[edit] Production
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).[citation needed] An important production method for acetaldehyde is the Wacker process.
The hydration of acetylene, catalyzed by mercury salts gives ethenol, which tautomerizes to acetaldehyde. This process was conducted on an industrial scale prior to the Wacker process.[3]
[edit] Reactions
Acetaldehyde is a common 2-carbon building block in organic synthesis.[4] 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.[5] Grignard reagents and organolithium compounds react with MeCHO to give hydroxyethyl derivatives.[6] In one of the more spectacular condensation reactions, three equivalents of formaldehyde add to MeCHO to give pentaerythritol, C(CH2OH)4.[7]
In a Strecker reaction, acetaldehyde condenses with cyanide and ammonia to give, after hydrolysis, the amino acid alanine.[8] 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.[9]
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”).[10]
[edit] Acetal derivatives
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,"[11] although acetal is used more widely to describe other compounds with the formula RCH(OR')2.
[edit] Biochemistry
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.
[edit] Hangover
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.[12] 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. Antabuse is used as a deterrent for alcoholics who wish to stay sober.
[edit] Tobacco addiction
Acetaldehyde is a significant constituent of tobacco smoke. It has been demonstrated to have a synergistic effect with nicotine, increasing the onset and tenacity of addiction to cigarette smoking, particularly in adolescents.[13][14]
[edit] Safety
Acetaldehyde is toxic when applied externally for prolonged periods, an irritant, and a probable carcinogen.[15] In addition, acetaldehyde is damaging to DNA[16] and causes abnormal muscle development as it binds to proteins.[17]
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. [18]
[edit] See also
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Wikimedia Commons has media related to: Category:Acetaldehyde |
[edit] References
- ^ How Hangovers Work, HowStuffWorks
- ^ March, J. “Organic Chemistry: Reactions, Mechanisms, and Structures” J. Wiley, New York: 1992. ISBN 0-471-58148-8.
- ^ Dmitry A. Ponomarev and Sergey M. Shevchenko (2007). "Hydration of Acetylene: A 125th Anniversary". J. Chem. Ed. 84 (10): 1725. http://jchemed.chem.wisc.edu/HS/Journal/Issues/2007/OctACS/ACSSub/p1725.pdf.
- ^ Sowin, T. J.; Melcher, L. M. ”Acetaldehyde” in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289
- ^ Behrens, C.; Paquette, L. A. (2004). "N-Benzyl-2,3-Azetidinedione". Org. Synth.; Coll. Vol. 10: 41.
- ^ Walter, L. A. (1955). "1-(α-Pyridyl)-2-Propanol". Org. Synth.; Coll. Vol. 3: 757.
- ^ Schurink, H. B. J. (1941). "Pentaerythritol". Org. Synth.; Coll. Vol. 1: 425.
- ^ Kendall, E. C. McKenzie, B. F. (1941). "dl-Alanine". Org. Synth.; Coll. Vol. 1: 21.
- ^ Wittig, G.; Hesse, A. (1988). "Directed Aldol Condensations: β-Phenylcinnamaldehyde". Org. Synth.; Coll. Vol. 6: 901.
- ^ Frank, R. L.; Pilgrim, F. J.; Riener, E. F. (1963). "5-Ethyl-2-Methylpyridine". Org. Synth.; Coll. Vol. 4: 451.
- ^ Adkins, H.; Nissen, B. H. (1941). "Acetal". Org. Synth.; Coll. Vol. 1: 1.
- ^ Xiao Q, Weiner H, Crabb DW (1996). "The mutation in the mitochondrial aldehyde dehydrogenase (ALDH2) gene responsible for alcohol-induced flushing increases turnover of the enzyme tetramers in a dominant fashion". J. Clin. Invest. 98 (9): 2027–32. doi:. PMID 8903321. http://www.jci.org/cgi/content/abstract/98/9/2027.
- ^ [http://drugabuse.gov/NIDA_notes/NNvol20N3/Study.html Study Points to Acetaldehyde-Nicotine Combination In Adolescent Addiction]
- ^ Nicotine's addictive hold increases when combined with other tobacco smoke chemicals, UCI study finds
- ^ Chemical Summary For Acetaldehyde, US Environmental Protection Agency
- ^ http://www.ist-world.org/ResultPublicationDetails.aspx?ResultPublicationId=2c488c559db74d8cae0c14ae5b65e14e
- ^ Nicholas S. Aberle, II, Larry Burd, Bonnie H. Zhao and Jun Ren (2004). "Acetaldehyde-induced cardiac contractile dysfunction may be alleviated by vitamin b1 but not by vitamins B6 or B12". Alcohol & Alcoholism 39 (5): 450–454. doi:. http://alcalc.oxfordjournals.org/cgi/content/full/39/5/450.
- ^ Smoking. (2006). Encyclopædia Britannica. Accessed 27 Oct 2006.
[edit] External links
- International Chemical Safety Card 0009
- National Pollutant Inventory - Acetaldehde
- NIOSH Pocket Guide to Chemical Hazards
- Methods for sampling and analysis
- IARC Monograph: "Acetaldehyde"
- Hal Kibbey, Genetic Influences on Alcohol Drinking and Alcoholism, Indiana University Research and Creative Activity, Vol. 17 no. 3.
- United States Food and Drug Administration (FDA) information for acetaldehyde
