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Acetaldehído
Lewis structure of acetaldehyde
Skeletal structure of acetaldehyde
Ball-and-stick model
Space-filling model
Nombres
Nombre IUPAC preferido
Acetaldehído [3]
Nombre IUPAC sistemático
Etanal [3]
Otros nombres
Aldehído acético
Etil aldehído [1]
Acetilaldehído [2]
Identificadores
Modelo 3D ( JSmol )
CHEBI
CHEMBL
ChemSpider
Tarjeta de información ECHA100.000.761 Edit this at Wikidata
Número CE
  • 200-836-8
KEGG
Número RTECS
  • AB1925000
UNII
  • EnChI = 1S / C2H4O / c1-2-3 / h2H, 1H3 checkY
    Clave: IKHGUXGNUITLKF-UHFFFAOYSA-N checkY
  • EnChI = 1 / C2H4O / c1-2-3 / h2H, 1H3
    Clave: IKHGUXGNUITLKF-UHFFFAOYAB
  • O = CC
  • CC = O
Propiedades
C 2 H 4 O
Masa molar44,053  g · mol −1
AparienciaLíquido incoloro
OlorEtéreo
Densidad0,784 g · cm −3 (20 ° C) [4]

0,7904–0,7928 g · cm −3 (10 ° C) [4]

Punto de fusion −123,37 ° C (−190,07 ° F; 149,78 K)
Punto de ebullición 20,2 ° C (68,4 ° F; 293,3 K)
miscible
Solubilidadmiscible con etanol , éter , benceno , tolueno , xileno , trementina , acetona
ligeramente soluble en cloroformo
log P-0,34
Presión de vapor740 mmHg (20 ° C) [5]
Acidez (p K a )13,57 (25 ° C, H 2 O) [6]
Susceptibilidad magnética (χ)
-.5153 −6 cm 3 / g
Índice de refracción ( n D )
1.3316
Viscosidad0,21 mPa-sa 20 ° C (0,253 mPa-sa 9,5 ° C) [7]
Estructura
Forma molecular
trigonal planar (sp²) en C 1
tetraédrico (sp³) en C 2
Momento bipolar
2,7 D
Termoquímica
Entropía molar estándar ( S o 298 )
250 J · mol −1 · K −1
Entalpía estándar de formación (Δ f H ⦵ 298 )
−166 kJ · mol −1
Peligros
Principales peligrospotencial carcinógeno ocupacional [9]
Ficha de datos de seguridadVer: página de datos
HMDB
Pictogramas GHS[8]
Declaraciones de peligro GHS
H224 , H319 , H335 , H351 [8]
Consejos de prudencia del SGA
P210 , P261 , P281 , P305 + 351 + 338 [8]
NFPA 704 (diamante de fuego)
3
4
3
punto de inflamabilidad-39,00 ° C; -38,20 ° F; 234,15 K
autoignición temperatura
175,00 ° C; 347,00 ° F; 448,15 K [5]
Límites explosivos4.0–60%
Dosis o concentración letal (LD, LC):
LD 50 ( dosis mediana )
1930 mg / kg (rata, oral)
LC 50 ( concentración media )
13.000 ppm (rata),
17.000 ppm (hámster),
20.000 ppm (rata) [9]
NIOSH (límites de exposición a la salud de EE. UU.):
PEL (permitido)
200 ppm (360 mg / m 3 ) [5]
IDLH (peligro inmediato)
2000 ppm [5] [9]
Compuestos relacionados
Aldehídos relacionados
Propionaldehído formaldehído
Compuestos relacionados
Óxido de etileno
Página de datos complementarios
Estructura y propiedades
Índice de refracción ( n ),
constante dieléctrica (ε r ), etc.

Datos termodinámicos
Comportamiento de fase
sólido-líquido-gas
Datos espectrales
UV , IR , RMN , MS
Salvo que se indique lo contrario, los datos se proporcionan para materiales en su estado estándar (a 25 ° C [77 ° F], 100 kPa).
checkY verificar  ( ¿qué es   ?)checkY☒N
Referencias de Infobox

El etanal (nombre común acetaldehído ) es un compuesto químico orgánico con la fórmula CH 3 CHO , a veces abreviado por los químicos como MeCHO (Me = metilo ). Es uno de los aldehídos más importantes , se encuentra ampliamente en la naturaleza y se produce a gran escala en la industria. El acetaldehído se encuentra naturalmente en el café, el pan y la fruta madura, [10] y es producido por las plantas. También se produce por la oxidación parcial del etanol por la enzima hepática alcohol deshidrogenasa y es una causa que contribuye a la resaca después del alcohol.consumo. Las vías de exposición incluyen el aire, el agua, la tierra o las aguas subterráneas, así como la bebida y el humo. [11] El consumo de disulfiram inhibe la acetaldehído deshidrogenasa , la enzima responsable del metabolismo del acetaldehído, lo que hace que se acumule en el cuerpo.

La Agencia Internacional para la Investigación del Cáncer (IARC) ha incluido el acetaldehído como carcinógeno del Grupo 1 . [12] El acetaldehído es "una de las toxinas del aire que se encuentran con mayor frecuencia con un riesgo de cáncer superior a uno en un millón". [13]

Historia [ editar ]

El acetaldehído fue observado por primera vez por el farmacéutico / químico sueco Carl Wilhelm Scheele (1774); [14] luego fue investigado por los químicos franceses Antoine François, conde de Fourcroy y Louis Nicolas Vauquelin (1800), [15] y los químicos alemanes Johann Wolfgang Döbereiner (1821, 1822, 1832) [16] y Justus von Liebig ( 1835). [17] [18] En 1835, Liebig lo llamó "aldehído"; [19] el nombre fue posteriormente modificado a "acetaldehído". [20]

Producción [ editar ]

En 2003, la producción mundial fue de alrededor de 1 millón de toneladas. Antes de 1962, el etanol y el acetileno eran las principales fuentes de acetaldehído. Desde entonces, el etileno es la materia prima dominante . [21]

El principal método de producción es la oxidación del etileno mediante el proceso Wacker , que implica la oxidación del etileno mediante un sistema homogéneo de paladio / cobre:

2 CH 2 = CH 2 + O 2 → 2 CH 3 CHO

En la década de 1970, la capacidad mundial del proceso de oxidación directa de Wacker-Hoechst superó los 2 millones de toneladas anuales.

Pueden prepararse cantidades más pequeñas mediante la oxidación parcial de etanol en una reacción exotérmica. Este proceso generalmente se realiza sobre un catalizador de plata a aproximadamente 500–650 ° C. [21]

CH 3 CH 2 OH + 1 ⁄ 2 O 2 → CH 3 CHO + H 2 O

Este método es una de las rutas más antiguas para la preparación industrial de acetaldehído.

Otros métodos [ editar ]

Hidratación de acetileno [ editar ]

Prior to the Wacker process and the availability of cheap ethylene, acetaldehyde was produced by the hydration of acetylene.[22] This reaction is catalyzed by mercury(II) salts:

C2H2 + Hg2+ + H2O → CH3CHO + Hg

El mecanismo implica la intermediación del alcohol vinílico , que se tautomeriza a acetaldehído. La reacción se lleva a cabo a 90–95 ° C, y el acetaldehído formado se separa del agua y el mercurio y se enfría a 25–30 ° C. En el proceso de oxidación húmeda , se utiliza sulfato de hierro (III) para reoxidar el mercurio de nuevo a la sal de mercurio (II). El sulfato de hierro (II) resultante se oxida en un reactor separado con ácido nítrico . [21]

Deshidrogenación de etanol [ editar ]

Tradicionalmente, el acetaldehído se producía mediante la deshidrogenación parcial de etanol:

CH 3 CH 2 OH → CH 3 CHO + H 2

En este proceso endotérmico, el vapor de etanol pasa a 260-290 ° C sobre un catalizador a base de cobre. El proceso fue una vez atractivo debido al valor del coproducto de hidrógeno, [21] pero en los tiempos modernos no es económicamente viable.

Hidroformilación de metanol [ editar ]

La hidroformilación de metanol con catalizadores como sales de cobalto, níquel o hierro también produce acetaldehído, aunque este proceso no tiene importancia industrial. De manera similar, el acetaldehído no competitivo surge del gas de síntesis con una selectividad moderada. [21]

Reacciones [ editar ]

Tautomerización de acetaldehído en alcohol vinílico [ editar ]

Equilibrio tautomérico entre acetaldehído y alcohol vinílico.

Como muchos otros compuestos de carbonilo , el acetaldehído se tautomeriza para dar un enol ( alcohol vinílico ; nombre IUPAC: etenol):

CH 3 CH = O ⇌ CH 2 = CHOH ∆ H 298, g = +42,7 kJ / mol               

La constante de equilibrio es 6 × 10 −7 a temperatura ambiente, por lo que la cantidad relativa de la forma enol en una muestra de acetaldehído es muy pequeña. [23] A temperatura ambiente, el acetaldehído (CH 3 CH = O) es más estable que el alcohol vinílico (CH 2 = CHOH) en 42,7 kJ / mol: [24] En general, la tautomerización ceto-enólica ocurre lentamente pero es catalizada por ácidos.

La tautomerización ceto-enólica fotoinducida es viable en condiciones atmosféricas o estratosféricas. Esta foto-tautomerización es relevante para la atmósfera terrestre, porque se cree que el alcohol vinílico es un precursor de los ácidos carboxílicos en la atmósfera. [25] [26]

Reacciones de condensación [ editar ]

El acetaldehído es un electrófilo común en la síntesis orgánica . [27] En las reacciones de condensación, el acetaldehído es proquiral . Se utiliza principalmente como fuente del sintón "CH 3 C + H (OH)" en aldol y reacciones de condensación relacionadas. [28] Los reactivos de Grignard y los compuestos de organolitio reaccionan con MeCHO para dar derivados de hidroxietilo . [29] En una de las reacciones de condensación más espectaculares, se agregan tres equivalentes de formaldehído a MeCHO para dar pentaeritritol , C (CH 2 OH) 4. [30]

In a Strecker reaction, acetaldehyde condenses with cyanide and ammonia to give, after hydrolysis, the amino acid alanine.[31] Acetaldehyde can condense with amines to yield imines; for example, with cyclohexylamine to give N-ethylidenecyclohexylamine. These imines can be used to direct subsequent reactions like an aldol condensation.[32]

También es un componente básico en la síntesis de compuestos heterocíclicos . En un ejemplo, se convierte, tras el tratamiento con amoníaco , en 5-etil-2-metilpiridina ("aldehído-colidina"). [33]

Derivados del acetal [ editar ]

Oligómeros cíclicos de acetaldehído (CH 3 CHO) n : paraldehído ( n = 3, izquierda) y metaldehído ( n = 4, derecha)

Three molecules of acetaldehyde condense to form "paraldehyde", a cyclic trimer containing C-O single bonds. Similarly condensation of four molecules of acetaldehyde give the cyclic molecule metaldehyde. Paraldehyde can be produced in good yields, using a sulfuric acid catalyst. Metaldehyde is only obtained in a few percent yield and with cooling, often using HBr rather than H2SO4 as the catalyst. At -40 °C in the presence of acid catalysts, polyacetaldehyde is produced.[21]

Conversion of acetaldehyde to 1,1-diethoxyethane, R1 = CH3, R2 = CH3CH2

Acetaldehyde forms a stable acetal upon reaction with ethanol under conditions that favor dehydration. The product, CH3CH(OCH2CH3)2, is formally named 1,1-diethoxyethane but is commonly referred to as "acetal".[34] This can cause confusion as "acetal" is more commonly used to describe compounds with the functional groups RCH(OR')2 or RR'C(OR'')2 rather than referring to this specific compound – in fact, 1,1-diethoxyethane is also described as the diethyl acetal of acetaldehyde.

Precursor del ácido vinilfosfónico [ editar ]

El acetaldehído es un precursor del ácido vinilfosfónico , que se utiliza para fabricar adhesivos y membranas conductoras de iones . La secuencia de síntesis comienza con una reacción con tricloruro de fósforo : [35]

PCl 3 + CH 3 CHO → CH 3 CH (O - ) PCl 3 +
CH 3 CH (O - ) PCl 3 + + 2 CH 3 CO 2 H → CH 3 CH (Cl) PO (OH) 2 + 2 CH 3 COCl
CH3CH(Cl)PO(OH)2 → CH2=CHPO(OH)2 + HCl

Biochemistry[edit]

In the liver, the enzyme alcohol dehydrogenase oxidizes ethanol into acetaldehyde, which is then further oxidized into harmless acetic acid by acetaldehyde dehydrogenase. These two oxidation reactions are coupled with the reduction of NAD+ to NADH.[36] In the brain, the enzyme catalase is primarily responsible for oxidizing ethanol to acetaldehyde, and alcohol dehydrogenase plays a minor role.[36] The last steps of alcoholic fermentation in bacteria, plants, and yeast involve the conversion of pyruvate into acetaldehyde and carbon dioxide 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.

Uses[edit]

Traditionally, acetaldehyde was mainly used as a precursor to acetic acid. This application has declined because acetic acid is produced more efficiently from methanol by the Monsanto and Cativa processes. Acetaldehyde is an important precursor to pyridine derivatives, pentaerythritol, and crotonaldehyde. Urea and acetaldehyde combine to give a useful resin. Acetic anhydride reacts with acetaldehyde to give ethylidene diacetate, a precursor to vinyl acetate, which is used to produce polyvinyl acetate.[21]

The global market for acetaldehyde is declining. Demand has been impacted by changes in the production of plasticizer alcohols, which has shifted because n-butyraldehyde is less often produced from acetaldehyde, instead being generated by hydroformylation of propylene. Likewise, acetic acid, once produced from acetaldehyde, is made predominantly by the lower-cost methanol carbonylation process.[37] The impact on demand has led to increase in prices and thus slowdown in the market.

Production of Acetaldehyde

Consumption of acetaldehyde (103 t) in 2003[21]
(* Included in others -glyoxal/glyoxalic acid, crotonaldehyde, lactic acid, n-butanol, 2-ethylhexanol)

ProductUSAMexicoW. EuropeJapanTotal
Acetic Acid/Acetic anhydride-118947147
Acetate esters35854224321
Pentaerythritol26–431180
Pyridine and pyridine bases73–10*83
Peracetic acid23––*23
1,3-Butylene glycol14––*14
Others53108098
Total17622206362766

China is the largest consumer of acetaldehyde in the world, accounting for almost half of global consumption in 2012. Major use has been the production of acetic acid. Other uses such as pyridines and pentaerythritol are expected to grow faster than acetic acid, but the volumes are not large enough to offset the decline in acetic acid. As a consequence, overall acetaldehyde consumption in China may grow slightly at 1.6% per year through 2018. Western Europe is the second-largest consumer of acetaldehyde worldwide, accounting for 20% of world consumption in 2012. As with China, the Western European acetaldehyde market is expected to increase only very slightly at 1% per year during 2012–2018. However, Japan could emerge as a potential consumer for acetaldehyde in next five years due to newfound use in commercial production of butadiene. The supply of butadiene has been volatile in Japan and the rest of Asia. This should provide the much needed boost to the flat market, as of 2013.[38]

Safety[edit]

Exposure limits[edit]

The threshold limit value is 25ppm (STEL/ceiling value) and the MAK (Maximum Workplace Concentration) is 50 ppm. At 50 ppm acetaldehyde, no irritation or local tissue damage in the nasal mucosa is observed. When taken up by the organism, acetaldehyde is metabolized rapidly in the liver to acetic acid. Only a small proportion is exhaled unchanged. After intravenous injection, the half-life in the blood is approximately 90 seconds.[21]

Dangers[edit]

Toxicity[edit]

No serious cases of acute intoxication have been recorded.[21] Acetaldehyde naturally breaks down in the human body[11] but has been shown to excrete in urine of rats.[39]

Irritation[edit]

Acetaldehyde is an irritant of the skin, eyes, mucous membranes, throat, and respiratory tract. This occurs at concentrations as low as 1000 ppm. Symptoms of exposure to this compound include nausea, vomiting, and headache. These symptoms may not happen immediately. The perception threshold for acetaldehyde in air is in the range between 0.07 and 0.25 ppm.[21] At such concentrations, the fruity odor of acetaldehyde is apparent. Conjunctival irritations have been observed after a 15-minute exposure to concentrations of 25 and 50 ppm, but transient conjunctivitis and irritation of the respiratory tract have been reported after exposure to 200 ppm acetaldehyde for 15 minutes.

Carcinogenicity[edit]

Acetaldehyde is carcinogenic in humans.[40][41] In 1988 the International Agency for Research on Cancer stated, "There is sufficient evidence for the carcinogenicity of acetaldehyde (the major metabolite of ethanol) in experimental animals."[42] In October 2009 the International Agency for Research on Cancer updated the classification of acetaldehyde stating that acetaldehyde included in and generated endogenously from alcoholic beverages is a Group I human carcinogen.[43] In addition, acetaldehyde is damaging to DNA[44] and causes abnormal muscle development as it binds to proteins.[45]

Aggravating factors[edit]

Alzheimer's disease[edit]

People with a genetic deficiency for the enzyme responsible for the conversion of acetaldehyde into acetic acid may have a greater risk of Alzheimer's disease. "These results indicate that the ALDH2 deficiency is a risk factor for LOAD [late-onset Alzheimer's disease] ..."[46]

Genetic conditions[edit]

A study of 818 heavy drinkers found that those exposed to more acetaldehyde than normal through a genetic variant of the gene encoding for alcohol dehydrogenase are at greater risk of developing cancers of the upper gastrointestinal tract and liver.[47]

Disulfiram[edit]

The drug disulfiram (Antabuse) prevents the oxidation of acetaldehyde to acetic acid. Antabuse is sometimes used as a deterrent for alcoholics wishing to stay sober.

Sources of exposure[edit]

Indoor air[edit]

Acetaldehyde is a potential contaminant in workplace, indoors, and ambient environments. Moreover, the majority of humans spend more than 90% of their time in indoor environments, increasing any exposure and the risk to human health.[48]

In a study in France, the mean indoor concentration of acetaldehydes measured in 16 homes was approximately seven times higher than the outside acetaldehyde concentration. The living room had a mean of 18.1±17.5 μg m−3 and the bedroom was 18.2±16.9 μg m−3, whereas the outdoor air had a mean concentration of 2.3±2.6 μg m−3.[citation needed]

It has been concluded that volatile organic compounds (VOC) such as benzene, formaldehyde, acetaldehyde, toluene, and xylenes have to be considered priority pollutants with respect to their health effects. It has been pointed that in renovated or completely new buildings, the VOCs concentration levels are often several orders of magnitude higher. The main sources of acetaldehydes in homes include building materials, laminate, linoleum, wooden varnished, and cork/pine flooring. It is also found in plastic water-based and matt emulsion paints, in wood ceilings, and wooden, particle-board, plywood, pine wood, and chipboard furniture.[49]

Outdoor air[edit]

The use of acetaldehyde is widespread in different industries, and it may be released into waste water or the air during production, use, transportation and storage. Sources of acetaldehyde include fuel combustion emissions from stationary internal combustion engines and power plants that burn fossil fuels, wood, or trash, oil and gas extraction, refineries, cement kilns, lumber and wood mills and paper mills. Acetaldehyde is also present in automobile and diesel exhaust.[50] As a result, acetaldehyde is "one of the most frequently found air toxics with cancer risk greater than one in a million".[13]

Tobacco smoke[edit]

Natural tobacco polysaccharides, including cellulose, have been shown to be the primary precursors making acetaldehyde a significant constituent of tobacco smoke.[51][52] It has been demonstrated to have a synergistic effect with nicotine in rodent studies of addiction.[53][54] Acetaldehyde is also the most abundant carcinogen in tobacco smoke; it is dissolved into the saliva while smoking.

Cannabis smoke[edit]

Acetaldehyde has been found in cannabis smoke. This finding emerged through the use of new chemical techniques that demonstrated the acetaldehyde present was causing DNA damage in laboratory settings.[55]

Alcohol consumption[edit]

Many microbes produce acetaldehyde from ethanol, but they have a lower capacity to eliminate the acetaldehyde, which can lead to the accumulation of acetaldehyde in saliva, stomach acid, and intestinal contents. Fermented food and many alcoholic beverages can also contain significant amounts of acetaldehyde. Acetaldehyde, derived from mucosal or microbial oxidation of ethanol, tobacco smoke, and diet, appears to act as a cumulative carcinogen in the upper digestive tract of humans.[56] According to European Commission's Scientific Committee on Consumer Safety's (SCCS) "Opinion on Acetaldehyde" (2012) the cosmetic products special risk limit is 5 mg/l and acetaldehyde should not be used in mouth-washing products.[57]

Plastics[edit]

Acetaldehyde is also created by thermal degradation or ultraviolet photo-degradation of some thermoplastic polymers during or after manufacture. One common example occurs when a bottle of water is left in a hot car for a few hours on a hot, sunny day, and one notices its strange sweet taste in the water from the breakdown of the polyethylene terephthalate (PETE) container.[58] The water industry generally recognizes 20–40 ppb as the taste/odor threshold for acetaldehyde. The level at which an average consumer could detect acetaldehyde is still considerably lower than any toxicity.[59]

Candida Overgrowth[edit]

Candida albicans in patients with potentially carcinogenic oral diseases has been shown to produce acetaldehyde in quantities sufficient to cause problems.[60]

See also[edit]

  • Alcohol dehydrogenase
  • Disulfiram-like drug
  • Formaldehyde
  • Paraldehyde
  • Wine fault

References[edit]

  1. ^ SciFinderScholar (accessed 4 November 2009). Acetaldehyde (75-07-0) Substance Detail.
  2. ^ Molecular Pathology and Diagnostics of Cancer p. 190
  3. ^ a b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 908. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
  4. ^ a b Stoffdaten Acetaldehyd bei Celanese Chemicals. Archived 17 May 2008 at the Wayback Machine as of December 1999.
  5. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0001". National Institute for Occupational Safety and Health (NIOSH).
  6. ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN 9781498754293.
  7. ^ "Acetaldehyde".
  8. ^ a b c Sigma-Aldrich Co., Acetaldehyde. Retrieved on 2013-07-20.
  9. ^ a b c "Acetaldehyde". NIOSH. 4 December 2014. Retrieved 12 February 2015.
  10. ^ Uebelacker, Michael; Lachenmeier, Dirk (13 June 2011). "Quantitative Determination of Acetaldehyde in Foods Using Automated Digestion with Simulated Gastric Fluid Followed by Headspace Gas Chromatography". Journal of Automated Methods and Management in Chemistry. 2011: 907317. doi:10.1155/2011/907317. PMC 3124883. PMID 21747735.
  11. ^ a b "Chemicals in the Environment: Acetaldehyde (CAS NO. 75-07-0)". epa.gov. Office of Pollution Prevention and Toxics, United States Environmental Protection Agency. August 1994. Archived from the original on 17 August 2002. Retrieved 22 January 2011.
  12. ^ List of IARC Group 1 carcinogens
  13. ^ a b Zhou, Ying; Li, Chaoyang; Huijbregts, Mark A. J.; Mumtaz, M. Moiz (7 October 2015). "Carcinogenic Air Toxics Exposure and Their Cancer-Related Health Impacts in the United States". PLOS One. 10 (10): e0140013. Bibcode:2015PLoSO..1040013Z. doi:10.1371/journal.pone.0140013. PMC 4596837. PMID 26444872.
  14. ^ Scheele, C. W. (1774) "Om Brunsten eller Magnesia nigra och dess egenskaper" (On brown-stone or black magnesia [i.e., manganese ore] and its properties), Kungliga Svenska vetenskapsakademiens handlingar (Proceedings of the Royal Swedish Academy of Sciences), 35 : 89–116; 177–194. On pages 109–110, Scheele mentions that refluxing ("digesting") ethanol (Alkohol vini) with manganese dioxide (Brunsten) and either hydrochloric acid (Spirtus salis) or sulfuric acid (Spiritus Vitrioli) produces a smell like "Aether nitri" (ethanol treated with nitric acid). Later investigators realized that Scheele had produced acetaldehyde.
  15. ^ Note:
    • Dabit, a pharmacist in Nantes, France, performed a series of experiments and concluded that acetaldehyde was formed when hydrogen in ethanol combined with oxygen in sulfuric acid to form water: Dabit (1800) "Extrait du mémoire du cit. Dabit sur l'éther" (Extract of the memoir by citizen Dabit on ether), Annales de Chimie, 34 : 289–305.
    • Fourcroy and Vauquelin stated that sulfuric acid was not consumed in the production of acetaldehyde: Fourcroy and Vauquelin (1800), "Sur l'éther préparé à la manière du cit. Dabit" (On the ether prepared in the way of citizen Dabit), Annales de Chimie, 34 : 318-332.
  16. ^ See:
    • (Döbereiner) (1821) "Neue Aether" (A new ether), Journal für Chemie und Physik, 32 : 269–270. Döbereiner named the new "ether" "Sauerstoffäther" (oxygen-ether).
    • (Döbereiner) (1822) "Döbereiner's Apparat zur Darstellung des Sauerstoffaethers" (Döbereiner's apparatus for the preparation of oxygen-ether), Journal für Chemie und Physik, 34 : 124–125.
    • Döbereiner, J. W. (1832) "Bildung des Sauerstoff-Aethers durch atmosphärische Oxidation des Alkohols" (Formation of oxy-ether by atmospheric oxidation of alcohol), Journal für Chemie und Physik, 64 : 466–468. In this paper, Döbereiner made acetaldehyde by exposing ethanol vapor to air in the presence of platinum black.
  17. ^ Liebig, Justus (1835) "Ueber die Producte der Oxydation des Alkohols" (On the products of oxidation of alcohol [i.e., ethanol]), Annalen der Chemie, 14 : 133–167.
  18. ^ Brock, William H. (1997) Justus von Liebig: The Chemical Gatekeeper. Cambridge, England: Cambridge University Press, pp. 83–84.
  19. ^ Liebig, J. (1835) "Sur les produits de l'oxidation de l'alcool" (On the products of the oxidation of alcohol), Annales de Chimie et de Physique, 59 : 289–327. From p. 290: "Je le décrirai dans ce mémoire sous le nom d'aldehyde; ce nom est formé de alcool dehydrogenatus." (I will describe it in this memoir by the name of aldehyde; this name is formed from alcohol dehydrogenatus.)
  20. ^ The name change occurred at least as early as 1868. See, for example: Eugen F. von Gorup-Besanez, ed., Lehrbuch der organischen Chemie für den Unterricht auf Universitäten ... [Textbook of Organic Chemistry for Instruction at Universities ...], 3rd ed. (Braunschweig, Germany: Friedrich Vieweg und Sohn, 1868), vol. 2, p. 88.
  21. ^ a b c d e f g h i j k Eckert, Marc et al. (2007) "Acetaldehyde" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. doi:10.1002/14356007.a01_031.pub2
  22. ^ Dmitry A. Ponomarev; Sergey M. Shevchenko (2007). "Hydration of Acetylene: A 125th Anniversary" (PDF). J. Chem. Educ. 84 (10): 1725. Bibcode:2007JChEd..84.1725P. doi:10.1021/ed084p1725.
  23. ^ Keeffe, J. R.; Kresge, A. J.; Schepp, N. P. (1990). "Keto-enol equilibrium constants of simple monofunctional aldehydes and ketones in aqueous solution". Journal of the American Chemical Society. 112 (12): 4862–4868. doi:10.1021/ja00168a035.
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External links[edit]

  • International Chemical Safety Card 0009
  • 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
  • Acetaldehyde production process flow sheet by ethylene oxidation method