Difference between revisions of "Acetaldehyde"

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[[File:Acetaldehyde lewis.png|thumb|152x152px]]
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'''Acetaldehyde''' is the organic compound with chemical formula CH<sub>3</sub>CHO. It is the second-simplest aldehyde and finds use as a building block in organic synthesis.
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| Name = Acetaldehyde
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| Reference =
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| IUPACName = Acetaldehyde
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| PIN = Acetaldehyde
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| SystematicName = Ethanal
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| OtherNames = Acetic aldehyde<br>Ethyl aldehyde<br>Acetylaldehyde
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| Section1 = {{Chembox Identifiers
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| 3DMet =
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| Abbreviations =
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| Section2 = {{Chembox Properties
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| AtmosphericOHRateConstant =
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| Appearance = Colorless volatile liquid
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| BoilingPt =
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| BoilingPtC = 20.2
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| BoilingPt_ref =
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| BoilingPt_notes =
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| Density = 0.7928 g/cm<sup>3</sup> (10 °C)<br>0.784 g/cm<sup>3</sup> (20 °C)
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| Formula = C<sub>2</sub>H<sub>4</sub>O<br>CH<sub>3</sub>CHO
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| HenryConstant =
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| LogP =
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| MolarMass = 44.05 g/mol
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| MeltingPt =
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| MeltingPtC = −123.37
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| Odor = Ether-like
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| pKa = 13.57
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| pKb =
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| Solubility = Miscible
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| SolubleOther = Reacts with ammines<br>Miscible with glacial [[acetic acid]], [[acetone]], [[benzene]], [[diethyl ether]], [[ethanol]], [[ethyl acetate]], [[gasoline]], [[methanol]], [[toluene]], turpentine, [[xylene]]<br>Slightly soluble in [[chloroform]]
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| VaporPressure = 740 mmHg (20 °C)
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| Section3 = {{Chembox Structure
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| Coordination =
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| CrystalStruct =
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| MolShape = trigonal planar (sp²) at C<sub>1</sub><br />tetrahedral (sp³) at C<sub>2</sub>
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| Section4 = {{Chembox Thermochemistry
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| DeltaGf =
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| DeltaHc =
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| DeltaHf = −166 kJ/mol
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| Entropy = 250 J·mol<sup>−1</sup>·K<sup>−1</sup>
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| Section6 = {{Chembox Hazards
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| AutoignitionPt = 175 °C (347 °F; 448.15 K)
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| ExploLimits = 4.0–60%
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| ExternalMSDS = [https://www.docdroid.net/yUCvWsq/acetaldehyde-sa.pdf.html Sigma-Aldrich]
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| FlashPt = −39 °C (−38.2 °F; 234.15 K)
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| LD50 = 1,930 mg/kg (rat, oral)
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| LC50 = 13,000 ppm (rat)<br> 17,000 ppm (hamster)<br> 20,000 ppm (rat)
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| OtherCompounds = [[Formaldehyde]]<br>[[Propionaldehyde]]
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'''Acetaldehyde''' is the organic compound with chemical formula '''CH<sub>3</sub>CHO'''. It is the second-simplest aldehyde and finds use as a building block in organic synthesis.
  
 
==Properties==
 
==Properties==
 
===Chemical===
 
===Chemical===
−
 
 
Depending on reaction conditions, the oxidation of acetaldehyde by oxygen variously co-produces [[acetic anhydride]] and [[acetic acid]] via the intermediate [[peracetic acid]]. The process relies on a catalyst containing metal ions and is typically conducted by introduction of gaseous oxygen into liquid acetaldehyde.
 
Depending on reaction conditions, the oxidation of acetaldehyde by oxygen variously co-produces [[acetic anhydride]] and [[acetic acid]] via the intermediate [[peracetic acid]]. The process relies on a catalyst containing metal ions and is typically conducted by introduction of gaseous oxygen into liquid acetaldehyde.
  
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==Preparation==
 
==Preparation==
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Industrially, acetaldehyde is produced via the oxidation of [[ethylene|ethene]] over a copper-palladium catalyst. Two routes exist from ethanol, the first an exothermic, self-sustaining oxidation reaction using a copper or silver catalyst at a temperature of 500-650°C:
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Industrially, acetaldehyde is produced via the oxidation of [[ethylene|ethene]] over a copper-palladium catalyst.
  
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2CH<sub>3</sub>CH<sub>2</sub>OH + O<sub>2</sub> → 2CH<sub>3</sub>CHO + 2H<sub>2</sub>O
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:2 CH<sub>2</sub>=CH<sub>2</sub> + O<sub>2</sub> → 2 CH<sub>3</sub>CHO
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Two routes exist from [[ethanol]], the first an exothermic, self-sustaining oxidation reaction using a copper or silver catalyst at a temperature of 500-650°C:
 +
 
 +
:2 CH<sub>3</sub>CH<sub>2</sub>OH + O<sub>2</sub> → 2 CH<sub>3</sub>CHO + 2 H<sub>2</sub>O
  
 
The second method of preparing acetaldehyde from ethanol involves its dehydrogenation at a temperature of of 260-290 °C, again over a catalyst of copper. This route is endothermic, requiring constant and uniform heating, but has the advantage of not requiring oxygen input, which also reduces the risk of fire.
 
The second method of preparing acetaldehyde from ethanol involves its dehydrogenation at a temperature of of 260-290 °C, again over a catalyst of copper. This route is endothermic, requiring constant and uniform heating, but has the advantage of not requiring oxygen input, which also reduces the risk of fire.
  
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CH<sub>3</sub>CH<sub>2</sub>OH → CH<sub>3</sub>CHO + H<sub>2</sub><ref>Ullmann's Encyclopedia Of Industrial Chemistry, Wiley-VCH (2007)</ref>
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: CH<sub>3</sub>CH<sub>2</sub>OH → CH<sub>3</sub>CHO + H<sub>2</sub><ref>Ullmann's Encyclopedia Of Industrial Chemistry, Wiley-VCH (2007)</ref>
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During the synthesis of [[1,4-Dioxane|dioxane]] from [[ethylene glycol]] using conc. [[sulfuric acid]] as catalyst, small amounts of acetaldehyde will be produced. However you will need to convert large amounts of ethylene glycol into dioxane to get a significant amount of acetaldehyde.
  
 
==Projects==
 
==Projects==
 
*[[Pentaerythritol]] synthesis
 
*[[Pentaerythritol]] synthesis
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*Crotonaldehyde synthesis
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*Synthesis of [[glyoxal]]
  
 
==Handling==
 
==Handling==
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===Storage===
 
===Storage===
 
Acetaldehyde must be stored in a highly temperature-controlled environment given its low boiling point, and should also be kept in a separate cabinet or secondary container in a well-ventilated space, always away from potential sources of ignition.
 
Acetaldehyde must be stored in a highly temperature-controlled environment given its low boiling point, and should also be kept in a separate cabinet or secondary container in a well-ventilated space, always away from potential sources of ignition.
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Another option is to store it into a metal pressurized container, such as a [[lecture bottle]].
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Small amounts of niacinamide are sometimes used as stabilizer.<ref>https://www.sigmaaldrich.com/catalog/product/sial/w200320</ref>
  
 
===Disposal===
 
===Disposal===
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Acetaldehyde can be safely burned.
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Acetaldehyde can be safely burned. Do this outside.
  
 
==References==
 
==References==
 
<references/>
 
<references/>
 
===Relevant Sciencemadness threads===
 
===Relevant Sciencemadness threads===
 +
*[http://www.sciencemadness.org/talk/viewthread.php?tid=55 Acetaldehyde synthesis]
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*[http://www.sciencemadness.org/talk/viewthread.php?tid=79224 Preparation of Acetaldehyde]
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*[http://www.sciencemadness.org/talk/viewthread.php?tid=12767 Smell of Acetaldehyde - What Products?]
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*[http://www.sciencemadness.org/talk/viewthread.php?tid=23343 Acetaldehyde DANGER!!]
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[[Category:Chemical compounds]]
 
[[Category:Chemical compounds]]
 
[[Category:Organic compounds]]
 
[[Category:Organic compounds]]
 
[[Category:Aldehydes]]
 
[[Category:Aldehydes]]
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[[Category:Fragrant compounds]]
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[[Category:Volatile chemicals]]
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[[Category:Carcinogenic]]
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[[Category:Contact poisons]]
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[[Category:Liquids]]
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[[Category:Air-sensitive materials]]

Latest revision as of 21:30, 17 August 2020

Acetaldehyde
Acetaldehyde lewis.png
Names
IUPAC name
Acetaldehyde
Preferred IUPAC name
Acetaldehyde
Systematic IUPAC name
Ethanal
Other names
Acetic aldehyde
Ethyl aldehyde
Acetylaldehyde
Properties
C2H4O
CH3CHO
Molar mass 44.05 g/mol
Appearance Colorless volatile liquid
Odor Ether-like
Density 0.7928 g/cm3 (10 °C)
0.784 g/cm3 (20 °C)
Melting point −123.37 °C (−190.07 °F; 149.78 K)
Boiling point 20.2 °C (68.4 °F; 293.3 K)
Miscible
Solubility Reacts with ammines
Miscible with glacial acetic acid, acetone, benzene, diethyl ether, ethanol, ethyl acetate, gasoline, methanol, toluene, turpentine, xylene
Slightly soluble in chloroform
Vapor pressure 740 mmHg (20 °C)
Acidity (pKa) 13.57
Thermochemistry
250 J·mol−1·K−1
−166 kJ/mol
Hazards
Safety data sheet Sigma-Aldrich
Flash point −39 °C (−38.2 °F; 234.15 K)
Lethal dose or concentration (LD, LC):
1,930 mg/kg (rat, oral)
13,000 ppm (rat)
17,000 ppm (hamster)
20,000 ppm (rat)
Related compounds
Related compounds
 Formaldehyde
Propionaldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Acetaldehyde is the organic compound with chemical formula CH3CHO. It is the second-simplest aldehyde and finds use as a building block in organic synthesis.

Properties

Chemical

Depending on reaction conditions, the oxidation of acetaldehyde by oxygen variously co-produces acetic anhydride and acetic acid via the intermediate peracetic acid. The process relies on a catalyst containing metal ions and is typically conducted by introduction of gaseous oxygen into liquid acetaldehyde.

Physical

Acetaldehyde is a transparent, volatile, and extremely flammable liquid at room temperature that boils at only 20.2°C (68.4°F), making it difficult to store. The characteristic odor of acetaldehyde is sweet and reminiscent of green apple. Acetaldehyde has a flash point of only −39°C, making it absolutely crucial that any significant amount is kept away from possible ignition sources.

Availability

No over-the-counter source of acetaldehyde is known, and sources are unlikely due to the difficulty and danger of prolonged storage.

Preparation

Industrially, acetaldehyde is produced via the oxidation of ethene over a copper-palladium catalyst.

2 CH2=CH2 + O2 → 2 CH3CHO

Two routes exist from ethanol, the first an exothermic, self-sustaining oxidation reaction using a copper or silver catalyst at a temperature of 500-650°C:

2 CH3CH2OH + O2 → 2 CH3CHO + 2 H2O

The second method of preparing acetaldehyde from ethanol involves its dehydrogenation at a temperature of of 260-290 °C, again over a catalyst of copper. This route is endothermic, requiring constant and uniform heating, but has the advantage of not requiring oxygen input, which also reduces the risk of fire.

CH3CH2OH → CH3CHO + H2[1]

During the synthesis of dioxane from ethylene glycol using conc. sulfuric acid as catalyst, small amounts of acetaldehyde will be produced. However you will need to convert large amounts of ethylene glycol into dioxane to get a significant amount of acetaldehyde.

Projects

Handling

Safety

Acetaldehyde is designated a probable carcinogen and is many times more toxic than ethanol, which it is a metabolite of. With a high chance of vaporization and a flash point of only −39 °C, acetaldehyde represents a significant fire hazard, and care should be made that all potential sources of ignition are kept away.

Storage

Acetaldehyde must be stored in a highly temperature-controlled environment given its low boiling point, and should also be kept in a separate cabinet or secondary container in a well-ventilated space, always away from potential sources of ignition.

Another option is to store it into a metal pressurized container, such as a lecture bottle.

Small amounts of niacinamide are sometimes used as stabilizer.[2]

Disposal

Acetaldehyde can be safely burned. Do this outside.

References

  1. ↑ Ullmann's Encyclopedia Of Industrial Chemistry, Wiley-VCH (2007)
  2. ↑ https://www.sigmaaldrich.com/catalog/product/sial/w200320

Relevant Sciencemadness threads

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