View source for Acrolein

{{Chembox
| Name = Acrolein
| Reference = 
| IUPACName = Prop-2-enal
| PIN = 
| SystematicName = 
| OtherNames = Acraldehyde<br>Acrylaldehyde<br>Acrylic aldehyde<br>Allyl Aldehyde<br>Ethylene aldehyde
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| Section1 = {{Chembox Identifiers
| 3DMet = 
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  }}
| Section2 = {{Chembox Properties
| AtmosphericOHRateConstant = 
| Appearance = Colorless to yellowish liquid
| BoilingPt = 
| BoilingPtC = 53
| BoilingPt_ref = 
| BoilingPt_notes = 
| Density = 0.839 g/cm<sup>3</sup>
| Formula = C<sub>3</sub>H<sub>4</sub>O
| HenryConstant = 
| LogP = 
| MolarMass = 56.06 g/mol
| MeltingPt = 
| MeltingPtC = −88
| MeltingPt_ref = 
| MeltingPt_notes = 
| Odor = Acrid, burnt fat-like
| pKa = 
| pKb = 
| Solubility = 20 g/100 ml (20 °C)
| SolubleOther = Miscible in [[acetone]], [[benzene]], [[diethyl ether]], [[ethanol]], [[methylcyclohexane]]<br>Slightly soluble in [[chloroform]]
| Solvent = 
| VaporPressure = 210 mmHg
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| Section3 = {{Chembox Structure
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| Section4 = {{Chembox Thermochemistry
| DeltaGf = 
| DeltaHc = -1,633.83 kJ/mol
| DeltaHf = -65.314 kJ/mol
| Entropy = 
| HeatCapacity = 69.31 J·mol<sup>−1</sup>·K<sup>−1</sup>
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| Section5 = {{Chembox Explosive
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| Section6 = {{Chembox Hazards
| AutoignitionPt = 278 °C
| ExploLimits = 2.8-31%
| ExternalMSDS = [https://www.docdroid.net/qsmrC2j/acrolein-sa.pdf.html Sigma-Aldrich]
| FlashPt = −26 °C
| LD50 = 
| LC50 = 875 ppm (mouse, 1 min)<br>175 ppm (mouse, 10 min)<br>150 ppm (dog, 30 min)<br>8 ppm (rat, 4 hr)<br>375 ppm (rat, 10 min)<br>25.4 ppm (hamster, 4 hr)<br>131 ppm (rat, 30 min)
| MainHazards = Highly poisonous and irritant
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| Section7 = {{Chembox Related
| OtherAnions = 
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| OtherFunction = 
| OtherFunction_label = 
| OtherCompounds = [[Propionaldehyde]]
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}}
'''Acrolein''' or '''propenal''' ('''C<sub>3</sub>H<sub>4</sub>O''') is the simplest unsaturated aldehyde. It is a colourless liquid with a piercing, disagreeable, acrid smell reminiscent of burnt fat.

==Properties==
===Chemical===
Acrolein will polymerize in contact with light or a strong base.

===Physical===
Acrolein is a colorless to slight yellowish liquid, with a strong unpleasant odor, reminiscent of burnt fat.

==Availability==
While some chemical suppliers will sell acrolein, it is extremely difficult to get hold of.

==Preparation==
Can be prepared by dehydration of [[glycerol]].<ref>https://www.youtube.com/watch?v=7oAcT4Duun4</ref>

Oxidation of propene will also give acrolein.

==Projects==
*Make 1-octen-3-ol
*Make [[propanol]]<ref>http://pubs.rsc.org/en/Content/ArticleLanding/2016/RA/c6ra02682f#!divAbstract</ref>

==Handling==
===Safety===
Acrolein is highly toxic and irritant. Wear proper protection and work in a well ventilated place or in a fumehood. Normal respirators do not block it, so you'll have to use a different type of breathing mask.

===Storage===
Acrolein should be stored in amber bottles, away from light or bases. [[Hydroquinone]] is added as a stabilizer. However, it should be noted that acrolein will polymerize in several days.

===Disposal===
Acrolein can be neutralized with a base, such as sodium hydroxide.

==References==
<references/>
===Relevant Sciencemadness threads===
*[http://www.sciencemadness.org/talk/viewthread.php?tid=212 Glycerol to Propionic Acid: A Chemical Safari Tour.]
*[http://www.sciencemadness.org/talk/viewthread.php?tid=7036 Valorizing the Glycerol from Biodiesel Production]

[[Category:Chemical compounds]]
[[Category:Organic compounds]]
[[Category:Aldehydes]]
[[Category:Volatile chemicals]]
[[Category:Materials unstable in basic solution]]
[[Category:Light-sensitive chemicals]]
[[Category:Foul smelling compounds]]
[[Category:Carcinogenic]]
[[Category:Things that should NOT be messed with except by professionals]]
[[Category:Choking agents]]
[[Category:Liquids]]