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Concept
Acrolein
Summary
Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a piercing, acrid smell. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fat breaking down into acrolein. It is produced industrially from propene and mainly used as a biocide and a building block to other chemical compounds, such as the amino acid methionine.
Acrolein was first named and characterized as an aldehyde by the Swedish chemist Jöns Jacob Berzelius in 1839. He had been working with it as a thermal degradation product of glycerol, a material used in the manufacture of soap. The name is a contraction of ‘acrid’ (referring to its pungent smell) and ‘oleum’ (referring to its oil-like consistency). In the 20th century, acrolein became an important intermediate for the industrial production of acrylic acid and acrylic plastics.
Acrolein is prepared industrially by oxidation of propene. The process uses air as the source of oxygen and requires metal oxides as heterogeneous catalysts:
About 500,000 tons of acrolein are produced in this way annually in North America, Europe, and Japan. Additionally, all acrylic acid is produced via the transient formation of acrolein.
Propane represents a promising but challenging feedstock for the synthesis of acrolein (and acrylic acid).The main challenge is in fact the overoxidation to this acid.
When glycerol (also called glycerin) is heated to 280 °C, it decomposes into acrolein:
(CH2OH)2CHOH → CH2=CHCHO + 2 H2O
This route is attractive when glycerol is co-generated in the production of biodiesel from vegetable oils or animal fats. The dehydration of glycerol has been demonstrated but has not proven competitive with the route from petrochemicals.
The original industrial route to acrolein, developed by Degussa, involves condensation of formaldehyde and acetaldehyde:
HCHO + CH3CHO → CH2=CHCHO + H2O
Acrolein may also be produced on lab scale by the action of potassium bisulfate on glycerol (glycerine).
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