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Propionaldehyde or propanal is the aldehyde and is a structural isomer of acetone. It is a colourless liquid with a slightly irritating, fruity odour.
Propionaldehyde is mainly produced industrially through hydroformylation, by combining synthesis gas (carbon monoxide and hydrogen) with ethylene using a metal (typically rhodium) catalyst:
In this way, several hundred thousand tons are produced annually.[1]
Propionaldehyde may also be prepared by oxidizing propanol with a mixture of sulfuric acid and potassium dichromate. The reflux condenser contains water heated at 60 °C, which condenses unreacted propanol, but allows propionaldehyde to pass. The propionaldehyde vapor is immediately condensed into a suitable receiver. In this arrangement, any propionaldehyde formed is immediately removed from the reactor, thus it does not get over-oxidized to propionic acid.[2]
It is principally used as a precursor to trimethylolethane (CH3C(CH2OH)3) through a condensation reaction with formaldehyde; this triol is an important intermediate in the production of alkyd resins. Other applications include reduction to propanol and oxidation to propionic acid.[1]
Condensation of propionaldehyde with imine with LDA produces CH3CHLiCH=N-t-Bu, which in turn condenses with aldehydes.[3]
Astronomers have detected propionaldehyde in the molecular cloud Sagittarius B2 near the center of the Milky Way Galaxy, about 26,000 light years from Earth.[4][5][6] Because molecules emit energy at specific frequencies, researchers were able to identify propionaldehyde and the related compound, acrolein, by measuring radio waves emitted by the cloud.
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