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Open Access Articles- Top Results for Propionaldehyde

Propionaldehyde

Not to be confused with propanol.
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Propanal

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IUPAC name
Propanal
Systematic IUPAC name
Propionaldehyde
Other names
Methylacetaldehyde; propionic aldehyde; propaldehyde
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This page is a soft redirect.- C3H6O Molar mass 58.08 g mol−1 Appearance Colorless liquid
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Molecular shape C1, O: sp2

C2, C3: sp3

Dipole moment 2.52 D colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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EU classification Extremely Flammable F+ Irritant Xi R-phrases R11, R36/37/38 S-phrases S9, S16, S29 NFPA 704

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This page is a soft redirect. Related compounds

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Related aldehydes
Acetaldehyde
Butyraldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Propionaldehyde or propanal is the organic compound with the formula CH3CH2CHO. It is a saturated 3-carbon aldehyde and is a structural isomer of acetone. It is a colourless liquid with a slightly irritating, fruity odour.

Production

Propionaldehyde is mainly produced industrially through hydroformylation, by combining synthesis gas (carbon monoxide and hydrogen) with ethylene using a metal (typically rhodium) catalyst:

CO + H2 + C2H4 → CH3CH2CHO

In this way, several hundred thousand tons are produced annually.[1]

Laboratory preparation

Propionaldehyde may also be prepared by oxidizing 1-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]

Uses

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 tert-butylamine gives CH3CH2CH=N-t-Bu, a three-carbon building block used in organic synthesis. Deprotonation of this imine with LDA produces CH3CHLiCH=N-t-Bu, which in turn condenses with aldehydes.[3]

Interstellar occurrence

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.

References

  1. ^ a b Anthony J. Papa "Propanal" In Ullmann's Encyclopedia of Industrial Chemistry, 2011, WIley-VCH, Weinheim. doi:10.1002/14356007.a22_157.pub2
  2. ^ Charles D. Hurd and R. N. Meinert (1943). "Propionaldehyde". Org. Synth. ; Coll. Vol. 2, p. 541 
  3. ^ Peralta, M. M. "Propionaldehyde t-Butylimine" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289.
  4. ^ Scientists Discover Two New Interstellar Molecules: Point to Probable Pathways for Chemical Evolution in Space, National Radio Astronomy Observatory, June 21, 2004
  5. ^ Two newly found space molecules. By: Goho, Alexandra, Science News, 00368423, 7/24/2004, Vol. 166, Issue 4
  6. ^ Chemical Precursors to Life Found in Space Scientists say that a universal prebiotic chemistry may be at work

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