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Propionaldehyde

Propionaldehyde
Skeletal structure of propanal
Flat structure
Ball-and-stick model
Names
IUPAC name
Propanal
Systematic IUPAC name
Propanal
Other names
  • Methylacetaldehyde
  • Propionic aldehyde
  • Propaldehyde
Identifiers
123-38-6 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:17153 YesY
ChEMBL ChEMBL275626 YesY
ChemSpider 512 YesY
ECHA InfoCard 100.004.204
PubChem 527
UNII AMJ2B4M67V YesY
UN number 1275
Properties
C3H6O
Molar mass 58.08 g·mol−1
Appearance Colorless liquid
Pungent, fruity odor
Density 0.81 g cm−3
Melting point −81 °C (−114 °F; 192 K)
Boiling point 46 to 50 °C (115 to 122 °F; 319 to 323 K)
20 g/100 mL
-34.32·10−6 cm3/mol
Viscosity 0.6 cP at 20 °C
Structure
C1, O: sp2

C2, C3: sp3
2.52 D
Hazards
Extremely Flammable F+ Irritant Xi
R-phrases R11, R36/37/38
S-phrases S9, S16, S29
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g., phosphorus Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −26 °C (−15 °F; 247 K)
175 °C (347 °F; 448 K)
Related compounds
Related aldehydes
Acetaldehyde
Butyraldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

C2, C3: sp3

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 colorless liquid with a slightly irritating, fruity odor.

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.

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.

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.

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.


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