Propionaldehyde

Propanal

Names
IUPAC name Propanal
Systematic IUPAC name Propionaldehyde
Other names Methylacetaldehyde; propionic aldehyde; propaldehyde
Identifiers
CAS Registry Number	123-38-6 Y
ChEBI	CHEBI:17153 Y
ChEMBL	ChEMBL275626 Y
ChemSpider	512 Y
InChI InChI=1S/C3H6O/c1-2-3-4/h3H,2H2,1H3 Y Key: NBBJYMSMWIIQGU-UHFFFAOYSA-N Y InChI=1/C3H6O/c1-2-3-4/h3H,2H2,1H3 Key: NBBJYMSMWIIQGU-UHFFFAOYAZ
Jmol-3D images	Image
PubChem	527
SMILES CCC=O
UNII	AMJ2B4M67V Y
UN number	1275
Properties
Chemical formula	C3H6O
Molar mass	58.08 g mol−1
Appearance	Colorless liquid Pungent, malty odor
Density	0.81 g cm−3
Melting point	−81 °C (−114 °F; 192 K)
Boiling point	46 °C (115 °F; 319 K)
Solubility in water	20 g/100 mL
Viscosity	0.6 cP at 20 °C
Structure
Molecular shape	C1, O: sp2 C2, C3: sp3
Dipole moment	2.52 D
Hazards
EU classification	F+ Xi
R-phrases	R11, R36/37/38
S-phrases	S9, S16, S29
NFPA 704	3 2 2
Flash point	−26 °C (−15 °F; 247 K)
Autoignition temperature	175 °C (347 °F; 448 K)
Related compounds
Related aldehydes	Acetaldehyde Butyraldehyde
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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. ↑ 1.0 1.1 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

Molecules detected in outer space Molecules Diatomic Aluminium monochloride Aluminium monofluoride Aluminium monoxide Argon hydride Carbon monophosphide Carbon monosulfide Carbon monoxide Carborundum Cyanogen radical Diatomic carbon Fluoromethylidynium Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Iron(II) oxide Magnesium monohydride cation Methylidyne radical Nitric oxide Nitrogen (molecular) Nitrogen monohydride Nitrogen sulfide Oxygen (molecular) Phosphorus monoxide Phosphorus nitride Potassium chloride Silicon carbide Silicon mononitride Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfur monohydride Sulfur monoxide Titanium oxide Triatomic Aluminium hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Ethynyl radical Formyl radical Hydrogen cyanide Hydrogen isocyanide (HCN) Hydrogen isocyanide (HNC) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene radical N2H+ Nitrous oxide Nitroxyl Ozone Phosphaethyne Potassium cyanide Protonated molecular hydrogen Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide Silicon naphthalocyanine Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water Four atoms Acetylene Ammonia Cyanic acid Cyanoethynyl Cyclopropynylidyne Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Methylene amidogen Methyl radical Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thioformaldehyde Tricarbon monoxide Tricarbon sulfide Thiocyanic acid Five atoms Ammonium Ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Protonated formaldehyde Silane Silicon-carbide cluster Six atoms Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC4N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene Seven atoms Acetaldehyde Acrylonitrile Cyanodiacetylene Ethylene oxide Hexatriynyl radical Methylacetylene Methylamine Vinyl alcohol Eight atoms Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Heptatrienyl radical Hexapentaenylidene Methylcyanoacetylene Methyl formate Propenal Nine atoms Acetamide Cyanohexatriyne Cyanotriacetylene Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Propionitrile Ten atoms or more Acetone Benzene Buckminsterfullerene (C60 fullerene) ("bucky-ball") C70 fullerene Cyanodecapentayne Cyanopentaacetylene Cyanotetra-acetylene Ethylene glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propanal n-Propyl cyanide Pyrimidine Deuterated molecules Ammonia Ammonium ion Formaldehyde Formyl radical Heavy water Hydrogen cyanide Hydrogen deuteride Hydrogen isocyanide Methylacetylene N2D+ Trihydrogen cation Unconfirmed Anthracene Dihydroxyacetone Ethyl methyl ether Glycine Graphene H2NCO+ Linear C5 Naphthalene cation Phosphine Pyrene Silylidine Related Abiogenesis Astrobiology Astrochemistry Atomic and molecular astrophysics Chemical formula Circumstellar envelope Cosmic dust Cosmic ray Cosmochemistry Diffuse interstellar band Extraterrestrial life Extraterrestrial liquid water Forbidden mechanism Helium hydride ion Homochirality Intergalactic dust Interplanetary medium Interstellar medium Iron–sulfur world theory Kerogen Life Molecules in stars Nexus for Exoplanet System Science Organic compound Outer space PAH world hypothesis Panspermia Polycyclic aromatic hydrocarbon (PAH) RNA world hypothesis Spectroscopy Tholin Book:Chemistry Category:Astrochemistry Category:Molecules Portal:Astrobiology Portal:Chemistry